treatments-xml/data/03/9A/CE/039ACE712C6F61725331FD8A168DBF7D.xml

<document id="1720B5320EB1FAE15F97E1F171DF60CA" ID-DOI="10.1016/j.phytochem.2022.113471" ID-ISSN="1873-3700" ID-Zenodo-Dep="8160618" IM.bibliography_approvedBy="juliana" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="juliana" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1689692017716" checkinUser="felipe" docAuthor="Kılınc, Hilal, Masullo, Milena, Lauro, Gianluigi, D’Urso, Gilda, Alankus, Ozgen, Bifulco, Giuseppe &amp; Piacente, Sonia" docDate="2023" docId="039ACE712C6F61725331FD8A168DBF7D" docLanguage="en" docName="Phytochemistry.205.113471.pdf" docOrigin="Phytochemistry (113471) 205" docSource="http://dx.doi.org/10.1016/j.phytochem.2022.113471" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.3:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="3" docTitle="Scabiosa atropurpurea subsp. methanol" docType="treatment" docVersion="2" lastPageNumber="7" masterDocId="FFA3B6092C6E61745355FC681412BA28" masterDocTitle="Scabiosa atropurpurea: A rich source of iridoids with α-glucosidase inhibitory activity evaluated by in vitro and in silico studies" masterLastPageNumber="113471" masterPageNumber="113471" pageNumber="2" updateTime="1689858957558" updateUser="ExternalLinkService">
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<mods:title id="BF938556389D1C6BD464FCB6B2CBE736">Scabiosa atropurpurea: A rich source of iridoids with α-glucosidase inhibitory activity evaluated by in vitro and in silico studies</mods:title>
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<mods:namePart id="C39B9C96ABFF0C84B66E3B9B9A76B2E0">Kılınc, Hilal</mods:namePart>
<mods:affiliation id="59DA387795ACB0717411844DF35ED830">, Milena Masullo &amp; Dokuz Eylul University Engineering Faculty Department of Geological Engineering, Buca, ˙ Izmir, 35370, Turkey</mods:affiliation>
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<mods:namePart id="873D459D12B627C18EC27A90DE3AA0D7">Masullo, Milena</mods:namePart>
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<mods:namePart id="2E8D862042F5CC6B825CC4FD76F01994">Lauro, Gianluigi</mods:namePart>
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<mods:namePart id="4FDD8DE81FC5779A65AA733E11FA6E72">D’Urso, Gilda</mods:namePart>
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<mods:namePart id="DEC57078235AAA111B76963E495C7206">Alankus, Ozgen</mods:namePart>
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<mods:namePart id="E80686455F775554E8D9B9AC84FD87C5">Bifulco, Giuseppe</mods:namePart>
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<mods:namePart id="D43E8B1F792F25E4F8814680B8021F54">Piacente, Sonia</mods:namePart>
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<mods:title id="478895930999CE674AFE4E7DD32840D9">Phytochemistry</mods:title>
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<emphasis id="B947A3752C6F61755331FD8A16B7BBDE" bold="true" box="[100,677,482,502]" italics="true" pageId="1" pageNumber="2">
2.1. LC-MS analysis of 
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methanol extract
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To broaden the knowledge of the specialised metabolites occurring in 
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<emphasis id="B947A3752C6F617553D5FE5E151DB861" bold="true" box="[128,271,566,585]" italics="true" pageId="1" pageNumber="2">S. atropurpurea</emphasis>
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, an in-depth phytochemical investigation has been developed in the present work. The methanol extract of 
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<emphasis id="B947A3752C6F61755122FE3A1690B84D" bold="true" box="[631,642,594,613]" italics="true" pageId="1" pageNumber="2">S</emphasis>
. 
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was initially subjected to a preliminary analysis using an extremely sensitive analytical technique like liquid chromatography coupled with high-resolution tandem mass spectrometry in negative ionisation mode, using a mass spectrometer with an electrospray source coupled to an orbitrap mass analyser (LC-ESI/LTQOrbitrap/MS). The LC-MS profile (
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), obtained using a mobile phase made up of a gradient of acetonitrile and water both acidified with 0.1% formic acid, highlighted the presence of 28 main chromatographic peaks corresponding to compounds belonging to the flavonoid, phenylpropanoid, and iridoid classes. Some of the main peaks were putatively attributed based on their accurate masses, characteristic fragmentation pattern, and by comparing the obtained results with data reported in literature and databases (database “KNApSAcK) on the 
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species
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(
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). Analysis of the LC-ESI/HR-MS 
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spectra of compounds 
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, 
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, 
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showed a typical fragmentation pattern with neutral losses of 132, 146, and 162 Da ascribable to flavones (apigenin, diosmetin, and luteolin) and flavonols (kaempferol and quercetin) glycosylated with sugar units corresponding to pentose, deoxyhexose and hexose units, respectively; in addition, a neutral loss of 120 Da corresponding to a C-linked hexose unit could be observed for compound 
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. Compounds 
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, 
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, and 
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showed a typical fragmentation pattern observed for compounds belonging to the phenylpropanoid class. Tandem mass spectra of the [M-H] 
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ion at 
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515 of compounds 
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and 
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showed an identical fragmentation to that reported in literature (
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) for dicaffeoylquinic acid with a peak [M-caffeoyl-H] 
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at 
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353, indicating the loss of a caffeoyl unit. Compounds 
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, 
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, 
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, 
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, 
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, 
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showed an accurate mass ascribable to iridoid molecular formulae. In some cases, the fragmentation pattern of these compounds allowed us to ascertain the presence of sugar units linked to the aglycone moiety suggesting their structure as iridoid glycosides. In other cases, the fragmentation pattern, along with the molecular formula, suggested the occurrence of bis-iridoids which are made up of two iridoid moieties. They can be formed by dimerization of iridoids and secoiridoids. Based on this approach, it was not possible to assign the exact structure of all specialised metabolites, and it was also observed that some compounds, including 
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, 
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, and 
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, exhibited accurate masses that were not traceable among compounds already reported in the literature for 
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<emphasis id="B947A3752C6F617556FCFD961772B805" bold="true" italics="true" pageId="1" pageNumber="2">Scabiosa</emphasis>
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genus. With the aim to obtain an in-depth knowledge of the constituents of the methanol extract and unambiguously attribute the peaks occurring in the LC-MS profile, a phytochemical investigation of the extract was performed.
</paragraph>
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<emphasis id="B947A3752C6F61755067FED11196B8E4" bold="true" box="[818,1412,697,716]" italics="true" pageId="1" pageNumber="2">2.2. Isolation and characterisation of specialised metabolites from</emphasis>
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<taxonomicName id="4C3304E42C6F61755067FEBD17E8B8C1" box="[818,1018,725,745]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6F61755067FEBD17E8B8C1" bold="true" box="[818,1018,725,745]" italics="true" pageId="1" pageNumber="2">Scabiosa atropurpurea</emphasis>
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The methanol extract of 
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<emphasis id="B947A3752C6F6175571CFF6510CAB909" bold="true" box="[1097,1240,781,801]" italics="true" pageId="1" pageNumber="2">S. atropurpurea</emphasis>
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was fractionated by size exclusion chromatography through Sephadex LH-20. Then the fractions were further purified by HPLC-UV and RI, obtaining pure compounds whose structures were characterised by spectroscopic methods, including 1D- (
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, 
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C, TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC, and ROESY) experiments and ESI-MS analysis (
<bibRefCitation id="EFA202962C6F61755663FFF11770B9E0" author="Benavides, A. &amp; Montoro, P. &amp; Bassarello, C. &amp; Piacente, S. &amp; Pizza, C." pageId="1" pageNumber="2" pagination="639 - 647" refId="ref9640" refString="Benavides, A., Montoro, P., Bassarello, C., Piacente, S., Pizza, C., 2006. Catechin derivatives in Jatropha macrantha stems: characterisation and LC / ESI / MS / MS quali-quantitative analysis. J. Pharm. Biomed. Anal. 40, 639 - 647. https: // doi. org / 10.1016 / j. jpba. 2005.10.004." type="journal article" year="2006">Benavides et al., 2006</bibRefCitation>
). All the isolated and identified metabolites are reported in 
<tableCitation id="C6B14ADC2C6F61755067FFB8176BB9CC" box="[818,889,976,996]" captionStart="Table 1" captionStartId="2.[100,150,150,166]" captionTargetPageId="2" captionText="Table 1 Compounds identified in Scabiosa atropurpurea extract by LC-ESI-FT-MS, LC-ESI-FT-MS/MS analysis and NMR spectroscopy." httpUri="http://table.plazi.org/id/DF4C2FEF2C6C61765331FCFE106DBAE8" pageId="1" pageNumber="2" tableUuid="DF4C2FEF2C6C61765331FCFE106DBAE8">Table 1</tableCitation>
. The chemical investigation revealed that compounds 
<emphasis id="B947A3752C6F617556DDFFB81186B9CB" bold="true" box="[1416,1428,976,995]" pageId="1" pageNumber="2">1</emphasis>
, 
<emphasis id="B947A3752C6F617556F7FFB811BCB9CB" bold="true" box="[1442,1454,976,995]" pageId="1" pageNumber="2">4</emphasis>
, 
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, 
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7 
<emphasis id="B947A3752C6F6175506BFF85175BBE29" bold="true" box="[830,841,1005,1025]" italics="true" pageId="1" pageNumber="2">–</emphasis>
9
</emphasis>
, and 
<emphasis id="B947A3752C6F617550DCFF8417B0B9D7" bold="true" box="[905,930,1004,1023]" pageId="1" pageNumber="2">15</emphasis>
were already reported in 
<taxonomicName id="4C3304E42C6F617557C1FF84110DBE28" box="[1172,1311,1004,1024]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6F617557C1FF84110DBE28" bold="true" box="[1172,1311,1004,1024]" italics="true" pageId="1" pageNumber="2">S. atropurpurea</emphasis>
</taxonomicName>
, while compounds 
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2 
<emphasis id="B947A3752C6F6175506BF860175BBE34" bold="true" box="[830,841,1032,1052]" italics="true" pageId="1" pageNumber="2">–</emphasis>
3
</emphasis>
, 
<emphasis id="B947A3752C6F61755037F860178DBE33" bold="true" box="[866,927,1032,1052]" pageId="1" pageNumber="2">
12 
<emphasis id="B947A3752C6F6175502EF8601794BE34" bold="true" box="[891,902,1032,1052]" italics="true" pageId="1" pageNumber="2">–</emphasis>
14
</emphasis>
, 
<emphasis id="B947A3752C6F617550F9F86017D7BE33" bold="true" box="[940,965,1032,1051]" pageId="1" pageNumber="2">18</emphasis>
, and 
<emphasis id="B947A3752C6F617550A9F8601007BE33" bold="true" box="[1020,1045,1032,1051]" pageId="1" pageNumber="2">20</emphasis>
were reported in other species of the 
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<emphasis id="B947A3752C6F617556D7F86011DDBE33" bold="true" box="[1410,1487,1032,1051]" italics="true" pageId="1" pageNumber="2">Scabiosa</emphasis>
</taxonomicName>
genus. Noteworthy, compounds 
<emphasis id="B947A3752C6F61755708F84C107BBE1F" bold="true" box="[1117,1129,1060,1079]" pageId="1" pageNumber="2">6</emphasis>
, 
<emphasis id="B947A3752C6F61755721F84C109FBE1F" bold="true" box="[1140,1165,1060,1079]" pageId="1" pageNumber="2">10</emphasis>
, 
<emphasis id="B947A3752C6F617557C2F84C10A2BE1F" bold="true" box="[1175,1200,1060,1079]" pageId="1" pageNumber="2">11</emphasis>
, 
<emphasis id="B947A3752C6F617557EEF84C10C6BE1F" bold="true" box="[1211,1236,1060,1079]" pageId="1" pageNumber="2">16</emphasis>
, 
<emphasis id="B947A3752C6F6175578BF84C10E5BE1F" bold="true" box="[1246,1271,1060,1079]" pageId="1" pageNumber="2">17</emphasis>
, 
<emphasis id="B947A3752C6F61755657F84C1109BE1F" bold="true" box="[1282,1307,1060,1079]" pageId="1" pageNumber="2">19</emphasis>
, 
<emphasis id="B947A3752C6F61755670F84C1170BE1F" bold="true" box="[1317,1378,1060,1080]" pageId="1" pageNumber="2">21–28</emphasis>
were found in 
<taxonomicName id="4C3304E42C6F61755019F82817CBBE7B" box="[844,985,1088,1107]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6F61755019F82817CBBE7B" bold="true" box="[844,985,1088,1107]" italics="true" pageId="1" pageNumber="2">S. atropurpurea</emphasis>
</taxonomicName>
for the first time, and among them, 
<emphasis id="B947A3752C6F6175566BF8281145BE7B" bold="true" box="[1342,1367,1088,1107]" pageId="1" pageNumber="2">23</emphasis>
, 
<emphasis id="B947A3752C6F61755630F828116CBE7B" bold="true" box="[1381,1406,1088,1107]" pageId="1" pageNumber="2">25</emphasis>
, and 
<emphasis id="B947A3752C6F617556E3F82811DDBE7B" bold="true" box="[1462,1487,1088,1107]" pageId="1" pageNumber="2">28</emphasis>
were undescribed compounds.
</paragraph>
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The molecular formula of compound 
<emphasis id="B947A3752C6F617557B0F81010ECBEA3" bold="true" box="[1253,1278,1144,1163]" pageId="1" pageNumber="2">23</emphasis>
was established as C 
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<subScript id="17B77D222C6F61755034F8F31761BE81" attach="both" box="[865,883,1179,1193]" fontSize="6" pageId="1" pageNumber="2">28</subScript>
O 
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by HR-ESI-MS (
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419.1548 [M-H] 
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, calcd for C 
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<collectionCode id="ED22E7A22C6F617556D3F8FC1184BE8F" box="[1414,1430,1172,1191]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="1" pageNumber="2" type="Herbarium">H</collectionCode>
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O 
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, 419.1553) and 
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C NMR data. The IR spectrum indicated the presence of OH (
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) and C––O (1705 and 
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). The 
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/ 
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spectrum showed a principal product ion at 
<emphasis id="B947A3752C6F61755724F88F1084BED2" bold="true" box="[1137,1174,1255,1274]" italics="true" pageId="1" pageNumber="2">m/z</emphasis>
239.09 [M-H-180] 
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originated by neutral loss of whole or mono-dehydrated hexose unit. The 
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NMR spectrum of 
<emphasis id="B947A3752C6C61765389FFA914E7B9FC" bold="true" box="[220,245,961,980]" pageId="2" pageNumber="3">23</emphasis>
showed signals for an olefinic proton at δ 7.44 (s), an acetal proton at δ 5.54 (1 
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, d, 
<emphasis id="B947A3752C6C6176522AFFB5159BB9D8" bold="true" box="[383,393,989,1008]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=8.5 Hz), a hemiacetal proton at δ 4.53 (1 
<collectionCode id="ED22E7A22C6C61765320FF911498BE24" box="[117,138,1017,1036]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
, d, 
<emphasis id="B947A3752C6C617653FFFF9114A6BE24" bold="true" box="[170,180,1017,1036]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=5.9, 5.2 Hz), a terminal vinyl group at δ 5.30 (1 
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, d, 
<emphasis id="B947A3752C6C617651E1FF9116ACBE24" bold="true" box="[692,702,1017,1036]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=10.5 Hz), 5.33 (1 
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, d, 
<emphasis id="B947A3752C6C61765256F87D151FBE00" bold="true" box="[259,269,1045,1064]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=17.7 Hz) and 5.76 (1 
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, ddd, 
<emphasis id="B947A3752C6C61765179F87D1624BE00" bold="true" box="[556,566,1045,1064]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=7.5, 10.5, 17.7 Hz). Further signals were observed at δ 1.67 (1 
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, ddd, 
<emphasis id="B947A3752C6C6176511FF8591646BE6C" bold="true" box="[586,596,1073,1092]" italics="true" pageId="2" pageNumber="3">J</emphasis>
= 14.0, 5.2, 4.0), 2.10 (1 
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, ddd, 
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=14.0, 5.9, 1.5), 2.69 (1 
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, brdt 
<emphasis id="B947A3752C6C61765160F825162DBE48" bold="true" box="[565,575,1101,1120]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=8.5, 7.5) and 2.94 (m). From the COSY spectrum the sequence 4.53 (H-7), 2.10 (H-6a), 1.67 (H-6b), 2.94 (H-5), 2.69 (H-9), 5.76 (H-8), 5.33 (H-10a) and 5.30 (H-10 b) of a secoiridoid skeleton could be deduced. In addition, signals corresponding to two methoxyl groups at δ 3.72 (3 
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, s) and 3.32 (3 
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, s) could be observed. In the 
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NMR spectrum, a signal corresponding to an anomeric proton at δ 4.71 (d, 
<emphasis id="B947A3752C6C617652CFF89C15B6BF2F" bold="true" box="[410,420,1268,1287]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=7.8 Hz) was present. The chemical shifts of all the individual protons of the sugar unit were ascertained from a combination of 1D-TOCSY and DQF-COSY spectral analysis, and the 
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C NMR chemical shifts of their attached carbons could be unambiguously assigned by HSQC (see 
<tableCitation id="C6B14ADC2C6C617652CEF90B15CDBF5E" box="[411,479,1379,1398]" captionStart="Table 2" captionStartId="3.[100,150,150,166]" captionTargetBox="[116,754,213,1942]" captionTargetPageId="3" captionText="Table 2 1H and 13C NMR data (J in Hz) of compounds 23, 25 and 28 (CD OD, 600 MHz). 3" httpUri="http://table.plazi.org/id/DF4C2FEF2C6D61775331FCFE1696BAEB" pageId="2" pageNumber="3" tableUuid="DF4C2FEF2C6D61775331FCFE1696BAEB">Table 2</tableCitation>
) (
<bibRefCitation id="EFA202962C6C617652A1F90B16ABBF5E" author="Gulcemal, D. &amp; Masullo, M. &amp; Bedir, E. &amp; Festa, M. &amp; Karayildirim, T. &amp; Alankus-Caliskan, O. &amp; Piacente, S." box="[500,697,1379,1399]" pageId="2" pageNumber="3" pagination="720 - 729" refId="ref10836" refString="Gulcemal, D., Masullo, M., Bedir, E., Festa, M., Karayildirim, T., Alankus-Caliskan, O., Piacente, S., 2012. Triterpene glycosides from Astragalus angustifolius. Planta Med. 78, 720 - 729. https: // doi. org / 10.1055 / s- 0031 - 1298337." type="journal article" year="2012">Gulcemal et al., 2012</bibRefCitation>
). These data demonstrated the presence of a terminal β- glucopyranosyl unit (
<bibRefCitation id="EFA202962C6C617651BCF9E8152ABF86" author="De Tommasi, N. &amp; Piacente, S. &amp; Gacs-Baitz, E. &amp; De Simone, F. &amp; Pizza, C. &amp; Aquino, R." pageId="2" pageNumber="3" pagination="323 - 327" refId="ref10126" refString="De Tommasi, N., Piacente, S., Gacs-Baitz, E., De Simone, F., Pizza, C., Aquino, R., 1998. Triterpenoid saponins from Spergularia ramosa. J. Nat. Prod. 61, 323 - 327. https: // doi. org / 10.1021 / np 970398 l." type="journal article" year="1998">De Tommasi et al., 1998</bibRefCitation>
). A detailed analysis of 2D NMR experiments revealed that the structure of compound 
<emphasis id="B947A3752C6C61765156F9DF160EBFE2" bold="true" box="[515,540,1463,1482]" pageId="2" pageNumber="3">23</emphasis>
was similar to that of secologanin-dimethyl-acetal (
<bibRefCitation id="EFA202962C6C617652D4F9BB1647BFCE" author="Damtoft, S. &amp; Franzyk, H. &amp; Jensen, S. R." box="[385,597,1491,1510]" pageId="2" pageNumber="3" pagination="773 - 784" refId="ref10070" refString="Damtoft, S., Franzyk, H., Jensen, S. R., 1995. Biosynthesis of iridoids in syringa and fraxinus: secoiridoid precursors. Phytochemistry 40, 773 - 784. https: // doi. org / 10.1016 / 0031 - 9422 (95) 00211 - O." type="journal article" year="1995">Damtoft et al., 1995</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6C6176513DF9BB1486BC2A" author="Machida, K. &amp; Asano, J. &amp; Kikuchi, M." pageId="2" pageNumber="3" pagination="111 - 114" refId="ref11962" refString="Machida, K., Asano, J., Kikuchi, M., 1995. Caeruleosides A and B, bis-iridoid glucosides from Lonicera caerulea. Phytochemistry 39, 111 - 114. https: // doi. org / 10.1016 / 0031 - 9422 (94) 00853 - L." type="journal article" year="1995">Machida et al., 1995</bibRefCitation>
), except for the replacement of a methoxy group at C-7 with a hydroxy group. On this basis, compound 
<emphasis id="B947A3752C6C61765173FA63162DBC36" bold="true" box="[550,575,1547,1566]" pageId="2" pageNumber="3">23</emphasis>
was identified as secologanin-methyl-hemiacetal, never reported before.
</paragraph>
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<emphasis id="B947A3752C6F61755266FBC4157EBD95" bold="true" box="[307,364,1964,1981]" pageId="1" pageNumber="2">Fig. 1.</emphasis>
LC-MS profile (Base Peak chromatogram) in negative ion mode of 
<taxonomicName id="4C3304E42C6F617550E5FBC410A9BD95" box="[944,1211,1964,1981]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="1" pageNumber="2" phylum="Tracheophyta" rank="subSpecies" species="atropurpurea" subSpecies="methanol">
<emphasis id="B947A3752C6F617550E5FBC41076BD94" bold="true" box="[944,1124,1964,1981]" italics="true" pageId="1" pageNumber="2">Scabiosa atropurpurea</emphasis>
methanol
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extract.
</paragraph>
</caption>
<caption id="DF4C2FEF2C6C61765331FCFE106DBAE8" ID-Table-UUID="DF4C2FEF2C6C61765331FCFE106DBAE8" httpUri="http://table.plazi.org/id/DF4C2FEF2C6C61765331FCFE106DBAE8" pageId="2" pageNumber="3" startId="2.[100,150,150,166]" targetBox="[116,1471,209,881]" targetIsTable="true" targetPageId="2" targetType="table">
<paragraph id="8B8C7F672C6C61765331FCFE14B5BA8F" blockId="2.[100,1151,150,193]" box="[100,167,150,167]" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765331FCFE14B5BA8F" bold="true" box="[100,167,150,167]" pageId="2" pageNumber="3">Table 1</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6C61765331FCD8106DBAE8" blockId="2.[100,1151,150,193]" box="[100,1151,175,193]" pageId="2" pageNumber="3">
Compounds identified in 
<taxonomicName id="4C3304E42C6C6176526EFCC715FCBAE8" box="[315,494,175,192]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6C6176526EFCC715FCBAE8" bold="true" box="[315,494,175,192]" italics="true" pageId="2" pageNumber="3">Scabiosa atropurpurea</emphasis>
</taxonomicName>
extract by LC-ESI-FT-MS, LC-ESI-FT-MS/MS analysis and NMR spectroscopy.
