1853 lines
187 KiB
XML
1853 lines
187 KiB
XML
<document id="0A3659DEA2D75D3A11FE2052A0BC1ED4" ID-CLB-Dataset="286381" ID-DOI="10.1016/j.phytochem.2014.08.015" ID-GBIF-Dataset="d09f2b64-5bdc-4aac-865b-39e9240fb571" ID-ISSN="1873-3700" ID-Zenodo-Dep="10491170" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="carolina" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="carolina" IM.taxonomicNames_approvedBy="carolina" IM.treatments_approvedBy="carolina" checkinTime="1704964880250" checkinUser="felipe" docAuthor="Galasso, Silvia, Pacifico, Severina, Kretschmer, Nadine, Pan, San-Po, Marciano, Sabina, Piccolella, Simona, Monaco, Pietro & Bauer, Rudolf" docDate="2014" docId="0012704D7F151C54FF94F8E7FDBCF885" docLanguage="en" docName="Phytochemistry.107.80-90.pdf" docOrigin="Phytochemistry 107" docSource="http://dx.doi.org/10.1016/j.phytochem.2014.08.015" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Thymus longicaulis C. Presl" docType="treatment" docVersion="3" lastPageNumber="87" masterDocId="FC2B08357F141C53FFE6FFE0FFA6FF93" masterDocTitle="Influence of seasonal variation on Thymus longicaulis C. Presl chemical composition and its antioxidant and anti-inflammatory properties" masterLastPageNumber="90" masterPageNumber="80" pageNumber="81" updateTime="1706224061070" updateUser="ExternalLinkService">
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<mods:titleInfo id="B411A142E95C5945C5D34198B8090552">
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<mods:title id="8C99F3D3FCBBFDF4C99D3472CCFEBE48">Influence of seasonal variation on Thymus longicaulis C. Presl chemical composition and its antioxidant and anti-inflammatory properties</mods:title>
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<mods:name id="2F09C5A5D57E12934774E2512694F5EA" type="personal">
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<mods:roleTerm id="26197AA0C7EBF8C162797C13D72BC43C">Author</mods:roleTerm>
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<mods:namePart id="87BDF89C4D83E4A8F1B106FCBA143BE9">Galasso, Silvia</mods:namePart>
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<mods:affiliation id="79A0854925D57F66EB7766F40C01ACE7">Department of Environmental Biological and Pharmaceutical Sciences and Technologies, Second University of Naples, Via Vivaldi 43, I- 81100 Caserta, Italy</mods:affiliation>
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<mods:namePart id="A27C646ED7DF6A7C971311B30B29D154">Pacifico, Severina</mods:namePart>
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<mods:namePart id="E4E63974208DFF9C9E624A9CACD82D1C">Kretschmer, Nadine</mods:namePart>
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<mods:roleTerm id="19629628A3AF50228A91944E1EBE0084">Author</mods:roleTerm>
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<mods:namePart id="A0D81222B2BC7204A71893156B23DE1F">Pan, San-Po</mods:namePart>
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<mods:namePart id="39E7593E512EBFD74C0C239C28FA9EC2">Marciano, Sabina</mods:namePart>
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</mods:name>
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<mods:name id="4ABC3558A2E980D2C608AB51A7C7E9D6" type="personal">
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<mods:roleTerm id="01FB8B959FADE2EC97EF56DF69442B43">Author</mods:roleTerm>
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<mods:namePart id="B3317537E58516904DC1928E7EC5BF83">Piccolella, Simona</mods:namePart>
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<mods:namePart id="883F5FC19C385876CFF203E45C00518B">Monaco, Pietro</mods:namePart>
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<mods:namePart id="42F7B67B8596430B241B61F67DD20240">Bauer, Rudolf</mods:namePart>
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<mods:typeOfResource id="71B5DE4755C1C65D140348826E02D681">text</mods:typeOfResource>
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<mods:title id="4E82C4913BB6B67EA1011F413AA727D6">Phytochemistry</mods:title>
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<mods:part id="0E88223B9C38542D1FB4830B301A12CE">
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<mods:date id="5B2579AA8BEE8C6CEE556F41E436ACC4">2014</mods:date>
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<mods:number id="873505590D799E200740012222CD7EE1">2014-11-30</mods:number>
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<mods:number id="FBA9547A1F7054EDB31EADE13CED6184">107</mods:number>
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<mods:start id="07809FFC2E80F9D5F2D2739FF60C18E8">80</mods:start>
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<mods:end id="125F40CE70A63B8985BAFAF6743517F3">90</mods:end>
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<mods:url id="5374C07F90F599E00CD6D60AC03C5CC8">http://dx.doi.org/10.1016/j.phytochem.2014.08.015</mods:url>
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<mods:classification id="B1D25C136C258884D99BE6256E3EFBF7">journal article</mods:classification>
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<mods:identifier id="648594851C0B36FBC6AD1F5DFE1340CE" type="CLB-Dataset">286381</mods:identifier>
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<mods:identifier id="3FD51CB9654449302E6395972DA10EA3" type="DOI">10.1016/j.phytochem.2014.08.015</mods:identifier>
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<mods:identifier id="CF5AA4B2E8F916816C6E18FD53242EF3" type="GBIF-Dataset">d09f2b64-5bdc-4aac-865b-39e9240fb571</mods:identifier>
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<mods:identifier id="F7878F4BE77B938A16F0B1495EEDF32F" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="9AC3EDA7C3AAD63699C01C6B34EAD51E" type="Zenodo-Dep">10491170</mods:identifier>
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<treatment id="0012704D7F151C54FF94F8E7FDBCF885" ID-DOI="http://doi.org/10.5281/zenodo.10570161" ID-Zenodo-Dep="10570161" LSID="urn:lsid:plazi:treatment:0012704D7F151C54FF94F8E7FDBCF885" httpUri="http://treatment.plazi.org/id/0012704D7F151C54FF94F8E7FDBCF885" lastPageId="7" lastPageNumber="87" pageId="1" pageNumber="81">
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<subSubSection id="C0A192D07F151C52FF94F8E7FD61F888" box="[114,711,1796,1819]" pageId="1" pageNumber="81" type="nomenclature">
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<paragraph id="8804C15B7F151C52FF94F8E7FD61F888" blockId="1.[114,711,1796,1819]" box="[114,711,1796,1819]" pageId="1" pageNumber="81">
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<heading id="D34C76377F151C52FF94F8E7FD61F888" box="[114,711,1796,1819]" fontSize="36" level="2" pageId="1" pageNumber="81" reason="3">
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||
<emphasis id="BACF1D497F151C52FF94F8E7FD61F888" box="[114,711,1796,1819]" italics="true" pageId="1" pageNumber="81">
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||
2.1. ESI MS
|
||
<superScript id="7FCE6C137F151C52FF3BF8E4FF40F882" attach="left" box="[221,230,1796,1809]" fontSize="5" pageId="1" pageNumber="81">n</superScript>
|
||
metabolic profiling of extracts from
|
||
<taxonomicName id="4FBBBAD87F151C52FDACF8E7FD61F888" ID-CoL="56R5N" authorityName="C. Presl" box="[586,711,1799,1819]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="1" pageNumber="81" phylum="Tracheophyta" rank="species" species="longicaulis">T. longicaulis</taxonomicName>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
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||
</subSubSection>
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||
<subSubSection id="C0A192D07F151C54FF77F8A0FCA9FB1C" lastPageId="7" lastPageNumber="87" pageId="1" pageNumber="81" type="description">
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<paragraph id="8804C15B7F151C52FF77F8A0FA7AFEAA" blockId="1.[113,783,1856,2017]" lastBlockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
In order to identify changes in the metabolic profile in wild plants of
|
||
<taxonomicName id="4FBBBAD87F151C52FF33F8BBFEFFF8FC" authority=", LC" authorityName="LC" box="[213,345,1883,1903]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="1" pageNumber="81" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F151C52FF33F8BBFEF3F8FC" box="[213,341,1883,1903]" italics="true" pageId="1" pageNumber="81">T. longicaulis</emphasis>
|
||
,
|
||
</taxonomicName>
|
||
LC–ESI-MS/MS analyses of hydroalcoholic extracts (Jul12, Oct12, Jan13, Apr13), prepared by the maceration accelerated with ultrasound of leaf samples of herbaceous species collected at different stages of its life cycle, were carried out. The maceration in H
|
||
<subScript id="143FC31E7F151C52FEFEF835FE87F872" attach="both" box="[280,289,2005,2017]" fontSize="5" pageId="1" pageNumber="81">2</subScript>
|
||
O:MeOH (1:1, v:v) facilitated the preparation of extracts in which polyphenols are abundant. Polyphenols are molecules highly biosynthesized in plants in which exercise primarily a defensive role against the overproduction of reactive oxygen species induced by abiotic stresses (
|
||
<bibRefCitation id="EC2ABCAA7F151C52FB4DFEEAFCD7FEAA" author="Gholizadeh, A. & Kohnehrouz, B. B." pageId="1" pageNumber="81" pagination="217 - 223" refId="ref12031" refString="Gholizadeh, A., Kohnehrouz, B. B., 2010. Activation of phenylalanine ammonia lyase as a key component of the antioxidative system of salt-challenged maize leaves. Braz. J. Plant Physiol. 22, 217 - 223." type="journal article" year="2010">Gholizadeh and Kohnehrouz, 2010</bibRefCitation>
|
||
). The metabolites identified are reported in
|
||
<figureCitation id="1080DDDE7F151C52FACCFEC6FAF9FEAA" box="[1322,1375,294,313]" captionStart="Fig" captionStartId="2.[515,541,1004,1018]" captionTargetBox="[115,1474,183,993]" captionTargetId="graphics-417@2.[794,976,492,630]" captionText="Fig. 1. Main metabolites identified in Thymus longicaulis extracts." figureDoi="http://doi.org/10.5281/zenodo.10570159" httpUri="https://zenodo.org/record/10570159/files/figure.png" pageId="1" pageNumber="81">Fig. 1</figureCitation>
|
||
and
|
||
<tableCitation id="C539F4E07F151C52FA69FEC6FA71FEAA" box="[1423,1495,294,313]" captionStart="Table 1" captionStartId="2.[87,131,1048,1062]" captionTargetPageId="2" captionText="Table 1 LC-MS/MS data of the main constituents of Thymus longicaulis extracts (Jul12, Oct12, Jan13, Apr13)." httpUri="http://table.plazi.org/id/DCC491D37F161C51FFB1FBF8FCD6FBAE" pageId="1" pageNumber="81" tableUuid="DCC491D37F161C51FFB1FBF8FCD6FBAE">Table 1</tableCitation>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FEA2FBB3FE57" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
Compound
|
||
<emphasis id="BACF1D497F151C52FC37FEA2FC78FEC6" bold="true" box="[977,990,322,341]" pageId="1" pageNumber="81">1</emphasis>
|
||
, was identified based on its fragmentation pattern, as quinic acid. In fact, the MS
|
||
<superScript id="7FCE6C137F151C52FB8EFEBAFBD7FEF5" attach="left" box="[1128,1137,346,358]" fontSize="5" pageId="1" pageNumber="81">2</superScript>
|
||
spectrum of the [M
|
||
<emphasis id="BACF1D497F151C52FADAFEBEFAEBFEE3" box="[1340,1357,350,368]" italics="true" pageId="1" pageNumber="81">—</emphasis>
|
||
H]
|
||
<emphasis id="BACF1D497F151C52FA83FEBAFAD7FEF5" box="[1381,1393,346,358]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FA83FEBAFAD7FEF5" attach="left" box="[1381,1393,346,358]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F151C52FA5FFEBDFA7BFEE2" box="[1465,1501,349,369]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
191 showed the ion at
|
||
<emphasis id="BACF1D497F151C52FBCCFE98FBE8FE1F" box="[1066,1102,376,396]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
173, resulting from the dehydration of the deprotonated molecular ion and the fragment ions at
|
||
<emphasis id="BACF1D497F151C52FA6DFE74FA09FE3B" box="[1419,1455,404,424]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
127 and 111 (
|
||
<bibRefCitation id="EC2ABCAA7F151C52FC47FE51FBAEFE57" author="Oen, H." box="[929,1032,433,452]" pageId="1" pageNumber="81" pagination="145 - 152" refId="ref13043" refString="Oen, H., 1985. Detection of non-volatile acids in sweet cherry fruits. Acta Agric. Scand. 35, 145 - 152." type="journal article" year="1985">Oen, 1985</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FE2DFA03FD1B" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
Compound
|
||
<emphasis id="BACF1D497F151C52FC31FE2DFC42FE73" bold="true" box="[983,996,461,480]" pageId="1" pageNumber="81">2</emphasis>
|
||
, eluted with a retention time of 1.52 min, was putatively identified as stachyose (Galoi1–6Galoi1–6Glcoi1–2Fru). The mass spectrum showed a peak at
|
||
<emphasis id="BACF1D497F151C52FB2EFDE4FB4AFD8B" box="[1224,1260,516,536]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
701, due to the adduct with chloride, [M+Cl]
|
||
<emphasis id="BACF1D497F151C52FBF2FDFDFB86FDBA" box="[1044,1056,541,553]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FBF2FDFDFB86FDBA" attach="none" box="[1044,1056,541,553]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
, whose fragmentation generated the deprotonated molecular ion at
|
||
<emphasis id="BACF1D497F151C52FBA7FDDCFBC3FDC3" box="[1089,1125,572,592]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
665 and a chlorinated adduct at
|
||
<emphasis id="BACF1D497F151C52FA5FFDDCFA7BFDC3" box="[1465,1501,572,592]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
539 formed by neutral loss of a fructose residue (162 Da) from the corresponding precursor [M+Cl]
|
||
<emphasis id="BACF1D497F151C52FB4FFD91FB13FDEE" box="[1193,1205,625,637]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FB4FFD91FB13FDEE" attach="left" box="[1193,1205,625,637]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F151C52FB23FD95FA31FD1B" author="Guan, B. & Cole, R. B." box="[1221,1431,629,648]" pageId="1" pageNumber="81" pagination="1119 - 1131" refId="ref12195" refString="Guan, B., Cole, R. B., 2008. MALDI linear-field reflectron TOF post-source decay analysis of underivatized oligosaccharides: determination of glycosidic linkages and anomeric configurations using anion attachment. J. Am. Soc. Mass Spectrom. 19, 1119 - 1131." type="journal article" year="2008">Guan and Cole, 2008</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FD71FB97FCF4" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
The metabolite
|
||
<emphasis id="BACF1D497F151C52FBE4FD70FBA9FD30" bold="true" box="[1026,1039,656,675]" pageId="1" pageNumber="81">3</emphasis>
|
||
, identified in the samples from July (Jul12), January (Jan13) and April (Apr13), was putatively identified as 12-hydroxyjasmonic acid hexoside (tuberonic acid), a molecule previously isolated from the leaves of
|
||
<taxonomicName id="4FBBBAD87F151C52FB22FD03FAD5FD64" box="[1220,1395,739,759]" class="Magnoliopsida" family="Lamiaceae" genus="Origanum" kingdom="Plantae" order="Lamiales" pageId="1" pageNumber="81" phylum="Tracheophyta" rank="species" species="vulgare">
|
||
<emphasis id="BACF1D497F151C52FB22FD03FAD5FD64" box="[1220,1395,739,759]" italics="true" pageId="1" pageNumber="81">Origanum vulgare</emphasis>
|
||
</taxonomicName>
|
||
and other
|
||
<taxonomicName id="4FBBBAD87F151C52FCD9FD1FFC18FC87" box="[831,958,767,788]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="1" pageNumber="81" phylum="Tracheophyta" rank="species" species="undetermined">
|
||
<emphasis id="BACF1D497F151C52FCD9FD1FFC2CFC80" box="[831,906,767,787]" italics="true" pageId="1" pageNumber="81">Thymus</emphasis>
|
||
spp.