</paragraph>
</caption>
<paragraph id="8B8C7F672C6C61765321FCBD10C9B947" pageId="2" pageNumber="3">
<table id="F9338DC72C6C9E8B5321FCB911ADB959" box="[116,1471,209,881]" gridcols="8" gridrows="29" pageId="2" pageNumber="3">
<tr id="35037D252C6C9E8B5321FCB911ADBACB" box="[116,1471,209,227]" gridrow="0" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FCB914AABACB" box="[116,184,209,227]" gridcol="0" gridrow="0" pageId="2" pageNumber="3">Numbers</th>
<th id="76D214592C6C9E8B53A4FCB9150EBACB" box="[241,284,209,227]" gridcol="1" gridrow="0" pageId="2" pageNumber="3">Rt</th>
<th id="76D214592C6C9E8B5203FCB9158CBACB" box="[342,414,209,227]" gridcol="2" gridrow="0" pageId="2" pageNumber="3">[M-H] -</th>
<th id="76D214592C6C9E8B5282FCB9160DBACB" box="[471,543,209,227]" gridcol="3" gridrow="0" pageId="2" pageNumber="3">[M+46] -</th>
<th id="76D214592C6C9E8B510CFCB916FABACB" box="[601,744,209,227]" gridcol="4" gridrow="0" pageId="2" pageNumber="3">Molecular Formula</th>
<th id="76D214592C6C9E8B5077FCB91755BACB" box="[802,839,209,227]" gridcol="5" gridrow="0" pageId="2" pageNumber="3">ppm</th>
<th id="76D214592C6C9E8B50D5FCB91023BACB" box="[896,1073,209,227]" gridcol="6" gridrow="0" pageId="2" pageNumber="3">MS/MS</th>
<th id="76D214592C6C9E8B573EFCB911ADBACB" box="[1131,1471,209,227]" gridcol="7" gridrow="0" pageId="2" pageNumber="3">Identity</th>
</tr>
<tr id="35037D252C6C9E8B5321FC9011ADBB20" box="[116,1471,248,264]" gridrow="1" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FC9014AABB20" box="[116,184,248,264]" gridcol="0" gridrow="1" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FC90146CBB2E" bold="true" box="[116,126,248,262]" pageId="2" pageNumber="3">1</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FC90150EBB20" box="[241,284,248,264]" gridcol="1" gridrow="1" pageId="2" pageNumber="3">5.11</td>
<td id="76D214592C6C9E8B5203FC90158CBB20" box="[342,414,248,264]" gridcol="2" gridrow="1" pageId="2" pageNumber="3">375.1302</td>
<td id="76D214592C6C9E8B510CFC9016FABB20" box="[601,744,248,264]" gridcol="4" gridrow="1" pageId="2" pageNumber="3">C16 H24 O10</td>
<td id="76D214592C6C9E8B5077FC901755BB20" box="[802,839,248,264]" gridcol="5" gridrow="1" pageId="2" pageNumber="3">4.3</td>
<td id="76D214592C6C9E8B50D5FC901023BB20" box="[896,1073,248,264]" gridcol="6" gridrow="1" pageId="2" pageNumber="3">283/199</td>
<td id="76D214592C6C9E8B573EFC9011ADBB20" box="[1131,1471,248,264]" gridcol="7" gridrow="1" pageId="2" pageNumber="3">loganic acid</td>
</tr>
<tr id="35037D252C6C9E8B5321FD6611ADBB37" box="[116,1471,270,287]" gridrow="2" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FD6614AABB37" box="[116,184,270,287]" gridcol="0" gridrow="2" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD66146CBB34" bold="true" box="[116,126,270,284]" pageId="2" pageNumber="3">2</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD66150EBB37" box="[241,284,270,287]" gridcol="1" gridrow="2" pageId="2" pageNumber="3">5.55</td>
<td id="76D214592C6C9E8B5203FD66158CBB37" box="[342,414,270,287]" gridcol="2" gridrow="2" pageId="2" pageNumber="3">389.1019</td>
<td id="76D214592C6C9E8B510CFD6616FABB37" box="[601,744,270,287]" gridcol="4" gridrow="2" pageId="2" pageNumber="3">C16 H22 O11</td>
<td id="76D214592C6C9E8B5077FD661755BB37" box="[802,839,270,287]" gridcol="5" gridrow="2" pageId="2" pageNumber="3">3</td>
<td id="76D214592C6C9E8B50D5FD661023BB37" box="[896,1073,270,287]" gridcol="6" gridrow="2" pageId="2" pageNumber="3">345/209/165/121</td>
<td id="76D214592C6C9E8B573EFD6611ADBB37" box="[1131,1471,270,287]" gridcol="7" gridrow="2" pageId="2" pageNumber="3">eustomoside</td>
</tr>
<tr id="35037D252C6C9E8B5321FD4D11ADBB1E" box="[116,1471,293,310]" gridrow="3" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FD4D14AABB1E" box="[116,184,293,310]" gridcol="0" gridrow="3" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD4D146CBB1B" bold="true" box="[116,126,293,307]" pageId="2" pageNumber="3">3</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD4D150EBB1E" box="[241,284,293,310]" gridcol="1" gridrow="3" pageId="2" pageNumber="3">5.94</td>
<td id="76D214592C6C9E8B5203FD4D158CBB1E" box="[342,414,293,310]" gridcol="2" gridrow="3" pageId="2" pageNumber="3">373.1143</td>
<td id="76D214592C6C9E8B510CFD4D16FABB1E" box="[601,744,293,310]" gridcol="4" gridrow="3" pageId="2" pageNumber="3">C16 H22 O10</td>
<td id="76D214592C6C9E8B5077FD4D1755BB1E" box="[802,839,293,310]" gridcol="5" gridrow="3" pageId="2" pageNumber="3">3.8</td>
<td id="76D214592C6C9E8B50D5FD4D1023BB1E" box="[896,1073,293,310]" gridcol="6" gridrow="3" pageId="2" pageNumber="3">211</td>
<td id="76D214592C6C9E8B573EFD4D11ADBB1E" box="[1131,1471,293,310]" gridcol="7" gridrow="3" pageId="2" pageNumber="3">secologanic acid</td>
</tr>
<tr id="35037D252C6C9E8B5321FD5411ADBB65" box="[116,1471,316,333]" gridrow="4" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FD5414AABB65" box="[116,184,316,333]" gridcol="0" gridrow="4" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD54146CBB62" bold="true" box="[116,126,316,330]" pageId="2" pageNumber="3">4</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD54150EBB65" box="[241,284,316,333]" gridcol="1" gridrow="4" pageId="2" pageNumber="3">6.53</td>
<td id="76D214592C6C9E8B5203FD54158CBB65" box="[342,414,316,333]" gridcol="2" gridrow="4" pageId="2" pageNumber="3">353.0881</td>
<td id="76D214592C6C9E8B510CFD5416FABB65" box="[601,744,316,333]" gridcol="4" gridrow="4" pageId="2" pageNumber="3">C16 H18 O9</td>
<td id="76D214592C6C9E8B5077FD541755BB65" box="[802,839,316,333]" gridcol="5" gridrow="4" pageId="2" pageNumber="3">3.9</td>
<td id="76D214592C6C9E8B50D5FD541023BB65" box="[896,1073,316,333]" gridcol="6" gridrow="4" pageId="2" pageNumber="3">191</td>
<td id="76D214592C6C9E8B573EFD5411ADBB65" box="[1131,1471,316,333]" gridcol="7" gridrow="4" pageId="2" pageNumber="3">4-caffeoylquinic acid</td>
</tr>
<tr id="35037D252C6C9E8B5321FD3B11ADBB4C" box="[116,1471,339,356]" gridrow="5" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FD3B14AABB4C" box="[116,184,339,356]" gridcol="0" gridrow="5" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD3B146CBB49" bold="true" box="[116,126,339,353]" pageId="2" pageNumber="3">5</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD3B150EBB4C" box="[241,284,339,356]" gridcol="1" gridrow="5" pageId="2" pageNumber="3">6.87</td>
<td id="76D214592C6C9E8B5203FD3B158CBB4C" box="[342,414,339,356]" gridcol="2" gridrow="5" pageId="2" pageNumber="3">357.1194</td>
<td id="76D214592C6C9E8B5282FD3B160DBB4C" box="[471,543,339,356]" gridcol="3" gridrow="5" pageId="2" pageNumber="3">403.1247</td>
<td id="76D214592C6C9E8B510CFD3B16FABB4C" box="[601,744,339,356]" gridcol="4" gridrow="5" pageId="2" pageNumber="3">C16 H22 O9</td>
<td id="76D214592C6C9E8B5077FD3B1755BB4C" box="[802,839,339,356]" gridcol="5" gridrow="5" pageId="2" pageNumber="3">4.01</td>
<td id="76D214592C6C9E8B50D5FD3B1023BB4C" box="[896,1073,339,356]" gridcol="6" gridrow="5" pageId="2" pageNumber="3">371/223/179/121</td>
<td id="76D214592C6C9E8B573EFD3B11ADBB4C" box="[1131,1471,339,356]" gridcol="7" gridrow="5" pageId="2" pageNumber="3">sweroside</td>
</tr>
<tr id="35037D252C6C9E8B5321FD0211ADBB52" box="[116,1471,362,378]" gridrow="6" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FD0214AABB52" box="[116,184,362,378]" gridcol="0" gridrow="6" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD02146CBB50" bold="true" box="[116,126,362,376]" pageId="2" pageNumber="3">6</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD02150EBB52" box="[241,284,362,378]" gridcol="1" gridrow="6" pageId="2" pageNumber="3">7.59</td>
<td id="76D214592C6C9E8B5203FD02158CBB52" box="[342,414,362,378]" gridcol="2" gridrow="6" pageId="2" pageNumber="3">433.1353</td>
<td id="76D214592C6C9E8B510CFD0216FABB52" box="[601,744,362,378]" gridcol="4" gridrow="6" pageId="2" pageNumber="3">C18 H26 O12</td>
<td id="76D214592C6C9E8B5077FD021755BB52" box="[802,839,362,378]" gridcol="5" gridrow="6" pageId="2" pageNumber="3">2.8</td>
<td id="76D214592C6C9E8B50D5FD021023BB52" box="[896,1073,362,378]" gridcol="6" gridrow="6" pageId="2" pageNumber="3">301</td>
<td id="76D214592C6C9E8B573EFD0211ADBB52" box="[1131,1471,362,378]" gridcol="7" gridrow="6" pageId="2" pageNumber="3">
quercetin 3- 
<emphasis id="B947A3752C6C61765793FD0210C0BB50" bold="true" box="[1222,1234,362,376]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D arabinopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FDE911ADBBB9" box="[116,1471,385,401]" gridrow="7" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FDE914AABBB9" box="[116,184,385,401]" gridcol="0" gridrow="7" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FDE9146CBBA7" bold="true" box="[116,126,385,399]" pageId="2" pageNumber="3">7</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FDE9150EBBB9" box="[241,284,385,401]" gridcol="1" gridrow="7" pageId="2" pageNumber="3">7.96</td>
<td id="76D214592C6C9E8B5203FDE9158CBBB9" box="[342,414,385,401]" gridcol="2" gridrow="7" pageId="2" pageNumber="3">593.1515</td>
<td id="76D214592C6C9E8B5282FDE9160DBBB9" box="[471,543,385,401]" gridcol="3" gridrow="7" pageId="2" pageNumber="3">613.2142</td>
<td id="76D214592C6C9E8B510CFDE916FABBB9" box="[601,744,385,401]" gridcol="4" gridrow="7" pageId="2" pageNumber="3">C27 H30 O15</td>
<td id="76D214592C6C9E8B5077FDE91755BBB9" box="[802,839,385,401]" gridcol="5" gridrow="7" pageId="2" pageNumber="3">1.5</td>
<td id="76D214592C6C9E8B50D5FDE91023BBB9" box="[896,1073,385,401]" gridcol="6" gridrow="7" pageId="2" pageNumber="3">284/198</td>
<td id="76D214592C6C9E8B573EFDE911ADBBB9" box="[1131,1471,385,401]" gridcol="7" gridrow="7" pageId="2" pageNumber="3">
kaempferol 3- 
<emphasis id="B947A3752C6C61765781FDE910F2BBA7" bold="true" box="[1236,1248,385,399]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D- rhamnoglucopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FDF011ADBB80" box="[116,1471,408,424]" gridrow="8" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FDF014AABB80" box="[116,184,408,424]" gridcol="0" gridrow="8" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FDF0146CBB8E" bold="true" box="[116,126,408,422]" pageId="2" pageNumber="3">8</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FDF0150EBB80" box="[241,284,408,424]" gridcol="1" gridrow="8" pageId="2" pageNumber="3">8.21</td>
<td id="76D214592C6C9E8B5203FDF0158CBB80" box="[342,414,408,424]" gridcol="2" gridrow="8" pageId="2" pageNumber="3">593.1516</td>
<td id="76D214592C6C9E8B510CFDF016FABB80" box="[601,744,408,424]" gridcol="4" gridrow="8" pageId="2" pageNumber="3">C27 H30 O15</td>
<td id="76D214592C6C9E8B5077FDF01755BB80" box="[802,839,408,424]" gridcol="5" gridrow="8" pageId="2" pageNumber="3">2.6</td>
<td id="76D214592C6C9E8B50D5FDF01023BB80" box="[896,1073,408,424]" gridcol="6" gridrow="8" pageId="2" pageNumber="3">575/357/339</td>
<td id="76D214592C6C9E8B573EFDF011ADBB80" box="[1131,1471,408,424]" gridcol="7" gridrow="8" pageId="2" pageNumber="3">
luteolin 7- 
<emphasis id="B947A3752C6C617657ECFDF010D7BB8E" bold="true" box="[1209,1221,408,422]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D- rhamnoglucopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FDC611ADBB97" box="[116,1471,430,447]" gridrow="9" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FDC614AABB97" box="[116,184,430,447]" gridcol="0" gridrow="9" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FDC6146CBB94" bold="true" box="[116,126,430,444]" pageId="2" pageNumber="3">9</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FDC6150EBB97" box="[241,284,430,447]" gridcol="1" gridrow="9" pageId="2" pageNumber="3">8.33</td>
<td id="76D214592C6C9E8B5203FDC6158CBB97" box="[342,414,430,447]" gridcol="2" gridrow="9" pageId="2" pageNumber="3">447.0935</td>
<td id="76D214592C6C9E8B510CFDC616FABB97" box="[601,744,430,447]" gridcol="4" gridrow="9" pageId="2" pageNumber="3">C21 H20 O11</td>
<td id="76D214592C6C9E8B5077FDC61755BB97" box="[802,839,430,447]" gridcol="5" gridrow="9" pageId="2" pageNumber="3">3.0</td>
<td id="76D214592C6C9E8B50D5FDC61023BB97" box="[896,1073,430,447]" gridcol="6" gridrow="9" pageId="2" pageNumber="3">429/357/327</td>
<td id="76D214592C6C9E8B573EFDC611ADBB97" box="[1131,1471,430,447]" gridcol="7" gridrow="9" pageId="2" pageNumber="3">
luteolin-7- 
<emphasis id="B947A3752C6C617657ECFDC610D7BB94" bold="true" box="[1209,1221,430,444]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D-glucopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FDAD11ADBBFE" box="[116,1471,453,470]" gridrow="10" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FDAD14AABBFE" box="[116,184,453,470]" gridcol="0" gridrow="10" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FDAD149ABBFB" bold="true" box="[116,136,453,467]" pageId="2" pageNumber="3">10</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FDAD150EBBFE" box="[241,284,453,470]" gridcol="1" gridrow="10" pageId="2" pageNumber="3">8.45</td>
<td id="76D214592C6C9E8B5203FDAD158CBBFE" box="[342,414,453,470]" gridcol="2" gridrow="10" pageId="2" pageNumber="3">461.1093</td>
<td id="76D214592C6C9E8B510CFDAD16FABBFE" box="[601,744,453,470]" gridcol="4" gridrow="10" pageId="2" pageNumber="3">C22 H22 O11</td>
<td id="76D214592C6C9E8B5077FDAD1755BBFE" box="[802,839,453,470]" gridcol="5" gridrow="10" pageId="2" pageNumber="3">3.19</td>
<td id="76D214592C6C9E8B50D5FDAD1023BBFE" box="[896,1073,453,470]" gridcol="6" gridrow="10" pageId="2" pageNumber="3">341/313/298</td>
<td id="76D214592C6C9E8B573EFDAD11ADBBFE" box="[1131,1471,453,470]" gridcol="7" gridrow="10" pageId="2" pageNumber="3">diosmetin 6-C- glucopyranoside</td>
</tr>
<tr id="35037D252C6C9E8B5321FDB411ADBBC5" box="[116,1471,476,493]" gridrow="11" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FDB414AABBC5" box="[116,184,476,493]" gridcol="0" gridrow="11" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FDB4149ABBC2" bold="true" box="[116,136,476,490]" pageId="2" pageNumber="3">11</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FDB4150EBBC5" box="[241,284,476,493]" gridcol="1" gridrow="11" pageId="2" pageNumber="3">8.81</td>
<td id="76D214592C6C9E8B5203FDB4158CBBC5" box="[342,414,476,493]" gridcol="2" gridrow="11" pageId="2" pageNumber="3">529.1351</td>
<td id="76D214592C6C9E8B510CFDB416FABBC5" box="[601,744,476,493]" gridcol="4" gridrow="11" pageId="2" pageNumber="3">C26 H25 O12</td>
<td id="76D214592C6C9E8B5077FDB41755BBC5" box="[802,839,476,493]" gridcol="5" gridrow="11" pageId="2" pageNumber="3">1.92</td>
<td id="76D214592C6C9E8B50D5FDB41023BBC5" box="[896,1073,476,493]" gridcol="6" gridrow="11" pageId="2" pageNumber="3">367/173</td>
<td id="76D214592C6C9E8B573EFDB411ADBBC5" box="[1131,1471,476,493]" gridcol="7" gridrow="11" pageId="2" pageNumber="3">
4- 
<emphasis id="B947A3752C6C6176572FFDB41094BBC2" bold="true" box="[1146,1158,476,490]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-feruloyl-5- 
<emphasis id="B947A3752C6C6176578FFDB410F4BBC2" bold="true" box="[1242,1254,476,490]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-caffeoylquinic acid acid
</td>
</tr>
<tr id="35037D252C6C9E8B5321FD9B11ADB82C" box="[116,1471,499,516]" gridrow="12" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FD9B14AAB82C" box="[116,184,499,516]" gridcol="0" gridrow="12" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FD9B149AB829" bold="true" box="[116,136,499,513]" pageId="2" pageNumber="3">12</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FD9B150EB82C" box="[241,284,499,516]" gridcol="1" gridrow="12" pageId="2" pageNumber="3">9.05</td>
<td id="76D214592C6C9E8B5203FD9B158CB82C" box="[342,414,499,516]" gridcol="2" gridrow="12" pageId="2" pageNumber="3">577.1570</td>
<td id="76D214592C6C9E8B510CFD9B16FAB82C" box="[601,744,499,516]" gridcol="4" gridrow="12" pageId="2" pageNumber="3">C27H30O14</td>
<td id="76D214592C6C9E8B5077FD9B1755B82C" box="[802,839,499,516]" gridcol="5" gridrow="12" pageId="2" pageNumber="3">3.1</td>
<td id="76D214592C6C9E8B50D5FD9B1023B82C" box="[896,1073,499,516]" gridcol="6" gridrow="12" pageId="2" pageNumber="3">431</td>
<td id="76D214592C6C9E8B573EFD9B11ADB82C" box="[1131,1471,499,516]" gridcol="7" gridrow="12" pageId="2" pageNumber="3">
apigenin-7- 
<emphasis id="B947A3752C6C61765795FD9B10DEB829" bold="true" box="[1216,1228,499,513]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D -rhamnoglucopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FE6211ADB832" box="[116,1471,522,538]" gridrow="13" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FE6214AAB832" box="[116,184,522,538]" gridcol="0" gridrow="13" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE62149AB830" bold="true" box="[116,136,522,536]" pageId="2" pageNumber="3">13</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE62150EB832" box="[241,284,522,538]" gridcol="1" gridrow="13" pageId="2" pageNumber="3">9.10</td>
<td id="76D214592C6C9E8B5203FE62158CB832" box="[342,414,522,538]" gridcol="2" gridrow="13" pageId="2" pageNumber="3">747.2730</td>
<td id="76D214592C6C9E8B5282FE62160DB832" box="[471,543,522,538]" gridcol="3" gridrow="13" pageId="2" pageNumber="3">793.2783</td>
<td id="76D214592C6C9E8B510CFE6216FAB832" box="[601,744,522,538]" gridcol="4" gridrow="13" pageId="2" pageNumber="3">C33 H48 O19</td>
<td id="76D214592C6C9E8B5077FE621755B832" box="[802,839,522,538]" gridcol="5" gridrow="13" pageId="2" pageNumber="3">1.4</td>
<td id="76D214592C6C9E8B50D5FE621023B832" box="[896,1073,522,538]" gridcol="6" gridrow="13" pageId="2" pageNumber="3">585/485/283</td>
<td id="76D214592C6C9E8B573EFE6211ADB832" box="[1131,1471,522,538]" gridcol="7" gridrow="13" pageId="2" pageNumber="3">sylvestroside I</td>
</tr>
<tr id="35037D252C6C9E8B5321FE4911ADB819" box="[116,1471,545,561]" gridrow="14" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FE4914AAB819" box="[116,184,545,561]" gridcol="0" gridrow="14" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE49149AB807" bold="true" box="[116,136,545,559]" pageId="2" pageNumber="3">14</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE49150EB819" box="[241,284,545,561]" gridcol="1" gridrow="14" pageId="2" pageNumber="3">9.29</td>
<td id="76D214592C6C9E8B5203FE49158CB819" box="[342,414,545,561]" gridcol="2" gridrow="14" pageId="2" pageNumber="3">463.0883</td>
<td id="76D214592C6C9E8B510CFE4916FAB819" box="[601,744,545,561]" gridcol="4" gridrow="14" pageId="2" pageNumber="3">C21 H20 O12</td>
<td id="76D214592C6C9E8B5077FE491755B819" box="[802,839,545,561]" gridcol="5" gridrow="14" pageId="2" pageNumber="3">2.8</td>
<td id="76D214592C6C9E8B50D5FE491023B819" box="[896,1073,545,561]" gridcol="6" gridrow="14" pageId="2" pageNumber="3">301</td>
<td id="76D214592C6C9E8B573EFE4911ADB819" box="[1131,1471,545,561]" gridcol="7" gridrow="14" pageId="2" pageNumber="3">
quercetin 3- 
<emphasis id="B947A3752C6C61765793FE4910C0B807" bold="true" box="[1222,1234,545,559]" italics="true" pageId="2" pageNumber="3">O</emphasis>
-β- D glucopyranoside
</td>
</tr>
<tr id="35037D252C6C9E8B5321FE5011ADB860" box="[116,1471,568,584]" gridrow="15" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FE5014AAB860" box="[116,184,568,584]" gridcol="0" gridrow="15" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE50149AB86E" bold="true" box="[116,136,568,582]" pageId="2" pageNumber="3">15</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE50150EB860" box="[241,284,568,584]" gridcol="1" gridrow="15" pageId="2" pageNumber="3">9.97</td>
<td id="76D214592C6C9E8B5203FE50158CB860" box="[342,414,568,584]" gridcol="2" gridrow="15" pageId="2" pageNumber="3">745.2572</td>
<td id="76D214592C6C9E8B5282FE50160DB860" box="[471,543,568,584]" gridcol="3" gridrow="15" pageId="2" pageNumber="3">791.2625</td>
<td id="76D214592C6C9E8B510CFE5016FAB860" box="[601,744,568,584]" gridcol="4" gridrow="15" pageId="2" pageNumber="3">C33 H46 O19</td>
<td id="76D214592C6C9E8B5077FE501755B860" box="[802,839,568,584]" gridcol="5" gridrow="15" pageId="2" pageNumber="3">1.6</td>
<td id="76D214592C6C9E8B50D5FE501023B860" box="[896,1073,568,584]" gridcol="6" gridrow="15" pageId="2" pageNumber="3">629/495/459/283</td>
<td id="76D214592C6C9E8B573EFE5011ADB860" box="[1131,1471,568,584]" gridcol="7" gridrow="15" pageId="2" pageNumber="3">cantleyoside</td>
</tr>
<tr id="35037D252C6C9E8B5321FE2611ADB877" box="[116,1471,590,607]" gridrow="16" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FE2614AAB877" box="[116,184,590,607]" gridcol="0" gridrow="16" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE26149AB874" bold="true" box="[116,136,590,604]" pageId="2" pageNumber="3">16</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE26150EB877" box="[241,284,590,607]" gridcol="1" gridrow="16" pageId="2" pageNumber="3">10.09</td>
<td id="76D214592C6C9E8B5203FE26158CB877" box="[342,414,590,607]" gridcol="2" gridrow="16" pageId="2" pageNumber="3">585.2200</td>
<td id="76D214592C6C9E8B5282FE26160DB877" box="[471,543,590,607]" gridcol="3" gridrow="16" pageId="2" pageNumber="3">631.2251</td>
<td id="76D214592C6C9E8B510CFE2616FAB877" box="[601,744,590,607]" gridcol="4" gridrow="16" pageId="2" pageNumber="3">C27 H38 O14</td>
<td id="76D214592C6C9E8B5077FE261755B877" box="[802,839,590,607]" gridcol="5" gridrow="16" pageId="2" pageNumber="3">2.8</td>
<td id="76D214592C6C9E8B50D5FE261023B877" box="[896,1073,590,607]" gridcol="6" gridrow="16" pageId="2" pageNumber="3">473/283</td>
<td id="76D214592C6C9E8B573EFE2611ADB877" box="[1131,1471,590,607]" gridcol="7" gridrow="16" pageId="2" pageNumber="3">laciniatoside V</td>
</tr>
<tr id="35037D252C6C9E8B5321FE0D11ADB85E" box="[116,1471,613,630]" gridrow="17" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FE0D14AAB85E" box="[116,184,613,630]" gridcol="0" gridrow="17" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE0D149AB85B" bold="true" box="[116,136,613,627]" pageId="2" pageNumber="3">17</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE0D150EB85E" box="[241,284,613,630]" gridcol="1" gridrow="17" pageId="2" pageNumber="3">10.57</td>
<td id="76D214592C6C9E8B5203FE0D158CB85E" box="[342,414,613,630]" gridcol="2" gridrow="17" pageId="2" pageNumber="3">615.2302</td>
<td id="76D214592C6C9E8B5282FE0D160DB85E" box="[471,543,613,630]" gridcol="3" gridrow="17" pageId="2" pageNumber="3">661.2358</td>
<td id="76D214592C6C9E8B510CFE0D16FAB85E" box="[601,744,613,630]" gridcol="4" gridrow="17" pageId="2" pageNumber="3">C28 H40 O15</td>
<td id="76D214592C6C9E8B5077FE0D1755B85E" box="[802,839,613,630]" gridcol="5" gridrow="17" pageId="2" pageNumber="3">3.8</td>
<td id="76D214592C6C9E8B50D5FE0D1023B85E" box="[896,1073,613,630]" gridcol="6" gridrow="17" pageId="2" pageNumber="3">583/373</td>
<td id="76D214592C6C9E8B573EFE0D11ADB85E" box="[1131,1471,613,630]" gridcol="7" gridrow="17" pageId="2" pageNumber="3">laciniatoside VI</td>
</tr>
<tr id="35037D252C6C9E8B5321FE1411ADB8A5" box="[116,1471,636,653]" gridrow="18" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FE1414AAB8A5" box="[116,184,636,653]" gridcol="0" gridrow="18" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE14149AB8A2" bold="true" box="[116,136,636,650]" pageId="2" pageNumber="3">18</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE14150EB8A5" box="[241,284,636,653]" gridcol="1" gridrow="18" pageId="2" pageNumber="3">10.68</td>
<td id="76D214592C6C9E8B5203FE14158CB8A5" box="[342,414,636,653]" gridcol="2" gridrow="18" pageId="2" pageNumber="3">515.1203</td>
<td id="76D214592C6C9E8B510CFE1416FAB8A5" box="[601,744,636,653]" gridcol="4" gridrow="18" pageId="2" pageNumber="3">C25 H24 O12</td>
<td id="76D214592C6C9E8B5077FE141755B8A5" box="[802,839,636,653]" gridcol="5" gridrow="18" pageId="2" pageNumber="3">3.6</td>
<td id="76D214592C6C9E8B50D5FE141023B8A5" box="[896,1073,636,653]" gridcol="6" gridrow="18" pageId="2" pageNumber="3">353/299</td>
<td id="76D214592C6C9E8B573EFE1411ADB8A5" box="[1131,1471,636,653]" gridcol="7" gridrow="18" pageId="2" pageNumber="3">3,4-dicaffeoylquinic acid</td>
</tr>
<tr id="35037D252C6C9E8B5321FEFB11ADB88C" box="[116,1471,659,676]" gridrow="19" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FEFB14AAB88C" box="[116,184,659,676]" gridcol="0" gridrow="19" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FEFB149AB889" bold="true" box="[116,136,659,673]" pageId="2" pageNumber="3">19</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FEFB150EB88C" box="[241,284,659,676]" gridcol="1" gridrow="19" pageId="2" pageNumber="3">10.80</td>
<td id="76D214592C6C9E8B5203FEFB158CB88C" box="[342,414,659,676]" gridcol="2" gridrow="19" pageId="2" pageNumber="3">791.2991</td>
<td id="76D214592C6C9E8B5282FEFB160DB88C" box="[471,543,659,676]" gridcol="3" gridrow="19" pageId="2" pageNumber="3">837.3035</td>
<td id="76D214592C6C9E8B510CFEFB16FAB88C" box="[601,744,659,676]" gridcol="4" gridrow="19" pageId="2" pageNumber="3">C35 H52 O20</td>
<td id="76D214592C6C9E8B5077FEFB1755B88C" box="[802,839,659,676]" gridcol="5" gridrow="19" pageId="2" pageNumber="3">1.5</td>
<td id="76D214592C6C9E8B50D5FEFB1023B88C" box="[896,1073,659,676]" gridcol="6" gridrow="19" pageId="2" pageNumber="3">629/495</td>
<td id="76D214592C6C9E8B573EFEFB11ADB88C" box="[1131,1471,659,676]" gridcol="7" gridrow="19" pageId="2" pageNumber="3">cantleyoside dimethyl acetal</td>
</tr>