|
||
</taxonomicName>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F151C52FC29FCE0FB6DFC80" author="Koukoulitsa, C. & Karioti, A. & Bergonzi, M. C. & Pescitelli, G. & Di Bari, L. & Skaltsa, H." box="[975,1227,768,788]" pageId="1" pageNumber="81" pagination="5388 - 5392" refId="ref12743" refString="Koukoulitsa, C., Karioti, A., Bergonzi, M. C., Pescitelli, G., Di Bari, L., Skaltsa, H., 2006. Polar constituents from the aerial parts of Origanum vulgare L. ssp. hirtum growing wild in Greece. J. Agric. Food Chem. 54, 5388 - 5392." type="journal article" year="2006">Koukoulitsa et al., 2006</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="EC2ABCAA7F151C52FB3FFCE0FA06FC80" author="Pereira, O. & Peres, A. & Silva, A. & Domingues, M. & Cardoso, S." box="[1241,1440,768,788]" pageId="1" pageNumber="81" pagination="1773 - 1780" refId="ref13262" refString="Pereira, O., Peres, A., Silva, A., Domingues, M., Cardoso, S., 2013. Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC - UV and ESI-MS combined method. Food Res. Int. 54, 1773 - 1780." type="journal article" year="2013">Pereira et al., 2013</bibRefCitation>
|
||
). The mass spectrum showed the [M–H]
|
||
<emphasis id="BACF1D497F151C52FB7EFCF8FB02FCB7" box="[1176,1188,792,804]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FB7EFCF8FB02FCB7" attach="left" box="[1176,1188,792,804]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F151C52FB0CFCFBFAABFCBC" box="[1258,1293,795,815]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
387 which provided the ion at
|
||
<emphasis id="BACF1D497F151C52FC40FCD7FC6FFCD8" box="[934,969,823,843]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
207 as base peak. This latter, due to CO
|
||
<subScript id="143FC31E7F151C52FABCFCA1FAC5FCDE" attach="left" box="[1370,1379,833,845]" fontSize="5" pageId="1" pageNumber="81">2</subScript>
|
||
loss, generated the ion at
|
||
<emphasis id="BACF1D497F151C52FC3DFCB3FC59FCF4" box="[987,1023,851,871]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
163.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FC90FAA6FB42" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
MS
|
||
<superScript id="7FCE6C137F151C52FC98FC8CFC2EFCEB" attach="left" box="[894,904,876,888]" fontSize="5" pageId="1" pageNumber="81">n</superScript>
|
||
spectra of compound
|
||
<emphasis id="BACF1D497F151C52FB8DFC90FBDEFC10" bold="true" box="[1131,1144,880,899]" pageId="1" pageNumber="81">4</emphasis>
|
||
were in accordance with the presence of a
|
||
<emphasis id="BACF1D497F151C52FC41FC6AFC71FC0D" box="[935,983,906,927]" italics="true" pageId="1" pageNumber="81">bis -C</emphasis>
|
||
-glycosylated flavone. The MS spectrum exhibited the deprotonated molecule at
|
||
<emphasis id="BACF1D497F151C52FB90FC46FB3CFC29" box="[1142,1178,934,954]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
593, which produced MS
|
||
<superScript id="7FCE6C137F151C52FA47FC43FA0CFC3C" attach="left" box="[1441,1450,931,943]" fontSize="5" pageId="1" pageNumber="81">2</superScript>
|
||
ions at
|
||
<emphasis id="BACF1D497F151C52FCBFFC22FCDBFC45" box="[857,893,962,982]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
473 [M–H-120]
|
||
<emphasis id="BACF1D497F151C52FBC7FC20FB8BFC5F" box="[1057,1069,960,972]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FBC7FC20FB8BFC5F" attach="left" box="[1057,1069,960,972]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
(base peak;
|
||
<bibRefCitation id="EC2ABCAA7F151C52FB56FC24FAF6FC45" author="Han, J. & Ye, M. & Qiao, X. & Xu, M. & Wang, B. - R. & Guo, D. - A." box="[1200,1360,963,983]" pageId="1" pageNumber="81" pagination="516 - 525" refId="ref12293" refString="Han, J., Ye, M., Qiao, X., Xu, M., Wang, B. - R., Guo, D. - A., 2008. Characterization of phenolic compounds in the chinese herbal drug Artemisia annua by liquid chromatography coupled to electrospray ionization mass spectrometry. J. Pharm. Biomed. Anal. 47, 516 - 525." type="journal article" year="2008">Han et al., 2008</bibRefCitation>
|
||
) and
|
||
<emphasis id="BACF1D497F151C52FA6AFC22FA09FC45" box="[1420,1455,962,982]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
341 and 311. The loss of 120 Da allowed us to hypothesize the presence of a hexose residue linked by C-C bond to apigenin (341 = [aglycone+71]
|
||
<emphasis id="BACF1D497F151C52FC7DFBF3FC01FB8C" box="[923,935,1043,1055]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FC7DFBF3FC01FB8C" attach="none" box="[923,935,1043,1055]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
; 311 [aglycone+41]
|
||
<emphasis id="BACF1D497F151C52FB9CFBF3FB20FB8C" box="[1146,1158,1043,1055]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FB9CFBF3FB20FB8C" attach="none" box="[1146,1158,1043,1055]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
). Further collision of the ion at
|
||
<emphasis id="BACF1D497F151C52FCD9FBD2FCC5FBD5" box="[831,867,1074,1094]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
473 yielded
|
||
<emphasis id="BACF1D497F151C52FC0CFBD2FBA8FBD5" box="[1002,1038,1074,1094]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
353 (loss of 120 Da) indicating the presence of a second
|
||
<emphasis id="BACF1D497F151C52FC5CFBAEFC60FBF1" box="[954,966,1102,1122]" italics="true" pageId="1" pageNumber="81">C</emphasis>
|
||
-hexosyl moiety. The fragment ion at
|
||
<emphasis id="BACF1D497F151C52FAAFFBAEFACBFBF1" box="[1353,1389,1102,1122]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
383 [aglycone+113] allowed us to confirm the aglycone identity (
|
||
<bibRefCitation id="EC2ABCAA7F151C52FA6DFB8BFC14FB09" author="Ferreres, F. & Silva, B. M. & Andrade, P. B. & Seabra, R. M. & Ferreira, M. A." pageId="1" pageNumber="81" pagination="352 - 359" refId="ref11896" refString="Ferreres, F., Silva, B. M., Andrade, P. B., Seabra, R. M., Ferreira, M. A., 2003. Approach to the study of C - glycosyl flavones by ion trap HPLC-PAD-ESI / MS / MS: application to seeds of quince (Cydonia oblonga). Phytochem. Anal. 14, 352 - 359." type="journal article" year="2003">Ferreres et al., 2003</bibRefCitation>
|
||
). As
|
||
<emphasis id="BACF1D497F151C52FC0FFB66FC53FB09" box="[1001,1013,1158,1178]" italics="true" pageId="1" pageNumber="81">C</emphasis>
|
||
-linked saccharide residues were found only in the C-6 and/or C-8 positions of flavone skeletons, compound
|
||
<emphasis id="BACF1D497F151C52FA29FB42FA7AFB26" bold="true" box="[1487,1500,1186,1205]" pageId="1" pageNumber="81">4</emphasis>
|
||
was assigned as apigenin-6,8-di-
|
||
<emphasis id="BACF1D497F151C52FB6DFB5DFB31FB42" box="[1163,1175,1213,1233]" italics="true" pageId="1" pageNumber="81">C</emphasis>
|
||
-hexoside.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FB3AFA92FACE" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
The mass spectrum of the metabolite
|
||
<emphasis id="BACF1D497F151C52FB30FB3AFB45FB7E" bold="true" box="[1238,1251,1242,1261]" pageId="1" pageNumber="81">5</emphasis>
|
||
is in agreement with the presence of pinoresinol dihexoside (
|
||
<bibRefCitation id="EC2ABCAA7F151C52FB35FB16FA3CFA9A" author="Eyles, A. & Jones, W. & Riedl, K. & Herms, D. A. & Cipollini, D. & Schwartz, S. & Chan, K. & Bonello, P." box="[1235,1434,1270,1290]" pageId="1" pageNumber="81" pagination="1430 - 1448" refId="ref11732" refString="Eyles, A., Jones, W., Riedl, K., Herms, D. A., Cipollini, D., Schwartz, S., Chan, K., Bonello, P., 2007. Comparative phloem chemistry of manchurian (F. mandshurica) and two north american ash species (F. americana and F. pennsylvanica). J. Chem. Ecol. 33, 1430 - 1448." type="journal article" year="2007">Eyles et al., 2007</bibRefCitation>
|
||
). The fragmentation of the deprotonated molecular ion [M–H]
|
||
<emphasis id="BACF1D497F151C52FA61FAEEFA35FA89" box="[1415,1427,1294,1306]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FA61FAEEFA35FA89" attach="left" box="[1415,1427,1294,1306]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="BACF1D497F151C52FA5FFAF1FA7BFAB6" box="[1465,1501,1297,1317]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
681 led to the formation of fragment ions at
|
||
<emphasis id="BACF1D497F151C52FAEBFACDFA97FAD2" box="[1293,1329,1325,1345]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
519 and 357 for subsequent loss of two hexose residues (162 Da).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8FA86FC14F9CB" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
Compound
|
||
<emphasis id="BACF1D497F151C52FC37FA86FC78FAEA" bold="true" box="[977,990,1382,1401]" pageId="1" pageNumber="81">6</emphasis>
|
||
showed the [M–H]
|
||
<emphasis id="BACF1D497F151C52FB78FA82FB0CFAFD" box="[1182,1194,1378,1390]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FB78FA82FB0CFAFD" attach="left" box="[1182,1194,1378,1390]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F151C52FB0BFA85FAB7FAEA" box="[1261,1297,1381,1401]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
693. Typical neutral losses of hexose moieties bound to a phenolic oxygen atoms as 162 Da (
|
||
<bibRefCitation id="EC2ABCAA7F151C52FC73FA7EFB9DFA22" author="Ricci, A. & Fiorentino, A. & Piccolella, S. & D'Abrosca, B. & Pacifico, S. & Monaco, P." box="[917,1083,1438,1457]" pageId="1" pageNumber="81" pagination="979 - 985" refId="ref13357" refString="Ricci, A., Fiorentino, A., Piccolella, S., D'Abrosca, B., Pacifico, S., Monaco, P., 2010. Structural discrimination of isomeric tetrahydrofuran lignan glycosides by tandem mass spectrometry. Rapid Commun. Mass Spectrom. 24, 979 - 985." type="journal article" year="2010">Ricci et al., 2010</bibRefCitation>
|
||
) provided MS
|
||
<superScript id="7FCE6C137F151C52FB2AFA7AFB73FA35" attach="left" box="[1228,1237,1434,1446]" fontSize="5" pageId="1" pageNumber="81">2</superScript>
|
||
fragment ions at
|
||
<emphasis id="BACF1D497F151C52FA6DFA7CFA09FA23" box="[1419,1455,1436,1456]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
521 and 359. This latter provided, besides others, the fragment ion at
|
||
<emphasis id="BACF1D497F151C52FCD9FA34FCC5FA7B" box="[831,867,1492,1512]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
329 according to the loss of 30 Da, reasonably
|
||
<collectingCountry id="F0AC81CB7F151C52FABBFA35FADCFA7B" box="[1373,1402,1493,1512]" name="Switzerland" pageId="1" pageNumber="81">CH</collectingCountry>
|
||
<subScript id="143FC31E7F151C52FA9CFA3EFA25FA79" attach="both" box="[1402,1411,1502,1514]" fontSize="5" pageId="1" pageNumber="81">2</subScript>
|
||
O. These findings, in line with
|
||
<bibRefCitation id="EC2ABCAA7F151C52FBF4FA11FABFF997" author="Ricci, A. & Piccolella, S." box="[1042,1305,1521,1540]" pageId="1" pageNumber="81" refId="ref13413" refString="Ricci, A., Piccolella, S., 2012. From the collisionally induced dissociation to the enzyme-mediated reactions: the electron flux within the lignan furanic ring. In: Tandem Mass Spectrometry - Applications and Principles, Dr Jeevan Prasain (Ed.)." type="book" year="2012">Ricci and Piccolella (2012)</bibRefCitation>
|
||
which investigated the fragmentation mechanisms of furofuranic (FUR) and tetrahydrofuranic (THF) lignans, were in accordance with lariciresinol dihexoside.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F151C52FCB8F981FA7BF84C" blockId="1.[831,1501,182,2015]" pageId="1" pageNumber="81">
|
||
Compounds
|
||
<emphasis id="BACF1D497F151C52FC3AF981FC4FF9E7" bold="true" box="[988,1001,1633,1652]" pageId="1" pageNumber="81">8</emphasis>
|
||
and
|
||
<emphasis id="BACF1D497F151C52FBFAF981FB93F9E7" bold="true" box="[1052,1077,1633,1652]" pageId="1" pageNumber="81">12</emphasis>
|
||
were putatively identified on the basis of their fragmentation pattern and relative retention times, as rosmarinic acid (
|
||
<emphasis id="BACF1D497F151C52FC2EF979FC47F93F" bold="true" box="[968,993,1689,1708]" pageId="1" pageNumber="81">12</emphasis>
|
||
) and its hexosyl (
|
||
<emphasis id="BACF1D497F151C52FB74F979FB39F93F" bold="true" box="[1170,1183,1689,1708]" pageId="1" pageNumber="81">8</emphasis>
|
||
) derivative. The mass spectrum of the metabolite
|
||
<emphasis id="BACF1D497F151C52FC13F954FBA8F954" bold="true" box="[1013,1038,1716,1735]" pageId="1" pageNumber="81">12</emphasis>
|
||
showed the [M–H]
|
||
<emphasis id="BACF1D497F151C52FB32F951FB46F92E" box="[1236,1248,1713,1725]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FB32F951FB46F92E" attach="left" box="[1236,1248,1713,1725]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F151C52FACCF953FAE8F954" box="[1322,1358,1715,1735]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
359. The MS
|
||
<superScript id="7FCE6C137F151C52FA35F951FA7AF92E" attach="left" box="[1491,1500,1713,1725]" fontSize="5" pageId="1" pageNumber="81">2</superScript>
|
||
spectrum of the precursor ion showed fragment ions at
|
||
<emphasis id="BACF1D497F151C52FA6CF92FFA08F970" box="[1418,1454,1743,1763]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
223 (due to the loss of a 3,4-dihydroxy vinylbenzene),
|
||
<emphasis id="BACF1D497F151C52FAA4F90BFAC0F96C" box="[1346,1382,1771,1791]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
197, corresponding to oi- hydroxyhydrocaffeoyl moiety, and at
|
||
<emphasis id="BACF1D497F151C52FAB0F8E7FADCF888" box="[1366,1402,1799,1819]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
179 [caffeic acid-H]
|
||
<emphasis id="BACF1D497F151C52FC53F8C1FC67F8BE" box="[949,961,1825,1837]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FC53F8C1FC67F8BE" attach="right" box="[949,961,1825,1837]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
. The fragmentation of the ion at
|
||
<emphasis id="BACF1D497F151C52FAFCF8C3FA9BF8A4" box="[1306,1341,1827,1847]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
197 generated, in the MS
|
||
<superScript id="7FCE6C137F151C52FC78F8DCFC01F8DB" attach="left" box="[926,935,1852,1864]" fontSize="5" pageId="1" pageNumber="81">3</superScript>
|
||
experiment, a fragment ion [M–H]
|
||
<emphasis id="BACF1D497F151C52FAE2F8DCFAB6F8DB" box="[1284,1296,1852,1864]" italics="true" pageId="1" pageNumber="81">
|
||
<superScript id="7FCE6C137F151C52FAE2F8DCFAB6F8DB" attach="left" box="[1284,1296,1852,1864]" fontSize="5" pageId="1" pageNumber="81">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="BACF1D497F151C52FAC8F8DFFAF4F8C0" box="[1326,1362,1855,1875]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
521 provided for the compound
|
||
<emphasis id="BACF1D497F151C52FC1EF8BCFBA3F8FC" bold="true" box="[1016,1029,1884,1903]" pageId="1" pageNumber="81">8</emphasis>
|
||
the ion at
|
||
<emphasis id="BACF1D497F151C52FB89F8BBFB35F8FC" box="[1135,1171,1883,1903]" italics="true" pageId="1" pageNumber="81">m/z</emphasis>
|
||
359 (rosmarinic acid), leaving to assume the presence of a hexosyl derivative of the metabolite
|
||
<emphasis id="BACF1D497F151C52FA5BF898FA70F818" bold="true" box="[1469,1494,1912,1931]" pageId="1" pageNumber="81">12</emphasis>
|
||
. The glycosylation could take place on of the aromatic unit of the oi- hydroxyhydrocaffeoyl moiety since it was recently observed that the bond of the hexose to the caffeic moiety provides a fragment at
|
||
</paragraph>
|
||
<caption id="DCC491D37F161C51FDE5FC0CFBBEFC68" ID-DOI="http://doi.org/10.5281/zenodo.10570159" ID-Zenodo-Dep="10570159" box="[515,1048,1004,1019]" httpUri="https://zenodo.org/record/10570159/files/figure.png" pageId="2" pageNumber="82" startId="2.[515,541,1004,1018]" targetBox="[115,1474,183,993]" targetPageId="2" targetType="figure">
|
||
<paragraph id="8804C15B7F161C51FDE5FC0CFBBEFC68" blockId="2.[515,1048,1004,1019]" box="[515,1048,1004,1019]" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FDE5FC0CFD93FC69" bold="true" box="[515,565,1004,1018]" pageId="2" pageNumber="82">Fig. 1.</emphasis>
|
||
Main metabolites identified in
|
||
<taxonomicName id="4FBBBAD87F161C51FCDFFC0CFC6BFC68" box="[825,973,1004,1019]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="2" pageNumber="82" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F161C51FCDFFC0CFC6BFC68" box="[825,973,1004,1019]" italics="true" pageId="2" pageNumber="82">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DCC491D37F161C51FFB1FBF8FCD6FBAE" ID-Table-UUID="DCC491D37F161C51FFB1FBF8FCD6FBAE" httpUri="http://table.plazi.org/id/DCC491D37F161C51FFB1FBF8FCD6FBAE" pageId="2" pageNumber="82" startId="2.[87,131,1048,1062]" targetBox="[110,1451,1104,1911]" targetIsTable="true" targetPageId="2" targetType="table">
|
||
<paragraph id="8804C15B7F161C51FFB1FBF8FF35FBB5" blockId="2.[87,880,1048,1085]" box="[87,147,1048,1062]" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FFB1FBF8FF35FBB5" bold="true" box="[87,147,1048,1062]" pageId="2" pageNumber="82">Table 1</emphasis>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F161C51FFB1FBCFFCD6FBAE" blockId="2.[87,880,1048,1085]" box="[87,880,1070,1085]" pageId="2" pageNumber="82">
|
||
LC-MS/MS data of the main constituents of
|
||
<taxonomicName id="4FBBBAD87F161C51FE55FBCEFDE5FBAE" box="[435,579,1070,1085]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="2" pageNumber="82" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F161C51FE55FBCEFDE5FBAE" box="[435,579,1070,1085]" italics="true" pageId="2" pageNumber="82">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts (Jul12, Oct12, Jan13, Apr13).