<tr id="35037D252C6C9E8B5321FEC211ADB892" box="[116,1471,682,698]" gridrow="20" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FEC214AAB892" box="[116,184,682,698]" gridcol="0" gridrow="20" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FEC2149AB890" bold="true" box="[116,136,682,696]" pageId="2" pageNumber="3">20</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FEC2150EB892" box="[241,284,682,698]" gridcol="1" gridrow="20" pageId="2" pageNumber="3">11.02</td>
<td id="76D214592C6C9E8B5203FEC2158CB892" box="[342,414,682,698]" gridcol="2" gridrow="20" pageId="2" pageNumber="3">515.1201</td>
<td id="76D214592C6C9E8B510CFEC216FAB892" box="[601,744,682,698]" gridcol="4" gridrow="20" pageId="2" pageNumber="3">C25 H24 O12</td>
<td id="76D214592C6C9E8B5077FEC21755B892" box="[802,839,682,698]" gridcol="5" gridrow="20" pageId="2" pageNumber="3">3.2</td>
<td id="76D214592C6C9E8B50D5FEC21023B892" box="[896,1073,682,698]" gridcol="6" gridrow="20" pageId="2" pageNumber="3">353/299</td>
<td id="76D214592C6C9E8B573EFEC211ADB892" box="[1131,1471,682,698]" gridcol="7" gridrow="20" pageId="2" pageNumber="3">3,5-dicaffeoylquinic acid</td>
</tr>
<tr id="35037D252C6C9E8B5321FEA911ADB8F9" box="[116,1471,705,721]" gridrow="21" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FEA914AAB8F9" box="[116,184,705,721]" gridcol="0" gridrow="21" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FEA9149AB8E7" bold="true" box="[116,136,705,719]" pageId="2" pageNumber="3">21</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FEA9150EB8F9" box="[241,284,705,721]" gridcol="1" gridrow="21" pageId="2" pageNumber="3">11.14</td>
<td id="76D214592C6C9E8B5203FEA9158CB8F9" box="[342,414,705,721]" gridcol="2" gridrow="21" pageId="2" pageNumber="3">583.2039</td>
<td id="76D214592C6C9E8B510CFEA916FAB8F9" box="[601,744,705,721]" gridcol="4" gridrow="21" pageId="2" pageNumber="3">C27 H36 O14</td>
<td id="76D214592C6C9E8B5077FEA91755B8F9" box="[802,839,705,721]" gridcol="5" gridrow="21" pageId="2" pageNumber="3">3</td>
<td id="76D214592C6C9E8B50D5FEA91023B8F9" box="[896,1073,705,721]" gridcol="6" gridrow="21" pageId="2" pageNumber="3">373/551</td>
<td id="76D214592C6C9E8B573EFEA911ADB8F9" box="[1131,1471,705,721]" gridcol="7" gridrow="21" pageId="2" pageNumber="3">sylvestroside IV</td>
</tr>
<tr id="35037D252C6C9E8B5321FEBF11ADB8C0" box="[116,1471,727,744]" gridrow="22" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FEBF14AAB8C0" box="[116,184,727,744]" gridcol="0" gridrow="22" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FEBF149AB8CD" bold="true" box="[116,136,727,741]" pageId="2" pageNumber="3">22</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FEBF150EB8C0" box="[241,284,727,744]" gridcol="1" gridrow="22" pageId="2" pageNumber="3">11.37</td>
<td id="76D214592C6C9E8B5203FEBF158CB8C0" box="[342,414,727,744]" gridcol="2" gridrow="22" pageId="2" pageNumber="3">583.2039</td>
<td id="76D214592C6C9E8B510CFEBF16FAB8C0" box="[601,744,727,744]" gridcol="4" gridrow="22" pageId="2" pageNumber="3">C27 H36 O14</td>
<td id="76D214592C6C9E8B5077FEBF1755B8C0" box="[802,839,727,744]" gridcol="5" gridrow="22" pageId="2" pageNumber="3">2.9</td>
<td id="76D214592C6C9E8B50D5FEBF1023B8C0" box="[896,1073,727,744]" gridcol="6" gridrow="22" pageId="2" pageNumber="3">373/551</td>
<td id="76D214592C6C9E8B573EFEBF11ADB8C0" box="[1131,1471,727,744]" gridcol="7" gridrow="22" pageId="2" pageNumber="3">sylvestroside III</td>
</tr>
<tr id="35037D252C6C9E8B5321FE8611ADB8D7" box="[116,1471,750,767]" gridrow="23" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FE8614AAB8D7" box="[116,184,750,767]" gridcol="0" gridrow="23" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FE86149AB8D4" bold="true" box="[116,136,750,764]" pageId="2" pageNumber="3">23</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FE86150EB8D7" box="[241,284,750,767]" gridcol="1" gridrow="23" pageId="2" pageNumber="3">11.48</td>
<td id="76D214592C6C9E8B5203FE86158CB8D7" box="[342,414,750,767]" gridcol="2" gridrow="23" pageId="2" pageNumber="3">419.1548</td>
<td id="76D214592C6C9E8B510CFE8616FAB8D7" box="[601,744,750,767]" gridcol="4" gridrow="23" pageId="2" pageNumber="3">C18 H28 O11</td>
<td id="76D214592C6C9E8B5077FE861755B8D7" box="[802,839,750,767]" gridcol="5" gridrow="23" pageId="2" pageNumber="3">1.2</td>
<td id="76D214592C6C9E8B50D5FE861023B8D7" box="[896,1073,750,767]" gridcol="6" gridrow="23" pageId="2" pageNumber="3">239/213/195</td>
<td id="76D214592C6C9E8B573EFE8611ADB8D7" box="[1131,1471,750,767]" gridcol="7" gridrow="23" pageId="2" pageNumber="3">secologanin-methyl-hemiacetal</td>
</tr>
<tr id="35037D252C6C9E8B5321FF6D11ADB93E" box="[116,1471,773,790]" gridrow="24" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FF6D14AAB93E" box="[116,184,773,790]" gridcol="0" gridrow="24" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FF6D149AB93B" bold="true" box="[116,136,773,787]" pageId="2" pageNumber="3">24</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FF6D150EB93E" box="[241,284,773,790]" gridcol="1" gridrow="24" pageId="2" pageNumber="3">12.69</td>
<td id="76D214592C6C9E8B5203FF6D158CB93E" box="[342,414,773,790]" gridcol="2" gridrow="24" pageId="2" pageNumber="3">629.2460</td>
<td id="76D214592C6C9E8B510CFF6D16FAB93E" box="[601,744,773,790]" gridcol="4" gridrow="24" pageId="2" pageNumber="3">C29 H42 O15</td>
<td id="76D214592C6C9E8B5077FF6D1755B93E" box="[802,839,773,790]" gridcol="5" gridrow="24" pageId="2" pageNumber="3">3</td>
<td id="76D214592C6C9E8B50D5FF6D1023B93E" box="[896,1073,773,790]" gridcol="6" gridrow="24" pageId="2" pageNumber="3">583/473</td>
<td id="76D214592C6C9E8B573EFF6D11ADB93E" box="[1131,1471,773,790]" gridcol="7" gridrow="24" pageId="2" pageNumber="3">sylvestroside III dimethyl acetal</td>
</tr>
<tr id="35037D252C6C9E8B5321FF7411ADB905" box="[116,1471,796,813]" gridrow="25" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FF7414AAB905" box="[116,184,796,813]" gridcol="0" gridrow="25" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FF74149AB902" bold="true" box="[116,136,796,810]" pageId="2" pageNumber="3">25</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FF74150EB905" box="[241,284,796,813]" gridcol="1" gridrow="25" pageId="2" pageNumber="3">13.73</td>
<td id="76D214592C6C9E8B5203FF74158CB905" box="[342,414,796,813]" gridcol="2" gridrow="25" pageId="2" pageNumber="3">875.3870</td>
<td id="76D214592C6C9E8B510CFF7416FAB905" box="[601,744,796,813]" gridcol="4" gridrow="25" pageId="2" pageNumber="3">C48 H60 O15</td>
<td id="76D214592C6C9E8B5077FF741755B905" box="[802,839,796,813]" gridcol="5" gridrow="25" pageId="2" pageNumber="3">2.55</td>
<td id="76D214592C6C9E8B50D5FF741023B905" box="[896,1073,796,813]" gridcol="6" gridrow="25" pageId="2" pageNumber="3">831/713/495/459/503</td>
<td id="76D214592C6C9E8B573EFF7411ADB905" box="[1131,1471,796,813]" gridcol="7" gridrow="25" pageId="2" pageNumber="3">atropurpurin A</td>
</tr>
<tr id="35037D252C6C9E8B5321FF5B11ADB96B" box="[116,1471,819,835]" gridrow="26" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FF5B14AAB96B" box="[116,184,819,835]" gridcol="0" gridrow="26" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FF5B149AB969" bold="true" box="[116,136,819,833]" pageId="2" pageNumber="3">26</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FF5B150EB96B" box="[241,284,819,835]" gridcol="1" gridrow="26" pageId="2" pageNumber="3">13.78</td>
<td id="76D214592C6C9E8B5203FF5B158CB96B" box="[342,414,819,835]" gridcol="2" gridrow="26" pageId="2" pageNumber="3">713.3360</td>
<td id="76D214592C6C9E8B510CFF5B16FAB96B" box="[601,744,819,835]" gridcol="4" gridrow="26" pageId="2" pageNumber="3">C35H54O15</td>
<td id="76D214592C6C9E8B5077FF5B1755B96B" box="[802,839,819,835]" gridcol="5" gridrow="26" pageId="2" pageNumber="3">2.6</td>
<td id="76D214592C6C9E8B50D5FF5B1023B96B" box="[896,1073,819,835]" gridcol="6" gridrow="26" pageId="2" pageNumber="3">551</td>
<td id="76D214592C6C9E8B573EFF5B11ADB96B" box="[1131,1471,819,835]" gridcol="7" gridrow="26" pageId="2" pageNumber="3">pteroceside A</td>
</tr>
<tr id="35037D252C6C9E8B5321FF2211ADB972" box="[116,1471,842,858]" gridrow="27" pageId="2" pageNumber="3">
<th id="76D214592C6C9E8B5321FF2214AAB972" box="[116,184,842,858]" gridcol="0" gridrow="27" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FF22149AB970" bold="true" box="[116,136,842,856]" pageId="2" pageNumber="3">27</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FF22150EB972" box="[241,284,842,858]" gridcol="1" gridrow="27" pageId="2" pageNumber="3">14.57</td>
<td id="76D214592C6C9E8B5203FF22158CB972" box="[342,414,842,858]" gridcol="2" gridrow="27" pageId="2" pageNumber="3">671.1465</td>
<td id="76D214592C6C9E8B5282FF22160DB972" box="[471,543,842,858]" gridcol="3" gridrow="27" pageId="2" pageNumber="3">717.3350</td>
<td id="76D214592C6C9E8B510CFF2216FAB972" box="[601,744,842,858]" gridcol="4" gridrow="27" pageId="2" pageNumber="3">C32 H48 O15</td>
<td id="76D214592C6C9E8B5077FF221755B972" box="[802,839,842,858]" gridcol="5" gridrow="27" pageId="2" pageNumber="3">3.07</td>
<td id="76D214592C6C9E8B50D5FF221023B972" box="[896,1073,842,858]" gridcol="6" gridrow="27" pageId="2" pageNumber="3">461/495/281</td>
<td id="76D214592C6C9E8B573EFF2211ADB972" box="[1131,1471,842,858]" gridcol="7" gridrow="27" pageId="2" pageNumber="3">pteroceside C</td>
</tr>
<tr id="35037D252C6C9E8B5321FF0811ADB959" box="[116,1471,864,881]" gridrow="28" pageId="2" pageNumber="3" rowspan-3="1">
<th id="76D214592C6C9E8B5321FF0814AAB959" box="[116,184,864,881]" gridcol="0" gridrow="28" pageId="2" pageNumber="3">
<emphasis id="B947A3752C6C61765321FF08149AB946" bold="true" box="[116,136,864,878]" pageId="2" pageNumber="3">28</emphasis>
</th>
<td id="76D214592C6C9E8B53A4FF08150EB959" box="[241,284,864,881]" gridcol="1" gridrow="28" pageId="2" pageNumber="3">14.69</td>
<td id="76D214592C6C9E8B5203FF08158CB959" box="[342,414,864,881]" gridcol="2" gridrow="28" pageId="2" pageNumber="3">833.3356</td>
<td id="76D214592C6C9E8B510CFF0816FAB959" box="[601,744,864,881]" gridcol="4" gridrow="28" pageId="2" pageNumber="3">C45 H54 O15</td>
<td id="76D214592C6C9E8B5077FF081755B959" box="[802,839,864,881]" gridcol="5" gridrow="28" pageId="2" pageNumber="3">2.6</td>
<td id="76D214592C6C9E8B50D5FF081023B959" box="[896,1073,864,881]" gridcol="6" gridrow="28" pageId="2" pageNumber="3">671/495/459</td>
<td id="76D214592C6C9E8B573EFF0811ADB959" box="[1131,1471,864,881]" gridcol="7" gridrow="28" pageId="2" pageNumber="3">atropurpurin B</td>
</tr>
</table>
</paragraph>
<paragraph id="8B8C7F672C6C617653D1FA2A119DBC2A" blockId="2.[100,771,927,1957]" lastBlockId="2.[818,1488,933,1957]" pageId="2" pageNumber="3">
The molecular formula of compound 
<emphasis id="B947A3752C6C6176514DFA2A1623BC7D" bold="true" box="[536,561,1602,1621]" pageId="2" pageNumber="3">25</emphasis>
was established as C 
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O 
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by HR-ESI-MS (
<emphasis id="B947A3752C6C6176522AFA3615B6BC59" bold="true" box="[383,420,1630,1649]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
875.3870 [M-H] 
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, calcd for C 
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<collectionCode id="ED22E7A22C6C61765331FA131466BCA6" box="[100,116,1659,1678]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
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O 
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875.3854) and the 
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C NMR data. The IR spectrum indicated the presence of OH (
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) and C––O (1705 and 
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). The 
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/ 
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spectrum of this compound showed several main product ions: at 
<emphasis id="B947A3752C6C617651B2FADA147FBCC9" bold="true" italics="true" pageId="2" pageNumber="3">m/ z</emphasis>
831.25 [M-H-44] 
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, 713.33 [M-H-162] 
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corresponding to the loss of one hexose unit, and others at 
<emphasis id="B947A3752C6C61765237FA821595BCD5" bold="true" box="[354,391,1770,1789]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
495.21 [M-H-380] 
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, 459.29 [M-H-416] 
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and 503.38 [M-H-372] 
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, which only after characterisation by NMR could be attributed to the loss of a glycosidated iridoid moiety. The 
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NMR spectrum showed characteristic signals for two olefinic protons at δ 7.47 and 7.45 (each, s), three acetal protons at δ 5.54 (1 
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, d, 
<emphasis id="B947A3752C6C6176512BFB32169ABD45" bold="true" box="[638,648,1882,1901]" italics="true" pageId="2" pageNumber="3">J</emphasis>
= 8.5 Hz), δ 5.32 (1 
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, d, 
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= 8.5 Hz), and δ 4.60 (1 
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, dd, 
<emphasis id="B947A3752C6C61765176FB1E163FBDA1" bold="true" box="[547,557,1910,1929]" italics="true" pageId="2" pageNumber="3">J</emphasis>
= 5.9, 5.2 Hz), a secondary methyl group at δ 1.10 (3 
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, d, 
<emphasis id="B947A3752C6C61765296FBF915DFBD8C" bold="true" box="[451,461,1937,1956]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=6.8 Hz), a terminal vinyl group at δ 5.30 (1 
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, d, 
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= 10.5 Hz), 5.35 (1 
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, d, 
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= 17.7 Hz) and 5.76 (1 
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, ddd, 
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= 7.5, 10.5, 17.7 Hz), and signals corresponding to one carbomethoxy group at δ 3.72 (3 
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, s). Moreover, signals corresponding to two butyloxy moieties at δ 3.63 and 3.44 (each 2 
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, m), 1.55 (4 
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, m), 1.42 (4 
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, m) and 0.97 (6 
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, t, 
<emphasis id="B947A3752C6C61765746F87D100FBE00" bold="true" box="[1043,1053,1045,1064]" italics="true" pageId="2" pageNumber="3">J</emphasis>
=7.4 Hz) were evident. The 
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NMR spectrum showed for the sugar region signals corresponding to two anomeric protons at δ 4.70 (2 
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, d, 
<emphasis id="B947A3752C6C61765776F825103FBE48" bold="true" box="[1059,1069,1101,1120]" italics="true" pageId="2" pageNumber="3">J</emphasis>
= 7.8 Hz). These data, in combination with 1D-TOCSY, HSQC, HMBC, DQF-COSY correlations, demonstrated the presence of two terminal β- glucopyranosyl units (see 
<tableCitation id="C6B14ADC2C6C61765671F8EC1178BEBF" box="[1316,1386,1156,1175]" captionStart="Table 2" captionStartId="3.[100,150,150,166]" captionTargetBox="[116,754,213,1942]" captionTargetPageId="3" captionText="Table 2 1H and 13C NMR data (J in Hz) of compounds 23, 25 and 28 (CD OD, 600 MHz). 3" httpUri="http://table.plazi.org/id/DF4C2FEF2C6D61775331FCFE1696BAEB" pageId="2" pageNumber="3" tableUuid="DF4C2FEF2C6D61775331FCFE1696BAEB">Table 2</tableCitation>
). All these results indicated the presence of an iridoid glucoside unit and a secoiridoid glucoside unit in the molecule (Kirmizibekmez et al., 2012); these spectroscopic features were similar to those of cantleyoside-dimethyl-acetal (
<bibRefCitation id="EFA202962C6C61765707F89C1139BF2F" author="Gulcemal, D. &amp; Masullo, M. &amp; Alankus-Caliskan, O. &amp; Karayildirim, T. &amp; Senol, S. G. &amp; Piacente, S. &amp; Bedir, E." box="[1106,1323,1268,1287]" pageId="2" pageNumber="3" pagination="239 - 243" refId="ref10763" refString="Gulcemal, D., Masullo, M., Alankus-Caliskan, O., Karayildirim, T., Senol, S. G., Piacente, S., Bedir, E., 2010. Monoterpenoid glucoindole alkaloids and iridoids from Pterocephalus pinardii. Magn. Reson. Chem. 48, 239 - 243. https: // doi. org / 10.1002 / mrc. 2559." type="journal article" year="2010">Gulcemal et al., 2010</bibRefCitation>
), except for the absence of two methoxyl groups. In the HMBC spectrum, the proton signals at δ 7.45 (H-3), 3.72 (-OCH 
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), and 3.16 (H-5) showed long range correlations with the carbon resonance at δ 169.0 (C-11), while the proton signals at δ 3.44, 3.63 and 2.97 (H-5ꞌ) displayed long range correlations with the carbon resonance at δ 103.8 (C-7ꞌ), indicating the occurrence of the two butyloxy groups at C-7ꞌ. This linkage was also confirmed by the low-frequency shift of H-7ꞌ (δ 4.60) and C-7 (δ 103.8); these evidences suggested that compound 
<emphasis id="B947A3752C6C617657EAF9BB10CABFCE" bold="true" box="[1215,1240,1491,1510]" pageId="2" pageNumber="3">25</emphasis>
was made up of a loganin unit and a secologanin derived moiety (
<bibRefCitation id="EFA202962C6C617657FFF9871190BC2A" author="Sohretoglu, D. &amp; Masullo, M. &amp; Piacente, S. &amp; Kirmizibekmez, H." box="[1194,1410,1519,1538]" pageId="2" pageNumber="3" pagination="69 - 72" refId="ref12601" refString="Sohretoglu, D., Masullo, M., Piacente, S., Kirmizibekmez, H., 2013. Iridoids, monoterpenoid glucoindole alkaloids and flavonoids from Vinca major. Biochem. Systemat. Ecol. 49, 69 - 72. https: // doi. org / 10.1016 / j. bse. 2013.03.028." type="journal article" year="2013">Sohretoglu et al., 2013</bibRefCitation>
).
</paragraph>
<paragraph id="8B8C7F672C6C61765004FA631167BCED" blockId="2.[818,1488,933,1957]" pageId="2" pageNumber="3">
The site of linkage among the two units was confirmed by the HMBC experiment, which showed a strong correlation between the proton signals at δ 7.47 (H-3ꞌ), 5.24 (H-7), and 2.97 (H-5ꞌ) with the carbon resonance at δ 168.2 (C-11ꞌ). These data indicated that the carboxylic group (C-11ꞌ) of the secologanin derived moiety was linked to the C-7 hydroxyl group of the loganin unit. Therefore, compound 
<emphasis id="B947A3752C6C617656D3FAFE118DBC81" bold="true" box="[1414,1439,1686,1705]" pageId="2" pageNumber="3">25</emphasis>
was established, as reported in 
<figureCitation id="130863E22C6C6176577AFADA1077BCED" box="[1071,1125,1714,1733]" captionStart="Fig" captionStartId="4.[572,602,1913,1930]" captionTargetBox="[285,1302,149,1885]" captionTargetId="graphics-784@4.[704,863,1005,1225]" captionTargetPageId="4" captionText="Fig. 2. Iridoids isolated from Scabiosa atropurpurea." figureDoi="http://doi.org/10.5281/zenodo.8160622" httpUri="https://zenodo.org/record/8160622/files/figure.png" pageId="2" pageNumber="3">Fig. 2</figureCitation>
, and named atropurpurin A.
</paragraph>
<paragraph id="8B8C7F672C6C61775004FAA61119B9A4" blockId="2.[818,1488,933,1957]" lastBlockId="3.[818,1487,805,908]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
The molecular formula of compound 
<emphasis id="B947A3752C6C617657B0FAA610ECBCC9" bold="true" box="[1253,1278,1742,1761]" pageId="2" pageNumber="3">28</emphasis>
was established as C 
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<collectionCode id="ED22E7A22C6C61765004FA821773BCD5" box="[849,865,1770,1789]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
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O 
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by HR-ESI-MS (
<emphasis id="B947A3752C6C61765764FA821044BCD5" bold="true" box="[1073,1110,1770,1789]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
833.3356 [M-H] 
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, calcd for C 
<subScript id="17B77D222C6C61765621FA991194BCD7" attach="both" box="[1396,1414,1777,1791]" fontSize="6" pageId="2" pageNumber="3">45</subScript>
<collectionCode id="ED22E7A22C6C617656D3FA821184BCD5" box="[1414,1430,1770,1789]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
<subScript id="17B77D222C6C617656C3FA9911BABCD7" attach="both" box="[1430,1448,1777,1791]" fontSize="6" pageId="2" pageNumber="3">53</subScript>
O 
<subScript id="17B77D222C6C617656E2FA9911DBBCD7" attach="left" box="[1463,1481,1777,1791]" fontSize="6" pageId="2" pageNumber="3">15</subScript>
, 833.3387) and 
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C NMR data. Compound 
<emphasis id="B947A3752C6C6176579EFB6E10F6BD31" bold="true" box="[1227,1252,1798,1817]" pageId="2" pageNumber="3">28</emphasis>
differed from 
<emphasis id="B947A3752C6C61765626FB6E119EBD31" bold="true" box="[1395,1420,1798,1817]" pageId="2" pageNumber="3">25</emphasis>
for 42 uma (C 
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<collectionCode id="ED22E7A22C6C617650D7FB4A1780BD1D" box="[898,914,1826,1845]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
<subScript id="17B77D222C6C617650C4FB411788BD1F" attach="left" box="[913,922,1833,1847]" fontSize="6" pageId="2" pageNumber="3">6</subScript>
). The 
<collectionCode id="ED22E7A22C6C61765088FB4A17EEBD1D" box="[989,1020,1826,1845]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="2" pageNumber="3" type="Herbarium">MS</collectionCode>
/ 
<collectionCode id="ED22E7A22C6C61765756FB4A1030BD1D" box="[1027,1058,1826,1845]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="2" pageNumber="3" type="Herbarium">MS</collectionCode>
spectrum of this compound showed a main peak at 
<emphasis id="B947A3752C6C6176502AFB5617B6BD79" bold="true" box="[895,932,1854,1873]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
671.26 [M-H-162] 
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, corresponding to the loss of a hexose unit and other main peaks at 
<emphasis id="B947A3752C6C61765711FB31107BBD44" bold="true" box="[1092,1129,1881,1900]" italics="true" pageId="2" pageNumber="3">m/z</emphasis>
495.27 [M-H-338] 
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and 459.31 [M-H-374] 
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, that only after the NMR characterisation could be attributed to the loss of the iridoid unit. A comparison of 
<superScript id="7C46D22F2C6C617657BAFBE410EABDB2" attach="right" box="[1263,1272,1932,1946]" fontSize="6" pageId="2" pageNumber="3">1</superScript>
<collectionCode id="ED22E7A22C6C617657ADFBFA111ABD8D" box="[1272,1288,1938,1957]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="2" pageNumber="3" type="Herbarium">H</collectionCode>
NMR and 
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C NMR spectroscopic data of 
<emphasis id="B947A3752C6D617750ADFF4D1003B910" bold="true" box="[1016,1041,805,824]" pageId="3" pageNumber="4">25</emphasis>
and 
<emphasis id="B947A3752C6D61775768FF4D1044B910" bold="true" box="[1085,1110,805,824]" pageId="3" pageNumber="4">28</emphasis>
revealed that 
<emphasis id="B947A3752C6D6177578DFF4D10E3B910" bold="true" box="[1240,1265,805,824]" pageId="3" pageNumber="4">28</emphasis>
was structurally closely related to 
<emphasis id="B947A3752C6D617750C7FF2917B9B97C" bold="true" box="[914,939,833,852]" pageId="3" pageNumber="4">25</emphasis>
, with the replacement of a butyloxy moiety at C-7ꞌ with a methyloxy group (δ 3.33). Therefore, the structure of 
<emphasis id="B947A3752C6D61775663FF35115DB958" bold="true" box="[1334,1359,861,880]" pageId="3" pageNumber="4">28</emphasis>
, named atropurpurin B, was determined, as reported in 
<figureCitation id="130863E22C6D6177579AFF111119B9A4" box="[1231,1291,889,908]" captionStart="Fig" captionStartId="4.[572,602,1913,1930]" captionTargetBox="[285,1302,149,1885]" captionTargetId="graphics-784@4.[704,863,1005,1225]" captionTargetPageId="4" captionText="Fig. 2. Iridoids isolated from Scabiosa atropurpurea." figureDoi="http://doi.org/10.5281/zenodo.8160622" httpUri="https://zenodo.org/record/8160622/files/figure.png" pageId="3" pageNumber="4">Fig. 2.</figureCitation>
</paragraph>
<caption id="DF4C2FEF2C6D61775331FCFE1696BAEB" ID-Table-UUID="DF4C2FEF2C6D61775331FCFE1696BAEB" httpUri="http://table.plazi.org/id/DF4C2FEF2C6D61775331FCFE1696BAEB" pageId="3" pageNumber="4" startId="3.[100,150,150,166]" targetBox="[116,754,213,1942]" targetIsTable="true" targetPageId="3" targetType="table">
<paragraph id="8B8C7F672C6D61775331FCFE1711BAE9" pageId="3" pageNumber="4">
<emphasis id="B947A3752C6D61775331FCFE14B5BA8F" bold="true" box="[100,167,150,167]" pageId="3" pageNumber="4">Table 2</emphasis>
<superScript id="7C46D22F2C6D61775331FCC3147EBA9F" attach="right" box="[100,108,171,183]" fontSize="5" pageId="3" pageNumber="4">1</superScript>
H and 
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C NMR data (
<emphasis id="B947A3752C6D61775276FCD8153EBAE8" bold="true" box="[291,300,176,192]" italics="true" pageId="3" pageNumber="4">J</emphasis>
in Hz) of compounds 
<emphasis id="B947A3752C6D617752B7FCD815EABAE9" bold="true" box="[482,504,176,193]" pageId="3" pageNumber="4">23</emphasis>
, 
<emphasis id="B947A3752C6D61775157FCD8160ABAE9" bold="true" box="[514,536,176,193]" pageId="3" pageNumber="4">25</emphasis>
and 
<emphasis id="B947A3752C6D61775115FCD81644BAE9" bold="true" box="[576,598,176,193]" pageId="3" pageNumber="4">28</emphasis>
(CD OD, 600 MHz).