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F161C51FF88FBB5FD45F8E5" pageId="2" pageNumber="82">
|
||
<table id="FABB33FB7F16E3ACFF88FBB0FA0DF8E4" box="[110,1451,1104,1911]" gridcols="10" gridrows="35" pageId="2" pageNumber="82">
|
||
<tr id="368BC3197F16E3ACFF88FBB0FA0DFBF7" box="[110,1451,1104,1124]" gridrow="0" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88FBB0FF32FBF7" box="[110,148,1104,1124]" gridcol="0" gridrow="0" pageId="2" pageNumber="82">Peak</th>
|
||
<th id="755AAA657F16E3ACFF4CFBB0FF71FBF7" box="[170,215,1104,1124]" gridcol="1" gridrow="0" pageId="2" pageNumber="82">RT</th>
|
||
<th id="755AAA657F16E3ACFF08FBB0FEF0FBF7" box="[238,342,1104,1124]" gridcol="2" gridrow="0" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FF08FBB4FF51FBF0" box="[238,247,1108,1123]" italics="true" pageId="2" pageNumber="82">λ</emphasis>
|
||
max (nm)
|
||
</th>
|
||
<th id="755AAA657F16E3ACFE8AFBB0FE08FBF7" box="[364,430,1104,1124]" gridcol="3" gridrow="0" pageId="2" pageNumber="82">
|
||
[M
|
||
<emphasis id="BACF1D497F161C51FE65FBB5FE36FBF0" box="[387,400,1109,1123]" italics="true" pageId="2" pageNumber="82">—</emphasis>
|
||
H]
|
||
<emphasis id="BACF1D497F161C51FE42FBB1FE08FBC9" box="[420,430,1105,1114]" italics="true" pageId="2" pageNumber="82">—</emphasis>
|
||
</th>
|
||
<th id="755AAA657F16E3ACFE23FBB0FC25FBF7" box="[453,899,1104,1124]" gridcol="4" gridrow="0" pageId="2" pageNumber="82">
|
||
MS
|
||
<emphasis id="BACF1D497F161C51FE38FBB0FE43FBC8" box="[478,485,1104,1115]" italics="true" pageId="2" pageNumber="82">n</emphasis>
|
||
</th>
|
||
<th id="755AAA657F16E3ACFC7CFBB0FB35FBF7" box="[922,1171,1104,1124]" gridcol="5" gridrow="0" pageId="2" pageNumber="82">Tentative assignment</th>
|
||
<th id="755AAA657F16E3ACFB49FBB0FB7FFBF7" box="[1199,1241,1104,1124]" gridcol="6" gridrow="0" pageId="2" pageNumber="82">Jul12</th>
|
||
<th id="755AAA657F16E3ACFB09FBB0FAB9FBF7" box="[1263,1311,1104,1124]" gridcol="7" gridrow="0" pageId="2" pageNumber="82">Oct12</th>
|
||
<th id="755AAA657F16E3ACFAD0FBB0FAC2FBF7" box="[1334,1380,1104,1124]" gridcol="8" gridrow="0" pageId="2" pageNumber="82">Jan13</th>
|
||
<th id="755AAA657F16E3ACFA9CFBB0FA0DFBF7" box="[1402,1451,1104,1124]" gridcol="9" gridrow="0" pageId="2" pageNumber="82">Apr13</th>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB8CFA0DFBE9" box="[110,1451,1132,1146]" gridrow="1" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88FB8CFA0DFBE9" box="[110,1451,1132,1146]" colspan="10" colspanRight="9" gridcol="0" gridrow="1" pageId="2" pageNumber="82">(min)</th>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB6DFA0DFB0F" box="[110,1451,1165,1180]" gridrow="2" pageId="2" pageNumber="82" rowspan-8="1">
|
||
<th id="755AAA657F16E3ACFF88FB6DFF32FB0F" box="[110,148,1165,1180]" gridcol="0" gridrow="2" pageId="2" pageNumber="82">1</th>
|
||
<td id="755AAA657F16E3ACFF4CFB6DFF71FB0F" box="[170,215,1165,1180]" gridcol="1" gridrow="2" pageId="2" pageNumber="82">1.50</td>
|
||
<td id="755AAA657F16E3ACFF08FB6DFEF0FB0F" box="[238,342,1165,1180]" gridcol="2" gridrow="2" pageId="2" pageNumber="82">209</td>
|
||
<td id="755AAA657F16E3ACFE8AFB6DFE08FB0F" box="[364,430,1165,1180]" gridcol="3" gridrow="2" pageId="2" pageNumber="82">191</td>
|
||
<td id="755AAA657F16E3ACFE23FB6DFC25FB0F" box="[453,899,1165,1180]" gridcol="4" gridrow="2" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FB6DFE56FB08" bold="true" box="[453,496,1165,1179]" pageId="2" pageNumber="82">173 (</emphasis>
|
||
<emphasis id="BACF1D497F161C51FE09FB6EFDA6FB0F" box="[495,512,1166,1180]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
93);
|
||
<emphasis id="BACF1D497F161C51FDC1FB6DFDE0FB08" bold="true" box="[551,582,1165,1179]" pageId="2" pageNumber="82">127</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FDB4FB6EFDC5FB0F" box="[594,611,1166,1180]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
109;99;85;83;81);
|
||
<emphasis id="BACF1D497F161C51FD18FB6DFCBBFB08" bold="true" box="[766,797,1165,1179]" pageId="2" pageNumber="82">111</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFB6DFB35FB0F" box="[922,1171,1165,1180]" gridcol="5" gridrow="2" pageId="2" pageNumber="82">Quinic acid</td>
|
||
<td id="755AAA657F16E3ACFB49FB6DFB7FFB0F" box="[1199,1241,1165,1180]" gridcol="6" gridrow="2" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09FB6DFAB9FB0F" box="[1263,1311,1165,1180]" gridcol="7" gridrow="2" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFB6DFA0DFB0F" box="[1402,1451,1165,1180]" gridcol="9" gridrow="2" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB44FA0DFB20" box="[110,1451,1188,1203]" gridrow="3" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FB44FC25FB20" box="[453,899,1188,1203]" gridcol="4" gridrow="3" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFB45FE7AFB20" box="[459,476,1189,1203]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
96;93;81;67)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB5BFA0DFB59" box="[110,1451,1211,1226]" gridrow="4" pageId="2" pageNumber="82" rowspan-7="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88FB5BFF32FB59" box="[110,148,1211,1226]" gridcol="0" gridrow="4" pageId="2" pageNumber="82">2</th>
|
||
<td id="755AAA657F16E3ACFF4CFB5BFF71FB59" box="[170,215,1211,1226]" gridcol="1" gridrow="4" pageId="2" pageNumber="82">1.52</td>
|
||
<td id="755AAA657F16E3ACFF08FB5BFEF0FB59" box="[238,342,1211,1226]" gridcol="2" gridrow="4" pageId="2" pageNumber="82">338;346</td>
|
||
<td id="755AAA657F16E3ACFE8AFB5BFE08FB59" box="[364,430,1211,1226]" gridcol="3" gridrow="4" pageId="2" pageNumber="82">701</td>
|
||
<td id="755AAA657F16E3ACFE23FB5BFC25FB59" box="[453,899,1211,1226]" gridcol="4" gridrow="4" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FB5BFE42FB5A" bold="true" box="[453,484,1211,1225]" pageId="2" pageNumber="82">665</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FB5CFDA6FB59" box="[495,512,1212,1226]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
485;443;383;341;323;321;221;203;179);
|
||
<emphasis id="BACF1D497F161C51FCB1FB5BFCD0FB5A" bold="true" box="[855,886,1211,1225]" pageId="2" pageNumber="82">539</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFB5BFB35FB59" box="[922,1171,1211,1226]" gridcol="5" gridrow="4" pageId="2" pageNumber="82">Stachyose</td>
|
||
<td id="755AAA657F16E3ACFB49FB5BFB7FFB59" box="[1199,1241,1211,1226]" gridcol="6" gridrow="4" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FB5BFAC2FB59" box="[1334,1380,1211,1226]" gridcol="8" gridrow="4" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB32FA0DFB73" box="[110,1451,1234,1248]" gridrow="5" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FB32FC25FB73" box="[453,899,1234,1248]" gridcol="4" gridrow="5" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFB32FE7AFB73" box="[459,476,1234,1248]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
521;507;489;373;359;341;327;285;197;183;143)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB09FA0DFB64" box="[110,1451,1257,1271]" gridrow="6" pageId="2" pageNumber="82" rowspan-7="1">
|
||
<th id="755AAA657F16E3ACFF88FB09FF32FB64" box="[110,148,1257,1271]" gridcol="0" gridrow="6" pageId="2" pageNumber="82">3</th>
|
||
<td id="755AAA657F16E3ACFF4CFB09FF71FB64" box="[170,215,1257,1271]" gridcol="1" gridrow="6" pageId="2" pageNumber="82">10.7</td>
|
||
<td id="755AAA657F16E3ACFF08FB09FEF0FB64" box="[238,342,1257,1271]" gridcol="2" gridrow="6" pageId="2" pageNumber="82">229</td>
|
||
<td id="755AAA657F16E3ACFE8AFB09FE08FB64" box="[364,430,1257,1271]" gridcol="3" gridrow="6" pageId="2" pageNumber="82">387</td>
|
||
<td id="755AAA657F16E3ACFE23FB09FC25FB64" box="[453,899,1257,1271]" gridcol="4" gridrow="6" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FB09FE42FB64" bold="true" box="[453,484,1257,1271]" pageId="2" pageNumber="82">369</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FB09FDA6FB64" box="[495,512,1257,1271]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
207;163);
|
||
<emphasis id="BACF1D497F161C51FDB0FB09FDD3FB64" bold="true" box="[598,629,1257,1271]" pageId="2" pageNumber="82">207</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD67FB09FD34FB64" box="[641,658,1257,1271]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
189;163;145;109;81);
|
||
<emphasis id="BACF1D497F161C51FCAAFB09FCCDFB64" bold="true" box="[844,875,1257,1271]" pageId="2" pageNumber="82">163</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFB09FB35FB64" box="[922,1171,1257,1271]" gridcol="5" gridrow="6" pageId="2" pageNumber="82">12-Hydroxyjasmonic acid</td>
|
||
<td id="755AAA657F16E3ACFB49FB09FB7FFB64" box="[1199,1241,1257,1271]" gridcol="6" gridrow="6" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FB09FAC2FB64" box="[1334,1380,1257,1271]" gridcol="8" gridrow="6" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFB09FA0DFB64" box="[1402,1451,1257,1271]" gridcol="9" gridrow="6" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FB1EFA0DFA9D" box="[110,1451,1278,1294]" gridrow="7" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FB1EFC25FA9D" box="[453,899,1278,1294]" gridcol="4" gridrow="7" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFAE0FE7AFA9D" box="[459,476,1280,1294]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
145;135;109;107;95;81)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFB1EFB35FA9D" box="[922,1171,1278,1294]" gridcol="5" gridrow="7" pageId="2" pageNumber="82">
|
||
12-
|
||
<emphasis id="BACF1D497F161C51FC50FB1EFC64FA9D" box="[950,962,1278,1294]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexoside
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FAF5FA0DFAB6" box="[110,1451,1301,1317]" gridrow="8" pageId="2" pageNumber="82" rowspan-7="1">
|
||
<th id="755AAA657F16E3ACFF88FAF5FF32FAB6" box="[110,148,1301,1317]" gridcol="0" gridrow="8" pageId="2" pageNumber="82">4</th>
|
||
<td id="755AAA657F16E3ACFF4CFAF5FF71FAB6" box="[170,215,1301,1317]" gridcol="1" gridrow="8" pageId="2" pageNumber="82">12.7</td>
|
||
<td id="755AAA657F16E3ACFF08FAF5FEF0FAB6" box="[238,342,1301,1317]" gridcol="2" gridrow="8" pageId="2" pageNumber="82">218;284;343</td>
|
||
<td id="755AAA657F16E3ACFE8AFAF5FE08FAB6" box="[364,430,1301,1317]" gridcol="3" gridrow="8" pageId="2" pageNumber="82">593</td>
|
||
<td id="755AAA657F16E3ACFE23FAF5FC25FAB6" box="[453,899,1301,1317]" gridcol="4" gridrow="8" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FAF6FE42FAB7" bold="true" box="[453,484,1302,1316]" pageId="2" pageNumber="82">551</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FAF7FDA6FAB6" box="[495,512,1303,1317]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
503;473;417;397;235);
|
||
<emphasis id="BACF1D497F161C51FD22FAF6FD45FAB7" bold="true" box="[708,739,1302,1316]" pageId="2" pageNumber="82">473</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFAF5FB35FAB6" box="[922,1171,1301,1317]" gridcol="5" gridrow="8" pageId="2" pageNumber="82">
|
||
6.8-Di-
|
||
<emphasis id="BACF1D497F161C51FC35FAF5FC7BFAB6" box="[979,989,1301,1317]" italics="true" pageId="2" pageNumber="82">C</emphasis>
|
||
-hexosylapigenin
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FAF5FB7FFAB6" box="[1199,1241,1301,1317]" gridcol="6" gridrow="8" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FAF5FAC2FAB6" box="[1334,1380,1301,1317]" gridcol="8" gridrow="8" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFAF5FA0DFAB6" box="[1402,1451,1301,1317]" gridcol="9" gridrow="8" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FACDFA0DFAAF" box="[110,1451,1325,1340]" gridrow="9" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FACDFC25FAAF" box="[453,899,1325,1340]" gridcol="4" gridrow="9" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFACEFE7AFAAF" box="[459,476,1326,1340]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
383;353;325;297;283);
|
||
<emphasis id="BACF1D497F161C51FD46FACDFD19FAA8" bold="true" box="[672,703,1325,1339]" pageId="2" pageNumber="82">431</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD23FACEFD70FAAF" box="[709,726,1326,1340]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
341;311)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FAA4FA0DFAC0" box="[110,1451,1348,1363]" gridrow="10" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88FAA4FF32FAC0" box="[110,148,1348,1363]" gridcol="0" gridrow="10" pageId="2" pageNumber="82">5</th>
|
||
<td id="755AAA657F16E3ACFF4CFAA4FF71FAC0" box="[170,215,1348,1363]" gridcol="1" gridrow="10" pageId="2" pageNumber="82">14.1</td>
|
||
<td id="755AAA657F16E3ACFF08FAA4FEF0FAC0" box="[238,342,1348,1363]" gridcol="2" gridrow="10" pageId="2" pageNumber="82">229</td>
|
||
<td id="755AAA657F16E3ACFE8AFAA4FE08FAC0" box="[364,430,1348,1363]" gridcol="3" gridrow="10" pageId="2" pageNumber="82">681</td>
|
||
<td id="755AAA657F16E3ACFE23FAA4FC25FAC0" box="[453,899,1348,1363]" gridcol="4" gridrow="10" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FAA4FE42FAC1" bold="true" box="[453,484,1348,1362]" pageId="2" pageNumber="82">519</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FAA5FDA6FAC0" box="[495,512,1349,1363]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
357);
|
||
<emphasis id="BACF1D497F161C51FDD7FAA4FDF6FAC1" bold="true" box="[561,592,1348,1362]" pageId="2" pageNumber="82">357</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FDBAFAA5FDCBFAC0" box="[604,621,1349,1363]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
342;311;297;151;136)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFAA4FB35FAC0" box="[922,1171,1348,1363]" gridcol="5" gridrow="10" pageId="2" pageNumber="82">Pinoresinol dihexoside</td>
|
||
<td id="755AAA657F16E3ACFB49FAA4FB7FFAC0" box="[1199,1241,1348,1363]" gridcol="6" gridrow="10" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09FAA4FAB9FAC0" box="[1263,1311,1348,1363]" gridcol="7" gridrow="10" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FAA4FAC2FAC0" box="[1334,1380,1348,1363]" gridcol="8" gridrow="10" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFAA4FA0DFAC0" box="[1402,1451,1348,1363]" gridcol="9" gridrow="10" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FAB9FA0DFAFA" box="[110,1451,1369,1385]" gridrow="11" pageId="2" pageNumber="82" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88FAB9FF32FAFA" box="[110,148,1369,1385]" gridcol="0" gridrow="11" pageId="2" pageNumber="82">6</th>
|
||
<td id="755AAA657F16E3ACFF4CFAB9FF71FAFA" box="[170,215,1369,1385]" gridcol="1" gridrow="11" pageId="2" pageNumber="82">15.6</td>
|
||
<td id="755AAA657F16E3ACFF08FAB9FEF0FAFA" box="[238,342,1369,1385]" gridcol="2" gridrow="11" pageId="2" pageNumber="82">232</td>
|
||
<td id="755AAA657F16E3ACFE8AFAB9FE08FAFA" box="[364,430,1369,1385]" gridcol="3" gridrow="11" pageId="2" pageNumber="82">683</td>
|
||
<td id="755AAA657F16E3ACFE23FAB9FC25FAFA" box="[453,899,1369,1385]" gridcol="4" gridrow="11" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FABBFE42FAFA" bold="true" box="[453,484,1371,1385]" pageId="2" pageNumber="82">521</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FABBFDA6FAFA" box="[495,512,1371,1385]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
359;341;223;197);
|
||
<emphasis id="BACF1D497F161C51FD46FABBFD19FAFA" bold="true" box="[672,703,1371,1385]" pageId="2" pageNumber="82">359</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFAB9FB35FAFA" box="[922,1171,1369,1385]" gridcol="5" gridrow="11" pageId="2" pageNumber="82">
|
||
Lariciresinol
|
||
<emphasis id="BACF1D497F161C51FBE5FAB9FBA9FAFA" box="[1027,1039,1369,1385]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-dihexoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FAB9FB7FFAFA" box="[1199,1241,1369,1385]" gridcol="6" gridrow="11" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA92FA0DFA13" box="[110,1451,1394,1408]" gridrow="12" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FA92FC25FA13" box="[453,899,1394,1408]" gridcol="4" gridrow="12" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFA92FE7AFA13" box="[459,476,1394,1408]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
329;223;197;179;161;135)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA67FA0DFA04" box="[110,1451,1415,1431]" gridrow="13" pageId="2" pageNumber="82" rowspan-7="1">
|
||
<th id="755AAA657F16E3ACFF88FA67FF32FA04" box="[110,148,1415,1431]" gridcol="0" gridrow="13" pageId="2" pageNumber="82">7</th>
|
||
<td id="755AAA657F16E3ACFF4CFA67FF71FA04" box="[170,215,1415,1431]" gridcol="1" gridrow="13" pageId="2" pageNumber="82">16.5</td>
|
||
<td id="755AAA657F16E3ACFF08FA67FEF0FA04" box="[238,342,1415,1431]" gridcol="2" gridrow="13" pageId="2" pageNumber="82">218;284;343</td>
|
||
<td id="755AAA657F16E3ACFE8AFA67FE08FA04" box="[364,430,1415,1431]" gridcol="3" gridrow="13" pageId="2" pageNumber="82">463</td>
|
||
<td id="755AAA657F16E3ACFE23FA67FC25FA04" box="[453,899,1415,1431]" gridcol="4" gridrow="13" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FA69FE42FA04" bold="true" box="[453,484,1417,1431]" pageId="2" pageNumber="82">301</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FA69FDA6FA04" box="[495,512,1417,1431]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
283;255;229; 201;165)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFA67FB35FA04" box="[922,1171,1415,1431]" gridcol="5" gridrow="13" pageId="2" pageNumber="82">
|
||
Quercetin-
|
||
<emphasis id="BACF1D497F161C51FC16FA67FC5AFA04" box="[1008,1020,1415,1431]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FA67FB7FFA04" box="[1199,1241,1415,1431]" gridcol="6" gridrow="13" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FA67FAC2FA04" box="[1334,1380,1415,1431]" gridcol="8" gridrow="13" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFA67FA0DFA04" box="[1402,1451,1415,1431]" gridcol="9" gridrow="13" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA7EFA0DFA3D" box="[110,1451,1438,1454]" gridrow="14" pageId="2" pageNumber="82" rowspan-7="1">
|
||
<th id="755AAA657F16E3ACFF88FA7EFF32FA3D" box="[110,148,1438,1454]" gridcol="0" gridrow="14" pageId="2" pageNumber="82">8</th>
|
||
<td id="755AAA657F16E3ACFF4CFA7EFF71FA3D" box="[170,215,1438,1454]" gridcol="1" gridrow="14" pageId="2" pageNumber="82">17.7</td>
|
||
<td id="755AAA657F16E3ACFF08FA7EFEF0FA3D" box="[238,342,1438,1454]" gridcol="2" gridrow="14" pageId="2" pageNumber="82">224;329</td>
|
||
<td id="755AAA657F16E3ACFE8AFA7EFE08FA3D" box="[364,430,1438,1454]" gridcol="3" gridrow="14" pageId="2" pageNumber="82">521</td>
|
||
<td id="755AAA657F16E3ACFE23FA7EFC25FA3D" box="[453,899,1438,1454]" gridcol="4" gridrow="14" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FA7FFE42FA3E" bold="true" box="[453,484,1439,1453]" pageId="2" pageNumber="82">359</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FA40FDA6FA3D" box="[495,512,1440,1454]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
223;197;179; 161;133)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFA7EFB35FA3D" box="[922,1171,1438,1454]" gridcol="5" gridrow="14" pageId="2" pageNumber="82">
|
||
Rosmarinic acid
|
||
<emphasis id="BACF1D497F161C51FBC7FA7EFB8BFA3D" box="[1057,1069,1438,1454]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FA7EFB7FFA3D" box="[1199,1241,1438,1454]" gridcol="6" gridrow="14" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FA7EFAC2FA3D" box="[1334,1380,1438,1454]" gridcol="8" gridrow="14" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFA7EFA0DFA3D" box="[1402,1451,1438,1454]" gridcol="9" gridrow="14" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA55FA0DFA56" box="[110,1451,1461,1477]" gridrow="15" pageId="2" pageNumber="82" rowspan-7="1">
|
||
<th id="755AAA657F16E3ACFF88FA55FF32FA56" box="[110,148,1461,1477]" gridcol="0" gridrow="15" pageId="2" pageNumber="82">9</th>
|
||
<td id="755AAA657F16E3ACFF4CFA55FF71FA56" box="[170,215,1461,1477]" gridcol="1" gridrow="15" pageId="2" pageNumber="82">18.9</td>
|
||
<td id="755AAA657F16E3ACFF08FA55FEF0FA56" box="[238,342,1461,1477]" gridcol="2" gridrow="15" pageId="2" pageNumber="82">208;345</td>
|
||
<td id="755AAA657F16E3ACFE8AFA55FE08FA56" box="[364,430,1461,1477]" gridcol="3" gridrow="15" pageId="2" pageNumber="82">447</td>
|
||
<td id="755AAA657F16E3ACFE23FA55FC25FA56" box="[453,899,1461,1477]" gridcol="4" gridrow="15" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FA56FE42FA57" bold="true" box="[453,484,1462,1476]" pageId="2" pageNumber="82">285</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FA57FDA6FA56" box="[495,512,1463,1477]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
261;259;243;241;199;175;198/197)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFA55FB35FA56" box="[922,1171,1461,1477]" gridcol="5" gridrow="15" pageId="2" pageNumber="82">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F161C51FC05FA55FC49FA56" box="[995,1007,1461,1477]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FA55FB7FFA56" box="[1199,1241,1461,1477]" gridcol="6" gridrow="15" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FA55FAC2FA56" box="[1334,1380,1461,1477]" gridcol="8" gridrow="15" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFA55FA0DFA56" box="[1402,1451,1461,1477]" gridcol="9" gridrow="15" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA2CFA0DFA4F" box="[110,1451,1484,1500]" gridrow="16" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88FA2CFF32FA4F" box="[110,148,1484,1500]" gridcol="0" gridrow="16" pageId="2" pageNumber="82">10</th>
|
||
<td id="755AAA657F16E3ACFF4CFA2CFF71FA4F" box="[170,215,1484,1500]" gridcol="1" gridrow="16" pageId="2" pageNumber="82">19.4</td>
|
||
<td id="755AAA657F16E3ACFF08FA2CFEF0FA4F" box="[238,342,1484,1500]" gridcol="2" gridrow="16" pageId="2" pageNumber="82">225;261</td>
|
||
<td id="755AAA657F16E3ACFE8AFA2CFE08FA4F" box="[364,430,1484,1500]" gridcol="3" gridrow="16" pageId="2" pageNumber="82">461</td>
|
||
<td id="755AAA657F16E3ACFE23FA2CFC25FA4F" box="[453,899,1484,1500]" gridcol="4" gridrow="16" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FA2DFE42FA48" bold="true" box="[453,484,1485,1499]" pageId="2" pageNumber="82">285</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FA2EFDA6FA4F" box="[495,512,1486,1500]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
243;241;199;175;151;213;197/198)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFA2CFB35FA4F" box="[922,1171,1484,1500]" gridcol="5" gridrow="16" pageId="2" pageNumber="82">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F161C51FC05FA2CFC49FA4F" box="[995,1007,1484,1500]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexuronide
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FA2CFB7FFA4F" box="[1199,1241,1484,1500]" gridcol="6" gridrow="16" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09FA2CFAB9FA4F" box="[1263,1311,1484,1500]" gridcol="7" gridrow="16" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FA2CFAC2FA4F" box="[1334,1380,1484,1500]" gridcol="8" gridrow="16" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CFA2CFA0DFA4F" box="[1402,1451,1484,1500]" gridcol="9" gridrow="16" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA02FA0DFA61" box="[110,1451,1506,1522]" gridrow="17" pageId="2" pageNumber="82" rowspan-7="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88FA02FF32FA61" box="[110,148,1506,1522]" gridcol="0" gridrow="17" pageId="2" pageNumber="82">11</th>
|
||
<td id="755AAA657F16E3ACFF4CFA02FF71FA61" box="[170,215,1506,1522]" gridcol="1" gridrow="17" pageId="2" pageNumber="82">19.7</td>
|
||
<td id="755AAA657F16E3ACFF08FA02FEF0FA61" box="[238,342,1506,1522]" gridcol="2" gridrow="17" pageId="2" pageNumber="82">225;261;341</td>
|
||
<td id="755AAA657F16E3ACFE8AFA02FE08FA61" box="[364,430,1506,1522]" gridcol="3" gridrow="17" pageId="2" pageNumber="82">579</td>
|
||
<td id="755AAA657F16E3ACFE23FA02FC25FA61" box="[453,899,1506,1522]" gridcol="4" gridrow="17" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23FA04FE42FA61" bold="true" box="[453,484,1508,1522]" pageId="2" pageNumber="82">447</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09FA04FDA6FA61" box="[495,512,1508,1522]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
429;369;285);
|
||
<emphasis id="BACF1D497F161C51FD9DFA04FD3CFA61" bold="true" box="[635,666,1508,1522]" pageId="2" pageNumber="82">417</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD40FA04FD11FA61" box="[678,695,1508,1522]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
327;285);
|
||
<emphasis id="BACF1D497F161C51FCEBFA04FC8AFA61" bold="true" box="[781,812,1508,1522]" pageId="2" pageNumber="82">285</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CFA02FB35FA61" box="[922,1171,1506,1522]" gridcol="5" gridrow="17" pageId="2" pageNumber="82">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F161C51FC05FA02FC49FA61" box="[995,1007,1506,1522]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-hexosylpentoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49FA02FB7FFA61" box="[1199,1241,1506,1522]" gridcol="6" gridrow="17" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0FA02FAC2FA61" box="[1334,1380,1506,1522]" gridcol="8" gridrow="17" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88FA1BFA0DF99A" box="[110,1451,1531,1545]" gridrow="18" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23FA1BFC25F99A" box="[453,899,1531,1545]" gridcol="4" gridrow="18" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DFA1BFE7AF99A" box="[459,476,1531,1545]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
267;257;243;241;217;199;175;151;149;133;107)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F9F1FA0DF9B3" box="[110,1451,1553,1568]" gridrow="19" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88F9F1FF32F9B3" box="[110,148,1553,1568]" gridcol="0" gridrow="19" pageId="2" pageNumber="82">12</th>
|
||
<td id="755AAA657F16E3ACFF4CF9F1FF71F9B3" box="[170,215,1553,1568]" gridcol="1" gridrow="19" pageId="2" pageNumber="82">21.3</td>
|
||
<td id="755AAA657F16E3ACFF08F9F1FEF0F9B3" box="[238,342,1553,1568]" gridcol="2" gridrow="19" pageId="2" pageNumber="82">220;330</td>
|
||
<td id="755AAA657F16E3ACFE8AF9F1FE08F9B3" box="[364,430,1553,1568]" gridcol="3" gridrow="19" pageId="2" pageNumber="82">359</td>
|
||
<td id="755AAA657F16E3ACFE23F9F1FC25F9B3" box="[453,899,1553,1568]" gridcol="4" gridrow="19" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F9F2FE56F98C" bold="true" box="[453,496,1553,1568]" pageId="2" pageNumber="82">223 (</emphasis>
|
||
<emphasis id="BACF1D497F161C51FE09F9F2FDA6F9B3" box="[495,512,1554,1568]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
197;169);
|
||
<emphasis id="BACF1D497F161C51FDB0F9F2FDD3F9B3" bold="true" box="[598,629,1554,1568]" pageId="2" pageNumber="82">197</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD67F9F2FD34F9B3" box="[641,658,1554,1568]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
179);
|
||
<emphasis id="BACF1D497F161C51FD25F9F2FD44F9B3" bold="true" box="[707,738,1554,1568]" pageId="2" pageNumber="82">179</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF9F1FB35F9B3" box="[922,1171,1553,1568]" gridcol="5" gridrow="19" pageId="2" pageNumber="82">Rosmarinic acid</td>
|
||
<td id="755AAA657F16E3ACFB49F9F1FB7FF9B3" box="[1199,1241,1553,1568]" gridcol="6" gridrow="19" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09F9F1FAB9F9B3" box="[1263,1311,1553,1568]" gridcol="7" gridrow="19" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F9F1FAC2F9B3" box="[1334,1380,1553,1568]" gridcol="8" gridrow="19" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CF9F1FA0DF9B3" box="[1402,1451,1553,1568]" gridcol="9" gridrow="19" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F9C9FA0DF9A4" box="[110,1451,1577,1591]" gridrow="20" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F9C9FC25F9A4" box="[453,899,1577,1591]" gridcol="4" gridrow="20" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF9C9FE7AF9A4" box="[459,476,1577,1591]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
139;135;109;107);
|
||
<emphasis id="BACF1D497F161C51FD9DF9C9FD3CF9A4" bold="true" box="[635,666,1577,1591]" pageId="2" pageNumber="82">161</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD40F9C9FD11F9A4" box="[678,695,1577,1591]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
137;133;117;105)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F9DEFA0DF9DD" box="[110,1451,1598,1614]" gridrow="21" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88F9DEFF32F9DD" box="[110,148,1598,1614]" gridcol="0" gridrow="21" pageId="2" pageNumber="82">13</th>
|
||
<td id="755AAA657F16E3ACFF4CF9DEFF71F9DD" box="[170,215,1598,1614]" gridcol="1" gridrow="21" pageId="2" pageNumber="82">21.8</td>
|
||
<td id="755AAA657F16E3ACFF08F9DEFEF0F9DD" box="[238,342,1598,1614]" gridcol="2" gridrow="21" pageId="2" pageNumber="82">227</td>
|
||