</paragraph>
<caption id="DF4C2FEF2C6D61775067FCFE17CBBA8F" box="[818,985,149,167]" isContinuationCaption="true" pageId="3" pageNumber="4" startId="3.[818,868,150,166]" targetBox="[834,1471,187,751]" targetIsTable="true" targetPageId="3">
<paragraph id="8B8C7F672C6D61775067FCFE17CBBA8F" blockId="3.[818,985,149,167]" box="[818,985,149,167]" pageId="3" pageNumber="4">
<emphasis id="B947A3752C6D61775067FCFE1767BA8F" bold="true" box="[818,885,150,167]" pageId="3" pageNumber="4">Table 2</emphasis>
(
<emphasis id="B947A3752C6D617750D7FCFE17C2BA8F" bold="true" box="[898,976,150,167]" italics="true" pageId="3" pageNumber="4">continued</emphasis>
)
</paragraph>
</caption>
<paragraph id="8B8C7F672C6D61775129FCDF1696BAEB" box="[636,644,183,195]" pageId="3" pageNumber="4">
<subScript id="17B77D222C6D61775129FCDF1696BAEB" attach="right" box="[636,644,183,195]" fontSize="5" pageId="3" pageNumber="4">3</subScript>
</paragraph>
</caption>
<paragraph id="8B8C7F672C6D617750C5FCD311A0B8C7" pageId="3" pageNumber="4">
<table id="F9338DC72C6D9E8B5017FCD311ADB8C7" box="[834,1471,187,751]" gridcols="7" gridrows="24" pageId="3" pageNumber="4">
<tr id="35037D252C6D9E8B5017FCD311ADBAE1" box="[834,1471,187,201]" gridrow="0" pageId="3" pageNumber="4" rowspan-0="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
<th id="76D214592C6D9E8B50C5FCD317A3BAE1" box="[912,945,187,201]" gridcol="1" gridrow="0" pageId="3" pageNumber="4">23</th>
<th id="76D214592C6D9E8B5700FCD31092BAE1" box="[1109,1152,187,201]" gridcol="3" gridrow="0" pageId="3" pageNumber="4">25</th>
<th id="76D214592C6D9E8B564CFCD31156BAE1" box="[1305,1348,187,201]" gridcol="5" gridrow="0" pageId="3" pageNumber="4">28</th>
</tr>
<tr id="35037D252C6D9E8B5017FCB611ADBAC7" box="[834,1471,222,239]" gridrow="1" pageId="3" pageNumber="4" rowspan-0="1">
<td id="76D214592C6D9E8B50C5FCB617A3BAC7" box="[912,945,222,239]" gridcol="1" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B508CFCB6103BBAC7" box="[985,1065,222,239]" gridcol="2" gridrow="1" pageId="3" pageNumber="4">δH</td>
<td id="76D214592C6D9E8B5700FCB61092BAC7" box="[1109,1152,222,239]" gridcol="3" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B57CBFCB610E9BAC7" box="[1182,1275,222,239]" gridcol="4" gridrow="1" pageId="3" pageNumber="4">δH</td>
<td id="76D214592C6D9E8B564CFCB61156BAC7" box="[1305,1348,222,239]" gridcol="5" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B5637FCB611ADBAC7" box="[1378,1471,222,239]" gridcol="6" gridrow="1" pageId="3" pageNumber="4">δH</td>
</tr>
<tr id="35037D252C6D9E8B5017FD6911ADBB27" box="[834,1471,257,271]" gridrow="2" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFD69103BBB27" box="[985,1065,257,271]" gridcol="2" gridrow="2" pageId="3" pageNumber="4">3.38, dd</td>
<td id="76D214592C6D9E8B57CBFD6910E9BB27" box="[1182,1275,257,271]" gridcol="4" gridrow="2" pageId="3" pageNumber="4">3.38, dd</td>
<td id="76D214592C6D9E8B5637FD6911ADBB27" box="[1378,1471,257,271]" gridcol="6" gridrow="2" pageId="3" pageNumber="4">3.38, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FD7011ADBB0E" box="[834,1471,280,294]" gridrow="3" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFD70103BBB0E" box="[985,1065,280,294]" gridcol="2" gridrow="3" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B57CBFD7010E9BB0E" box="[1182,1275,280,294]" gridcol="4" gridrow="3" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B5637FD7011ADBB0E" box="[1378,1471,280,294]" gridcol="6" gridrow="3" pageId="3" pageNumber="4">(9.0, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FD4711ADBB15" box="[834,1471,303,317]" gridrow="4" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5017FD47175EBB15" box="[834,844,303,317]" gridcol="0" gridrow="4" pageId="3" pageNumber="4">4</th>
<td id="76D214592C6D9E8B50C5FD4717A3BB15" box="[912,945,303,317]" gridcol="1" gridrow="4" pageId="3" pageNumber="4">71.2</td>
<td id="76D214592C6D9E8B508CFD47103BBB15" box="[985,1065,303,317]" gridcol="2" gridrow="4" pageId="3" pageNumber="4">3.29, dd</td>
<td id="76D214592C6D9E8B5700FD471092BB15" box="[1109,1152,303,317]" gridcol="3" gridrow="4" pageId="3" pageNumber="4">71.9</td>
<td id="76D214592C6D9E8B57CBFD4710E9BB15" box="[1182,1275,303,317]" gridcol="4" gridrow="4" pageId="3" pageNumber="4">3.29, dd</td>
<td id="76D214592C6D9E8B564CFD471156BB15" box="[1305,1348,303,317]" gridcol="5" gridrow="4" pageId="3" pageNumber="4">71.9</td>
<td id="76D214592C6D9E8B5637FD4711ADBB15" box="[1378,1471,303,317]" gridcol="6" gridrow="4" pageId="3" pageNumber="4">3.29, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FD2E11ADBB7C" box="[834,1471,326,340]" gridrow="5" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFD2E103BBB7C" box="[985,1065,326,340]" gridcol="2" gridrow="5" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B57CBFD2E10E9BB7C" box="[1182,1275,326,340]" gridcol="4" gridrow="5" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B5637FD2E11ADBB7C" box="[1378,1471,326,340]" gridcol="6" gridrow="5" pageId="3" pageNumber="4">(9.0, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FD3511ADBB43" box="[834,1471,349,363]" gridrow="6" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5017FD35175EBB43" box="[834,844,349,363]" gridcol="0" gridrow="6" pageId="3" pageNumber="4">5</th>
<td id="76D214592C6D9E8B50C5FD3517A3BB43" box="[912,945,349,363]" gridcol="1" gridrow="6" pageId="3" pageNumber="4">78.2</td>
<td id="76D214592C6D9E8B508CFD35103BBB43" box="[985,1065,349,363]" gridcol="2" gridrow="6" pageId="3" pageNumber="4">3.33, m</td>
<td id="76D214592C6D9E8B5700FD351092BB43" box="[1109,1152,349,363]" gridcol="3" gridrow="6" pageId="3" pageNumber="4">78.6</td>
<td id="76D214592C6D9E8B57CBFD3510E9BB43" box="[1182,1275,349,363]" gridcol="4" gridrow="6" pageId="3" pageNumber="4">3.33, m</td>
<td id="76D214592C6D9E8B564CFD351156BB43" box="[1305,1348,349,363]" gridcol="5" gridrow="6" pageId="3" pageNumber="4">78.6</td>
<td id="76D214592C6D9E8B5637FD3511ADBB43" box="[1378,1471,349,363]" gridcol="6" gridrow="6" pageId="3" pageNumber="4">3.33, m</td>
</tr>
<tr id="35037D252C6D9E8B5017FD1B11ADBBAA" box="[834,1471,371,386]" gridrow="7" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5017FD1B175EBBAA" box="[834,844,371,386]" gridcol="0" gridrow="7" pageId="3" pageNumber="4">6</th>
<td id="76D214592C6D9E8B50C5FD1B17A3BBAA" box="[912,945,371,386]" gridcol="1" gridrow="7" pageId="3" pageNumber="4">62.5</td>
<td id="76D214592C6D9E8B508CFD1B103BBBAA" box="[985,1065,371,386]" gridcol="2" gridrow="7" pageId="3" pageNumber="4">3.92, dd</td>
<td id="76D214592C6D9E8B5700FD1B1092BBAA" box="[1109,1152,371,386]" gridcol="3" gridrow="7" pageId="3" pageNumber="4">62.5</td>
<td id="76D214592C6D9E8B57CBFD1B10E9BBAA" box="[1182,1275,371,386]" gridcol="4" gridrow="7" pageId="3" pageNumber="4">3.92, dd</td>
<td id="76D214592C6D9E8B564CFD1B1156BBAA" box="[1305,1348,371,386]" gridcol="5" gridrow="7" pageId="3" pageNumber="4">62.5</td>
<td id="76D214592C6D9E8B5637FD1B11ADBBAA" box="[1378,1471,371,386]" gridcol="6" gridrow="7" pageId="3" pageNumber="4">3.92, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FDE211ADBBB0" box="[834,1471,394,408]" gridrow="8" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFDE2103BBBB0" box="[985,1065,394,408]" gridcol="2" gridrow="8" pageId="3" pageNumber="4">(2.5, 12.0)</td>
<td id="76D214592C6D9E8B57CBFDE210E9BBB0" box="[1182,1275,394,408]" gridcol="4" gridrow="8" pageId="3" pageNumber="4">(2.5, 12.0)</td>
<td id="76D214592C6D9E8B5637FDE211ADBBB0" box="[1378,1471,394,408]" gridcol="6" gridrow="8" pageId="3" pageNumber="4">(2.5, 12.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FDC911ADBB87" box="[834,1471,417,431]" gridrow="9" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFDC9103BBB87" box="[985,1065,417,431]" gridcol="2" gridrow="9" pageId="3" pageNumber="4">3.70, dd</td>
<td id="76D214592C6D9E8B57CBFDC910E9BB87" box="[1182,1275,417,431]" gridcol="4" gridrow="9" pageId="3" pageNumber="4">3.70, dd</td>
<td id="76D214592C6D9E8B5637FDC911ADBB87" box="[1378,1471,417,431]" gridcol="6" gridrow="9" pageId="3" pageNumber="4">3.70, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FDD011ADBBEE" box="[834,1471,440,454]" gridrow="10" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B508CFDD0103BBBEE" box="[985,1065,440,454]" gridcol="2" gridrow="10" pageId="3" pageNumber="4">(4.5, 12.0)</td>
<td id="76D214592C6D9E8B57CBFDD010E9BBEE" box="[1182,1275,440,454]" gridcol="4" gridrow="10" pageId="3" pageNumber="4">(4.5, 12.0)</td>
<td id="76D214592C6D9E8B5637FDD011ADBBEE" box="[1378,1471,440,454]" gridcol="6" gridrow="10" pageId="3" pageNumber="4">(4.5, 12.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FDA511ADBBF5" box="[834,1471,461,477]" gridrow="11" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1">
<td id="76D214592C6D9E8B5700FDA510E9BBF5" box="[1109,1275,461,477]" colspan="2" colspanRight="1" gridcol="3" gridrow="11" pageId="3" pageNumber="4">β- D-GlcII (at C-1′)</td>
<td id="76D214592C6D9E8B564CFDA511ADBBF5" box="[1305,1471,461,477]" colspan="2" colspanRight="1" gridcol="5" gridrow="11" pageId="3" pageNumber="4">β- D-GlcII (at C-1′)</td>
</tr>
<tr id="35037D252C6D9E8B5017FD8E11ADBBDC" box="[834,1471,486,500]" gridrow="12" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FD8E175EBBDC" box="[834,844,486,500]" gridcol="0" gridrow="12" pageId="3" pageNumber="4">1</th>
<td id="76D214592C6D9E8B5700FD8E1092BBDC" box="[1109,1152,486,500]" gridcol="3" gridrow="12" pageId="3" pageNumber="4">100.3</td>
<td id="76D214592C6D9E8B57CBFD8E10E9BBDC" box="[1182,1275,486,500]" gridcol="4" gridrow="12" pageId="3" pageNumber="4">4.70, d (7.8)</td>
<td id="76D214592C6D9E8B564CFD8E1156BBDC" box="[1305,1348,486,500]" gridcol="5" gridrow="12" pageId="3" pageNumber="4">100.3</td>
<td id="76D214592C6D9E8B5637FD8E11ADBBDC" box="[1378,1471,486,500]" gridcol="6" gridrow="12" pageId="3" pageNumber="4">4.70, d (7.8)</td>
</tr>
<tr id="35037D252C6D9E8B5017FD9511ADB823" box="[834,1471,509,523]" gridrow="13" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FD95175EB823" box="[834,844,509,523]" gridcol="0" gridrow="13" pageId="3" pageNumber="4">2</th>
<td id="76D214592C6D9E8B5700FD951092B823" box="[1109,1152,509,523]" gridcol="3" gridrow="13" pageId="3" pageNumber="4">74.9</td>
<td id="76D214592C6D9E8B57CBFD9510E9B823" box="[1182,1275,509,523]" gridcol="4" gridrow="13" pageId="3" pageNumber="4">3.21, dd</td>
<td id="76D214592C6D9E8B564CFD951156B823" box="[1305,1348,509,523]" gridcol="5" gridrow="13" pageId="3" pageNumber="4">74.9</td>
<td id="76D214592C6D9E8B5637FD9511ADB823" box="[1378,1471,509,523]" gridcol="6" gridrow="13" pageId="3" pageNumber="4">3.21, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FE7B11ADB809" box="[834,1471,531,545]" gridrow="14" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFE7B10E9B809" box="[1182,1275,531,545]" gridcol="4" gridrow="14" pageId="3" pageNumber="4">(7.8, 9.0)</td>
<td id="76D214592C6D9E8B5637FE7B11ADB809" box="[1378,1471,531,545]" gridcol="6" gridrow="14" pageId="3" pageNumber="4">(7.8, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FE4211ADB810" box="[834,1471,554,568]" gridrow="15" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FE42175EB810" box="[834,844,554,568]" gridcol="0" gridrow="15" pageId="3" pageNumber="4">3</th>
<td id="76D214592C6D9E8B5700FE421092B810" box="[1109,1152,554,568]" gridcol="3" gridrow="15" pageId="3" pageNumber="4">78.4</td>
<td id="76D214592C6D9E8B57CBFE4210E9B810" box="[1182,1275,554,568]" gridcol="4" gridrow="15" pageId="3" pageNumber="4">3.38, dd</td>
<td id="76D214592C6D9E8B564CFE421156B810" box="[1305,1348,554,568]" gridcol="5" gridrow="15" pageId="3" pageNumber="4">78.4</td>
<td id="76D214592C6D9E8B5637FE4211ADB810" box="[1378,1471,554,568]" gridcol="6" gridrow="15" pageId="3" pageNumber="4">3.38, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FE2911ADB867" box="[834,1471,577,591]" gridrow="16" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFE2910E9B867" box="[1182,1275,577,591]" gridcol="4" gridrow="16" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B5637FE2911ADB867" box="[1378,1471,577,591]" gridcol="6" gridrow="16" pageId="3" pageNumber="4">(9.0, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FE3011ADB84E" box="[834,1471,600,614]" gridrow="17" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FE30175EB84E" box="[834,844,600,614]" gridcol="0" gridrow="17" pageId="3" pageNumber="4">4</th>
<td id="76D214592C6D9E8B5700FE301092B84E" box="[1109,1152,600,614]" gridcol="3" gridrow="17" pageId="3" pageNumber="4">71.2</td>
<td id="76D214592C6D9E8B57CBFE3010E9B84E" box="[1182,1275,600,614]" gridcol="4" gridrow="17" pageId="3" pageNumber="4">3.31, dd</td>
<td id="76D214592C6D9E8B564CFE301156B84E" box="[1305,1348,600,614]" gridcol="5" gridrow="17" pageId="3" pageNumber="4">71.2</td>
<td id="76D214592C6D9E8B5637FE3011ADB84E" box="[1378,1471,600,614]" gridcol="6" gridrow="17" pageId="3" pageNumber="4">3.31, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FE0711ADB855" box="[834,1471,623,637]" gridrow="18" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFE0710E9B855" box="[1182,1275,623,637]" gridcol="4" gridrow="18" pageId="3" pageNumber="4">(9.0, 9.0)</td>
<td id="76D214592C6D9E8B5637FE0711ADB855" box="[1378,1471,623,637]" gridcol="6" gridrow="18" pageId="3" pageNumber="4">(9.0, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FEEE11ADB8BC" box="[834,1471,646,660]" gridrow="19" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FEEE175EB8BC" box="[834,844,646,660]" gridcol="0" gridrow="19" pageId="3" pageNumber="4">5</th>
<td id="76D214592C6D9E8B5700FEEE1092B8BC" box="[1109,1152,646,660]" gridcol="3" gridrow="19" pageId="3" pageNumber="4">78.6</td>
<td id="76D214592C6D9E8B57CBFEEE10E9B8BC" box="[1182,1275,646,660]" gridcol="4" gridrow="19" pageId="3" pageNumber="4">3.33, m</td>
<td id="76D214592C6D9E8B564CFEEE1156B8BC" box="[1305,1348,646,660]" gridcol="5" gridrow="19" pageId="3" pageNumber="4">78.6</td>
<td id="76D214592C6D9E8B5637FEEE11ADB8BC" box="[1378,1471,646,660]" gridcol="6" gridrow="19" pageId="3" pageNumber="4">3.33, m</td>
</tr>
<tr id="35037D252C6D9E8B5017FEF411ADB883" box="[834,1471,668,683]" gridrow="20" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5017FEF4175EB883" box="[834,844,668,683]" gridcol="0" gridrow="20" pageId="3" pageNumber="4">6</th>
<td id="76D214592C6D9E8B5700FEF41092B883" box="[1109,1152,668,683]" gridcol="3" gridrow="20" pageId="3" pageNumber="4">62.5</td>
<td id="76D214592C6D9E8B57CBFEF410E9B883" box="[1182,1275,668,683]" gridcol="4" gridrow="20" pageId="3" pageNumber="4">3.92, dd</td>
<td id="76D214592C6D9E8B564CFEF41156B883" box="[1305,1348,668,683]" gridcol="5" gridrow="20" pageId="3" pageNumber="4">62.5</td>
<td id="76D214592C6D9E8B5637FEF411ADB883" box="[1378,1471,668,683]" gridcol="6" gridrow="20" pageId="3" pageNumber="4">3.92, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FEDB11ADB8E9" box="[834,1471,691,705]" gridrow="21" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFEDB10E9B8E9" box="[1182,1275,691,705]" gridcol="4" gridrow="21" pageId="3" pageNumber="4">(2.5, 12.0)</td>
<td id="76D214592C6D9E8B5637FEDB11ADB8E9" box="[1378,1471,691,705]" gridcol="6" gridrow="21" pageId="3" pageNumber="4">(2.5, 12.0)</td>
</tr>
<tr id="35037D252C6D9E8B5017FEA211ADB8F0" box="[834,1471,714,728]" gridrow="22" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFEA210E9B8F0" box="[1182,1275,714,728]" gridcol="4" gridrow="22" pageId="3" pageNumber="4">3.70, dd</td>
<td id="76D214592C6D9E8B5637FEA211ADB8F0" box="[1378,1471,714,728]" gridcol="6" gridrow="22" pageId="3" pageNumber="4">3.70, dd</td>
</tr>
<tr id="35037D252C6D9E8B5017FE8911ADB8C7" box="[834,1471,737,751]" gridrow="23" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B57CBFE8910E9B8C7" box="[1182,1275,737,751]" gridcol="4" gridrow="23" pageId="3" pageNumber="4">(4.5, 12.0)</td>
<td id="76D214592C6D9E8B5637FE8911ADB8C7" box="[1378,1471,737,751]" gridcol="6" gridrow="23" pageId="3" pageNumber="4">(4.5, 12.0)</td>
</tr>
</table>
</paragraph>
<paragraph id="8B8C7F672C6D61775396FCBD167FBDBE" pageId="3" pageNumber="4">
<table id="F9338DC72C6D9E8B5321FCBD16E0BDBE" box="[116,754,213,1942]" gridcols="7" gridrows="74" pageId="3" pageNumber="4">
<tr id="35037D252C6D9E8B5321FCBD16E0BACB" box="[116,754,213,227]" gridrow="0" pageId="3" pageNumber="4" rowspan-0="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
<th id="76D214592C6D9E8B5396FCBD14FCBACB" box="[195,238,213,227]" gridcol="1" gridrow="0" pageId="3" pageNumber="4">23</th>
<th id="76D214592C6D9E8B52D2FCBD15A0BACB" box="[391,434,213,227]" gridcol="3" gridrow="0" pageId="3" pageNumber="4">25</th>
<th id="76D214592C6D9E8B5119FCBD1665BACB" box="[588,631,213,227]" gridcol="5" gridrow="0" pageId="3" pageNumber="4">28</th>
</tr>
<tr id="35037D252C6D9E8B5321FC9016E0BB20" box="[116,754,248,264]" gridrow="1" pageId="3" pageNumber="4" rowspan-0="1">
<td id="76D214592C6D9E8B5396FC9014FCBB20" box="[195,238,248,264]" gridcol="1" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B5259FC90157BBB20" box="[268,361,248,264]" gridcol="2" gridrow="1" pageId="3" pageNumber="4">δH</td>
<td id="76D214592C6D9E8B52D2FC9015A0BB20" box="[391,434,248,264]" gridcol="3" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B5284FC90163CBB20" box="[465,558,248,264]" gridcol="4" gridrow="1" pageId="3" pageNumber="4">δH</td>
<td id="76D214592C6D9E8B5119FC901665BB20" box="[588,631,248,264]" gridcol="5" gridrow="1" pageId="3" pageNumber="4">δC</td>
<td id="76D214592C6D9E8B51C0FC9016E0BB20" box="[661,754,248,264]" gridcol="6" gridrow="1" pageId="3" pageNumber="4">δH</td>
</tr>
<tr id="35037D252C6D9E8B5321FD7316E0BB01" box="[116,754,283,297]" gridrow="2" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FD7314B6BB01" box="[116,164,283,297]" gridcol="0" gridrow="2" pageId="3" pageNumber="4">1</th>
<td id="76D214592C6D9E8B5396FD7314FCBB01" box="[195,238,283,297]" gridcol="1" gridrow="2" pageId="3" pageNumber="4">97.2</td>
<td id="76D214592C6D9E8B5259FD73157BBB01" box="[268,361,283,297]" gridcol="2" gridrow="2" pageId="3" pageNumber="4">5.54, d (8.5)</td>
<td id="76D214592C6D9E8B52D2FD7315A0BB01" box="[391,434,283,297]" gridcol="3" gridrow="2" pageId="3" pageNumber="4">97.6</td>
<td id="76D214592C6D9E8B5284FD73163CBB01" box="[465,558,283,297]" gridcol="4" gridrow="2" pageId="3" pageNumber="4">5.32, d (8.5)</td>
<td id="76D214592C6D9E8B5119FD731665BB01" box="[588,631,283,297]" gridcol="5" gridrow="2" pageId="3" pageNumber="4">97.6</td>
<td id="76D214592C6D9E8B51C0FD7316E0BB01" box="[661,754,283,297]" gridcol="6" gridrow="2" pageId="3" pageNumber="4">5.32, d (8.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321FD5A16E0BB68" box="[116,754,306,320]" gridrow="3" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1" rowspan-4="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FD5A14B6BB68" box="[116,164,306,320]" gridcol="0" gridrow="3" pageId="3" pageNumber="4">2</th>
<td id="76D214592C6D9E8B52D2FD5A15A0BB68" box="[391,434,306,320]" gridcol="3" gridrow="3" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B5119FD5A1665BB68" box="[588,631,306,320]" gridcol="5" gridrow="3" pageId="3" pageNumber="4">–</td>
</tr>
<tr id="35037D252C6D9E8B5321FD2016E0BB7F" box="[116,754,328,343]" gridrow="4" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FD2014B6BB7F" box="[116,164,328,343]" gridcol="0" gridrow="4" pageId="3" pageNumber="4">3</th>
<td id="76D214592C6D9E8B5396FD2014FCBB7F" box="[195,238,328,343]" gridcol="1" gridrow="4" pageId="3" pageNumber="4">153.0</td>
<td id="76D214592C6D9E8B5259FD20157BBB7F" box="[268,361,328,343]" gridcol="2" gridrow="4" pageId="3" pageNumber="4">7.44, s</td>
<td id="76D214592C6D9E8B52D2FD2015A0BB7F" box="[391,434,328,343]" gridcol="3" gridrow="4" pageId="3" pageNumber="4">152.9</td>
<td id="76D214592C6D9E8B5284FD20163CBB7F" box="[465,558,328,343]" gridcol="4" gridrow="4" pageId="3" pageNumber="4">7.45, s</td>
<td id="76D214592C6D9E8B5119FD201665BB7F" box="[588,631,328,343]" gridcol="5" gridrow="4" pageId="3" pageNumber="4">152.9</td>
<td id="76D214592C6D9E8B51C0FD2016E0BB7F" box="[661,754,328,343]" gridcol="6" gridrow="4" pageId="3" pageNumber="4">7.45, s</td>
</tr>
<tr id="35037D252C6D9E8B5321FD3716E0BB46" box="[116,754,351,366]" gridrow="5" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FD3714B6BB46" box="[116,164,351,366]" gridcol="0" gridrow="5" pageId="3" pageNumber="4">4</th>
<td id="76D214592C6D9E8B5396FD3714FCBB46" box="[195,238,351,366]" gridcol="1" gridrow="5" pageId="3" pageNumber="4">113.1</td>
<td id="76D214592C6D9E8B5259FD37157BBB46" box="[268,361,351,366]" gridcol="2" gridrow="5" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B52D2FD3715A0BB46" box="[391,434,351,366]" gridcol="3" gridrow="5" pageId="3" pageNumber="4">112.0</td>
<td id="76D214592C6D9E8B5284FD37163CBB46" box="[465,558,351,366]" gridcol="4" gridrow="5" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B5119FD371665BB46" box="[588,631,351,366]" gridcol="5" gridrow="5" pageId="3" pageNumber="4">112.0</td>
<td id="76D214592C6D9E8B51C0FD3716E0BB46" box="[661,754,351,366]" gridcol="6" gridrow="5" pageId="3" pageNumber="4">–</td>
</tr>
<tr id="35037D252C6D9E8B5321FD1E16E0BBAC" box="[116,754,374,388]" gridrow="6" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FD1E14B6BBAC" box="[116,164,374,388]" gridcol="0" gridrow="6" pageId="3" pageNumber="4">5</th>
<td id="76D214592C6D9E8B5396FD1E14FCBBAC" box="[195,238,374,388]" gridcol="1" gridrow="6" pageId="3" pageNumber="4">29.1</td>
<td id="76D214592C6D9E8B5259FD1E157BBBAC" box="[268,361,374,388]" gridcol="2" gridrow="6" pageId="3" pageNumber="4">2.94, m</td>
<td id="76D214592C6D9E8B52D2FD1E15A0BBAC" box="[391,434,374,388]" gridcol="3" gridrow="6" pageId="3" pageNumber="4">33.0</td>
<td id="76D214592C6D9E8B5284FD1E163CBBAC" box="[465,558,374,388]" gridcol="4" gridrow="6" pageId="3" pageNumber="4">3.16, td</td>
<td id="76D214592C6D9E8B5119FD1E1665BBAC" box="[588,631,374,388]" gridcol="5" gridrow="6" pageId="3" pageNumber="4">33.0</td>
<td id="76D214592C6D9E8B51C0FD1E16E0BBAC" box="[661,754,374,388]" gridcol="6" gridrow="6" pageId="3" pageNumber="4">3.16, td</td>
</tr>
<tr id="35037D252C6D9E8B5321FDE516E0BBB3" box="[116,754,397,411]" gridrow="7" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FDE5163CBBB3" box="[465,558,397,411]" gridcol="4" gridrow="7" pageId="3" pageNumber="4">(8.0, 8.0,</td>
<td id="76D214592C6D9E8B51C0FDE516E0BBB3" box="[661,754,397,411]" gridcol="6" gridrow="7" pageId="3" pageNumber="4">(8.0, 8.0,</td>
</tr>
<tr id="35037D252C6D9E8B5321FDCC16E0BB9A" box="[116,754,420,434]" gridrow="8" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FDCC163CBB9A" box="[465,558,420,434]" gridcol="4" gridrow="8" pageId="3" pageNumber="4">6.0)</td>
<td id="76D214592C6D9E8B51C0FDCC16E0BB9A" box="[661,754,420,434]" gridcol="6" gridrow="8" pageId="3" pageNumber="4">6.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FDD316E0BBE1" box="[116,754,443,457]" gridrow="9" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FDD314B6BBE1" box="[116,164,443,457]" gridcol="0" gridrow="9" pageId="3" pageNumber="4">6</th>
<td id="76D214592C6D9E8B5396FDD314FCBBE1" box="[195,238,443,457]" gridcol="1" gridrow="9" pageId="3" pageNumber="4">33.0</td>
<td id="76D214592C6D9E8B5259FDD3157BBBE1" box="[268,361,443,457]" gridcol="2" gridrow="9" pageId="3" pageNumber="4">2.10, ddd</td>
<td id="76D214592C6D9E8B52D2FDD315A0BBE1" box="[391,434,443,457]" gridcol="3" gridrow="9" pageId="3" pageNumber="4">40.6</td>
<td id="76D214592C6D9E8B5284FDD3163CBBE1" box="[465,558,443,457]" gridcol="4" gridrow="9" pageId="3" pageNumber="4">2.36, dd</td>
<td id="76D214592C6D9E8B5119FDD31665BBE1" box="[588,631,443,457]" gridcol="5" gridrow="9" pageId="3" pageNumber="4">40.6</td>
<td id="76D214592C6D9E8B51C0FDD316E0BBE1" box="[661,754,443,457]" gridcol="6" gridrow="9" pageId="3" pageNumber="4">2.36, dd</td>
</tr>
<tr id="35037D252C6D9E8B5321FDB916E0BBC8" box="[116,754,465,480]" gridrow="10" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FDB9157BBBC8" box="[268,361,465,480]" gridcol="2" gridrow="10" pageId="3" pageNumber="4">(14.0, 5.9,</td>
<td id="76D214592C6D9E8B5284FDB9163CBBC8" box="[465,558,465,480]" gridcol="4" gridrow="10" pageId="3" pageNumber="4">(14.0, 8.0)</td>
<td id="76D214592C6D9E8B51C0FDB916E0BBC8" box="[661,754,465,480]" gridcol="6" gridrow="10" pageId="3" pageNumber="4">(14.0, 8.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FD8016E0BBDF" box="[116,754,488,503]" gridrow="11" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FD80157BBBDF" box="[268,361,488,503]" gridcol="2" gridrow="11" pageId="3" pageNumber="4">1.5)</td>
<td id="76D214592C6D9E8B5284FD80163CBBDF" box="[465,558,488,503]" gridcol="4" gridrow="11" pageId="3" pageNumber="4">1.78, ddd</td>
<td id="76D214592C6D9E8B51C0FD8016E0BBDF" box="[661,754,488,503]" gridcol="6" gridrow="11" pageId="3" pageNumber="4">1.78, ddd</td>
</tr>
<tr id="35037D252C6D9E8B5321FD9716E0B825" box="[116,754,511,525]" gridrow="12" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FD97157BB825" box="[268,361,511,525]" gridcol="2" gridrow="12" pageId="3" pageNumber="4">1.67, ddd</td>