<td id="755AAA657F16E3ACFE8AF9DEFE08F9DD" box="[364,430,1598,1614]" gridcol="3" gridrow="21" pageId="2" pageNumber="82">417</td>
|
||
<td id="755AAA657F16E3ACFE23F9DEFC25F9DD" box="[453,899,1598,1614]" gridcol="4" gridrow="21" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F9DFFE42F9DE" bold="true" box="[453,484,1599,1613]" pageId="2" pageNumber="82">285</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09F9A0FDA6F9DD" box="[495,512,1600,1614]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
243;241;199; 175;151;226; 213; 199)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF9DEFB35F9DD" box="[922,1171,1598,1614]" gridcol="5" gridrow="21" pageId="2" pageNumber="82">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F161C51FC05F9DEFC49F9DD" box="[995,1007,1598,1614]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-pentoside
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49F9DEFB7FF9DD" box="[1199,1241,1598,1614]" gridcol="6" gridrow="21" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09F9DEFAB9F9DD" box="[1263,1311,1598,1614]" gridcol="7" gridrow="21" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F9DEFAC2F9DD" box="[1334,1380,1598,1614]" gridcol="8" gridrow="21" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CF9DEFA0DF9DD" box="[1402,1451,1598,1614]" gridcol="9" gridrow="21" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F9B6FA0DF9F6" box="[110,1451,1622,1637]" gridrow="22" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88F9B6FF32F9F6" box="[110,148,1622,1637]" gridcol="0" gridrow="22" pageId="2" pageNumber="82">14</th>
|
||
<td id="755AAA657F16E3ACFF4CF9B6FF71F9F6" box="[170,215,1622,1637]" gridcol="1" gridrow="22" pageId="2" pageNumber="82">22.8</td>
|
||
<td id="755AAA657F16E3ACFF08F9B6FEF0F9F6" box="[238,342,1622,1637]" gridcol="2" gridrow="22" pageId="2" pageNumber="82">225;324</td>
|
||
<td id="755AAA657F16E3ACFE8AF9B6FE08F9F6" box="[364,430,1622,1637]" gridcol="3" gridrow="22" pageId="2" pageNumber="82">555</td>
|
||
<td id="755AAA657F16E3ACFE23F9B6FC25F9F6" box="[453,899,1622,1637]" gridcol="4" gridrow="22" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F9B6FE42F9F7" bold="true" box="[453,484,1622,1636]" pageId="2" pageNumber="82">493</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09F9B7FDA6F9F6" box="[495,512,1623,1637]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
359;357;313; 223;197;179; 161)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF9B6FB35F9F6" box="[922,1171,1622,1637]" gridcol="5" gridrow="22" pageId="2" pageNumber="82">Salvianolic acid K</td>
|
||
<td id="755AAA657F16E3ACFB49F9B6FB7FF9F6" box="[1199,1241,1622,1637]" gridcol="6" gridrow="22" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09F9B6FAB9F9F6" box="[1263,1311,1622,1637]" gridcol="7" gridrow="22" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F9B6FAC2F9F6" box="[1334,1380,1622,1637]" gridcol="8" gridrow="22" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CF9B6FA0DF9F6" box="[1402,1451,1622,1637]" gridcol="9" gridrow="22" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F98CFA0DF9EF" box="[110,1451,1644,1660]" gridrow="23" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88F98CFF32F9EF" box="[110,148,1644,1660]" gridcol="0" gridrow="23" pageId="2" pageNumber="82">15</th>
|
||
<td id="755AAA657F16E3ACFF4CF98CFF71F9EF" box="[170,215,1644,1660]" gridcol="1" gridrow="23" pageId="2" pageNumber="82">24.4</td>
|
||
<td id="755AAA657F16E3ACFF08F98CFEF0F9EF" box="[238,342,1644,1660]" gridcol="2" gridrow="23" pageId="2" pageNumber="82">228</td>
|
||
<td id="755AAA657F16E3ACFE8AF98CFE08F9EF" box="[364,430,1644,1660]" gridcol="3" gridrow="23" pageId="2" pageNumber="82">591</td>
|
||
<td id="755AAA657F16E3ACFE23F98CFC25F9EF" box="[453,899,1644,1660]" gridcol="4" gridrow="23" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F98DFE42F9E8" bold="true" box="[453,484,1645,1659]" pageId="2" pageNumber="82">531</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE08F98EFE59F9EF" box="[494,511,1646,1660]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
513; 417; 399; 285);
|
||
<emphasis id="BACF1D497F161C51FD4AF98DFD6DF9E8" bold="true" box="[684,715,1645,1659]" pageId="2" pageNumber="82">285</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FD30F98EFD41F9EF" box="[726,743,1646,1660]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
241;199; 175; 151)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF98CFB35F9EF" box="[922,1171,1644,1660]" gridcol="5" gridrow="23" pageId="2" pageNumber="82">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F161C51FC05F98CFC49F9EF" box="[995,1007,1644,1660]" italics="true" pageId="2" pageNumber="82">O</emphasis>
|
||
-
|
||
</td>
|
||
<td id="755AAA657F16E3ACFB49F98CFB7FF9EF" box="[1199,1241,1644,1660]" gridcol="6" gridrow="23" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09F98CFAB9F9EF" box="[1263,1311,1644,1660]" gridcol="7" gridrow="23" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F98CFAC2F9EF" box="[1334,1380,1644,1660]" gridcol="8" gridrow="23" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CF98CFA0DF9EF" box="[1402,1451,1644,1660]" gridcol="9" gridrow="23" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F964FA0DF901" box="[110,1451,1668,1682]" gridrow="24" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFC7CF964FB35F901" box="[922,1171,1668,1682]" gridcol="5" gridrow="24" pageId="2" pageNumber="82">(acetylpentosyl)pentoside</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F97BFA0DF93A" box="[110,1451,1691,1705]" gridrow="25" pageId="2" pageNumber="82" rowspan-6="1" rowspan-8="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88F97BFF32F93A" box="[110,148,1691,1705]" gridcol="0" gridrow="25" pageId="2" pageNumber="82">16</th>
|
||
<td id="755AAA657F16E3ACFF4CF97BFF71F93A" box="[170,215,1691,1705]" gridcol="1" gridrow="25" pageId="2" pageNumber="82">25.8</td>
|
||
<td id="755AAA657F16E3ACFF08F97BFEF0F93A" box="[238,342,1691,1705]" gridcol="2" gridrow="25" pageId="2" pageNumber="82">231;330</td>
|
||
<td id="755AAA657F16E3ACFE8AF97BFE08F93A" box="[364,430,1691,1705]" gridcol="3" gridrow="25" pageId="2" pageNumber="82">283</td>
|
||
<td id="755AAA657F16E3ACFE23F97BFC25F93A" box="[453,899,1691,1705]" gridcol="4" gridrow="25" pageId="2" pageNumber="82">268</td>
|
||
<td id="755AAA657F16E3ACFC7CF97BFB35F93A" box="[922,1171,1691,1705]" gridcol="5" gridrow="25" pageId="2" pageNumber="82">Methylapigenin</td>
|
||
<td id="755AAA657F16E3ACFB09F97BFAB9F93A" box="[1263,1311,1691,1705]" gridcol="7" gridrow="25" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F94FFA0DF952" box="[110,1451,1711,1729]" gridrow="26" pageId="2" pageNumber="82" rowspan-2="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88F94FFF32F952" box="[110,148,1711,1729]" gridcol="0" gridrow="26" pageId="2" pageNumber="82">17</th>
|
||
<td id="755AAA657F16E3ACFF4CF94FFF71F952" box="[170,215,1711,1729]" gridcol="1" gridrow="26" pageId="2" pageNumber="82">27.4</td>
|
||
<td id="755AAA657F16E3ACFE8AF94FFE08F952" box="[364,430,1711,1729]" gridcol="3" gridrow="26" pageId="2" pageNumber="82">697</td>
|
||
<td id="755AAA657F16E3ACFE23F94FFC25F952" box="[453,899,1711,1729]" gridcol="4" gridrow="26" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F952FE42F953" bold="true" box="[453,484,1714,1728]" pageId="2" pageNumber="82">535</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09F952FDA6F953" box="[495,512,1714,1728]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
517;503;475;359;337;323;253;211;197);
|
||
<emphasis id="BACF1D497F161C51FCB1F952FCD0F953" bold="true" box="[855,886,1714,1728]" pageId="2" pageNumber="82">323</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF94FFB35F952" box="[922,1171,1711,1729]" gridcol="5" gridrow="26" pageId="2" pageNumber="82">(oi-</td>
|
||
<td id="755AAA657F16E3ACFB49F94FFB7FF952" box="[1199,1241,1711,1729]" gridcol="6" gridrow="26" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F929FA0DF944" box="[110,1451,1737,1751]" gridrow="27" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F929FC25F944" box="[453,899,1737,1751]" gridcol="4" gridrow="27" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF929FE7AF944" box="[459,476,1737,1751]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
305;263;251;221;203;179;177;161;109)
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF929FB35F944" box="[922,1171,1737,1751]" gridcol="5" gridrow="27" pageId="2" pageNumber="82">Hydroxyhydroferuloylcaffeoyl)</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F93FFA0DF97E" box="[110,1451,1759,1773]" gridrow="28" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFC7CF93FFB35F97E" box="[922,1171,1759,1773]" gridcol="5" gridrow="28" pageId="2" pageNumber="82">caffeoyl hexoside</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F916FA0DF896" box="[110,1451,1782,1797]" gridrow="29" pageId="2" pageNumber="82">
|
||
<th id="755AAA657F16E3ACFF88F916FF32F896" box="[110,148,1782,1797]" gridcol="0" gridrow="29" pageId="2" pageNumber="82">18</th>
|
||
<td id="755AAA657F16E3ACFF4CF916FF71F896" box="[170,215,1782,1797]" gridcol="1" gridrow="29" pageId="2" pageNumber="82">31.2</td>
|
||
<td id="755AAA657F16E3ACFF08F916FEF0F896" box="[238,342,1782,1797]" gridcol="2" gridrow="29" pageId="2" pageNumber="82">229</td>
|
||
<td id="755AAA657F16E3ACFE8AF916FE08F896" box="[364,430,1782,1797]" gridcol="3" gridrow="29" pageId="2" pageNumber="82">493</td>
|
||
<td id="755AAA657F16E3ACFE23F916FC25F896" box="[453,899,1782,1797]" gridcol="4" gridrow="29" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F916FE42F897" bold="true" box="[453,484,1782,1796]" pageId="2" pageNumber="82">359</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09F917FDA6F896" box="[495,512,1783,1797]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
341;315;249;223;197;179;161;133);
|
||
<emphasis id="BACF1D497F161C51FCD5F916FCF4F897" bold="true" box="[819,850,1782,1796]" pageId="2" pageNumber="82">295</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF916FB35F896" box="[922,1171,1782,1797]" gridcol="5" gridrow="29" pageId="2" pageNumber="82">Isosalvianolic acid A</td>
|
||
<td id="755AAA657F16E3ACFB49F916FB7FF896" box="[1199,1241,1782,1797]" gridcol="6" gridrow="29" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFB09F916FAB9F896" box="[1263,1311,1782,1797]" gridcol="7" gridrow="29" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F916FAC2F896" box="[1334,1380,1782,1797]" gridcol="8" gridrow="29" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFA9CF916FA0DF896" box="[1402,1451,1782,1797]" gridcol="9" gridrow="29" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F8EDFA0DF88F" box="[110,1451,1805,1820]" gridrow="30" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F8EDFC25F88F" box="[453,899,1805,1820]" gridcol="4" gridrow="30" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF8EEFE7AF88F" box="[459,476,1806,1820]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
293;277;267;251;185;159;157;147;109);
|
||
<emphasis id="BACF1D497F161C51FCD5F8EDFCF4F888" bold="true" box="[819,850,1805,1819]" pageId="2" pageNumber="82">161</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F8C4FA0DF8A1" box="[110,1451,1828,1842]" gridrow="31" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F8C4FC25F8A1" box="[453,899,1828,1842]" gridcol="4" gridrow="31" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF8C4FE7AF8A1" box="[459,476,1828,1842]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
137;133;117;105)
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F8DBFA0DF8DA" box="[110,1451,1851,1865]" gridrow="32" pageId="2" pageNumber="82" rowspan-2="1" rowspan-6="1" rowspan-9="1">
|
||
<th id="755AAA657F16E3ACFF88F8DBFF32F8DA" box="[110,148,1851,1865]" gridcol="0" gridrow="32" pageId="2" pageNumber="82">19</th>
|
||
<td id="755AAA657F16E3ACFF4CF8DBFF71F8DA" box="[170,215,1851,1865]" gridcol="1" gridrow="32" pageId="2" pageNumber="82">36.7</td>
|
||
<td id="755AAA657F16E3ACFE8AF8DBFE08F8DA" box="[364,430,1851,1865]" gridcol="3" gridrow="32" pageId="2" pageNumber="82">555</td>
|
||
<td id="755AAA657F16E3ACFE23F8DBFC25F8DA" box="[453,899,1851,1865]" gridcol="4" gridrow="32" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FE23F8DBFE42F8DA" bold="true" box="[453,484,1851,1865]" pageId="2" pageNumber="82">493</emphasis>
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE09F8DBFDA6F8DA" box="[495,512,1851,1865]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
359;357;316;269;161);
|
||
<emphasis id="BACF1D497F161C51FD22F8DBFD45F8DA" bold="true" box="[708,739,1851,1865]" pageId="2" pageNumber="82">359</emphasis>
|
||
</td>
|
||
<td id="755AAA657F16E3ACFC7CF8DBFB35F8DA" box="[922,1171,1851,1865]" gridcol="5" gridrow="32" pageId="2" pageNumber="82">Salvianolic acid K (isomer)</td>
|
||
<td id="755AAA657F16E3ACFB09F8DBFAB9F8DA" box="[1263,1311,1851,1865]" gridcol="7" gridrow="32" pageId="2" pageNumber="82">+</td>
|
||
<td id="755AAA657F16E3ACFAD0F8DBFAC2F8DA" box="[1334,1380,1851,1865]" gridcol="8" gridrow="32" pageId="2" pageNumber="82">+</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F8B1FA0DF8F3" box="[110,1451,1873,1888]" gridrow="33" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F8B1FC25F8F3" box="[453,899,1873,1888]" gridcol="4" gridrow="33" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF8B2FE7AF8F3" box="[459,476,1874,1888]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
341;315;249;223;197;179;161;133);
|
||
<emphasis id="BACF1D497F161C51FCE8F8B1FC8BF8CC" bold="true" box="[782,813,1873,1887]" pageId="2" pageNumber="82">225</emphasis>
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F16E3ACFF88F888FA0DF8E4" box="[110,1451,1896,1911]" gridrow="34" pageId="2" pageNumber="82" rowspan-0="1" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-5="1" rowspan-6="1" rowspan-7="1" rowspan-8="1" rowspan-9="1">
|
||
<td id="755AAA657F16E3ACFE23F888FC25F8E4" box="[453,899,1896,1911]" gridcol="4" gridrow="34" pageId="2" pageNumber="82">
|
||
(
|
||
<emphasis id="BACF1D497F161C51FE2DF889FE7AF8E4" box="[459,476,1897,1911]" italics="true" pageId="2" pageNumber="82">+</emphasis>
|
||
207;165;153;149;125;95;81;79)
|
||
</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F161C50FFB1F848FEFDFF75" blockId="2.[87,757,1960,2008]" lastBlockId="3.[113,784,182,2015]" lastPageId="3" lastPageNumber="83" pageId="2" pageNumber="82">
|
||
<emphasis id="BACF1D497F161C51FFB1F848FFDDF82F" box="[87,123,1960,1980]" italics="true" pageId="2" pageNumber="82">m/z</emphasis>
|
||
341 (
|
||
<bibRefCitation id="EC2ABCAA7F161C51FF58F849FE32F82F" author="Sakalem, M. E. & Negri, G. & Tabach, R." box="[190,404,1961,1981]" pageId="2" pageNumber="82" pagination="1219 - 1232" refId="ref13669" refString="Sakalem, M. E., Negri, G., Tabach, R., 2012. Chemical composition of hydroethanolic extracts from five species of the Passiflora genus. Braz. J. Pharmacog. 22, 1219 - 1232." type="journal article" year="2012">Sakalem et al., 2012</bibRefCitation>
|
||
), which was not detected in our analyses. Recently Vallverdú-Queralt et al., (2014), evaluating the phytochemical composition of herbaceous species with broad culinary uses such as rosemary, oregano, thyme and bay leaf, showed the presence of the hexosyl derivative of rosmarinic acid only in rosemary and oregano.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FF0EFE15FD8B" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The glycosylated flavonoids constitute the majority of polyphenols in spices. Glycosylated flavonoids were commonly observed. The UV spectrum, which showed two absorption bands at 284 and
|
||
<quantity id="4F436CBE7F171C50FF78FEA2FF4AFEC6" box="[158,236,322,341]" metricMagnitude="-7" metricUnit="m" metricValue="3.4299999999999997" pageId="3" pageNumber="83" unit="nm" value="343.0">343 nm</quantity>
|
||
, relating to the conjugations in the B and A rings of a flavonoid nucleus, together with the MS/MS data allowed the identification of the metabolite
|
||
<emphasis id="BACF1D497F171C50FE5DFE9AFE6EFE1E" bold="true" box="[443,456,378,397]" pageId="3" pageNumber="83">7</emphasis>
|
||
as quercetin-3-
|
||
<emphasis id="BACF1D497F171C50FD8DFE98FDDCFE1F" box="[619,634,376,396]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-hexoside. The deprotonated molecular ion, [M–H]
|
||
<emphasis id="BACF1D497F171C50FE15FE72FE59FE0D" box="[499,511,402,414]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FE15FE72FE59FE0D" attach="none" box="[499,511,402,414]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
, at
|
||
<emphasis id="BACF1D497F171C50FDD0FE74FDFCFE3B" box="[566,602,404,424]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
463 dissociated generating the fragment ion at
|
||
<emphasis id="BACF1D497F171C50FE5BFE50FE47FE57" box="[445,481,432,452]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
301 as base peak (
|
||
<emphasis id="BACF1D497F171C50FD56FE52FD67FE57" box="[688,705,434,452]" italics="true" pageId="3" pageNumber="83">—</emphasis>
|
||
162 Da) (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FF9CFE2DFEEBFE73" author="Hossain, M. B. & Rai, D. K. & Brunton, N. P. & Martin-Diana, A. B. & Barry-Ryan, C." box="[122,333,461,481]" pageId="3" pageNumber="83" pagination="10576 - 10581" refId="ref12419" refString="Hossain, M. B., Rai, D. K., Brunton, N. P., Martin-Diana, A. B., Barry-Ryan, C., 2010. Characterization of phenolic composition in lamiaceae spices by LC - ESI-MS / MS. J. Agric. Food Chem. 58, 10576 - 10581." type="journal article" year="2010">Hossain et al., 2010</bibRefCitation>
|
||
). The presence of the molecule is widely reported as constituent of species belonging to the Labiatae family (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FF9CFDE5FE01FD8B" author="Vallverdu-Queralt, A. & Regueiroc, J. & Martinez-Huelamo, M. & Rinaldi Alvarenga, J. F. & Neto Leal, L. & Lamuela-Raventos, R. M." box="[122,423,517,536]" pageId="3" pageNumber="83" pagination="299 - 307" refId="ref13942" refString="Vallverdu-Queralt, A., Regueiroc, J., Martinez-Huelamo, M., Rinaldi Alvarenga, J. F., Neto Leal, L., Lamuela-Raventos, R. M., 2014. A comprehensive study on the phenolic profile of widely used culinary herbs and spices: rosemary, thyme, oregano, cinnamon, cumin and bay. Food Chem. 154, 299 - 307." type="journal article" year="2014">Vallverdú-Queralt et al., 2014</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FDC1FF60FDFF" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The mass spectra of the metabolites
|
||
<emphasis id="BACF1D497F171C50FDE8FDC1FDBDFDA7" bold="true" box="[526,539,545,564]" pageId="3" pageNumber="83">9</emphasis>
|
||
,
|
||
<emphasis id="BACF1D497F171C50FDCEFDC1FDE7FDA7" bold="true" box="[552,577,545,564]" pageId="3" pageNumber="83">10</emphasis>
|
||
,
|
||
<emphasis id="BACF1D497F171C50FDA9FDC1FDCEFDA7" bold="true" box="[591,616,545,564]" pageId="3" pageNumber="83">11</emphasis>
|
||
and
|
||
<emphasis id="BACF1D497F171C50FD79FDC1FD1EFDA7" bold="true" box="[671,696,545,564]" pageId="3" pageNumber="83">15</emphasis>
|
||
were in agreement with the presence of glycosylated derivatives of flavone luteolin.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FD95FCA9FCBC" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The MS
|
||
<superScript id="7FCE6C137F171C50FF3DFD91FF42FDEE" attach="left" box="[219,228,625,637]" fontSize="5" pageId="3" pageNumber="83">2</superScript>
|
||
spectrum of metabolite
|
||
<emphasis id="BACF1D497F171C50FE3DFD94FE4EFD14" bold="true" box="[475,488,628,647]" pageId="3" pageNumber="83">9</emphasis>
|
||
([M–H]
|
||
<emphasis id="BACF1D497F171C50FDDEFD91FDE2FDEE" box="[568,580,625,637]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FDDEFD91FDE2FDEE" attach="left" box="[568,580,625,637]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="BACF1D497F171C50FD85FD94FD21FD1B" box="[611,647,628,648]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
447) showed the ion at
|
||
<emphasis id="BACF1D497F171C50FF07FD6FFEA2FD30" box="[225,260,655,675]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
<quantity id="4F436CBE7F171C50FEEBFD70FEF6FD37" box="[269,336,656,676]" metricMagnitude="0" metricUnit="m" metricValue="7.239" pageId="3" pageNumber="83" unit="in" value="285.0">285 in</quantity>
|
||
agreement with the presence of a hexosyl derivative of the flavone luteolin, identified on the basis of the MS
|
||
<superScript id="7FCE6C137F171C50FF77FD24FF3CFD43" attach="left" box="[145,154,708,720]" fontSize="5" pageId="3" pageNumber="83">3</superScript>
|
||
fragmentation pattern. The molecule has recently been reported as a component of
|
||
<emphasis id="BACF1D497F171C50FE47FD03FDA7FD64" box="[417,513,739,759]" italics="true" pageId="3" pageNumber="83">
|
||
<taxonomicName id="4FBBBAD87F171C50FE47FD03FE4AFD64" box="[417,492,739,759]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="genus">Thymus</taxonomicName>
|
||
x
|
||
</emphasis>
|
||
<taxonomicName id="4FBBBAD87F171C50FDEDFD03FF0AFC80" authority="(Pereira et al., 2013)" baseAuthorityName="Pereira" baseAuthorityYear="2013" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="citriodorus">
|
||
<emphasis id="BACF1D497F171C50FDEDFD03FDD5FD64" box="[523,627,739,759]" italics="true" pageId="3" pageNumber="83">citriodorus</emphasis>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F171C50FD62FD04FF02FC80" author="Pereira, O. & Peres, A. & Silva, A. & Domingues, M. & Cardoso, S." pageId="3" pageNumber="83" pagination="1773 - 1780" refId="ref13262" refString="Pereira, O., Peres, A., Silva, A., Domingues, M., Cardoso, S., 2013. Simultaneous characterization and quantification of phenolic compounds in Thymus x citriodorus using a validated HPLC - UV and ESI-MS combined method. Food Res. Int. 54, 1773 - 1780." type="journal article" year="2013">Pereira et al., 2013</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
and identified by 1D and 2D NMR spectroscopic techniques in
|
||
<taxonomicName id="4FBBBAD87F171C50FF6AFCFBFCADFCBC" authority="subsp. sipyleus var. sipyleus (Ozgen et al., 2011)" baseAuthorityName="Ozgen" baseAuthorityYear="2011" box="[140,779,795,815]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="variety" species="sipyleus" subSpecies="sipyleus" variety="sipyleus">
|
||
<emphasis id="BACF1D497F171C50FF6AFCFBFE8FFCBC" box="[140,297,795,815]" italics="true" pageId="3" pageNumber="83">Thymus sipyleus</emphasis>
|
||
subsp.
|
||
<emphasis id="BACF1D497F171C50FE93FCFBFE67FCBC" box="[373,449,795,815]" italics="true" pageId="3" pageNumber="83">sipyleus</emphasis>
|
||
var.
|
||
<emphasis id="BACF1D497F171C50FE15FCFBFD99FCBC" box="[499,575,795,815]" italics="true" pageId="3" pageNumber="83">sipyleus</emphasis>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F171C50FDA8FCFBFCA4FCBC" author="Ozgen, U. & Mavi, A. & Terzi, Z. & Kazaz, C. & Kaya, Y. & Secen, H." box="[590,770,795,815]" pageId="3" pageNumber="83" pagination="12 - 21" refId="ref13070" refString="Ozgen, U., Mavi, A., Terzi, Z., Kazaz, C., As ¸ ci, A., Kaya, Y., Secen, H., 2011. Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp. sipyleus var. sipyleus. Rec. Nat. Prod. 5, 12 - 21." type="journal article" year="2011">Özgen et al., 2011</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FCD8FD71FC0C" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The metabolite
|
||
<emphasis id="BACF1D497F171C50FECDFCD8FEE2FCD8" bold="true" box="[299,324,824,843]" pageId="3" pageNumber="83">10</emphasis>
|
||
was putatively identified as luteolin-7-
|
||
<emphasis id="BACF1D497F171C50FD2DFCD7FD7CFCD8" box="[715,730,823,843]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-hexuronide, previously identified as constituent of
|
||
<taxonomicName id="4FBBBAD87F171C50FDA3FCB3FE90FC10" authority="(Ismaili et al., 2002)" baseAuthorityName="Ismaili" baseAuthorityYear="2002" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="broussonettii">
|
||
<emphasis id="BACF1D497F171C50FDA3FCB3FCA9FCF4" box="[581,783,851,871]" italics="true" pageId="3" pageNumber="83">Thymus broussonettii</emphasis>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F171C50FF9FFC90FE88FC10" author="Ismaili, H. & Sosa, S. & Brkic, D. & Fkih-Tetouani, S. & Ilidrissi, A. & Touati, D. & Aquino, R. P. & Tubaro, A." box="[121,302,880,899]" pageId="3" pageNumber="83" pagination="1137 - 1140" refId="ref12579" refString="Ismaili, H., Sosa, S., Brkic, D., Fkih-Tetouani, S., Ilidrissi, A., Touati, D., Aquino, R. P., Tubaro, A., 2002. Topical anti-inflammatory activity of extracts and compounds from Thymus broussonettii. J. Pharm. Pharmacol. 54, 1137 - 1140." type="journal article" year="2002">Ismaili et al., 2002</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
and
|
||
<taxonomicName id="4FBBBAD87F171C50FE81FC8FFD28FC10" authority="(Ozgen et al., 2011)" baseAuthorityName="Ozgen" baseAuthorityYear="2011" box="[359,654,879,899]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="sipyleus">
|
||
<emphasis id="BACF1D497F171C50FE81FC8FFE6EFC10" box="[359,456,879,899]" italics="true" pageId="3" pageNumber="83">T. sipyleus</emphasis>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F171C50FE33FC8FFD23FC10" author="Ozgen, U. & Mavi, A. & Terzi, Z. & Kazaz, C. & Kaya, Y. & Secen, H." box="[469,645,879,899]" pageId="3" pageNumber="83" pagination="12 - 21" refId="ref13070" refString="Ozgen, U., Mavi, A., Terzi, Z., Kazaz, C., As ¸ ci, A., Kaya, Y., Secen, H., 2011. Relationship between chemical structure and antioxidant activity of luteolin and its glycosides isolated from Thymus sipyleus subsp. sipyleus var. sipyleus. Rec. Nat. Prod. 5, 12 - 21." type="journal article" year="2011">Özgen et al., 2011</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
. The [M–H]
|
||
<emphasis id="BACF1D497F171C50FCE5FC8CFCA9FCEB" box="[771,783,876,888]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FCE5FC8CFCA9FCEB" attach="none" box="[771,783,876,888]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F171C50FF54FC6AFF72FC0D" box="[178,212,906,926]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
461 provided the ion at
|
||
<emphasis id="BACF1D497F171C50FE29FC6AFE54FC0D" box="[463,498,906,926]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
285 by loss of 176 Da.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FC47FCB6FBD5" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The mass spectrum of the metabolite
|
||
<emphasis id="BACF1D497F171C50FDE1FC47FD86FC29" bold="true" box="[519,544,935,954]" pageId="3" pageNumber="83">11</emphasis>
|
||
was in accordance with the presence of a disaccharide derivative of luteolin. In fact, the collision of the deprotonated molecular ion at
|
||
<emphasis id="BACF1D497F171C50FDCEFC3EFDEAFC61" box="[552,588,990,1010]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
579 gave fragment ions at
|
||
<emphasis id="BACF1D497F171C50FF5BFC1AFF46FB9D" box="[189,224,1018,1038]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
417 and 285. The neutral loss of 162 Da suggested the presence of a hexose residue linked to a pentosyl derivative of luteolin, which for subsequent loss of 132 Da gave the flavone aglycone.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FBAFFF40FACE" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
Compound
|
||
<emphasis id="BACF1D497F171C50FEE3FBAFFEB8FBF1" bold="true" box="[261,286,1103,1122]" pageId="3" pageNumber="83">13</emphasis>
|
||
([M–H]
|
||
<emphasis id="BACF1D497F171C50FE88FBABFEDCFBC4" box="[366,378,1099,1111]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FE88FBABFEDCFBC4" attach="left" box="[366,378,1099,1111]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
at
|
||
<emphasis id="BACF1D497F171C50FE7CFBAEFE18FBF1" box="[410,446,1102,1122]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
417) was putatively identified as pentosyl luteolin. The fragmentation of the [M–H]
|
||
<emphasis id="BACF1D497F171C50FD9FFB87FD23FBE0" box="[633,645,1127,1139]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FD9FFB87FD23FBE0" attach="left" box="[633,645,1127,1139]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
ion gave the ion at
|
||
<emphasis id="BACF1D497F171C50FF57FB66FF73FB09" box="[177,213,1158,1178]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
285 for the loss of a neutral residue of 132 Da (pentose). The collision of the ion at
|
||
<emphasis id="BACF1D497F171C50FE64FB41FE00FB26" box="[386,422,1185,1205]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
285 gave, also in this case, several typical luteolin fragment ions (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FE54FB5EFD6CFB41" author="Gouveia, S. & Castilho, P." box="[434,714,1214,1234]" pageId="3" pageNumber="83" pagination="170 - 181" refId="ref12156" refString="Gouveia, S., Castilho, P., 2013. Artemisia annua L.: essential oil and acetone extract composition and antioxidant capacity. Ind. Crop. Prod. 45, 170 - 181." type="journal article" year="2013">Gouveia and Castilho, 2013</bibRefCitation>