<td id="76D214592C6D9E8B5284FD97163CB825" box="[465,558,511,525]" gridcol="4" gridrow="12" pageId="3" pageNumber="4">(14.0, 6.0,</td>
<td id="76D214592C6D9E8B51C0FD9716E0B825" box="[661,754,511,525]" gridcol="6" gridrow="12" pageId="3" pageNumber="4">(14.0, 6.0,</td>
</tr>
<tr id="35037D252C6D9E8B5321FE7E16E0B80C" box="[116,754,534,548]" gridrow="13" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FE7E157BB80C" box="[268,361,534,548]" gridcol="2" gridrow="13" pageId="3" pageNumber="4">(14.0, 5.2,</td>
<td id="76D214592C6D9E8B5284FE7E163CB80C" box="[465,558,534,548]" gridcol="4" gridrow="13" pageId="3" pageNumber="4">5.0)</td>
<td id="76D214592C6D9E8B51C0FE7E16E0B80C" box="[661,754,534,548]" gridcol="6" gridrow="13" pageId="3" pageNumber="4">5.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FE4516E0B813" box="[116,754,557,571]" gridrow="14" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FE45157BB813" box="[268,361,557,571]" gridcol="2" gridrow="14" pageId="3" pageNumber="4">4.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FE2C16E0B87A" box="[116,754,580,594]" gridrow="15" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FE2C14B6B87A" box="[116,164,580,594]" gridcol="0" gridrow="15" pageId="3" pageNumber="4">7</th>
<td id="76D214592C6D9E8B5396FE2C14FCB87A" box="[195,238,580,594]" gridcol="1" gridrow="15" pageId="3" pageNumber="4">103.8</td>
<td id="76D214592C6D9E8B5259FE2C157BB87A" box="[268,361,580,594]" gridcol="2" gridrow="15" pageId="3" pageNumber="4">4.53, dd</td>
<td id="76D214592C6D9E8B52D2FE2C15A0B87A" box="[391,434,580,594]" gridcol="3" gridrow="15" pageId="3" pageNumber="4">78.9</td>
<td id="76D214592C6D9E8B5284FE2C163CB87A" box="[465,558,580,594]" gridcol="4" gridrow="15" pageId="3" pageNumber="4">5.24, br t</td>
<td id="76D214592C6D9E8B5119FE2C1665B87A" box="[588,631,580,594]" gridcol="5" gridrow="15" pageId="3" pageNumber="4">78.9</td>
<td id="76D214592C6D9E8B51C0FE2C16E0B87A" box="[661,754,580,594]" gridcol="6" gridrow="15" pageId="3" pageNumber="4">5.24, br t</td>
</tr>
<tr id="35037D252C6D9E8B5321FE3216E0B840" box="[116,754,602,616]" gridrow="16" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FE32157BB840" box="[268,361,602,616]" gridcol="2" gridrow="16" pageId="3" pageNumber="4">(5.9, 5.2)</td>
<td id="76D214592C6D9E8B5284FE32163CB840" box="[465,558,602,616]" gridcol="4" gridrow="16" pageId="3" pageNumber="4">(5.0)</td>
<td id="76D214592C6D9E8B51C0FE3216E0B840" box="[661,754,602,616]" gridcol="6" gridrow="16" pageId="3" pageNumber="4">(5.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FE1916E0B8A8" box="[116,754,625,640]" gridrow="17" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FE1914B6B8A8" box="[116,164,625,640]" gridcol="0" gridrow="17" pageId="3" pageNumber="4">8</th>
<td id="76D214592C6D9E8B5396FE1914FCB8A8" box="[195,238,625,640]" gridcol="1" gridrow="17" pageId="3" pageNumber="4">135.7</td>
<td id="76D214592C6D9E8B5259FE19157BB8A8" box="[268,361,625,640]" gridcol="2" gridrow="17" pageId="3" pageNumber="4">5.76, ddd</td>
<td id="76D214592C6D9E8B52D2FE1915A0B8A8" box="[391,434,625,640]" gridcol="3" gridrow="17" pageId="3" pageNumber="4">41.2</td>
<td id="76D214592C6D9E8B5284FE19163CB8A8" box="[465,558,625,640]" gridcol="4" gridrow="17" pageId="3" pageNumber="4">2.17, m</td>
<td id="76D214592C6D9E8B5119FE191665B8A8" box="[588,631,625,640]" gridcol="5" gridrow="17" pageId="3" pageNumber="4">41.2</td>
<td id="76D214592C6D9E8B51C0FE1916E0B8A8" box="[661,754,625,640]" gridcol="6" gridrow="17" pageId="3" pageNumber="4">2.17, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FEE016E0B8BE" box="[116,754,648,662]" gridrow="18" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FEE0157BB8BE" box="[268,361,648,662]" gridcol="2" gridrow="18" pageId="3" pageNumber="4">(7.5, 10.5,</td>
</tr>
<tr id="35037D252C6D9E8B5321FEF716E0B885" box="[116,754,671,685]" gridrow="19" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FEF7157BB885" box="[268,361,671,685]" gridcol="2" gridrow="19" pageId="3" pageNumber="4">17.7)</td>
</tr>
<tr id="35037D252C6D9E8B5321FEDE16E0B8EC" box="[116,754,694,708]" gridrow="20" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FEDE14B6B8EC" box="[116,164,694,708]" gridcol="0" gridrow="20" pageId="3" pageNumber="4">9</th>
<td id="76D214592C6D9E8B5396FEDE14FCB8EC" box="[195,238,694,708]" gridcol="1" gridrow="20" pageId="3" pageNumber="4">44.3</td>
<td id="76D214592C6D9E8B5259FEDE157BB8EC" box="[268,361,694,708]" gridcol="2" gridrow="20" pageId="3" pageNumber="4">2.69, brdt</td>
<td id="76D214592C6D9E8B52D2FEDE15A0B8EC" box="[391,434,694,708]" gridcol="3" gridrow="20" pageId="3" pageNumber="4">47.5</td>
<td id="76D214592C6D9E8B5284FEDE163CB8EC" box="[465,558,694,708]" gridcol="4" gridrow="20" pageId="3" pageNumber="4">2.12, ddd</td>
<td id="76D214592C6D9E8B5119FEDE1665B8EC" box="[588,631,694,708]" gridcol="5" gridrow="20" pageId="3" pageNumber="4">47.5</td>
<td id="76D214592C6D9E8B51C0FEDE16E0B8EC" box="[661,754,694,708]" gridcol="6" gridrow="20" pageId="3" pageNumber="4">2.12, ddd</td>
</tr>
<tr id="35037D252C6D9E8B5321FEA516E0B8F3" box="[116,754,717,731]" gridrow="21" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FEA5157BB8F3" box="[268,361,717,731]" gridcol="2" gridrow="21" pageId="3" pageNumber="4">(8.5, 7.5)</td>
<td id="76D214592C6D9E8B5284FEA5163CB8F3" box="[465,558,717,731]" gridcol="4" gridrow="21" pageId="3" pageNumber="4">(10.8, 8.5,</td>
<td id="76D214592C6D9E8B51C0FEA516E0B8F3" box="[661,754,717,731]" gridcol="6" gridrow="21" pageId="3" pageNumber="4">(10.8, 8.5,</td>
</tr>
<tr id="35037D252C6D9E8B5321FE8C16E0B8DA" box="[116,754,740,754]" gridrow="22" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FE8C163CB8DA" box="[465,558,740,754]" gridcol="4" gridrow="22" pageId="3" pageNumber="4">8.0)</td>
<td id="76D214592C6D9E8B51C0FE8C16E0B8DA" box="[661,754,740,754]" gridcol="6" gridrow="22" pageId="3" pageNumber="4">8.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FE9216E0B921" box="[116,754,762,777]" gridrow="23" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FE9214B6B921" box="[116,164,762,777]" gridcol="0" gridrow="23" pageId="3" pageNumber="4">10</th>
<td id="76D214592C6D9E8B5396FE9214FCB921" box="[195,238,762,777]" gridcol="1" gridrow="23" pageId="3" pageNumber="4">120.0</td>
<td id="76D214592C6D9E8B5259FE92157BB921" box="[268,361,762,777]" gridcol="2" gridrow="23" pageId="3" pageNumber="4">5.33,</td>
<td id="76D214592C6D9E8B52D2FE9215A0B921" box="[391,434,762,777]" gridcol="3" gridrow="23" pageId="3" pageNumber="4">13.4</td>
<td id="76D214592C6D9E8B5284FE92163CB921" box="[465,558,762,777]" gridcol="4" gridrow="23" pageId="3" pageNumber="4">1.10, d (6.8)</td>
<td id="76D214592C6D9E8B5119FE921665B921" box="[588,631,762,777]" gridcol="5" gridrow="23" pageId="3" pageNumber="4">13.4</td>
<td id="76D214592C6D9E8B51C0FE9216E0B921" box="[661,754,762,777]" gridcol="6" gridrow="23" pageId="3" pageNumber="4">1.10, d (6.8)</td>
</tr>
<tr id="35037D252C6D9E8B5321FF7916E0B937" box="[116,754,785,799]" gridrow="24" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FF79157BB937" box="[268,361,785,799]" gridcol="2" gridrow="24" pageId="3" pageNumber="4">d (17.7)</td>
</tr>
<tr id="35037D252C6D9E8B5321FF4016E0B91E" box="[116,754,808,822]" gridrow="25" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FF40157BB91E" box="[268,361,808,822]" gridcol="2" gridrow="25" pageId="3" pageNumber="4">5.30,</td>
</tr>
<tr id="35037D252C6D9E8B5321FF5716E0B965" box="[116,754,831,845]" gridrow="26" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5259FF57157BB965" box="[268,361,831,845]" gridcol="2" gridrow="26" pageId="3" pageNumber="4">d (10.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321FF3E16E0B94C" box="[116,754,854,868]" gridrow="27" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FF3E14B6B94C" box="[116,164,854,868]" gridcol="0" gridrow="27" pageId="3" pageNumber="4">11</th>
<td id="76D214592C6D9E8B5396FF3E14FCB94C" box="[195,238,854,868]" gridcol="1" gridrow="27" pageId="3" pageNumber="4">168.2</td>
<td id="76D214592C6D9E8B5259FF3E157BB94C" box="[268,361,854,868]" gridcol="2" gridrow="27" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B52D2FF3E15A0B94C" box="[391,434,854,868]" gridcol="3" gridrow="27" pageId="3" pageNumber="4">169.0</td>
<td id="76D214592C6D9E8B5284FF3E163CB94C" box="[465,558,854,868]" gridcol="4" gridrow="27" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B5119FF3E1665B94C" box="[588,631,854,868]" gridcol="5" gridrow="27" pageId="3" pageNumber="4">169.0</td>
<td id="76D214592C6D9E8B51C0FF3E16E0B94C" box="[661,754,854,868]" gridcol="6" gridrow="27" pageId="3" pageNumber="4">–</td>
</tr>
<tr id="35037D252C6D9E8B5321FF0516E0B955" box="[116,754,877,893]" gridrow="28" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FF0514B6B955" box="[116,164,877,893]" gridcol="0" gridrow="28" pageId="3" pageNumber="4">
-OCH 
<subScript id="17B77D222C6D617753C8FF1B14B6B955" attach="left" box="[157,164,883,893]" fontSize="4" pageId="3" pageNumber="4">3</subScript>
</th>
<td id="76D214592C6D9E8B5396FF0514FCB955" box="[195,238,877,893]" gridcol="1" gridrow="28" pageId="3" pageNumber="4">51.8</td>
<td id="76D214592C6D9E8B5259FF05157BB955" box="[268,361,877,893]" gridcol="2" gridrow="28" pageId="3" pageNumber="4">3.72, s</td>
<td id="76D214592C6D9E8B52D2FF0515A0B955" box="[391,434,877,893]" gridcol="3" gridrow="28" pageId="3" pageNumber="4">51.5</td>
<td id="76D214592C6D9E8B5284FF05163CB955" box="[465,558,877,893]" gridcol="4" gridrow="28" pageId="3" pageNumber="4">3.72, s</td>
<td id="76D214592C6D9E8B5119FF051665B955" box="[588,631,877,893]" gridcol="5" gridrow="28" pageId="3" pageNumber="4">51.5</td>
<td id="76D214592C6D9E8B51C0FF0516E0B955" box="[661,754,877,893]" gridcol="6" gridrow="28" pageId="3" pageNumber="4">3.72, s</td>
</tr>
<tr id="35037D252C6D9E8B5321FFEC16E0B9BA" box="[116,754,900,914]" gridrow="29" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FFEC14B6B9BA" box="[116,164,900,914]" gridcol="0" gridrow="29" pageId="3" pageNumber="4">1’</th>
<td id="76D214592C6D9E8B52D2FFEC15A0B9BA" box="[391,434,900,914]" gridcol="3" gridrow="29" pageId="3" pageNumber="4">97.2</td>
<td id="76D214592C6D9E8B5284FFEC163CB9BA" box="[465,558,900,914]" gridcol="4" gridrow="29" pageId="3" pageNumber="4">5.54, d (8.5)</td>
<td id="76D214592C6D9E8B5119FFEC1665B9BA" box="[588,631,900,914]" gridcol="5" gridrow="29" pageId="3" pageNumber="4">97.2</td>
<td id="76D214592C6D9E8B51C0FFEC16E0B9BA" box="[661,754,900,914]" gridcol="6" gridrow="29" pageId="3" pageNumber="4">5.54, d (8.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321FFD916E0B997" box="[116,754,945,959]" gridrow="30" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FFD916E0B997" box="[116,754,945,959]" colspan="7" colspanRight="6" gridcol="0" gridrow="30" pageId="3" pageNumber="4">2’</th>
</tr>
<tr id="35037D252C6D9E8B5321FFA016E0B9FE" box="[116,754,968,982]" gridrow="31" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FFA014B6B9FE" box="[116,164,968,982]" gridcol="0" gridrow="31" pageId="3" pageNumber="4">3’</th>
<td id="76D214592C6D9E8B52D2FFA015A0B9FE" box="[391,434,968,982]" gridcol="3" gridrow="31" pageId="3" pageNumber="4">153.4</td>
<td id="76D214592C6D9E8B5284FFA0163CB9FE" box="[465,558,968,982]" gridcol="4" gridrow="31" pageId="3" pageNumber="4">7.47, s</td>
<td id="76D214592C6D9E8B5119FFA01665B9FE" box="[588,631,968,982]" gridcol="5" gridrow="31" pageId="3" pageNumber="4">
<geoCoordinate id="EE0719A02C6D61775119FFA01665B9FE" box="[588,631,968,982]" degrees="153.4" direction="south" orientation="latitude" pageId="3" pageNumber="4" precision="5555" value="-153.4">153.4</geoCoordinate>
</td>
<td id="76D214592C6D9E8B51C0FFA016E0B9FE" box="[661,754,968,982]" gridcol="6" gridrow="31" pageId="3" pageNumber="4">7.47, s</td>
</tr>
<tr id="35037D252C6D9E8B5321FFB716E0B9C5" box="[116,754,991,1005]" gridrow="32" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FFB714B6B9C5" box="[116,164,991,1005]" gridcol="0" gridrow="32" pageId="3" pageNumber="4">4’</th>
<td id="76D214592C6D9E8B52D2FFB715A0B9C5" box="[391,434,991,1005]" gridcol="3" gridrow="32" pageId="3" pageNumber="4">113.1</td>
<td id="76D214592C6D9E8B5284FFB7163CB9C5" box="[465,558,991,1005]" gridcol="4" gridrow="32" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B5119FFB71665B9C5" box="[588,631,991,1005]" gridcol="5" gridrow="32" pageId="3" pageNumber="4">113.1</td>
<td id="76D214592C6D9E8B51C0FFB716E0B9C5" box="[661,754,991,1005]" gridcol="6" gridrow="32" pageId="3" pageNumber="4">–</td>
</tr>
<tr id="35037D252C6D9E8B5321FF9E16E0BE2C" box="[116,754,1014,1028]" gridrow="33" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FF9E14B6BE2C" box="[116,164,1014,1028]" gridcol="0" gridrow="33" pageId="3" pageNumber="4">5’</th>
<td id="76D214592C6D9E8B52D2FF9E15A0BE2C" box="[391,434,1014,1028]" gridcol="3" gridrow="33" pageId="3" pageNumber="4">29.5</td>
<td id="76D214592C6D9E8B5284FF9E163CBE2C" box="[465,558,1014,1028]" gridcol="4" gridrow="33" pageId="3" pageNumber="4">2.97, m</td>
<td id="76D214592C6D9E8B5119FF9E1665BE2C" box="[588,631,1014,1028]" gridcol="5" gridrow="33" pageId="3" pageNumber="4">29.5</td>
<td id="76D214592C6D9E8B51C0FF9E16E0BE2C" box="[661,754,1014,1028]" gridcol="6" gridrow="33" pageId="3" pageNumber="4">2.97, m</td>
</tr>
<tr id="35037D252C6D9E8B5321F86516E0BE33" box="[116,754,1037,1051]" gridrow="34" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F86514B6BE33" box="[116,164,1037,1051]" gridcol="0" gridrow="34" pageId="3" pageNumber="4">6’</th>
<td id="76D214592C6D9E8B52D2F86515A0BE33" box="[391,434,1037,1051]" gridcol="3" gridrow="34" pageId="3" pageNumber="4">34.0</td>
<td id="76D214592C6D9E8B5284F865163CBE33" box="[465,558,1037,1051]" gridcol="4" gridrow="34" pageId="3" pageNumber="4">2.13, ddd</td>
<td id="76D214592C6D9E8B5119F8651665BE33" box="[588,631,1037,1051]" gridcol="5" gridrow="34" pageId="3" pageNumber="4">34.0</td>
<td id="76D214592C6D9E8B51C0F86516E0BE33" box="[661,754,1037,1051]" gridcol="6" gridrow="34" pageId="3" pageNumber="4">2.13, ddd</td>
</tr>
<tr id="35037D252C6D9E8B5321F84C16E0BE1A" box="[116,754,1060,1074]" gridrow="35" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F84C163CBE1A" box="[465,558,1060,1074]" gridcol="4" gridrow="35" pageId="3" pageNumber="4">(14.0, 6.3,</td>
<td id="76D214592C6D9E8B51C0F84C16E0BE1A" box="[661,754,1060,1074]" gridcol="6" gridrow="35" pageId="3" pageNumber="4">(14.0, 6.3,</td>
</tr>
<tr id="35037D252C6D9E8B5321F85216E0BE60" box="[116,754,1082,1096]" gridrow="36" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F852163CBE60" box="[465,558,1082,1096]" gridcol="4" gridrow="36" pageId="3" pageNumber="4">1.5)</td>
<td id="76D214592C6D9E8B51C0F85216E0BE60" box="[661,754,1082,1096]" gridcol="6" gridrow="36" pageId="3" pageNumber="4">1.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321F83916E0BE77" box="[116,754,1105,1119]" gridrow="37" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F839163CBE77" box="[465,558,1105,1119]" gridcol="4" gridrow="37" pageId="3" pageNumber="4">1.68, ddd</td>
<td id="76D214592C6D9E8B51C0F83916E0BE77" box="[661,754,1105,1119]" gridcol="6" gridrow="37" pageId="3" pageNumber="4">1.68, ddd</td>
</tr>
<tr id="35037D252C6D9E8B5321F80016E0BE5E" box="[116,754,1128,1142]" gridrow="38" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F800163CBE5E" box="[465,558,1128,1142]" gridcol="4" gridrow="38" pageId="3" pageNumber="4">(14.0, 5.2,</td>
<td id="76D214592C6D9E8B51C0F80016E0BE5E" box="[661,754,1128,1142]" gridcol="6" gridrow="38" pageId="3" pageNumber="4">(14.0, 5.2,</td>
</tr>
<tr id="35037D252C6D9E8B5321F81716E0BEA5" box="[116,754,1151,1165]" gridrow="39" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F817163CBEA5" box="[465,558,1151,1165]" gridcol="4" gridrow="39" pageId="3" pageNumber="4">4.0)</td>
<td id="76D214592C6D9E8B51C0F81716E0BEA5" box="[661,754,1151,1165]" gridcol="6" gridrow="39" pageId="3" pageNumber="4">4.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321F8FE16E0BE8C" box="[116,754,1174,1188]" gridrow="40" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F8FE14B6BE8C" box="[116,164,1174,1188]" gridcol="0" gridrow="40" pageId="3" pageNumber="4">7’</th>
<td id="76D214592C6D9E8B52D2F8FE15A0BE8C" box="[391,434,1174,1188]" gridcol="3" gridrow="40" pageId="3" pageNumber="4">103.8</td>
<td id="76D214592C6D9E8B5284F8FE163CBE8C" box="[465,558,1174,1188]" gridcol="4" gridrow="40" pageId="3" pageNumber="4">4.60, dd</td>
<td id="76D214592C6D9E8B5119F8FE1665BE8C" box="[588,631,1174,1188]" gridcol="5" gridrow="40" pageId="3" pageNumber="4">103.8</td>
<td id="76D214592C6D9E8B51C0F8FE16E0BE8C" box="[661,754,1174,1188]" gridcol="6" gridrow="40" pageId="3" pageNumber="4">4.60, dd</td>
</tr>
<tr id="35037D252C6D9E8B5321F8C516E0BE93" box="[116,754,1197,1211]" gridrow="41" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F8C5163CBE93" box="[465,558,1197,1211]" gridcol="4" gridrow="41" pageId="3" pageNumber="4">(5.9, 5.2)</td>
<td id="76D214592C6D9E8B51C0F8C516E0BE93" box="[661,754,1197,1211]" gridcol="6" gridrow="41" pageId="3" pageNumber="4">(5.9, 5.2)</td>
</tr>
<tr id="35037D252C6D9E8B5321F8AB16E0BEFA" box="[116,754,1219,1234]" gridrow="42" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F8AB14B6BEFA" box="[116,164,1219,1234]" gridcol="0" gridrow="42" pageId="3" pageNumber="4">8’</th>
<td id="76D214592C6D9E8B52D2F8AB15A0BEFA" box="[391,434,1219,1234]" gridcol="3" gridrow="42" pageId="3" pageNumber="4">136.0</td>
<td id="76D214592C6D9E8B5284F8AB163CBEFA" box="[465,558,1219,1234]" gridcol="4" gridrow="42" pageId="3" pageNumber="4">5.76, ddd</td>
<td id="76D214592C6D9E8B5119F8AB1665BEFA" box="[588,631,1219,1234]" gridcol="5" gridrow="42" pageId="3" pageNumber="4">136.0</td>
<td id="76D214592C6D9E8B51C0F8AB16E0BEFA" box="[661,754,1219,1234]" gridcol="6" gridrow="42" pageId="3" pageNumber="4">5.76, ddd</td>
</tr>
<tr id="35037D252C6D9E8B5321F8B216E0BEC0" box="[116,754,1242,1256]" gridrow="43" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F8B2163CBEC0" box="[465,558,1242,1256]" gridcol="4" gridrow="43" pageId="3" pageNumber="4">(7.5, 10.5,</td>
<td id="76D214592C6D9E8B51C0F8B216E0BEC0" box="[661,754,1242,1256]" gridcol="6" gridrow="43" pageId="3" pageNumber="4">(7.5, 10.5,</td>
</tr>
<tr id="35037D252C6D9E8B5321F89916E0BED7" box="[116,754,1265,1279]" gridrow="44" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F899163CBED7" box="[465,558,1265,1279]" gridcol="4" gridrow="44" pageId="3" pageNumber="4">17.7)</td>
<td id="76D214592C6D9E8B51C0F89916E0BED7" box="[661,754,1265,1279]" gridcol="6" gridrow="44" pageId="3" pageNumber="4">17.7)</td>
</tr>
<tr id="35037D252C6D9E8B5321F96016E0BF3E" box="[116,754,1288,1302]" gridrow="45" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F96014B6BF3E" box="[116,164,1288,1302]" gridcol="0" gridrow="45" pageId="3" pageNumber="4">9’</th>
<td id="76D214592C6D9E8B52D2F96015A0BF3E" box="[391,434,1288,1302]" gridcol="3" gridrow="45" pageId="3" pageNumber="4">45.5</td>
<td id="76D214592C6D9E8B5284F960163CBF3E" box="[465,558,1288,1302]" gridcol="4" gridrow="45" pageId="3" pageNumber="4">2.71, brdt</td>
<td id="76D214592C6D9E8B5119F9601665BF3E" box="[588,631,1288,1302]" gridcol="5" gridrow="45" pageId="3" pageNumber="4">45.5</td>
<td id="76D214592C6D9E8B51C0F96016E0BF3E" box="[661,754,1288,1302]" gridcol="6" gridrow="45" pageId="3" pageNumber="4">2.71, brdt</td>
</tr>
<tr id="35037D252C6D9E8B5321F97716E0BF05" box="[116,754,1311,1325]" gridrow="46" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F977163CBF05" box="[465,558,1311,1325]" gridcol="4" gridrow="46" pageId="3" pageNumber="4">(8.5, 7.5)</td>
<td id="76D214592C6D9E8B51C0F97716E0BF05" box="[661,754,1311,1325]" gridcol="6" gridrow="46" pageId="3" pageNumber="4">(8.5, 7.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321F95E16E0BF6C" box="[116,754,1334,1348]" gridrow="47" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F95E14B6BF6C" box="[116,164,1334,1348]" gridcol="0" gridrow="47" pageId="3" pageNumber="4">10’</th>
<td id="76D214592C6D9E8B52D2F95E15A0BF6C" box="[391,434,1334,1348]" gridcol="3" gridrow="47" pageId="3" pageNumber="4">120.0</td>
<td id="76D214592C6D9E8B5284F95E163CBF6C" box="[465,558,1334,1348]" gridcol="4" gridrow="47" pageId="3" pageNumber="4">5.35,</td>
<td id="76D214592C6D9E8B5119F95E1665BF6C" box="[588,631,1334,1348]" gridcol="5" gridrow="47" pageId="3" pageNumber="4">120.0</td>
<td id="76D214592C6D9E8B51C0F95E16E0BF6C" box="[661,754,1334,1348]" gridcol="6" gridrow="47" pageId="3" pageNumber="4">5.35,</td>
</tr>
<tr id="35037D252C6D9E8B5321F92516E0BF73" box="[116,754,1357,1371]" gridrow="48" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F925163CBF73" box="[465,558,1357,1371]" gridcol="4" gridrow="48" pageId="3" pageNumber="4">d (17.7)</td>
<td id="76D214592C6D9E8B51C0F92516E0BF73" box="[661,754,1357,1371]" gridcol="6" gridrow="48" pageId="3" pageNumber="4">d (17.7)</td>
</tr>
<tr id="35037D252C6D9E8B5321F90B16E0BF59" box="[116,754,1379,1393]" gridrow="49" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F90B163CBF59" box="[465,558,1379,1393]" gridcol="4" gridrow="49" pageId="3" pageNumber="4">5.30,</td>
<td id="76D214592C6D9E8B51C0F90B16E0BF59" box="[661,754,1379,1393]" gridcol="6" gridrow="49" pageId="3" pageNumber="4">5.30,</td>
</tr>
<tr id="35037D252C6D9E8B5321F91216E0BFA0" box="[116,754,1402,1416]" gridrow="50" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F912163CBFA0" box="[465,558,1402,1416]" gridcol="4" gridrow="50" pageId="3" pageNumber="4">d (10.5)</td>
<td id="76D214592C6D9E8B51C0F91216E0BFA0" box="[661,754,1402,1416]" gridcol="6" gridrow="50" pageId="3" pageNumber="4">d (10.5)</td>
</tr>
<tr id="35037D252C6D9E8B5321F9F916E0BFB7" box="[116,754,1425,1439]" gridrow="51" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F9F914B6BFB7" box="[116,164,1425,1439]" gridcol="0" gridrow="51" pageId="3" pageNumber="4">11’</th>
<td id="76D214592C6D9E8B52D2F9F915A0BFB7" box="[391,434,1425,1439]" gridcol="3" gridrow="51" pageId="3" pageNumber="4">168.2</td>
<td id="76D214592C6D9E8B5284F9F9163CBFB7" box="[465,558,1425,1439]" gridcol="4" gridrow="51" pageId="3" pageNumber="4">–</td>
<td id="76D214592C6D9E8B5119F9F91665BFB7" box="[588,631,1425,1439]" gridcol="5" gridrow="51" pageId="3" pageNumber="4">168.2</td>
<td id="76D214592C6D9E8B51C0F9F916E0BFB7" box="[661,754,1425,1439]" gridcol="6" gridrow="51" pageId="3" pageNumber="4">–</td>
</tr>
<tr id="35037D252C6D9E8B5321F9C016E0BF91" box="[116,754,1448,1465]" gridrow="52" pageId="3" pageNumber="4" rowspan-3="1" rowspan-4="1">
<th id="76D214592C6D9E8B5321F9C014B6BF91" box="[116,164,1448,1465]" gridcol="0" gridrow="52" pageId="3" pageNumber="4">
-OCH 
<subScript id="17B77D222C6D617753C8F9C714B6BF91" attach="left" box="[157,164,1455,1465]" fontSize="4" pageId="3" pageNumber="4">3</subScript>
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<td id="76D214592C6D9E8B5396F9C014FCBF91" box="[195,238,1448,1465]" gridcol="1" gridrow="52" pageId="3" pageNumber="4">53.2</td>
<td id="76D214592C6D9E8B5259F9C0157BBF91" box="[268,361,1448,1465]" gridcol="2" gridrow="52" pageId="3" pageNumber="4">3.32, s</td>
<td id="76D214592C6D9E8B5119F9C01665BF91" box="[588,631,1448,1465]" gridcol="5" gridrow="52" pageId="3" pageNumber="4">
<geoCoordinate id="EE0719A02C6D61775119F9C0167FBF9E" box="[588,621,1448,1462]" degrees="53.5" direction="south" orientation="latitude" pageId="3" pageNumber="4" precision="5555" value="-53.5">53.5</geoCoordinate>
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<td id="76D214592C6D9E8B51C0F9C016E0BF91" box="[661,754,1448,1465]" gridcol="6" gridrow="52" pageId="3" pageNumber="4">3.33, s</td>
</tr>
<tr id="35037D252C6D9E8B5321F9D716E0BFE5" box="[116,754,1471,1485]" gridrow="53" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F9D714B6BFE5" box="[116,164,1471,1485]" gridcol="0" gridrow="53" pageId="3" pageNumber="4">1’’</th>
<td id="76D214592C6D9E8B52D2F9D715A0BFE5" box="[391,434,1471,1485]" gridcol="3" gridrow="53" pageId="3" pageNumber="4">67.0</td>
<td id="76D214592C6D9E8B5284F9D7163CBFE5" box="[465,558,1471,1485]" gridcol="4" gridrow="53" pageId="3" pageNumber="4">3.63, m</td>
<td id="76D214592C6D9E8B5119F9D71665BFE5" box="[588,631,1471,1485]" gridcol="5" gridrow="53" pageId="3" pageNumber="4">67.0</td>
<td id="76D214592C6D9E8B51C0F9D716E0BFE5" box="[661,754,1471,1485]" gridcol="6" gridrow="53" pageId="3" pageNumber="4">3.63, m</td>
</tr>
<tr id="35037D252C6D9E8B5321F9BE16E0BFCC" box="[116,754,1494,1508]" gridrow="54" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284F9BE163CBFCC" box="[465,558,1494,1508]" gridcol="4" gridrow="54" pageId="3" pageNumber="4">3.44, m</td>
<td id="76D214592C6D9E8B51C0F9BE16E0BFCC" box="[661,754,1494,1508]" gridcol="6" gridrow="54" pageId="3" pageNumber="4">3.44, m</td>
</tr>
<tr id="35037D252C6D9E8B5321F98416E0BFD3" box="[116,754,1516,1531]" gridrow="55" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321F98414B6BFD3" box="[116,164,1516,1531]" gridcol="0" gridrow="55" pageId="3" pageNumber="4">2’’</th>
<td id="76D214592C6D9E8B52D2F98415A0BFD3" box="[391,434,1516,1531]" gridcol="3" gridrow="55" pageId="3" pageNumber="4">33.2</td>