|
||
) at
|
||
<emphasis id="BACF1D497F171C50FD13FB5DFFDDFB7E" italics="true" pageId="3" pageNumber="83">m/ z</emphasis>
|
||
199 ([M
|
||
<emphasis id="BACF1D497F171C50FF3FFB3BFF4CFB7E" box="[217,234,1243,1261]" italics="true" pageId="3" pageNumber="83">—</emphasis>
|
||
H–C
|
||
<subScript id="143FC31E7F171C50FEF2FB03FEBBFB7C" attach="right" box="[276,285,1251,1263]" fontSize="5" pageId="3" pageNumber="83">3</subScript>
|
||
O
|
||
<subScript id="143FC31E7F171C50FECBFB03FE90FB7C" attach="left" box="[301,310,1251,1263]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
–H
|
||
<subScript id="143FC31E7F171C50FEB5FB03FEFAFB7C" attach="both" box="[339,348,1251,1263]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
O]
|
||
<emphasis id="BACF1D497F171C50FE92FB37FE26FB70" box="[372,384,1239,1251]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FE92FB37FE26FB70" attach="none" box="[372,384,1239,1251]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
), 175 ([M
|
||
<emphasis id="BACF1D497F171C50FE0DFB3BFE5AFB7E" box="[491,508,1243,1261]" italics="true" pageId="3" pageNumber="83">—</emphasis>
|
||
H–C
|
||
<subScript id="143FC31E7F171C50FDC0FB03FD89FB7C" attach="right" box="[550,559,1251,1263]" fontSize="5" pageId="3" pageNumber="83">3</subScript>
|
||
O
|
||
<subScript id="143FC31E7F171C50FDD8FB03FDE1FB7C" attach="left" box="[574,583,1251,1263]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
–C
|
||
<subScript id="143FC31E7F171C50FD84FB03FDCDFB7C" attach="both" box="[610,619,1251,1263]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
H
|
||
<subScript id="143FC31E7F171C50FD9DFB03FD22FB7C" attach="both" box="[635,644,1251,1263]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
O]
|
||
<emphasis id="BACF1D497F171C50FD7AFB37FD0EFB70" box="[668,680,1239,1251]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FD7AFB37FD0EFB70" attach="none" box="[668,680,1239,1251]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
) and 241 ([M
|
||
<emphasis id="BACF1D497F171C50FF70FB17FF01FA9A" box="[150,167,1271,1289]" italics="true" pageId="3" pageNumber="83">—</emphasis>
|
||
H–CO
|
||
<subScript id="143FC31E7F171C50FF07FB1FFF4CFA98" attach="left" box="[225,234,1279,1291]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
]
|
||
<emphasis id="BACF1D497F171C50FF14FB13FF58FB6C" box="[242,254,1267,1279]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FF14FB13FF58FB6C" attach="none" box="[242,254,1267,1279]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
). Since the
|
||
<emphasis id="BACF1D497F171C50FE91FB15FE20FA9A" box="[375,390,1269,1289]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-glycosylation of flavones is favored at C-7 (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FF4EFAF2FE63FAB6" author="Cuyckens, F. & Claeys, M. J." box="[168,453,1298,1317]" pageId="3" pageNumber="83" pagination="1 - 15" refId="ref11492" refString="Cuyckens, F., Claeys, M. J., 2004. Mass spectrometry in the structural analysis of flavonoids. J. Mass Spectrom. 39, 1 - 15." type="journal article" year="2004">Cuyckens and Claeys, 2004</bibRefCitation>
|
||
), in the derivatives of luteolin identified the saccharide residue was tentatively positioned at C-7 carbon.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77FA86FE56F954" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
The fragmentation of the [M–H]
|
||
<emphasis id="BACF1D497F171C50FE3BFA82FE4FFAFD" box="[477,489,1378,1390]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FE3BFA82FE4FFAFD" attach="left" box="[477,489,1378,1390]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F171C50FDD0FA85FDFCFAEA" box="[566,602,1381,1401]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
591 provided for the compound
|
||
<emphasis id="BACF1D497F171C50FEF6FA61FE8FFA07" bold="true" box="[272,297,1409,1428]" pageId="3" pageNumber="83">15</emphasis>
|
||
the fragment ion at
|
||
<emphasis id="BACF1D497F171C50FDEEFA61FD8DFA06" box="[520,555,1409,1429]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
531. The neutral loss of 60 Da suggested the presence of an acetyl function linked to an alcohol one. Confirming this hypothesis, the collision of the ion at
|
||
<emphasis id="BACF1D497F171C50FF5EFA34FF7AFA7B" box="[184,220,1492,1512]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
531 provided, among other ions, the fragment ion at
|
||
<emphasis id="BACF1D497F171C50FF97FA10FF33F997" box="[113,149,1520,1540]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
399 [531–132]. The loss of an acetyl function esterified to an alcohol group of a pentose sugar could facilitate the conversion of the pentose sugar in 2H-dihydro-
|
||
<emphasis id="BACF1D497F171C50FE11F9C8FDA4F9AE" box="[503,514,1576,1597]" italics="true" pageId="3" pageNumber="83">γ</emphasis>
|
||
-pyran with formation of the ion at
|
||
<emphasis id="BACF1D497F171C50FF30F9A4FF5CF9CB" box="[214,250,1604,1624]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
513. The loss of the 2H-dihydro-
|
||
<emphasis id="BACF1D497F171C50FDA4F9A4FDEBF9CA" box="[578,589,1604,1625]" italics="true" pageId="3" pageNumber="83">γ</emphasis>
|
||
-pyran moiety generated the ion at
|
||
<emphasis id="BACF1D497F171C50FEC7F980FEE3F9E7" box="[289,325,1632,1652]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
399. The presence of the ion at
|
||
<emphasis id="BACF1D497F171C50FD6AF980FD16F9E7" box="[652,688,1632,1652]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
417 suggested, once again, the presence of a pentosyl derivative of luteolin. From these observations the metabolite
|
||
<emphasis id="BACF1D497F171C50FDC8F979FDE1F93F" bold="true" box="[558,583,1689,1708]" pageId="3" pageNumber="83">15</emphasis>
|
||
was identified as luteolin-7-
|
||
<emphasis id="BACF1D497F171C50FF38F953FF4BF954" box="[222,237,1715,1735]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-acetylpentosylpentoside.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77F930FDADF8FC" blockId="3.[113,784,182,2015]" pageId="3" pageNumber="83">
|
||
Compounds
|
||
<emphasis id="BACF1D497F171C50FEF7F930FE8CF970" bold="true" box="[273,298,1744,1763]" pageId="3" pageNumber="83">14</emphasis>
|
||
and
|
||
<emphasis id="BACF1D497F171C50FE84F930FEDDF970" bold="true" box="[354,379,1744,1763]" pageId="3" pageNumber="83">19</emphasis>
|
||
were identified as two isomers of salvianolic K acid (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FEF2F90DFE66F96C" author="Lu, Y. R. & Foo, L. Y." box="[276,448,1772,1792]" pageId="3" pageNumber="83" pagination="8223 - 8225" refId="ref12915" refString="Lu, Y. R., Foo, L. Y., 2001. Salvianolic acid L, a potent phenolic antioxidant from Salvia officinalis. Tetrahedron Lett. 42, 8223 - 8225." type="journal article" year="2001">Lu and Foo, 2001</bibRefCitation>
|
||
). The MS spectrum of both compounds showed the [M–H]
|
||
<emphasis id="BACF1D497F171C50FE66F8E5FE2AF882" box="[384,396,1797,1809]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FE66F8E5FE2AF882" attach="left" box="[384,396,1797,1809]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F171C50FE35F8E7FE51F888" box="[467,503,1799,1819]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
555, which, for subsequent decarboxylation and dehydration gave an ion at
|
||
<emphasis id="BACF1D497F171C50FD86F8C3FD25F8A4" box="[608,643,1827,1847]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
493. The loss of a 3,4-dihydroxyvinylbenzenic moiety generated the ion at
|
||
<emphasis id="BACF1D497F171C50FD0DF8DFFCA9F8C0" box="[747,783,1855,1875]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
359, which consisted in rosmarinic acid.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FF77F898FA21FF76" blockId="3.[113,784,182,2015]" lastBlockId="3.[831,1501,181,648]" pageId="3" pageNumber="83">
|
||
The deprotonated molecular ion, [M–H]
|
||
<emphasis id="BACF1D497F171C50FDC7F894FD8BF813" box="[545,557,1908,1920]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FDC7F894FD8BF813" attach="none" box="[545,557,1908,1920]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
, at
|
||
<emphasis id="BACF1D497F171C50FDB4F897FDD0F818" box="[594,630,1911,1931]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
283 relative to the metabolite
|
||
<emphasis id="BACF1D497F171C50FEEAF874FE83F834" bold="true" box="[268,293,1940,1959]" pageId="3" pageNumber="83">16</emphasis>
|
||
, isolated only in sample Oct12, has been identified as 4
|
||
<emphasis id="BACF1D497F171C50FF2DF84DFF69F82A" box="[203,207,1965,1977]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FF2DF84DFF69F82A" attach="none" box="[203,207,1965,1977]" fontSize="5" pageId="3" pageNumber="83">0</superScript>
|
||
</emphasis>
|
||
-metil-apigenin (acacetin). To confirm the UV spectrum showed two bands at 231 and
|
||
<quantity id="4F436CBE7F171C50FE52F82CFDA6F84C" box="[436,512,1996,2015]" metricMagnitude="-7" metricUnit="m" metricValue="3.3" pageId="3" pageNumber="83" unit="nm" value="330.0">330 nm</quantity>
|
||
and the spectrum MS/MS provided an abundant fragment at
|
||
<emphasis id="BACF1D497F171C50FB57FF55FB73FF5A" box="[1201,1237,181,201]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
268 probably formed by homolytic cleavage and loss of
|
||
<collectingCountry id="F0AC81CB7F171C50FB9BFF32FB3CFF76" box="[1149,1178,210,229]" name="Switzerland" pageId="3" pageNumber="83">CH</collectingCountry>
|
||
<emphasis id="BACF1D497F171C50FB7CFF2FFB04FF48" box="[1178,1186,207,219]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FB7CFF2FFB04FF48" attach="left" box="[1178,1186,207,219]" fontSize="5" pageId="3" pageNumber="83">•</superScript>
|
||
</emphasis>
|
||
<subScript id="143FC31E7F171C50FB7CFF3BFB05FF74" attach="left" box="[1178,1187,219,231]" fontSize="5" pageId="3" pageNumber="83">3</subScript>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F171C50FB55FF32FADFFF76" author="Hossain, M. B. & Rai, D. K. & Brunton, N. P. & Martin-Diana, A. B. & Barry-Ryan, C." box="[1203,1401,210,230]" pageId="3" pageNumber="83" pagination="10576 - 10581" refId="ref12419" refString="Hossain, M. B., Rai, D. K., Brunton, N. P., Martin-Diana, A. B., Barry-Ryan, C., 2010. Characterization of phenolic composition in lamiaceae spices by LC - ESI-MS / MS. J. Agric. Food Chem. 58, 10576 - 10581." type="journal article" year="2010">Hossain et al., 2010</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCB8FF0EFC16FD8B" blockId="3.[831,1501,181,648]" pageId="3" pageNumber="83">
|
||
Compound
|
||
<emphasis id="BACF1D497F171C50FC31FF0EFC56FE92" bold="true" box="[983,1008,238,257]" pageId="3" pageNumber="83">17</emphasis>
|
||
, present only in Jul12 sample, was putatively identified as a hydroxycinnamyl derivative: (oi- hydroxyhydroferuloylcaffeoyl)caffeoyl hexoside. The [M–H]
|
||
<emphasis id="BACF1D497F171C50FABDFEC2FAC1FEBD" box="[1371,1383,290,302]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FABDFEC2FAC1FEBD" attach="left" box="[1371,1383,290,302]" fontSize="5" pageId="3" pageNumber="83">—</superScript>
|
||
</emphasis>
|
||
ion at
|
||
<emphasis id="BACF1D497F171C50FA5FFEC5FA7BFEAA" box="[1465,1501,293,313]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
697 gave fragment ions at
|
||
<emphasis id="BACF1D497F171C50FBB4FEA1FBD0FEC6" box="[1106,1142,321,341]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
535 and 323. The loss of a residue of 162 suggested the presence of a caffeoyl residue probably esterified to a oi- hydroxyhydroferuloyl moiety. The electron delocalisation from the fragment at
|
||
<emphasis id="BACF1D497F171C50FBAFFE74FBCAFE3B" box="[1097,1132,404,424]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
535 could lead to the loss of a 2-(4- hydroxy-3-methoxyphenyl) acetaldehyde, a CO
|
||
<subScript id="143FC31E7F171C50FAC0FE5AFA89FE55" attach="left" box="[1318,1327,442,454]" fontSize="5" pageId="3" pageNumber="83">2</subScript>
|
||
unit and of one water molecule favoring the formation of the ion at
|
||
<emphasis id="BACF1D497F171C50FAA3FE2CFACFFE73" box="[1349,1385,460,480]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
323, which for cross-ring cleavage of the saccharide moiety, generated the ion at
|
||
<emphasis id="BACF1D497F171C50FCBFFDE4FCDBFD8B" box="[857,893,516,536]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
221.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCB8FDC1FA3BFD1B" blockId="3.[831,1501,181,648]" pageId="3" pageNumber="83">
|
||
The mass spectrum of the metabolite
|
||
<emphasis id="BACF1D497F171C50FB03FDC1FB58FDA7" bold="true" box="[1253,1278,545,564]" pageId="3" pageNumber="83">18</emphasis>
|
||
presented a deprotonated molecular ion at
|
||
<emphasis id="BACF1D497F171C50FBC3FDDCFBEFFDC3" box="[1061,1097,572,592]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
493, whose dissociation generated fragment ions at
|
||
<emphasis id="BACF1D497F171C50FC24FDB8FC40FDFF" box="[962,998,600,620]" italics="true" pageId="3" pageNumber="83">m/z</emphasis>
|
||
359 (rosmarinic acid) and
|
||
<quantity id="4F436CBE7F171C50FB14FDB9FA94FDFF" box="[1266,1330,601,620]" metricMagnitude="0" metricUnit="m" metricValue="7.492999999999999" pageId="3" pageNumber="83" unit="in" value="295.0">295 in</quantity>
|
||
accordance with the presence of the isosalvianolic A acid (
|
||
<bibRefCitation id="EC2ABCAA7F171C50FB03FD95FA29FD1B" author="Ruan, M. & Li, Y. & Li, X. & Luo, J. & Kong, L." box="[1253,1423,629,648]" pageId="3" pageNumber="83" pagination="184 - 189" refId="ref13602" refString="Ruan, M., Li, Y., Li, X., Luo, J., Kong, L., 2012. Qualitative and quantitative analysis of the major constituents in Chinese medicinal preparation Guan - Xin - Ning injection by HPLC - DAD-ESI-MS (n). J. Pharm. Biomed. Anal. 59, 184 - 189." type="journal article" year="2012">Ruan et al., 2012</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCD9FD4BFA85FD2C" blockId="3.[831,1315,683,703]" box="[831,1315,683,703]" pageId="3" pageNumber="83">
|
||
<heading id="D34C76377F171C50FCD9FD4BFA85FD2C" box="[831,1315,683,703]" fontSize="36" level="2" pageId="3" pageNumber="83" reason="3">
|
||
<emphasis id="BACF1D497F171C50FCD9FD4BFA85FD2C" box="[831,1315,683,703]" italics="true" pageId="3" pageNumber="83">
|
||
2.2. Quantitative analysis of
|
||