<td id="76D214592C6D9E8B5284F984163CBFD3" box="[465,558,1516,1531]" gridcol="4" gridrow="55" pageId="3" pageNumber="4">1.55, m</td>
<td id="76D214592C6D9E8B5119F9841665BFD3" box="[588,631,1516,1531]" gridcol="5" gridrow="55" pageId="3" pageNumber="4">33.2</td>
<td id="76D214592C6D9E8B51C0F98416E0BFD3" box="[661,754,1516,1531]" gridcol="6" gridrow="55" pageId="3" pageNumber="4">1.55, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FA6C16E0BC3A" box="[116,754,1540,1554]" gridrow="56" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FA6C163CBC3A" box="[465,558,1540,1554]" gridcol="4" gridrow="56" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617752B5FA6C15FDBC3A" box="[480,495,1540,1554]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
<td id="76D214592C6D9E8B51C0FA6C16E0BC3A" box="[661,754,1540,1554]" gridcol="6" gridrow="56" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617751F1FA6C16A1BC3A" box="[676,691,1540,1554]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FA7216E0BC01" box="[116,754,1562,1577]" gridrow="57" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FA7214B6BC01" box="[116,164,1562,1577]" gridcol="0" gridrow="57" pageId="3" pageNumber="4">3’’</th>
<td id="76D214592C6D9E8B52D2FA7215A0BC01" box="[391,434,1562,1577]" gridcol="3" gridrow="57" pageId="3" pageNumber="4">20.8</td>
<td id="76D214592C6D9E8B5284FA72163CBC01" box="[465,558,1562,1577]" gridcol="4" gridrow="57" pageId="3" pageNumber="4">1.42, m</td>
<td id="76D214592C6D9E8B5119FA721665BC01" box="[588,631,1562,1577]" gridcol="5" gridrow="57" pageId="3" pageNumber="4">20.8</td>
<td id="76D214592C6D9E8B51C0FA7216E0BC01" box="[661,754,1562,1577]" gridcol="6" gridrow="57" pageId="3" pageNumber="4">1.42, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FA5916E0BC17" box="[116,754,1585,1599]" gridrow="58" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FA59163CBC17" box="[465,558,1585,1599]" gridcol="4" gridrow="58" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617752B5FA5915FDBC17" box="[480,495,1585,1599]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
<td id="76D214592C6D9E8B51C0FA5916E0BC17" box="[661,754,1585,1599]" gridcol="6" gridrow="58" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617751F1FA5916A1BC17" box="[676,691,1585,1599]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FA2016E0BC7E" box="[116,754,1608,1622]" gridrow="59" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1">
<th id="76D214592C6D9E8B5321FA2014B6BC7E" box="[116,164,1608,1622]" gridcol="0" gridrow="59" pageId="3" pageNumber="4">4’’</th>
<td id="76D214592C6D9E8B52D2FA2015A0BC7E" box="[391,434,1608,1622]" gridcol="3" gridrow="59" pageId="3" pageNumber="4">14.6</td>
<td id="76D214592C6D9E8B5284FA20163CBC7E" box="[465,558,1608,1622]" gridcol="4" gridrow="59" pageId="3" pageNumber="4">0.97, t (7.4,</td>
<td id="76D214592C6D9E8B5119FA201665BC7E" box="[588,631,1608,1622]" gridcol="5" gridrow="59" pageId="3" pageNumber="4">14.6</td>
<td id="76D214592C6D9E8B51C0FA2016E0BC7E" box="[661,754,1608,1622]" gridcol="6" gridrow="59" pageId="3" pageNumber="4">0.97, t (7.4,</td>
</tr>
<tr id="35037D252C6D9E8B5321FA3716E0BC45" box="[116,754,1631,1645]" gridrow="60" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5284FA37163CBC45" box="[465,558,1631,1645]" gridcol="4" gridrow="60" pageId="3" pageNumber="4">
3 
<collectionCode id="ED22E7A22C6D6177528CFA3715FABC45" box="[473,488,1631,1645]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
<td id="76D214592C6D9E8B51C0FA3716E0BC45" box="[661,754,1631,1645]" gridcol="6" gridrow="60" pageId="3" pageNumber="4">
3 
<collectionCode id="ED22E7A22C6D617751C8FA3716BEBC45" box="[669,684,1631,1645]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FA1C16E0BCAC" box="[116,754,1652,1668]" gridrow="61" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FA1C14B6BCAC" box="[116,164,1652,1668]" gridcol="0" gridrow="61" pageId="3" pageNumber="4">1’’ꞌ</th>
<td id="76D214592C6D9E8B52D2FA1C15A0BCAC" box="[391,434,1652,1668]" gridcol="3" gridrow="61" pageId="3" pageNumber="4">67.0</td>
<td id="76D214592C6D9E8B5284FA1C163CBCAC" box="[465,558,1652,1668]" gridcol="4" gridrow="61" pageId="3" pageNumber="4">3.63, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FAE416E0BCB3" box="[116,754,1676,1691]" gridrow="62" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5284FAE4163CBCB3" box="[465,558,1676,1691]" gridcol="4" gridrow="62" pageId="3" pageNumber="4">3.45, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FACA16E0BC9A" box="[116,754,1698,1714]" gridrow="63" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FACA14B6BC9A" box="[116,164,1698,1714]" gridcol="0" gridrow="63" pageId="3" pageNumber="4">2’’ꞌ</th>
<td id="76D214592C6D9E8B52D2FACA15A0BC9A" box="[391,434,1698,1714]" gridcol="3" gridrow="63" pageId="3" pageNumber="4">33.2</td>
<td id="76D214592C6D9E8B5284FACA163CBC9A" box="[465,558,1698,1714]" gridcol="4" gridrow="63" pageId="3" pageNumber="4">1.55, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FAD216E0BCE0" box="[116,754,1722,1736]" gridrow="64" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5284FAD2163CBCE0" box="[465,558,1722,1736]" gridcol="4" gridrow="64" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617752B5FAD215FDBCE0" box="[480,495,1722,1736]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FAB816E0BCC8" box="[116,754,1744,1760]" gridrow="65" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FAB814B6BCC8" box="[116,164,1744,1760]" gridcol="0" gridrow="65" pageId="3" pageNumber="4">3’’ꞌ</th>
<td id="76D214592C6D9E8B52D2FAB815A0BCC8" box="[391,434,1744,1760]" gridcol="3" gridrow="65" pageId="3" pageNumber="4">20.8</td>
<td id="76D214592C6D9E8B5284FAB8163CBCC8" box="[465,558,1744,1760]" gridcol="4" gridrow="65" pageId="3" pageNumber="4">1.42, m</td>
</tr>
<tr id="35037D252C6D9E8B5321FA8016E0BCDE" box="[116,754,1768,1782]" gridrow="66" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5284FA80163CBCDE" box="[465,558,1768,1782]" gridcol="4" gridrow="66" pageId="3" pageNumber="4">
(2 
<collectionCode id="ED22E7A22C6D617752B5FA8015FDBCDE" box="[480,495,1768,1782]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FA9516E0BD25" box="[116,754,1789,1805]" gridrow="67" pageId="3" pageNumber="4" rowspan-1="1" rowspan-2="1" rowspan-5="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FA9514B6BD25" box="[116,164,1789,1805]" gridcol="0" gridrow="67" pageId="3" pageNumber="4">4’’ꞌ</th>
<td id="76D214592C6D9E8B52D2FA9515A0BD25" box="[391,434,1789,1805]" gridcol="3" gridrow="67" pageId="3" pageNumber="4">14.6</td>
<td id="76D214592C6D9E8B5284FA95163CBD25" box="[465,558,1789,1805]" gridcol="4" gridrow="67" pageId="3" pageNumber="4">0.97, t (7.4,</td>
</tr>
<tr id="35037D252C6D9E8B5321FB7E16E0BD0C" box="[116,754,1814,1828]" gridrow="68" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1">
<td id="76D214592C6D9E8B5284FB7E163CBD0C" box="[465,558,1814,1828]" gridcol="4" gridrow="68" pageId="3" pageNumber="4">
3 
<collectionCode id="ED22E7A22C6D6177528CFB7E15FABD0C" box="[473,488,1814,1828]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="3" pageNumber="4" type="Herbarium">H</collectionCode>
)
</td>
</tr>
<tr id="35037D252C6D9E8B5321FB4416E0BD12" box="[116,754,1836,1850]" gridrow="69" pageId="3" pageNumber="4" rowspan-0="1">
<td id="76D214592C6D9E8B5396FB44157BBD12" box="[195,361,1836,1850]" colspan="2" colspanRight="1" gridcol="1" gridrow="69" pageId="3" pageNumber="4">β- D-GlcI (at C-1)</td>
<td id="76D214592C6D9E8B52D2FB44163CBD12" box="[391,558,1836,1850]" colspan="2" colspanRight="1" gridcol="3" gridrow="69" pageId="3" pageNumber="4">β- D-GlcI (at C-1)</td>
<td id="76D214592C6D9E8B5119FB4416E0BD12" box="[588,754,1836,1850]" colspan="2" colspanRight="1" gridcol="5" gridrow="69" pageId="3" pageNumber="4">β- D-GlcI (at C-1)</td>
</tr>
<tr id="35037D252C6D9E8B5321FB2B16E0BD79" box="[116,754,1859,1873]" gridrow="70" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FB2B14B6BD79" box="[116,164,1859,1873]" gridcol="0" gridrow="70" pageId="3" pageNumber="4">1</th>
<td id="76D214592C6D9E8B5396FB2B14FCBD79" box="[195,238,1859,1873]" gridcol="1" gridrow="70" pageId="3" pageNumber="4">99.7</td>
<td id="76D214592C6D9E8B5259FB2B157BBD79" box="[268,361,1859,1873]" gridcol="2" gridrow="70" pageId="3" pageNumber="4">4.71, d (7.8)</td>
<td id="76D214592C6D9E8B52D2FB2B15A0BD79" box="[391,434,1859,1873]" gridcol="3" gridrow="70" pageId="3" pageNumber="4">100.3</td>
<td id="76D214592C6D9E8B5284FB2B163CBD79" box="[465,558,1859,1873]" gridcol="4" gridrow="70" pageId="3" pageNumber="4">4.70, d (7.8)</td>
<td id="76D214592C6D9E8B5119FB2B1665BD79" box="[588,631,1859,1873]" gridcol="5" gridrow="70" pageId="3" pageNumber="4">100.3</td>
<td id="76D214592C6D9E8B51C0FB2B16E0BD79" box="[661,754,1859,1873]" gridcol="6" gridrow="70" pageId="3" pageNumber="4">4.70, d (7.8)</td>
</tr>
<tr id="35037D252C6D9E8B5321FB3216E0BD40" box="[116,754,1882,1896]" gridrow="71" pageId="3" pageNumber="4">
<th id="76D214592C6D9E8B5321FB3214B6BD40" box="[116,164,1882,1896]" gridcol="0" gridrow="71" pageId="3" pageNumber="4">2</th>
<td id="76D214592C6D9E8B5396FB3214FCBD40" box="[195,238,1882,1896]" gridcol="1" gridrow="71" pageId="3" pageNumber="4">74.3</td>
<td id="76D214592C6D9E8B5259FB32157BBD40" box="[268,361,1882,1896]" gridcol="2" gridrow="71" pageId="3" pageNumber="4">3.22, dd</td>
<td id="76D214592C6D9E8B52D2FB3215A0BD40" box="[391,434,1882,1896]" gridcol="3" gridrow="71" pageId="3" pageNumber="4">74.9</td>
<td id="76D214592C6D9E8B5284FB32163CBD40" box="[465,558,1882,1896]" gridcol="4" gridrow="71" pageId="3" pageNumber="4">3.21, dd</td>
<td id="76D214592C6D9E8B5119FB321665BD40" box="[588,631,1882,1896]" gridcol="5" gridrow="71" pageId="3" pageNumber="4">74.9</td>
<td id="76D214592C6D9E8B51C0FB3216E0BD40" box="[661,754,1882,1896]" gridcol="6" gridrow="71" pageId="3" pageNumber="4">3.21, dd</td>
</tr>
<tr id="35037D252C6D9E8B5321FB1916E0BD57" box="[116,754,1905,1919]" gridrow="72" pageId="3" pageNumber="4" rowspan-0="1" rowspan-1="1" rowspan-3="1" rowspan-5="1">
<td id="76D214592C6D9E8B5259FB19157BBD57" box="[268,361,1905,1919]" gridcol="2" gridrow="72" pageId="3" pageNumber="4">(7.8, 9.0)</td>
<td id="76D214592C6D9E8B5284FB19163CBD57" box="[465,558,1905,1919]" gridcol="4" gridrow="72" pageId="3" pageNumber="4">(7.8, 9.0)</td>
<td id="76D214592C6D9E8B51C0FB1916E0BD57" box="[661,754,1905,1919]" gridcol="6" gridrow="72" pageId="3" pageNumber="4">(7.8, 9.0)</td>
</tr>
<tr id="35037D252C6D9E8B5321FBE016E0BDBE" box="[116,754,1928,1942]" gridrow="73" pageId="3" pageNumber="4" rowspan-2="1" rowspan-4="1" rowspan-6="1">
<th id="76D214592C6D9E8B5321FBE014B6BDBE" box="[116,164,1928,1942]" gridcol="0" gridrow="73" pageId="3" pageNumber="4">3</th>
<td id="76D214592C6D9E8B5396FBE014FCBDBE" box="[195,238,1928,1942]" gridcol="1" gridrow="73" pageId="3" pageNumber="4">78.8</td>
<td id="76D214592C6D9E8B52D2FBE015A0BDBE" box="[391,434,1928,1942]" gridcol="3" gridrow="73" pageId="3" pageNumber="4">78.4</td>
<td id="76D214592C6D9E8B5119FBE01665BDBE" box="[588,631,1928,1942]" gridcol="5" gridrow="73" pageId="3" pageNumber="4">78.4</td>
</tr>
</table>
</paragraph>
<paragraph id="8B8C7F672C6D61775067FFD011ADB9E3" blockId="3.[818,1471,951,971]" box="[818,1471,951,971]" pageId="3" pageNumber="4">
<emphasis id="B947A3752C6D61775067FFD011ADB9E3" bold="true" box="[818,1471,951,971]" italics="true" pageId="3" pageNumber="4">2.3. Evaluation of the total phenolic content and the antioxidant activity</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6D61775004FF8717A5BF8D" blockId="3.[818,1488,1007,1446]" pageId="3" pageNumber="4">
Considering the occurrence of phenolic compounds in the extract, the phenolic content and the antioxidant activity of the methanol extract of 
<taxonomicName id="4C3304E42C6D61775019F84F1004BE12" box="[844,1046,1063,1082]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D61775019F84F1004BE12" bold="true" box="[844,1046,1063,1082]" italics="true" pageId="3" pageNumber="4">Scabiosa atropurpurea</emphasis>
</taxonomicName>
were evaluated by spectrophotometric assays such as the Folin Ciocalteu assay and DPPH and TEAC tests (
<tableCitation id="C6B14ADC2C6D6177562FF82B11D3BE7E" box="[1402,1473,1091,1110]" captionStart="Table 3" captionStartId="5.[100,150,150,166]" captionTargetBox="[100,771,235,450]" captionTargetPageId="5" captionText="Table 3 Total phenolic content and radical scavenging activity of S. atropurpurea methanol extract in DPPH and TEAC assays." httpUri="http://table.plazi.org/id/DF4C2FEF2C6B61715331FCFE15A0BAF2" pageId="3" pageNumber="4" tableUuid="DF4C2FEF2C6B61715331FCFE15A0BAF2">Table 3</tableCitation>
). The total phenolic content of 
<taxonomicName id="4C3304E42C6D61775713F83710C3BE5A" box="[1094,1233,1119,1138]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D61775713F83710C3BE5A" bold="true" box="[1094,1233,1119,1138]" italics="true" pageId="3" pageNumber="4">S. atropurpurea</emphasis>
</taxonomicName>
extract, expressed as gallic acid equivalents (GAE), corresponded to 
<quantity id="4CCBD2822C6D617757E9F8131119BEA6" box="[1212,1291,1147,1166]" metricMagnitude="-6" metricUnit="kg" metricValue="7.6" pageId="3" pageNumber="4" unit="mg" value="7.6">7.60 mg</quantity>
of GAE/g of extract (
<bibRefCitation id="EFA202962C6D6177506FF8FF17F6BE82" author="Santos, C. C. D. &amp; Masullo, M. &amp; Cerulli, A. &amp; Mari, A. &amp; Estevam, C. D. &amp; Pizza, C. &amp; Piacente, S." box="[826,996,1175,1194]" pageId="3" pageNumber="4" pagination="45 - 51" refId="ref12508" refString="Santos, C. C. D., Masullo, M., Cerulli, A., Mari, A., Estevam, C. D., Pizza, C., Piacente, S., 2017. Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling. Phytochemistry 140, 45 - 51. https: // doi. org / 10.1016 / j. phytochem. 2017.04.008." type="journal article" year="2017">Santos et al., 2017</bibRefCitation>
). The TEAC value of the methanol extract, expressed as the concentration of the Trolox solution (mM) which has the same antioxidant activity as a 
<quantity id="4CCBD2822C6D6177574FF8A7105BBECA" box="[1050,1097,1231,1250]" metricMagnitude="-6" metricUnit="kg" metricValue="1.0" pageId="3" pageNumber="4" unit="mg" value="1.0">1 mg</quantity>
/mL solution of the tested extract (
<bibRefCitation id="EFA202962C6D617756C7F8A717B0BED6" author="Santos, C. C. D. &amp; Masullo, M. &amp; Cerulli, A. &amp; Mari, A. &amp; Estevam, C. D. &amp; Pizza, C. &amp; Piacente, S." pageId="3" pageNumber="4" pagination="45 - 51" refId="ref12508" refString="Santos, C. C. D., Masullo, M., Cerulli, A., Mari, A., Estevam, C. D., Pizza, C., Piacente, S., 2017. Isolation of antioxidant phenolics from Schinopsis brasiliensis based on a preliminary LC-MS profiling. Phytochemistry 140, 45 - 51. https: // doi. org / 10.1016 / j. phytochem. 2017.04.008." type="journal article" year="2017">Santos et al., 2017</bibRefCitation>
), was 0.28 mM. Quercetin 3- 
<emphasis id="B947A3752C6D61775791F88210C1BED5" bold="true" box="[1220,1235,1258,1277]" italics="true" pageId="3" pageNumber="4">O</emphasis>
-glucoside (TEAC = 0.663 mM) was used as the reference compound. The extract exhibited a concentration-dependent free radical scavenging activity expressed as EC 
<subScript id="17B77D222C6D6177501EF92D174FBF7B" attach="left" box="[843,861,1349,1363]" fontSize="6" pageId="3" pageNumber="4">50</subScript>
, μg/mL of sample required to decrease the initial DPPH 
<superScript id="7C46D22F2C6D61775622F9501192BF6E" attach="left" box="[1399,1408,1336,1350]" fontSize="6" pageId="3" pageNumber="4">•</superScript>
concentration by 50% (
<bibRefCitation id="EFA202962C6D6177508DF9321081BF45" author="Cerulli, A. &amp; Masullo, M. &amp; Montoro, P. &amp; Hosek, J. &amp; Pizza, C. &amp; Piacente, S." box="[984,1171,1370,1389]" pageId="3" pageNumber="4" pagination="168 - 178" refId="ref9842" refString="Cerulli, A., Masullo, M., Montoro, P., Hosek, J., Pizza, C., Piacente, S., 2018. Metabolite profiling of &quot; green &quot; extracts of Corylus avellana leaves by 1 H NMR spectroscopy and multivariate statistical analysis. J. Pharm. Biomed. Anal. 160, 168 - 178. https: // doi. org / 10.1016 / j. jpba. 2018.07.046." type="journal article" year="2018">Cerulli et al., 2018</bibRefCitation>
), corresponding to 4.80 μg/mL, comparable to that exerted by vitamin C used as reference compound (4.40 μg/mL).
</paragraph>
<paragraph id="8B8C7F672C6D61775067F9B81028BFCB" blockId="3.[818,1082,1488,1507]" box="[818,1082,1488,1507]" pageId="3" pageNumber="4">
<emphasis id="B947A3752C6D61775067F9B81028BFCB" bold="true" box="[818,1082,1488,1507]" italics="true" pageId="3" pageNumber="4">2.4. Anti-glucosidase activity</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6D61775004FA60107CBD96" blockId="3.[818,1488,1544,1983]" pageId="3" pageNumber="4">
The extracts of 
<taxonomicName id="4C3304E42C6D617750ABFA601080BC33" box="[1022,1170,1544,1563]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D617750ABFA601080BC33" bold="true" box="[1022,1170,1544,1563]" italics="true" pageId="3" pageNumber="4">S. atropurpurea</emphasis>
</taxonomicName>
and 
<taxonomicName id="4C3304E42C6D61775786FA60112CBC33" box="[1235,1342,1544,1563]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="arenaria">
<emphasis id="B947A3752C6D61775786FA60112CBC33" bold="true" box="[1235,1342,1544,1563]" italics="true" pageId="3" pageNumber="4">S. arenaria</emphasis>
</taxonomicName>
showed antihyperglycemic effects (
<bibRefCitation id="EFA202962C6D61775742FA4D1113BC1F" author="Bonet, M. A. &amp; Valles, J." box="[1047,1281,1572,1592]" pageId="3" pageNumber="4" pagination="130 - 147" refId="ref9785" refString="Bonet, M. A., Valles, J., 2007. Ethnobotany of montseny biosphere reserve (catalonia, iberian peninsula): plants used in veterinary medicine. J. Ethnopharmacol. 110, 130 - 147. https: // doi. org / 10.1016 / j. jep. 2006.09.016." type="journal article" year="2007">Bonet and Valles, 2007</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6D61775647FA4C11D3BC1F" author="Hlila, M. B. &amp; Mosbah, H. &amp; Majouli, K. &amp; Msaada, K. &amp; Ben Jannet, H. &amp; Aouni, M. &amp; Selmi, B." box="[1298,1473,1572,1592]" pageId="3" pageNumber="4" pagination="383 - 389" refId="ref11042" refString="Hlila, M. B., Mosbah, H., Majouli, K., Msaada, K., Ben Jannet, H., Aouni, M., Selmi, B., 2015. alpha-Glucosidase inhibition by Tunisian Scabiosa arenaria Forssk. extracts. Int. J. Biol. Macromol. 77, 383 - 389. https: // doi. org / 10.1016 / j. ijbiomac. 2015.03.035." type="journal article" year="2015">Hlila et al., 2015</bibRefCitation>
). Moreover, iridoid compounds were reported to have antidiabetic effects (
<bibRefCitation id="EFA202962C6D6177506FFA3417EABC47" author="Habtemariam, S." box="[826,1016,1628,1647]" pageId="3" pageNumber="4" refId="ref10902" refString="Habtemariam, S., 2017. Antidiabetic potential of monoterpenes: a case of small molecules punching above their weight. Int. J. Mol. Sci. 19 https: // doi. org / 10.3390 / ijms 19010004." type="book" year="2017">Habtemariam, 2017</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6D61775750FA3410A2BC47" author="Wang, C. C. &amp; Gong, X. &amp; Bo, A. &amp; Zhang, L. &amp; Zhang, M. X. &amp; Zang, E. H. &amp; Zhang, C. H. &amp; Li, M. H." box="[1029,1200,1628,1647]" pageId="3" pageNumber="4" refId="ref12730" refString="Wang, C. C., Gong, X., Bo, A., Zhang, L., Zhang, M. X., Zang, E. H., Zhang, C. H., Li, M. H., 2020. Iridoids: research advances in their phytochemistry, biological activities, and pharmacokinetics. Molecules 25. https: // doi. org / 10.3390 / molecules 25020287." type="journal volume" year="2020">Wang et al., 2020</bibRefCitation>
). Genipin and geniposide displayed potential antidiabetic effects in vitro, and the iridoids loganin, previously isolated also from 
<taxonomicName id="4C3304E42C6D61775714FAFC10B6BC8E" box="[1089,1188,1683,1703]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="hymettia">
<emphasis id="B947A3752C6D61775714FAFC10B6BC8E" bold="true" box="[1089,1188,1683,1703]" italics="true" pageId="3" pageNumber="4">S. hymettia</emphasis>
</taxonomicName>
, 
<taxonomicName id="4C3304E42C6D617757FBFAFC112ABC8F" box="[1198,1336,1684,1703]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D617757FBFAFC112ABC8F" bold="true" box="[1198,1336,1684,1703]" italics="true" pageId="3" pageNumber="4">S. atropurpurea</emphasis>
</taxonomicName>
, and 
<taxonomicName id="4C3304E42C6D6177563CFAFC11DDBC8E" box="[1385,1487,1683,1703]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="variifolia">
<emphasis id="B947A3752C6D6177563CFAFC11DDBC8E" bold="true" box="[1385,1487,1683,1703]" italics="true" pageId="3" pageNumber="4">S. variifolia</emphasis>
</taxonomicName>
was reported for its beneficial effect in the diabetic nephropathy control on in vivo studies involving mice with induced diabetes (
<bibRefCitation id="EFA202962C6D6177561CFAA31770BCD2" author="Habtemariam, S." pageId="3" pageNumber="4" refId="ref10902" refString="Habtemariam, S., 2017. Antidiabetic potential of monoterpenes: a case of small molecules punching above their weight. Int. J. Mol. Sci. 19 https: // doi. org / 10.3390 / ijms 19010004." type="book" year="2017">Habtemariam, 2017</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6D61775027FA8F1031BCD2" author="Pinto, D. C. G. A. &amp; Rahmouni, N. &amp; Beghidja, N. &amp; Silva, A. M. S." box="[882,1059,1767,1787]" pageId="3" pageNumber="4" pagination="110" refId="ref12392" refString="Pinto, D. C. G. A., Rahmouni, N., Beghidja, N., Silva, A. M. S., 2018. Scabiosa genus: a rich source of bioactive metabolites. Medicines 5, 110. https: // doi. org / 10.3390 / medicines 5040110." type="journal article" year="2018">Pinto et al., 2018</bibRefCitation>
). A recent report showed how the natural compound swertiamarin, isolated from 
<taxonomicName id="4C3304E42C6D617757F0FB6B111BBD3E" box="[1189,1289,1795,1814]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="hymettia">
<emphasis id="B947A3752C6D617757F0FB6B111BBD3E" bold="true" box="[1189,1289,1795,1814]" italics="true" pageId="3" pageNumber="4">S. hymettia</emphasis>
</taxonomicName>
, 
<taxonomicName id="4C3304E42C6D61775640FB6B11B2BD3E" box="[1301,1440,1795,1814]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D61775640FB6B11B2BD3E" bold="true" box="[1301,1440,1795,1814]" italics="true" pageId="3" pageNumber="4">S. atropurpurea</emphasis>
</taxonomicName>
, and 
<taxonomicName id="4C3304E42C6D61775067FB77178CBD1A" box="[818,926,1823,1842]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="variifolia">
<emphasis id="B947A3752C6D61775067FB77178CBD1A" bold="true" box="[818,926,1823,1842]" italics="true" pageId="3" pageNumber="4">S. variifolia</emphasis>
</taxonomicName>
regulated the peroxisome proliferator-activated receptor gamma (PPAR-) and increased insulin sensitivity (
<bibRefCitation id="EFA202962C6D61775650FB5311D3BD66" author="Habtemariam, S." box="[1285,1473,1851,1870]" pageId="3" pageNumber="4" refId="ref10902" refString="Habtemariam, S., 2017. Antidiabetic potential of monoterpenes: a case of small molecules punching above their weight. Int. J. Mol. Sci. 19 https: // doi. org / 10.3390 / ijms 19010004." type="book" year="2017">Habtemariam, 2017</bibRefCitation>
). Furthermore, it inhibited both α- amylase and α- glucosidase enzymes (
<bibRefCitation id="EFA202962C6D6177506FFB1B17CABDAE" author="Pinto, D. C. G. A. &amp; Rahmouni, N. &amp; Beghidja, N. &amp; Silva, A. M. S." box="[826,984,1907,1926]" pageId="3" pageNumber="4" pagination="110" refId="ref12392" refString="Pinto, D. C. G. A., Rahmouni, N., Beghidja, N., Silva, A. M. S., 2018. Scabiosa genus: a rich source of bioactive metabolites. Medicines 5, 110. https: // doi. org / 10.3390 / medicines 5040110." type="journal article" year="2018">Pinto et al., 2018</bibRefCitation>
). Based on these observations, the methanol extract of 
<taxonomicName id="4C3304E42C6D61775067FBE717D2BD8A" box="[818,960,1935,1954]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6D61775067FBE717D2BD8A" bold="true" box="[818,960,1935,1954]" italics="true" pageId="3" pageNumber="4">S. atropurpurea</emphasis>
</taxonomicName>
and the main iridoids were tested for their ability to inhibit the α- glucosidase enzyme.
</paragraph>
<caption id="DF4C2FEF2C6A61705169FB1117E5BDA2" ID-DOI="http://doi.org/10.5281/zenodo.8160622" ID-Zenodo-Dep="8160622" box="[572,1015,1913,1931]" httpUri="https://zenodo.org/record/8160622/files/figure.png" pageId="4" pageNumber="5" startId="4.[572,602,1913,1930]" targetBox="[285,1302,149,1885]" targetPageId="4" targetType="figure">
<paragraph id="8B8C7F672C6A61705169FB1117E5BDA2" blockId="4.[572,1015,1913,1931]" box="[572,1015,1913,1931]" pageId="4" pageNumber="5">
<emphasis id="B947A3752C6A61705169FB111664BDA3" bold="true" box="[572,630,1913,1931]" pageId="4" pageNumber="5">Fig. 2.</emphasis>
Iridoids isolated from 
<taxonomicName id="4C3304E42C6A6170506BFB1117E0BDA2" box="[830,1010,1913,1930]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="4" pageNumber="5" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6A6170506BFB1117E0BDA2" bold="true" box="[830,1010,1913,1930]" italics="true" pageId="4" pageNumber="5">Scabiosa atropurpurea</emphasis>
</taxonomicName>
.
</paragraph>
</caption>
<caption id="DF4C2FEF2C6B61715331FCFE15A0BAF2" ID-Table-UUID="DF4C2FEF2C6B61715331FCFE15A0BAF2" httpUri="http://table.plazi.org/id/DF4C2FEF2C6B61715331FCFE15A0BAF2" pageId="5" pageNumber="6" startId="5.[100,150,150,166]" targetBox="[100,771,235,450]" targetIsTable="true" targetPageId="5">
<paragraph id="8B8C7F672C6B61715331FCFE15A0BAF2" blockId="5.[100,770,150,218]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B61715331FCFE14B5BA8F" bold="true" box="[100,167,150,167]" pageId="5" pageNumber="6">Table 3</emphasis>
Total phenolic content and radical scavenging activity of 
<taxonomicName id="4C3304E42C6B61715118FCD816D9BAE8" box="[589,715,176,193]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715118FCD816D9BAE8" bold="true" box="[589,715,176,193]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
methanol extract in DPPH and TEAC assays.
</paragraph>
</caption>
<paragraph id="8B8C7F672C6B61715321FC8614B7BBEA" pageId="5" pageNumber="6">
<table id="F9338DC72C6B9E8B5331FC831711BBEA" box="[100,771,235,450]" gridcols="3" gridrows="7" pageId="5" pageNumber="6">
<tr id="35037D252C6B9E8B5331FC831711BAD4" box="[100,771,235,252]" gridrow="0" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FC831533BAD4" box="[100,289,235,252]" gridcol="0" gridrow="0" pageId="5" pageNumber="6">Total Phenolic Content</th>
<th id="76D214592C6B9E8B52FAFC831629BAD4" box="[431,571,235,252]" gridcol="1" gridrow="0" pageId="5" pageNumber="6">
DPPH 
<superScript id="7C46D22F2C6B6171528EFC8315F0BADB" attach="left" box="[475,482,235,243]" fontSize="4" pageId="5" pageNumber="6">•</superScript>
</th>
<th id="76D214592C6B9E8B5110FC831711BAD4" box="[581,771,235,252]" gridcol="2" gridrow="0" pageId="5" pageNumber="6">
ABTS 
<superScript id="7C46D22F2C6B61715195FC8316C1BADB" attach="left" box="[704,723,235,243]" fontSize="4" pageId="5" pageNumber="6">•+</superScript>
</th>
</tr>
<tr id="35037D252C6B9E8B5331FD651711BB0A" box="[100,771,269,290]" gridrow="1" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FD651533BB0A" box="[100,289,269,290]" gridcol="0" gridrow="1" pageId="5" pageNumber="6">
GAE 
<superScript id="7C46D22F2C6B617153C0FD651489BB3E" attach="left" box="[149,155,269,278]" fontSize="4" pageId="5" pageNumber="6">a</superScript>
SD 
<superScript id="7C46D22F2C6B617153E3FD6514AFBB3F" attach="left" box="[182,189,269,279]" fontSize="4" pageId="5" pageNumber="6">d</superScript>
</th>
<td id="76D214592C6B9E8B52FAFD651629BB0A" box="[431,571,269,290]" gridcol="1" gridrow="1" pageId="5" pageNumber="6">
EC 
<superScript id="7C46D22F2C6B61715287FD6515CBBB3F" attach="right" box="[466,473,269,279]" fontSize="4" pageId="5" pageNumber="6">b</superScript>
SD 
<superScript id="7C46D22F2C6B617152A6FD6515E8BB3F" attach="left" box="[499,506,269,279]" fontSize="4" pageId="5" pageNumber="6">d</superScript>
<subScript id="17B77D222C6B61715291FD7015C0BB0A" attach="left" box="[452,466,280,290]" fontSize="4" pageId="5" pageNumber="6">50</subScript>
</td>
<td id="76D214592C6B9E8B5110FD651711BB0A" box="[581,771,269,290]" gridcol="2" gridrow="1" pageId="5" pageNumber="6">
TEAC 
<superScript id="7C46D22F2C6B61715197FD6516DABB3E" attach="left" box="[706,712,269,278]" fontSize="4" pageId="5" pageNumber="6">c</superScript>
SD 
<superScript id="7C46D22F2C6B617151B4FD6516FABB3F" attach="left" box="[737,744,269,279]" fontSize="4" pageId="5" pageNumber="6">d</superScript>
</td>
</tr>
<tr id="35037D252C6B9E8B5331FD401711BB1F" box="[100,771,296,311]" gridrow="2" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FD401533BB1F" box="[100,289,296,311]" gridcol="0" gridrow="2" pageId="5" pageNumber="6">7.60 ± 0.26</th>
<td id="76D214592C6B9E8B52FAFD401629BB1F" box="[431,571,296,311]" gridcol="1" gridrow="2" pageId="5" pageNumber="6">4.80 ± 0.06</td>
<td id="76D214592C6B9E8B5110FD401711BB1F" box="[581,771,296,311]" gridcol="2" gridrow="2" pageId="5" pageNumber="6">0.28 ± 0.03</td>
</tr>
<tr id="35037D252C6B9E8B5331FD2F1711BB75" box="[100,771,327,349]" gridrow="3" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FD2F1711BB75" box="[100,771,327,349]" colspan="3" colspanRight="2" gridcol="0" gridrow="3" pageId="5" pageNumber="6">
<superScript id="7C46D22F2C6B61715326FD2F1468BB7B" attach="left" box="[115,122,327,339]" fontSize="5" pageId="5" pageNumber="6">a</superScript>
Values are expressed as gallic acid equivalents (GAE) mg/g of dried extract.
</th>
</tr>
<tr id="35037D252C6B9E8B5331FD091711BBB8" box="[100,771,353,400]" gridrow="4" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FD091711BBB8" box="[100,771,353,400]" colspan="3" colspanRight="2" gridcol="0" gridrow="4" pageId="5" pageNumber="6">
<superScript id="7C46D22F2C6B61715326FD091469BB45" attach="left" box="[115,123,353,365]" fontSize="5" pageId="5" pageNumber="6">b</superScript>
Values are expressed as μg/mL. 
<superScript id="7C46D22F2C6B61715326FD121468BBAE" attach="right" box="[115,122,378,390]" fontSize="5" pageId="5" pageNumber="6">c</superScript>
Values are expressed as concentration (mM) of a standard Trolox solution
</th>
</tr>
<tr id="35037D252C6B9E8B5331FDF01711BB82" box="[100,771,408,426]" gridrow="5" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FDF01629BB82" box="[100,571,408,426]" colspan="2" colspanRight="1" gridcol="0" gridrow="5" pageId="5" pageNumber="6">exerting the same antioxidant activity of a 1 mg/mL</th>
<td id="76D214592C6B9E8B5110FDF01711BB82" box="[581,771,408,426]" gridcol="2" gridrow="5" pageId="5" pageNumber="6">solution of the tested</td>
</tr>
<tr id="35037D252C6B9E8B5331FDDA1711BBEA" box="[100,771,434,450]" gridrow="6" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B5331FDDA1711BBEA" box="[100,771,434,450]" colspan="3" colspanRight="2" gridcol="0" gridrow="6" pageId="5" pageNumber="6">extract.</th>
</tr>
</table>
</paragraph>
<paragraph id="8B8C7F672C6B61715326FDAF1641BBF5" box="[115,595,455,477]" pageId="5" pageNumber="6">
<tableNote id="76D57EE92C6B61715326FDAF1641BBF5" box="[115,595,455,477]" pageId="5" pageNumber="6" targetBox="[100,771,235,450]" targetPageId="5">
<superScript id="7C46D22F2C6B61715326FDAF1469BBFB" attach="left" box="[115,123,455,467]" fontSize="5" pageId="5" pageNumber="6">d</superScript>
Standard Deviation of three independent experiments.
</tableNote>
</paragraph>
<paragraph id="8B8C7F672C6B617153D1FE6D1671B963" blockId="5.[100,771,517,1178]" pageId="5" pageNumber="6">
α- glucosidase is a carbohydrate-hydrolase located in the brush border cells of the intestine, which acts on the 
<emphasis id="B947A3752C6B6171517CFE49162AB81C" bold="true" box="[553,568,545,564]" italics="true" pageId="5" pageNumber="6">O</emphasis>
-glucosidic α (1 → 4) linkage. The enzyme breaks down starch and glucose oligosaccharides into single α- glucose monosaccharides. Its inhibition reduces the digestion rate of carbohydrates, which are not broken down into glucose molecules, reducing glucose levels in the blood. Therefore, the α- glucosidase inhibitors represent a class of drugs used to control the glycemic level in non-insulin-dependent diabetes mellitus (
<typeStatus id="5488C1C52C6B617151E7FEA116CEB8F4" box="[690,732,713,732]" pageId="5" pageNumber="6">type</typeStatus>
2), particularly postprandial hyperglycemia. The result is a delay in the digestion of carbohydrates, which delays the passage of the circulating glucose to allow pancreatic β cells to increase insulin secretion, reducing the postprandial glycemic peak (
<bibRefCitation id="EFA202962C6B617152CCFF501647B963" author="Masullo, M. &amp; Lauro, G. &amp; Cerulli, A. &amp; Bifulco, G. &amp; Piacente, S." box="[409,597,824,844]" pageId="5" pageNumber="6" pagination="805660" refId="ref12158" refString="Masullo, M., Lauro, G., Cerulli, A., Bifulco, G., Piacente, S., 2022. Corylus avellana: a source of diarylheptanoids with alpha-glucosidase inhibitory activity evaluated by in vitro and in silico studies. Front. Plant Sci. 13, 805660 https: // doi. org / 10.3389 / fpls. 2022.805660." type="journal article" year="2022">Masullo et al., 2022</bibRefCitation>
).
</paragraph>
<paragraph id="8B8C7F672C6B617153D1FF3C1711BEB2" blockId="5.[100,771,517,1178]" pageId="5" pageNumber="6">
The methanol extract of 
<taxonomicName id="4C3304E42C6B617152D6FF3C1642B94F" box="[387,592,852,871]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B617152D6FF3C1642B94F" bold="true" box="[387,592,852,871]" italics="true" pageId="5" pageNumber="6">Scabiosa atropurpurea</emphasis>
</taxonomicName>
showed a potent inhibitory activity of α- glucosidase (value IC 
<subScript id="17B77D222C6B61715145FF1F1630B9AD" attach="left" box="[528,546,887,901]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
= 100 μg/mL) comparable to that exerted by acarbose (value IC 
<subScript id="17B77D222C6B61715158FFFB160DB989" attach="left" box="[525,543,915,929]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
= 175 μM), used as a positive control. The result obtained encouraged the evaluation of this activity also for eleven iridoids, isolated in higher amounts, including compounds 
<emphasis id="B947A3752C6B61715380FF8814F3B9DB" bold="true" box="[213,225,992,1011]" pageId="5" pageNumber="6">3</emphasis>
, 
<emphasis id="B947A3752C6B617153BBFF8814E8B9DB" bold="true" box="[238,250,992,1011]" pageId="5" pageNumber="6">5</emphasis>
, 
<emphasis id="B947A3752C6B61715253FF88150DB9DB" bold="true" box="[262,287,992,1011]" pageId="5" pageNumber="6">15</emphasis>
, 
<emphasis id="B947A3752C6B6171527FFF881551B9DB" bold="true" box="[298,323,992,1011]" pageId="5" pageNumber="6">16</emphasis>
, 
<emphasis id="B947A3752C6B6171521AFF88157AB9DB" bold="true" box="[335,360,992,1011]" pageId="5" pageNumber="6">19</emphasis>
, 
<emphasis id="B947A3752C6B61715226FF8815A2B9DB" bold="true" box="[371,432,992,1011]" pageId="5" pageNumber="6">23–28</emphasis>
. All compounds showed IC 
<subScript id="17B77D222C6B617151FAFF8F16D3B9DD" attach="left" box="[687,705,999,1013]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
values (in the range of 25.01–92.59 μM) lower than that observed for acarbose (
<tableCitation id="C6B14ADC2C6B61715339F87F14A1BE03" box="[108,179,1047,1067]" captionStart="Table 4" captionStartId="5.[203,253,1580,1596]" captionTargetBox="[219,651,1666,1969]" captionTargetPageId="5" captionText="Table 4 Antihyperglycemic activity of the main iridoids isolated from S. atropurpurea, expressed as IC50 (μM) value." httpUri="http://table.plazi.org/id/DF4C2FEF2C6B6171539EFA44166EBC58" pageId="5" pageNumber="6" tableUuid="DF4C2FEF2C6B6171539EFA44166EBC58">Table 4</tableCitation>
). For compound 
<emphasis id="B947A3752C6B61715203F87F157DBE02" bold="true" box="[342,367,1047,1066]" pageId="5" pageNumber="6">16</emphasis>
, the IC 
<subScript id="17B77D222C6B617152E6F87715D7BE05" attach="left" box="[435,453,1055,1069]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
value was 25.01 μM, seven times lower than that exhibited by acarbose. Also, compounds 
<emphasis id="B947A3752C6B617151F6F85C16BDBE6F" bold="true" box="[675,687,1076,1095]" pageId="5" pageNumber="6">5</emphasis>
and 
<emphasis id="B947A3752C6B617151BCF85B1710BE6E" bold="true" box="[745,770,1075,1094]" pageId="5" pageNumber="6">15</emphasis>
showed low IC 
<subScript id="17B77D222C6B617153ABF83E1502BE4C" attach="left" box="[254,272,1110,1124]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
values (27.50 μM and 30.20 μM, respectively). Therefore, these results suggested to investigate this extract and individual iridoids as potential active principles in the treatment of diabetes.
</paragraph>
<paragraph id="8B8C7F672C6B61715331F8BE15B8BEC1" blockId="5.[100,426,1238,1257]" box="[100,426,1238,1257]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B61715331F8BE15B8BEC1" bold="true" box="[100,426,1238,1257]" italics="true" pageId="5" pageNumber="6">2.5. Molecular docking experiments</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6B617153D1F966177DBAD3" blockId="5.[100,770,1294,1537]" lastBlockId="5.[818,1488,148,837]" pageId="5" pageNumber="6">
Starting from the promising inhibitory activities detected for the tested iridoids against α- glucosidase from 
<taxonomicName id="4C3304E42C6B617152A8F94216F0BF15" box="[509,738,1322,1341]" class="Tremellomycetes" family="Tremellaceae" genus="Saccharomyces" kingdom="Fungi" order="Tremellales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="cerevisiae">
<emphasis id="B947A3752C6B617152A8F94216F0BF15" bold="true" box="[509,738,1322,1341]" italics="true" pageId="5" pageNumber="6">Saccharomyces cerevisiae</emphasis>
</taxonomicName>
, 
<emphasis id="B947A3752C6B617151A4F9421483BF71" bold="true" italics="true" pageId="5" pageNumber="6">in silico</emphasis>
studies were performed to shed light on the molecular basis responsible for the ligand/protein interactions. In this context, we recently reported a 
<taxonomicName id="4C3304E42C6B61715269F915163BBFB9" box="[316,553,1405,1425]" class="Tremellomycetes" family="Tremellaceae" genus="Saccharomyces" kingdom="Fungi" order="Tremellales" pageId="5" pageNumber="6" phylum="Basidiomycota" rank="species" species="cerevisiae">
<emphasis id="B947A3752C6B61715269F915163BBFB9" bold="true" box="[316,553,1405,1425]" italics="true" pageId="5" pageNumber="6">Saccharomyces cerevisiae</emphasis>
</taxonomicName>
α- glucosidase model generated by homology modeling experiments (see Materials and Methods) (
<bibRefCitation id="EFA202962C6B6171539BF9DE1586BFE1" author="Masullo, M. &amp; Lauro, G. &amp; Cerulli, A. &amp; Bifulco, G. &amp; Piacente, S." box="[206,404,1462,1481]" pageId="5" pageNumber="6" pagination="805660" refId="ref12158" refString="Masullo, M., Lauro, G., Cerulli, A., Bifulco, G., Piacente, S., 2022. Corylus avellana: a source of diarylheptanoids with alpha-glucosidase inhibitory activity evaluated by in vitro and in silico studies. Front. Plant Sci. 13, 805660 https: // doi. org / 10.3389 / fpls. 2022.805660." type="journal article" year="2022">Masullo et al., 2022</bibRefCitation>
) since the absence of experimentally determined protein structure. Molecular docking experiments were then performed, focusing on the protein region involved in the catalytic activity of this enzyme that includes D214, E276, D349 (
<bibRefCitation id="EFA202962C6B6171560AFCFC1770BAEB" author="Jenis, J. &amp; Baiseitova, A. &amp; Yoon, S. H. &amp; Park, C. &amp; Kim, J. Y. &amp; Li, Z. P. &amp; Lee, K. W. &amp; Park, K. H." pageId="5" pageNumber="6" pagination="1623 - 1632" refId="ref11302" refString="Jenis, J., Baiseitova, A., Yoon, S. H., Park, C., Kim, J. Y., Li, Z. P., Lee, K. W., Park, K. H., 2019. Competitive α- glucosidase inhibitors, dihydrobenzoxanthones, from the barks of Artocarpus elasticus. J. Enzym. Inhib. Med. Chem. 34, 1623 - 1632. https: // doi. org / 10.1080 / 14756366.2019.1660653." type="journal article" year="2019">Jenis et al., 2019</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B61715026FCD8104EBAEB" author="Yamamoto, K. &amp; Miyake, H. &amp; Kusunoki, M. &amp; Osaki, S." box="[883,1116,176,195]" pageId="5" pageNumber="6" pagination="4205 - 4214" refId="ref12893" refString="Yamamoto, K., Miyake, H., Kusunoki, M., Osaki, S., 2010. Crystal structures of isomaltase from Saccharomyces cerevisiae and in complex with its competitive inhibitor maltose. FEBS J. 277, 4205 - 4214. https: // doi. org / 10.1111 / j. 1742 - 4658.2010.07810. x." type="journal article" year="2010">Yamamoto et al., 2010</bibRefCitation>
), also accounted in previous studies (
<bibRefCitation id="EFA202962C6B6171506FFCA317FDBAF6" author="Jabeen, F. &amp; Shehzadi, S. A. &amp; Fatmi, M. Q. &amp; Shaheen, S. &amp; Iqbal, L. &amp; Afza, N. &amp; Panda, S. S. &amp; Ansari, F. L." box="[826,1007,203,223]" pageId="5" pageNumber="6" pagination="1029 - 1038" refId="ref11204" refString="Jabeen, F., Shehzadi, S. A., Fatmi, M. Q., Shaheen, S., Iqbal, L., Afza, N., Panda, S. S., Ansari, F. L., 2016. Synthesis, in vitro and computational studies of 1,4 - disubstituted 1,2,3 - triazoles as potential alpha-glucosidase inhibitors. Bioorg. Med. Chem. Lett. 26, 1029 - 1038. https: // doi. org / 10.1016 / j. bmcl. 2015.12.033." type="journal article" year="2016">Jabeen et al., 2016</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B617150A9FCA4109CBAF6" author="Ma, H. &amp; Wang, L. &amp; Niesen, D. B. &amp; Cai, A. &amp; Cho, B. P. &amp; Tan, W. &amp; Gu, Q. &amp; Xu, J. &amp; Seeram, N. P." box="[1020,1166,203,223]" pageId="5" pageNumber="6" pagination="107904 - 107915" refId="ref11790" refString="Ma, H., Wang, L., Niesen, D. B., Cai, A., Cho, B. P., Tan, W., Gu, Q., Xu, J., Seeram, N. P., 2015. Structure activity related, mechanistic, and modeling studies of gallotannins containing a glucitol-core and alpha-glucosidase. RSC Adv. 5, 107904 - 107915. https: // doi. org / 10.1039 / C 5 RA 19014 B." type="journal article" year="2015">Ma et al., 2015</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B617157CFFCA3115DBAF6" author="Milella, L. &amp; Milazzo, S. &amp; De Leo, M. &amp; Vera Saltos, M. B. &amp; Faraone, I. &amp; Tuccinardi, T. &amp; Lapillo, M. &amp; De Tommasi, N. &amp; Braca, A." box="[1178,1359,203,223]" pageId="5" pageNumber="6" pagination="2104 - 2112" refId="ref12226" refString="Milella, L., Milazzo, S., De Leo, M., Vera Saltos, M. B., Faraone, I., Tuccinardi, T., Lapillo, M., De Tommasi, N., Braca, A., 2016. alpha-Glucosidase and alpha-Amylase Inhibitors from Arcytophyllum thymifolium. J. Nat. Prod. 79, 2104 - 2112. https: // doi. org / 10.1021 / acs. jnatprod. 6 b 00484." type="journal article" year="2016">Milella et al., 2016</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B61715609FCA41770BAD3" author="Wang, G. &amp; Peng, Y. &amp; Xie, Z. &amp; Wang, J. &amp; Chen, M." pageId="5" pageNumber="6" pagination="1477 - 1484" refId="ref12811" refString="Wang, G. - c., Peng, Y. - p., Xie, Z. - z., Wang, J., Chen, M., 2017. Synthesis, α- glucosidase inhibition and molecular docking studies of novel thiazolidine- 2,4 - dione or rhodanine derivatives. Med. Chem. Comm. 8, 1477 - 1484. https: // doi. org / 10.1039 / C 7 MD 00173 H." type="journal article" year="2017">Wang et al., 2017</bibRefCitation>
).
</paragraph>
<paragraph id="8B8C7F672C6B61715004FD6B10C0B96C" blockId="5.[818,1488,148,837]" pageId="5" pageNumber="6">
Docking poses of active compounds 
<emphasis id="B947A3752C6B617157F9FD6B10AABB3E" bold="true" box="[1196,1208,259,278]" pageId="5" pageNumber="6">3</emphasis>
, 
<emphasis id="B947A3752C6B61715790FD6B10C3BB3E" bold="true" box="[1221,1233,259,278]" pageId="5" pageNumber="6">5</emphasis>
, 
<emphasis id="B947A3752C6B6171578AFD6B10EABB3E" bold="true" box="[1247,1272,259,278]" pageId="5" pageNumber="6">15</emphasis>
, 
<emphasis id="B947A3752C6B61715650FD6B110CBB3E" bold="true" box="[1285,1310,259,278]" pageId="5" pageNumber="6">16</emphasis>
, 
<emphasis id="B947A3752C6B6171567EFD6B1156BB3E" bold="true" box="[1323,1348,259,278]" pageId="5" pageNumber="6">19</emphasis>
, 
<emphasis id="B947A3752C6B61715604FD6B119CBB3E" bold="true" box="[1361,1422,259,279]" pageId="5" pageNumber="6">23–28</emphasis>
(Glide software) (
<bibRefCitation id="EFA202962C6B617150C2FD771043BB1A" author="Friesner, R. A. &amp; Banks, J. L. &amp; Murphy, R. B. &amp; Halgren, T. A. &amp; Klicic, J. J. &amp; Mainz, D. T. &amp; Repasky, M. P. &amp; Knoll, E. H. &amp; Shelley, M. &amp; Perry, J. K. &amp; Shaw, D. E. &amp; Francis, P. &amp; Shenkin, P. S." box="[919,1105,287,307]" pageId="5" pageNumber="6" pagination="1739 - 1749" refId="ref10514" refString="Friesner, R. A., Banks, J. L., Murphy, R. B., Halgren, T. A., Klicic, J. J., Mainz, D. T., Repasky, M. P., Knoll, E. H., Shelley, M., Perry, J. K., Shaw, D. E., Francis, P., Shenkin, P. S., 2004. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med. Chem. 47, 1739 - 1749. https: // doi. org / 10.1021 / jm 0306430." type="journal article" year="2004">Friesner et al., 2004</bibRefCitation>
, 
<bibRefCitation id="EFA202962C6B61715709FD77109EBB1A" author="Friesner, R. A. &amp; Murphy, R. B. &amp; Repasky, M. P. &amp; Frye, L. L. &amp; Greenwood, J. R. &amp; Halgren, T. A. &amp; Sanschagrin, P. C. &amp; Mainz, D. T." box="[1116,1164,287,306]" pageId="5" pageNumber="6" pagination="6177 - 6196" refId="ref10649" refString="Friesner, R. A., Murphy, R. B., Repasky, M. P., Frye, L. L., Greenwood, J. R., Halgren, T. A., Sanschagrin, P. C., Mainz, D. T., 2006. Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J. Med. Chem. 49, 6177 - 6196. https: // doi. org / 10.1021 / jm 051256 o." type="journal article" year="2006">2006</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B617157C2FD771116BB1A" author="Glide, S." box="[1175,1284,287,306]" pageId="5" pageNumber="6" refId="ref10749" refString="Glide, S., 2021. LLC, New York, NY." type="book" year="2021">Glide, 2021</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B6171565BFD7711D5BB1A" author="Halgren, T. A. &amp; Murphy, R. B. &amp; Friesner, R. A. &amp; Beard, H. S. &amp; Frye, L. L. &amp; Pollard, W. T. &amp; Banks, J. L." box="[1294,1479,287,307]" pageId="5" pageNumber="6" pagination="1750 - 1759" refId="ref10945" refString="Halgren, T. A., Murphy, R. B., Friesner, R. A., Beard, H. S., Frye, L. L., Pollard, W. T., Banks, J. L., 2004. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J. Med. Chem. 47, 1750 - 1759. https: // doi. org / 10.1021 / jm 030644 s." type="journal article" year="2004">Halgren et al., 2004</bibRefCitation>
) were visually inspected in order to detect the ability of the tested compounds to establish an interaction pattern with the above reported key residues consistently with the observed biological activity (
<bibRefCitation id="EFA202962C6B6171562FFD1B1770BB8A" author="Ma, H. &amp; Wang, L. &amp; Niesen, D. B. &amp; Cai, A. &amp; Cho, B. P. &amp; Tan, W. &amp; Gu, Q. &amp; Xu, J. &amp; Seeram, N. P." pageId="5" pageNumber="6" pagination="107904 - 107915" refId="ref11790" refString="Ma, H., Wang, L., Niesen, D. B., Cai, A., Cho, B. P., Tan, W., Gu, Q., Xu, J., Seeram, N. P., 2015. Structure activity related, mechanistic, and modeling studies of gallotannins containing a glucitol-core and alpha-glucosidase. RSC Adv. 5, 107904 - 107915. https: // doi. org / 10.1039 / C 5 RA 19014 B." type="journal article" year="2015">Ma et al., 2015</bibRefCitation>
; 
<bibRefCitation id="EFA202962C6B61715039FDE71002BB8A" author="Wang, G. &amp; Peng, Y. &amp; Xie, Z. &amp; Wang, J. &amp; Chen, M." box="[876,1040,399,418]" pageId="5" pageNumber="6" pagination="1477 - 1484" refId="ref12811" refString="Wang, G. - c., Peng, Y. - p., Xie, Z. - z., Wang, J., Chen, M., 2017. Synthesis, α- glucosidase inhibition and molecular docking studies of novel thiazolidine- 2,4 - dione or rhodanine derivatives. Med. Chem. Comm. 8, 1477 - 1484. https: // doi. org / 10.1039 / C 7 MD 00173 H." type="journal article" year="2017">Wang et al., 2017</bibRefCitation>
). Specifically, all the output poses related to the screened compounds were filtered providing that one contact with D214 and/or E276 and/or D349 was established. As expected, such a condition was positively satisfied after this screening and interestingly, most of the compounds specifically featured a H-bond with at least one of these key residues, supporting the obtained biological data (
<tableCitation id="C6B14ADC2C6B61715635FE7211B7B805" box="[1376,1445,538,557]" captionStart="Table 4" captionStartId="5.[203,253,1580,1596]" captionTargetBox="[219,651,1666,1969]" captionTargetPageId="5" captionText="Table 4 Antihyperglycemic activity of the main iridoids isolated from S. atropurpurea, expressed as IC50 (μM) value." httpUri="http://table.plazi.org/id/DF4C2FEF2C6B6171539EFA44166EBC58" pageId="5" pageNumber="6" tableUuid="DF4C2FEF2C6B6171539EFA44166EBC58">Table 4</tableCitation>
). As reported in 
<figureCitation id="130863E22C6B617150CAFE5E17C1B861" box="[927,979,566,585]" captionStart="Fig" captionStartId="6.[100,130,569,586]" captionTargetBox="[208,1378,149,537]" captionTargetId="figure-1046@6.[206,1381,148,542]" captionTargetPageId="6" captionText="Fig. 3. Docking poses of A) 5 (colored by atom type: C green, O red, polar H light grey); B) 15 (colored by atom type: C light blue, O red, polar H light grey); C) 16 (colored by atom type: C orange, O red, polar H light grey), showing the most promising inhibitory activity against α-glucosidase from Saccharomyces cerevisiae (represented with light grey ribbons; key residues are reported as sticks and colored by atom type: C grey, O red, N blue, polar H light grey). H-bonds are represented with dotted green lines in the 3D representation (for interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article)." figureDoi="http://doi.org/10.5281/zenodo.8160624" httpUri="https://zenodo.org/record/8160624/files/figure.png" pageId="5" pageNumber="6">Fig. 3</figureCitation>
, selected poses for compounds 
<emphasis id="B947A3752C6B617157ADFE5E1116B861" bold="true" box="[1272,1284,566,585]" pageId="5" pageNumber="6">5</emphasis>
, 
<emphasis id="B947A3752C6B61715645FE5E113BB861" bold="true" box="[1296,1321,566,585]" pageId="5" pageNumber="6">15</emphasis>
, and 
<emphasis id="B947A3752C6B61715609FE5E1167B861" bold="true" box="[1372,1397,566,585]" pageId="5" pageNumber="6">16</emphasis>
, showing the lowest IC 
<subScript id="17B77D222C6B617150F8FE3117ADB84F" attach="left" box="[941,959,601,615]" fontSize="6" pageId="5" pageNumber="6">50</subScript>
values, highlighted their ability to interact via H-bonds with E276. In particular, compound 
<emphasis id="B947A3752C6B617157CDFE0610B6B8A9" bold="true" box="[1176,1188,622,641]" pageId="5" pageNumber="6">5</emphasis>
was able to establish this key interaction through the carbonyl moiety of its lactone chemical functions, whereas 
<emphasis id="B947A3752C6B61715096FECE17CEB891" bold="true" box="[963,988,678,697]" pageId="5" pageNumber="6">15</emphasis>
and 
<emphasis id="B947A3752C6B61715745FECE103BB891" bold="true" box="[1040,1065,678,697]" pageId="5" pageNumber="6">16</emphasis>
through their glucopyranosyl units. Also, a large set of contacts was detected with further residues (e.g., F157, F158, 
<collectionCode id="ED22E7A22C6B61715025FEB61793B8D9" box="[880,897,734,753]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="5" pageNumber="6" type="Herbarium">H</collectionCode>
239, E304, P309, R312, Q350) stabilising the ligand/protein binding; among them, compound 
<emphasis id="B947A3752C6B6171573FFE911091B924" bold="true" box="[1130,1155,761,780]" pageId="5" pageNumber="6">16</emphasis>
was also able to make an additional H-bond with E304 (
<figureCitation id="130863E22C6B617150A2FF7D103DB900" box="[1015,1071,789,808]" captionStart="Fig" captionStartId="6.[100,130,569,586]" captionTargetBox="[208,1378,149,537]" captionTargetId="figure-1046@6.[206,1381,148,542]" captionTargetPageId="6" captionText="Fig. 3. Docking poses of A) 5 (colored by atom type: C green, O red, polar H light grey); B) 15 (colored by atom type: C light blue, O red, polar H light grey); C) 16 (colored by atom type: C orange, O red, polar H light grey), showing the most promising inhibitory activity against α-glucosidase from Saccharomyces cerevisiae (represented with light grey ribbons; key residues are reported as sticks and colored by atom type: C grey, O red, N blue, polar H light grey). H-bonds are represented with dotted green lines in the 3D representation (for interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article)." figureDoi="http://doi.org/10.5281/zenodo.8160624" httpUri="https://zenodo.org/record/8160624/files/figure.png" pageId="5" pageNumber="6">Fig. 3</figureCitation>
) (
<bibRefCitation id="EFA202962C6B6171571DFF7D10E1B900" author="Jenis, J. &amp; Baiseitova, A. &amp; Yoon, S. H. &amp; Park, C. &amp; Kim, J. Y. &amp; Li, Z. P. &amp; Lee, K. W. &amp; Park, K. H." box="[1096,1267,789,809]" pageId="5" pageNumber="6" pagination="1623 - 1632" refId="ref11302" refString="Jenis, J., Baiseitova, A., Yoon, S. H., Park, C., Kim, J. Y., Li, Z. P., Lee, K. W., Park, K. H., 2019. Competitive α- glucosidase inhibitors, dihydrobenzoxanthones, from the barks of Artocarpus elasticus. J. Enzym. Inhib. Med. Chem. 34, 1623 - 1632. https: // doi. org / 10.1080 / 14756366.2019.1660653." type="journal article" year="2019">Jenis et al., 2019</bibRefCitation>
) through the terminal hydroxy function on the secoiridoid moiety.
</paragraph>
</subSubSection>
<subSubSection id="C3292CEC2C6B61715067FF02176EBC1E" pageId="5" pageNumber="6" type="discussion">
<paragraph id="8B8C7F672C6B61715067FF0217DEB955" blockId="5.[818,972,874,893]" box="[818,972,874,893]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B61715067FF0217DEB955" bold="true" box="[818,972,874,893]" pageId="5" pageNumber="6">3. Conclusions</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6B61715004FFCA176EBC1E" blockId="5.[818,1488,929,1590]" pageId="5" pageNumber="6">
In this study, three previously undescribed iridoids (
<emphasis id="B947A3752C6B61715669FFC91147B99C" bold="true" box="[1340,1365,929,948]" pageId="5" pageNumber="6">23</emphasis>
, 
<emphasis id="B947A3752C6B61715634FFC91168B99C" bold="true" box="[1377,1402,929,948]" pageId="5" pageNumber="6">25</emphasis>
and 
<emphasis id="B947A3752C6B617156FDFFC911D3B99C" bold="true" box="[1448,1473,929,948]" pageId="5" pageNumber="6">28</emphasis>
), with fourteen known iridoids, four known quinic acid derivatives and seven known flavonoids, were isolated and identified from 
<taxonomicName id="4C3304E42C6B61715067FF9D17AEBE21" box="[818,956,1013,1033]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715067FF9D17AEBE21" bold="true" box="[818,956,1013,1033]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
. This investigation confirms how plants belonging to the 
<taxonomicName id="4C3304E42C6B61715067F879176DBE0C" box="[818,895,1041,1060]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="genus">
<emphasis id="B947A3752C6B61715067F879176DBE0C" bold="true" box="[818,895,1041,1060]" italics="true" pageId="5" pageNumber="6">Scabiosa</emphasis>
</taxonomicName>
genus represent a source of flavonoids and iridoids. Interestingly, iridoids here reported are mainly bis-iridoids (
<emphasis id="B947A3752C6B61715677F8451129BE68" bold="true" box="[1314,1339,1069,1088]" pageId="5" pageNumber="6">13</emphasis>
, 
<emphasis id="B947A3752C6B61715612F8451172BE68" bold="true" box="[1351,1376,1069,1088]" pageId="5" pageNumber="6">15</emphasis>
, 
<emphasis id="B947A3752C6B61715639F8451197BE68" bold="true" box="[1388,1413,1069,1088]" pageId="5" pageNumber="6">16</emphasis>
, 
<emphasis id="B947A3752C6B617156C4F84511B8BE68" bold="true" box="[1425,1450,1069,1088]" pageId="5" pageNumber="6">17</emphasis>
, 
<emphasis id="B947A3752C6B617156E3F84511DDBE68" bold="true" box="[1462,1487,1069,1088]" pageId="5" pageNumber="6">19</emphasis>
and 
<emphasis id="B947A3752C6B61715009F821178BBE74" bold="true" box="[860,921,1097,1116]" pageId="5" pageNumber="6">21–28</emphasis>
), made up of one iridoid and one secoiridoid unit. From a literature search on the chemistry of 
<taxonomicName id="4C3304E42C6B617157D2F80D1113BE50" box="[1159,1281,1125,1144]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="undetermined">
<emphasis id="B947A3752C6B617157D2F80D10C6BE50" bold="true" box="[1159,1236,1125,1144]" italics="true" pageId="5" pageNumber="6">Scabiosa</emphasis>
spp.
</taxonomicName>
<taxonomicName id="4C3304E42C6B61715651F80D119DBE50" box="[1284,1423,1125,1144]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715651F80D119DBE50" bold="true" box="[1284,1423,1125,1144]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
can be considered the largest source of bis-iridoids. Therefore, considering the α- glucosidase inhibitory activity reported for iridoids, eleven iridoids and bis-iridoids isolated from 
<taxonomicName id="4C3304E42C6B61715710F8D010DDBEE4" box="[1093,1231,1208,1228]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715710F8D010DDBEE4" bold="true" box="[1093,1231,1208,1228]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
, including compounds 
<emphasis id="B947A3752C6B617156F3F8D011A0BEE3" bold="true" box="[1446,1458,1208,1227]" pageId="5" pageNumber="6">3</emphasis>
, 
<emphasis id="B947A3752C6B617156E8F8D111DBBEE4" bold="true" box="[1469,1481,1209,1228]" pageId="5" pageNumber="6">5</emphasis>
, 
<emphasis id="B947A3752C6B61715067F8BC1759BECF" bold="true" box="[818,843,1236,1255]" pageId="5" pageNumber="6">15</emphasis>
, 
<emphasis id="B947A3752C6B61715000F8BC177CBECF" bold="true" box="[853,878,1236,1255]" pageId="5" pageNumber="6">16</emphasis>
, 
<emphasis id="B947A3752C6B6171502DF8BC1783BECF" bold="true" box="[888,913,1236,1255]" pageId="5" pageNumber="6">19</emphasis>
, 
<emphasis id="B947A3752C6B617150CEF8BC17CABECF" bold="true" box="[923,984,1236,1256]" pageId="5" pageNumber="6">23–28</emphasis>
, were tested. 
<emphasis id="B947A3752C6B61715703F8BD108BBECF" bold="true" box="[1110,1177,1236,1256]" italics="true" pageId="5" pageNumber="6">In silico</emphasis>
investigation based on molecular docking experiments were carried out to evaluate the feasibility of selected compounds to 
<taxonomicName id="4C3304E42C6B61715742F9641079BF37" box="[1047,1131,1292,1311]" form="the" pageId="5" pageNumber="6" rank="form">form the</taxonomicName>
complex with α- glucosidase enzyme active site. In detail, the analysis of the binding modes was focused on evaluating the ability of the investigated compounds to interact with the key residues responsible for the catalytic activity of α- glucosidase. The obtained results suggest how the antihyperglycemic effects shown by 
<taxonomicName id="4C3304E42C6B61715067F9F017ADBF83" box="[818,959,1432,1451]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715067F9F017ADBF83" bold="true" box="[818,959,1432,1451]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
could be correlated to the occurrence of iridoid compounds. This work highlights the possibility of promoting 
<taxonomicName id="4C3304E42C6B61715613F9DC11DDBFEF" box="[1350,1487,1460,1479]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B61715613F9DC11DDBFEF" bold="true" box="[1350,1487,1460,1479]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
as a source of functional ingredients for the treatment of diabetes. Anyway, further studies are required to deeper address this point, as well as the possibility of exploring the use of these iridoids in this disease.
</paragraph>
</subSubSection>
<caption id="DF4C2FEF2C6B6171539EFA44166EBC58" ID-Table-UUID="DF4C2FEF2C6B6171539EFA44166EBC58" httpUri="http://table.plazi.org/id/DF4C2FEF2C6B6171539EFA44166EBC58" pageId="5" pageNumber="6" startId="5.[203,253,1580,1596]" targetBox="[219,651,1666,1969]" targetIsTable="true" targetPageId="5" targetType="table">
<paragraph id="8B8C7F672C6B6171539EFA44166EBC58" blockId="5.[203,667,1580,1649]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171539EFA44151CBC15" bold="true" box="[203,270,1580,1597]" pageId="5" pageNumber="6">Table 4</emphasis>
Antihyperglycemic activity of the main iridoids isolated from 
<taxonomicName id="4C3304E42C6B617153ACFA371564BC47" box="[249,374,1631,1648]" class="Magnoliopsida" family="Caprifoliaceae" genus="Scabiosa" kingdom="Plantae" order="Dipsacales" pageId="5" pageNumber="6" phylum="Tracheophyta" rank="species" species="atropurpurea">
<emphasis id="B947A3752C6B617153ACFA371564BC47" bold="true" box="[249,374,1631,1648]" italics="true" pageId="5" pageNumber="6">S. atropurpurea</emphasis>
</taxonomicName>
, expressed as IC 
<subScript id="17B77D222C6B61715156FA0D1601BC59" attach="left" box="[515,531,1637,1649]" fontSize="5" pageId="5" pageNumber="6">50</subScript>
(μM) value.
</paragraph>
</caption>
<subSubSection id="C3292CEC2C6B61725067FA34168DBF7D" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6" type="materials_examined">
<paragraph id="8B8C7F672C6B61715067FA3417CBBC47" blockId="5.[818,985,1628,1647]" box="[818,985,1628,1647]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B61715067FA3417CBBC47" bold="true" box="[818,985,1628,1647]" pageId="5" pageNumber="6">4. Experimental</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6B6171538EFAEB1696BD98" pageId="5" pageNumber="6">
<table id="F9338DC72C6B9E8B538EFAEA1699BD99" box="[219,651,1666,1969]" gridcols="2" gridrows="13" pageId="5" pageNumber="6">
<tr id="35037D252C6B9E8B538EFAEA1699BCBC" box="[219,651,1666,1684]" gridrow="0" pageId="5" pageNumber="6">
<th id="76D214592C6B9E8B538EFAEA1526BCBC" box="[219,308,1666,1684]" gridcol="0" gridrow="0" pageId="5" pageNumber="6">Compounds</th>
<th id="76D214592C6B9E8B5142FAEA1699BCBC" box="[535,651,1666,1684]" gridcol="1" gridrow="0" pageId="5" pageNumber="6">IC50 ± SD (μM)</th>
</tr>
<tr id="35037D252C6B9E8B538EFACE1699BC9D" box="[219,651,1702,1717]" gridrow="1" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFACE1526BC9D" box="[219,308,1702,1717]" gridcol="0" gridrow="1" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFACE14F7BC9C" bold="true" box="[219,229,1702,1716]" pageId="5" pageNumber="6">3</emphasis>
</td>
<td id="76D214592C6B9E8B5142FACE1699BC9D" box="[535,651,1702,1717]" gridcol="1" gridrow="1" pageId="5" pageNumber="6">58.82 ± 2.08</td>
</tr>
<tr id="35037D252C6B9E8B538EFAD51699BCE4" box="[219,651,1725,1740]" gridrow="2" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFAD51526BCE4" box="[219,308,1725,1740]" gridcol="0" gridrow="2" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFAD514F7BCE3" bold="true" box="[219,229,1725,1739]" pageId="5" pageNumber="6">5</emphasis>
</td>
<td id="76D214592C6B9E8B5142FAD51699BCE4" box="[535,651,1725,1740]" gridcol="1" gridrow="2" pageId="5" pageNumber="6">27.50 ± 2.80</td>
</tr>
<tr id="35037D252C6B9E8B538EFABC1699BCCB" box="[219,651,1748,1763]" gridrow="3" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFABC1526BCCB" box="[219,308,1748,1763]" gridcol="0" gridrow="3" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFABC14FDBCCA" bold="true" box="[219,239,1748,1762]" pageId="5" pageNumber="6">15</emphasis>
</td>
<td id="76D214592C6B9E8B5142FABC1699BCCB" box="[535,651,1748,1763]" gridcol="1" gridrow="3" pageId="5" pageNumber="6">30.20 ± 2.13</td>
</tr>
<tr id="35037D252C6B9E8B538EFA831699BCD2" box="[219,651,1771,1786]" gridrow="4" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFA831526BCD2" box="[219,308,1771,1786]" gridcol="0" gridrow="4" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFA8314FDBCD1" bold="true" box="[219,239,1771,1785]" pageId="5" pageNumber="6">16</emphasis>
</td>
<td id="76D214592C6B9E8B5142FA831699BCD2" box="[535,651,1771,1786]" gridcol="1" gridrow="4" pageId="5" pageNumber="6">25.01 ± 1.72</td>
</tr>
<tr id="35037D252C6B9E8B538EFB6A1699BD39" box="[219,651,1794,1809]" gridrow="5" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB6A1526BD39" box="[219,308,1794,1809]" gridcol="0" gridrow="5" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB6A14FDBD38" bold="true" box="[219,239,1794,1808]" pageId="5" pageNumber="6">19</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB6A1699BD39" box="[535,651,1794,1809]" gridcol="1" gridrow="5" pageId="5" pageNumber="6">35.64 ± 1.18</td>
</tr>
<tr id="35037D252C6B9E8B538EFB701699BD0F" box="[219,651,1816,1831]" gridrow="6" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB701526BD0F" box="[219,308,1816,1831]" gridcol="0" gridrow="6" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB7114FDBD0F" bold="true" box="[219,239,1817,1831]" pageId="5" pageNumber="6">23</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB701699BD0F" box="[535,651,1816,1831]" gridcol="1" gridrow="6" pageId="5" pageNumber="6">49.95 ± 1.08</td>
</tr>
<tr id="35037D252C6B9E8B538EFB471699BD16" box="[219,651,1839,1854]" gridrow="7" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB471526BD16" box="[219,308,1839,1854]" gridcol="0" gridrow="7" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB5814FDBD16" bold="true" box="[219,239,1840,1854]" pageId="5" pageNumber="6">24</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB471699BD16" box="[535,651,1839,1854]" gridcol="1" gridrow="7" pageId="5" pageNumber="6">32.36 ± 2.06</td>
</tr>
<tr id="35037D252C6B9E8B538EFB2E1699BD7D" box="[219,651,1862,1877]" gridrow="8" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB2E1526BD7D" box="[219,308,1862,1877]" gridcol="0" gridrow="8" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB2E14FDBD7C" bold="true" box="[219,239,1862,1876]" pageId="5" pageNumber="6">25</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB2E1699BD7D" box="[535,651,1862,1877]" gridcol="1" gridrow="8" pageId="5" pageNumber="6">86.96 ± 3.50</td>
</tr>
<tr id="35037D252C6B9E8B538EFB351699BD44" box="[219,651,1885,1900]" gridrow="9" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB351526BD44" box="[219,308,1885,1900]" gridcol="0" gridrow="9" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB3514FDBD43" bold="true" box="[219,239,1885,1899]" pageId="5" pageNumber="6">26</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB351699BD44" box="[535,651,1885,1900]" gridcol="1" gridrow="9" pageId="5" pageNumber="6">38.46 ± 2.08</td>
</tr>
<tr id="35037D252C6B9E8B538EFB1C1699BDAB" box="[219,651,1908,1923]" gridrow="10" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFB1C1526BDAB" box="[219,308,1908,1923]" gridcol="0" gridrow="10" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFB1C14FDBDAA" bold="true" box="[219,239,1908,1922]" pageId="5" pageNumber="6">27</emphasis>
</td>
<td id="76D214592C6B9E8B5142FB1C1699BDAB" box="[535,651,1908,1923]" gridcol="1" gridrow="10" pageId="5" pageNumber="6">82.01 ± 3.50</td>
</tr>
<tr id="35037D252C6B9E8B538EFBE31699BDB2" box="[219,651,1931,1946]" gridrow="11" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFBE31526BDB2" box="[219,308,1931,1946]" gridcol="0" gridrow="11" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B6171538EFBE314FDBDB1" bold="true" box="[219,239,1931,1945]" pageId="5" pageNumber="6">28</emphasis>
</td>
<td id="76D214592C6B9E8B5142FBE31699BDB2" box="[535,651,1931,1946]" gridcol="1" gridrow="11" pageId="5" pageNumber="6">92.59 ± 3.52</td>
</tr>
<tr id="35037D252C6B9E8B538EFBCA1699BD99" box="[219,651,1954,1969]" gridrow="12" pageId="5" pageNumber="6">
<td id="76D214592C6B9E8B538EFBCA1526BD99" box="[219,308,1954,1969]" gridcol="0" gridrow="12" pageId="5" pageNumber="6">acarbose</td>
<td id="76D214592C6B9E8B5142FBCA1699BD99" box="[535,651,1954,1969]" gridcol="1" gridrow="12" pageId="5" pageNumber="6">175.00 ± 3.50</td>
</tr>
</table>
</paragraph>
<paragraph id="8B8C7F672C6B61715067FAFC17E5BC8E" blockId="5.[818,1015,1683,1703]" box="[818,1015,1683,1703]" pageId="5" pageNumber="6">
<emphasis id="B947A3752C6B61715067FAFC17E5BC8E" bold="true" box="[818,1015,1683,1703]" italics="true" pageId="5" pageNumber="6">4.1. General methods</emphasis>
</paragraph>
<paragraph id="8B8C7F672C6B61725004FAA315CBB9BB" blockId="5.[818,1488,1739,1982]" lastBlockId="6.[100,771,729,1139]" lastPageId="6" lastPageNumber="7" pageId="5" pageNumber="6">
Optical rotations were obtained on a Jasco 2000 polarimeter. IR spectra were measured on a FTIR IFS-48 spectrometer (Bruker, BioSpinGmBH, Rheinstetten, 
<collectingCountry id="F3243FF72C6B6171577FFB6B1097BD3E" box="[1066,1157,1795,1814]" name="Germany" pageId="5" pageNumber="6">Germany</collectingCountry>
). NMR experiments were acquired in methanol- 
<emphasis id="B947A3752C6B617150FCFB7717A6BD1A" bold="true" box="[937,948,1823,1842]" italics="true" pageId="5" pageNumber="6">d</emphasis>
4 (99.95%, Sigma-Aldrich, Milan, 
<collectingCountry id="F3243FF72C6B617157A1FB771132BD1A" box="[1268,1312,1823,1842]" name="Italy" pageId="5" pageNumber="6">Italy</collectingCountry>
) on a Bruker DRX-600 spectrometer (Bruker BioSpinGmBH, Rheinstetten, 
<collectingCountry id="F3243FF72C6B61715624FB5311DBBD66" box="[1393,1481,1851,1870]" name="Germany" pageId="5" pageNumber="6">Germany</collectingCountry>
) equipped with a Bruker 
<quantity id="4CCBD2822C6B61715740FB3F1058BD42" box="[1045,1098,1879,1898]" metricMagnitude="-3" metricUnit="m" metricValue="5.0" pageId="5" pageNumber="6" unit="mm" value="5.0">5 mm</quantity>
<collectingCountry id="F3243FF72C6B61715705FB3F1063BD42" box="[1104,1137,1879,1898]" name="Turks and Caicos Islands" pageId="5" pageNumber="6">TCI</collectingCountry>
CryoProbe at 300 K. Data processing were carried out with Topspin 3.2 software. The ROESY spectra were acquired with tmix = 400 ms. HPLC separations were carried out on a Waters system (Milford, 
<collectingCountry id="F3243FF72C6B61715742FBC31050BD96" box="[1047,1090,1963,1982]" name="United States of America" pageId="5" pageNumber="6">USA</collectingCountry>
) equipped with a R-401 A refractive index detector, a Symmetry Prep TM-C18 (78 × 
<quantity id="4CCBD2822C686172514CFEB11662B8C5" box="[537,624,729,749]" metricMagnitude="-1" metricUnit="m" metricValue="3.0" pageId="6" pageNumber="7" unit="mm" value="300.0">300 mm</quantity>
, 7 μm). Semipreparative HPLC separations were carried out by using a Phenomenex C18 Synergy-Hydro-RP (
<quantity id="4CCBD2822C686172521EFF791589B90C" box="[331,411,785,804]" metricMagnitude="-1" metricUnit="m" metricValue="2.5" pageId="6" pageNumber="7" unit="mm" value="250.0">250 mm</quantity>
× 
<quantity id="4CCBD2822C68617252ECFF7915EDB90C" box="[441,511,785,804]" metricMagnitude="-2" metricUnit="m" metricValue="1.0" pageId="6" pageNumber="7" unit="mm" value="10.0">10 mm</quantity>
, 10 μm) column on an Agilent 1260 Infinity system (Agilent Technologies, Palo Alto, CA, 
<collectingCountry id="F3243FF72C686172519EFF4516EAB968" box="[715,760,813,832]" name="United States of America" pageId="6" pageNumber="7">USA</collectingCountry>
), equipped with a binary pump (G-1312C), and a UV detector (G-1314 B). The mobile phase consisted of solvent A (
<collectionCode id="ED22E7A22C68617252BFFF0D15E9B950" box="[490,507,869,888]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="7" type="Herbarium">H</collectionCode>
<subScript id="17B77D222C68617252AEFF041616B952" attach="both" box="[507,516,876,890]" fontSize="6" pageId="6" pageNumber="7">2</subScript>
O +0.1% formic acid) and solvent B (
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<subScript id="17B77D222C68617253B3FFE014FDB9BE" attach="both" box="[230,239,904,918]" fontSize="6" pageId="6" pageNumber="7">3</subScript>
CN + 0.1% formic acid).
</paragraph>
<caption id="DF4C2FEF2C6861725331FE5114DFB898" ID-DOI="http://doi.org/10.5281/zenodo.8160624" ID-Zenodo-Dep="8160624" httpUri="https://zenodo.org/record/8160624/files/figure.png" pageId="6" pageNumber="7" startId="6.[100,130,569,586]" targetBox="[208,1378,149,537]" targetPageId="6" targetType="figure">
<paragraph id="8B8C7F672C6861725331FE5114DFB898" blockId="6.[100,1487,568,688]" pageId="6" pageNumber="7">
<emphasis id="B947A3752C6861725331FE51148FB862" bold="true" box="[100,157,569,586]" pageId="6" pageNumber="7">Fig. 3.</emphasis>
Docking poses of A) 
<emphasis id="B947A3752C6861725201FE51154DB861" bold="true" box="[340,351,569,585]" pageId="6" pageNumber="7">5</emphasis>
(colored by atom type: C green, O red, polar H light grey); B) 
<emphasis id="B947A3752C6861725025FE511794B862" bold="true" box="[880,902,569,586]" pageId="6" pageNumber="7">15</emphasis>
(colored by atom type: C light blue, O red, polar H light grey); C) 
<emphasis id="B947A3752C68617256ECFE5111DDB862" bold="true" box="[1465,1487,569,586]" pageId="6" pageNumber="7">16</emphasis>
(colored by atom type: C orange, O red, polar H light grey), showing the most promising inhibitory activity against α- glucosidase from 
<taxonomicName id="4C3304E42C6861725657FE3A11DDB84C" box="[1282,1487,594,612]" class="Tremellomycetes" family="Tremellaceae" genus="Saccharomyces" kingdom="Fungi" order="Tremellales" pageId="6" pageNumber="7" phylum="Basidiomycota" rank="species" species="cerevisiae">
<emphasis id="B947A3752C6861725657FE3A11DDB84C" bold="true" box="[1282,1487,594,612]" italics="true" pageId="6" pageNumber="7">Saccharomyces cerevisiae</emphasis>
</taxonomicName>
(represented with light grey ribbons; key residues are reported as sticks and colored by atom type: C grey, O red, N blue, polar H light grey). H-bonds are represented with dotted green lines in the 3D representation (for interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article).
</paragraph>
</caption>
<paragraph id="8B8C7F672C68617253D1FFF5169EBE5B" blockId="6.[100,771,729,1139]" pageId="6" pageNumber="7">
TLC was performed on silica gel F 
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(Macherey-Nagel Deltek, Naples, 
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) plates (
<quantity id="4CCBD2822C6861725208FFD015BAB9E4" box="[349,424,952,972]" metricMagnitude="-1" metricUnit="m" metricValue="2.0" pageId="6" pageNumber="7" unit="cm" value="20.0">20 cm</quantity>
× 
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) and mixtures of CHCl 
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– 
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OH– 
<collectionCode id="ED22E7A22C68617253ACFFBD151BB9C0" box="[249,265,981,1000]" country="Finland" lsid="urn:lsid:biocol.org:col:15618" name="University of Helsinki" pageId="6" pageNumber="7" type="Herbarium">H</collectionCode>
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O (80:20:2, 70:30:3, 61:32:7) (VWR international PBI S. r.l., Milan, 
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) were used as mobile phases to obtain a separation distance of 
<quantity id="4CCBD2822C6861725387F864150BBE37" box="[210,281,1036,1055]" metricMagnitude="-2" metricUnit="m" metricValue="8.0" pageId="6" pageNumber="7" unit="mm" value="80.0">80 mm</quantity>
. Detection was carried out by spraying cerium (IV) sulphate followed by heating at 100 
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C for 5 min. HR/ESI-MS data were acquired on an LTQ Orbitrap XL mass spectrometer (Thermo Fisher Scientific, San Josѐ, 
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) operating in negative ion mode.
</paragraph>
<paragraph id="8B8C7F672C6861725331F8F21506BE85" blockId="6.[100,276,1178,1197]" box="[100,276,1178,1197]" pageId="6" pageNumber="7">
<emphasis id="B947A3752C6861725331F8F21506BE85" bold="true" box="[100,276,1178,1197]" italics="true" pageId="6" pageNumber="7">4.2. Plant material</emphasis>
</paragraph>
<paragraph id="8B8C7F672C68617253D1F8BA168DBF7D" blockId="6.[100,771,1234,1365]" pageId="6" pageNumber="7">
<materialsCitation id="3B5B753A2C68617253D1F8BA168DBF7D" collectionCode="Herbarium of Science Faculty" country="Turkey" latitude="38.327028" location="Urla" longitude="26.774579" pageId="6" pageNumber="7" specimenCode="EGE 40781" specimenCount="1" stateProvince="Urla">
Whole plants of 
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<emphasis id="B947A3752C6861725272F8BA15E3BECD" bold="true" box="[295,497,1234,1253]" italics="true" pageId="6" pageNumber="7">Scabiosa atropurpurea</emphasis>
L. subsp. 
<emphasis id="B947A3752C6861725102F8BA16BABECD" bold="true" box="[599,680,1234,1253]" italics="true" pageId="6" pageNumber="7">maritima</emphasis>
(L.)
</taxonomicName>
Arc. (
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) were collected in 
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(GPS coordinates latitude: 
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, longitude: 
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), 
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, 
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, dried in the shade and grounded. A voucher 
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was deposited in the 
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, Ege University, Izmir, Turkey (
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).
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</paragraph>
</subSubSection>
</treatment>
</document>