<taxonomicName id="4FBBBAD87F171C50FBB2FD4BFB74FD2C" box="[1108,1234,683,703]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="subSpecies" species="longicaulis" subSpecies="extracts">T. longicaulis</taxonomicName>
|
||
extracts
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCB8FD04FA1EFBF1" blockId="3.[831,1501,740,1122]" pageId="3" pageNumber="83">
|
||
The quantitative analysis allowed us to detect changes of the metabolic composition of the extracts from
|
||
<taxonomicName id="4FBBBAD87F171C50FB18FD1FFADDFC80" box="[1278,1403,767,787]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F171C50FB18FD1FFADDFC80" box="[1278,1403,767,787]" italics="true" pageId="3" pageNumber="83">T. longicaulis</emphasis>
|
||
</taxonomicName>
|
||
collected in the different four months (
|
||
<figureCitation id="1080DDDE7F171C50FB92FCFCFB0AFCBC" box="[1140,1196,796,815]" captionStart="Fig" captionStartId="4.[360,386,1201,1215]" captionTargetBox="[140,1424,182,1172]" captionTargetId="figure-111@4.[140,1425,181,1172]" captionTargetPageId="4" captionText="Fig. 2. TICs from Thymus longicaulis Jul12, Oct12, Jan13, Apr13 extracts and their relative MS spectrum." figureDoi="http://doi.org/10.5281/zenodo.10491172" httpUri="https://zenodo.org/record/10491172/files/figure.png" pageId="3" pageNumber="83">Fig. 2</figureCitation>
|
||
). The luteolin derivatives (
|
||
<emphasis id="BACF1D497F171C50FA23FCFBFA72FCBC" box="[1477,1492,795,815]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
- pentoside,
|
||
<emphasis id="BACF1D497F171C50FC48FCD7FC1BFCD8" box="[942,957,823,843]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-hexuronide and
|
||
<emphasis id="BACF1D497F171C50FB8AFCD7FBDDFCD8" box="[1132,1147,823,843]" italics="true" pageId="3" pageNumber="83">O</emphasis>
|
||
-acetylpentosylpentoside) and rosmarinic acid, salvianolic acid K and isosalvianolic acid A were determined in all the samples analyzed. The concentration of such molecules seems to be collection time and season dependent. In fact, comparing the data obtained from the four samples, it was particularly observed that an increase in the content of rosmarinic acid and its derivatives was often related to a decrease of the content of the luteolin pentosyl derivatives. Rosmarinic acid was considerably abundant in the sample Oct12: it amounted to
|
||
<quantity id="4F436CBE7F171C50FA6AFBF7FA7AFBB9" box="[1420,1500,1047,1066]" metricMagnitude="-6" metricUnit="kg" metricValue="3.03" pageId="3" pageNumber="83" unit="mg" value="3.03">3.03 mg</quantity>
|
||
quercetin equivalent for 1.0 g of fresh weight sample (
|
||
<tableCitation id="C539F4E07F171C50FA64FBD3FA69FBD5" box="[1410,1487,1075,1094]" captionStart="Table 2" captionStartId="4.[87,131,1275,1289]" captionTargetPageId="4" captionText="Table 2 LC MS quantitative analysis of the identified metabolites in the different Thymus longicaulis extracts (Jul12, Oct12, Jan13, Apr13). Data are expressed as quercetin equivalents (µg/ mL). n.d. = not detected." httpUri="http://table.plazi.org/id/DCC491D37F101C57FFB1FB1BFEB1FAA4" pageId="3" pageNumber="83" tableUuid="DCC491D37F101C57FFB1FB1BFEB1FAA4">Table 2</tableCitation>
|
||
). Jul12 sample contained the lowest amount of rosmarinic acid.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCD9FB66FAB1FB09" blockId="3.[831,1303,1158,1178]" box="[831,1303,1158,1178]" pageId="3" pageNumber="83">
|
||
<heading id="D34C76377F171C50FCD9FB66FAB1FB09" box="[831,1303,1158,1178]" fontSize="36" level="2" pageId="3" pageNumber="83" reason="3">
|
||
<emphasis id="BACF1D497F171C50FCD9FB66FAB1FB09" box="[831,1303,1158,1178]" italics="true" pageId="3" pageNumber="83">
|
||
2.3. Antioxidant activity of extracts
|
||
<taxonomicName id="4FBBBAD87F171C50FB7FFB66FAB1FB09" ID-CoL="56R5N" box="[1177,1303,1158,1178]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="longicaulis">T. longicaulis</taxonomicName>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C50FCB8FB5EFB53F888" blockId="3.[831,1501,1214,2016]" pageId="3" pageNumber="83">
|
||
The evaluation of the antioxidant capacity was carried out by using different methods given the current state of non-existence of a valid method for the determination of total antioxidant capacity of a system. One of the methods used, since the antioxidant activity of plant extracts often is related to their polyphenols amount, was the method of Folin and Ciocalteu Reagent. Although the results obtained by this method cannot be considered an absolute measure of the amount of phenolic material constituting the plant drug, they provide an indication of the reducing properties of the plant matrix. By interpolation on a calibration curve of gallic acid, it was possible to estimate the effective reducing capacity of the four
|
||
<taxonomicName id="4FBBBAD87F171C50FC7DFA10FBBCF997" box="[923,1050,1520,1540]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="3" pageNumber="83" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F171C50FC7DFA10FBBCF997" box="[923,1050,1520,1540]" italics="true" pageId="3" pageNumber="83">T. longicaulis</emphasis>
|
||
</taxonomicName>
|
||
hydroalcoholic extracts. It was determined that the total polyphenol content (TPC) value was clearly higher in Jul12 extract (115.7 GAE (mg)/g FW) than in the other collected extracts. The TPC value undergoes profound changes that seem to strongly depend on the collection time. In fact, comparing the data of Jul12 sample with those for remaining months, it emerged that the TPC value was reduced for more than half for the Oct12 extract (69.6 GAE (mg)/g FW) and reached its lowest level for Jan13 extract (54.4 GAE (mg)/g FW). The spring season (Apr13) seemed to favor a plant metabolic activity turned to polyphenolic compounds biosynthesis (62.9 GAE (mg)/g FW).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F171C56FCB8F8C4FE31FD41" blockId="3.[831,1501,1214,2016]" lastBlockId="5.[113,784,480,1252]" lastPageId="5" lastPageNumber="85" pageId="3" pageNumber="83">
|
||
As it is clear from
|
||
<tableCitation id="C539F4E07F171C50FBFFF8C4FBC5F8A4" box="[1049,1123,1828,1847]" captionStart="Table 3" captionStartId="5.[114,158,183,197]" captionTargetPageId="5" captionText="Table 3 D+ D+ ® ® Antioxidant activity of Thymus longicaulis extracts reported as ID50 values (µg/mL) vs ABTS and DPPH and TEAC values (Trolox Equivalents Antioxidant Capacity, µg Trolox per g of extract) from DPPH, ABTS, FE(III)RP. ORAC values are reported as µM Trolox® Equivalents." httpUri="http://table.plazi.org/id/DCC491D37F111C56FF94FF57FC24FF61" pageId="3" pageNumber="83" tableUuid="DCC491D37F111C56FF94FF57FC24FF61">Table 3</tableCitation>
|
||
, all the investigated extracts showed an effective reducing power of the radical species target ABTS
|
||
<superScript id="7FCE6C137F171C50FA47F8DCFA14F8DB" attach="left" box="[1441,1458,1852,1864]" fontSize="5" pageId="3" pageNumber="83">
|
||
<emphasis id="BACF1D497F171C50FA47F8DCFA0FF8DB" box="[1441,1449,1852,1864]" italics="true" pageId="3" pageNumber="83">•</emphasis>
|
||
+
|
||
</superScript>
|
||
and DPPH
|
||
<emphasis id="BACF1D497F171C50FC91F8B8FCD9F8F7" box="[887,895,1880,1892]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FC91F8B8FCD9F8F7" attach="left" box="[887,895,1880,1892]" fontSize="5" pageId="3" pageNumber="83">•</superScript>
|
||
</emphasis>
|
||
. The scavenging effectiveness seemed to be strongly dependent on the tested dose. Oct12 extract, whose polyphenolic profile analysis highlighted the massive presence of rosmarinic acid, showed an effective reducing power of the radical species target ABTS
|
||
<superScript id="7FCE6C137F171C50FC94F828FC25F847" attach="left" box="[882,899,1992,2004]" fontSize="5" pageId="3" pageNumber="83">
|
||
<emphasis id="BACF1D497F171C50FC94F828FCDCF847" box="[882,890,1992,2004]" italics="true" pageId="3" pageNumber="83">•</emphasis>
|
||
+
|
||
</superScript>
|
||
and DPPH
|
||
<emphasis id="BACF1D497F171C50FC1BF828FBA3F847" box="[1021,1029,1992,2004]" italics="true" pageId="3" pageNumber="83">
|
||
<superScript id="7FCE6C137F171C50FC1BF828FBA3F847" attach="left" box="[1021,1029,1992,2004]" fontSize="5" pageId="3" pageNumber="83">•</superScript>
|
||
</emphasis>
|
||
, quantifiable in the respective ID
|
||
<subScript id="143FC31E7F171C50FA9DF834FA2BF873" attach="left" box="[1403,1421,2004,2016]" fontSize="5" pageId="3" pageNumber="83">50</subScript>
|
||
values (8.91 µg/mL
|
||
<emphasis id="BACF1D497F101C57FF3FF8B6FF4BF8F9" box="[217,237,1878,1898]" italics="true" pageId="4" pageNumber="84">vs</emphasis>
|
||
. the ABTS radical cation and 9.50 µg/mL
|
||
<emphasis id="BACF1D497F101C57FD7CF8B6FD08F8F9" box="[666,686,1878,1898]" italics="true" pageId="4" pageNumber="84">vs</emphasis>
|
||
. DPPH radical). The scavenging effectiveness seemed to be strongly dependent on the tested dose: both the radicals were completely converted in their reduced form at 25.0 µg/mL dose. Rosmarinic acid antioxidant effectiveness was already reported; Fadel et al., (2011) showed that the antiradical activity of rosmarinic acid was much higher than that exerted by bioflavonoids. DFT studies revealed that the high antioxidant power of the molecule could be due to the abstraction of hydrogen atoms from the ortho hydroxyl groups, characterizing both its A and B rings (
|
||
<bibRefCitation id="EC2ABCAA7F101C57FAFCF827FA13F84A" author="Cao, H. & Cheng, W. X. & Li, C. & Pan, X. L. & Xie, X. G. & Li, T. H." box="[1306,1461,1990,2010]" pageId="4" pageNumber="84" pagination="177 - 183" refId="ref11297" refString="Cao, H., Cheng, W. X., Li, C., Pan, X. L., Xie, X. G., Li, T. H., 2005. DFT study on the antioxidant activity of rosmarinic acid. J. Mol. Struct. (THEOCHEM) 719, 177 - 183." type="journal article" year="2005">Cao et al., 2005</bibRefCitation>
|
||
). The sample Oct12 is the only one that contained as constituent acacetin, a well known antioxidant, anti-inflammatory and anticancer natural substance, recently proposed as a therapeutic agent for the treatment of neuropsychiatric disorders (
|
||
<bibRefCitation id="EC2ABCAA7F111C56FD8EFDD4FCA7FDD4" author="Lin, T. Y. & Huang, W. J. & Wu, C. C. & Lu, C. W. & Wang, S. J." box="[616,769,564,583]" pageId="5" pageNumber="85" pagination="88644" refId="ref12810" refString="Lin, T. Y., Huang, W. J., Wu, C. C., Lu, C. W., Wang, S. J., 2014. Acacetin inhibits glutamate release and prevents kainic acid-induced neurotoxicity in rats. Plos One 9, e 88644." type="journal article" year="2014">Lin et al., 2014</bibRefCitation>
|
||
). The evaluation of the Fe
|
||
<superScript id="7FCE6C137F111C56FE87FDACFED5FDCB" attach="left" box="[353,371,588,600]" fontSize="5" pageId="5" pageNumber="85">3+</superScript>
|
||
reducing power strongly correlated with the TPC values (
|
||
<tableCitation id="C539F4E07F111C56FEFFFD8BFEC3FDED" box="[281,357,619,638]" captionStart="Table 3" captionStartId="5.[114,158,183,197]" captionTargetPageId="5" captionText="Table 3 D+ D+ ® ® Antioxidant activity of Thymus longicaulis extracts reported as ID50 values (µg/mL) vs ABTS and DPPH and TEAC values (Trolox Equivalents Antioxidant Capacity, µg Trolox per g of extract) from DPPH, ABTS, FE(III)RP. ORAC values are reported as µM Trolox® Equivalents." httpUri="http://table.plazi.org/id/DCC491D37F111C56FF94FF57FC24FF61" pageId="5" pageNumber="85" tableUuid="DCC491D37F111C56FF94FF57FC24FF61">Table 3</tableCitation>
|
||
). In fact, it was observed that Jul12 contained the highest TEAC value (474.95 µg Trolox
|
||
<emphasis id="BACF1D497F111C56FDB8FD63FDCDFD03" box="[606,619,643,656]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FDB8FD63FDCDFD03" attach="left" box="[606,619,643,656]" fontSize="5" pageId="5" pageNumber="85">®</superScript>
|
||
</emphasis>
|
||
Equivalents per g of extract), followed by Oct12 sample (323.24 µg Trolox
|
||
<emphasis id="BACF1D497F111C56FCE4FD7FFCA9FD3F" box="[770,783,671,684]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FCE4FD7FFCA9FD3F" attach="left" box="[770,783,671,684]" fontSize="5" pageId="5" pageNumber="85">®</superScript>
|
||
</emphasis>
|
||
Equivalents per g of extract).
|
||
</paragraph>
|
||
<caption id="DCC491D37F101C57FE8EFB51FB15FB53" ID-DOI="http://doi.org/10.5281/zenodo.10491172" ID-Zenodo-Dep="10491172" box="[360,1203,1201,1216]" httpUri="https://zenodo.org/record/10491172/files/figure.png" pageId="4" pageNumber="84" startId="4.[360,386,1201,1215]" targetBox="[140,1424,182,1172]" targetPageId="4" targetType="figure">
|
||
<paragraph id="8804C15B7F101C57FE8EFB51FB15FB53" blockId="4.[360,1203,1201,1216]" box="[360,1203,1201,1216]" pageId="4" pageNumber="84">
|
||
<emphasis id="BACF1D497F101C57FE8EFB51FE3CFB2C" bold="true" box="[360,410,1201,1215]" pageId="4" pageNumber="84">Fig. 2.</emphasis>
|
||
TICs from
|
||
<taxonomicName id="4FBBBAD87F101C57FE10FB51FD01FB2C" authority="Jul" authorityName="Jul" box="[502,679,1201,1216]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="4" pageNumber="84" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F101C57FE10FB51FD2CFB53" box="[502,650,1201,1216]" italics="true" pageId="4" pageNumber="84">Thymus longicaulis</emphasis>
|
||
Jul
|
||
</taxonomicName>
|
||
12, Oct12, Jan13, Apr13 extracts and their relative MS spectrum.
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="DCC491D37F101C57FFB1FB1BFEB1FAA4" ID-Table-UUID="DCC491D37F101C57FFB1FB1BFEB1FAA4" httpUri="http://table.plazi.org/id/DCC491D37F101C57FFB1FB1BFEB1FAA4" pageId="4" pageNumber="84" startId="4.[87,131,1275,1289]" targetBox="[110,1451,1359,1818]" targetIsTable="true" targetPageId="4" targetType="table">
|
||
<paragraph id="8804C15B7F101C57FFB1FB1BFEB1FAA4" blockId="4.[87,1474,1275,1335]" pageId="4" pageNumber="84">
|
||
<emphasis id="BACF1D497F101C57FFB1FB1BFF35FA9A" bold="true" box="[87,147,1275,1289]" pageId="4" pageNumber="84">Table 2</emphasis>
|
||
LC MS quantitative analysis of the identified metabolites in the different
|
||
<taxonomicName id="4FBBBAD87F101C57FD69FAF1FCBBFAB3" box="[655,797,1297,1312]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="4" pageNumber="84" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F101C57FD69FAF1FCBBFAB3" box="[655,797,1297,1312]" italics="true" pageId="4" pageNumber="84">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts (Jul12, Oct12, Jan13, Apr13). Data are expressed as quercetin equivalents (µg/ mL). n.d. = not detected.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F101C57FF88FAAFFA3EF889" pageId="4" pageNumber="84">
|
||
<table id="FABB33FB7F10E3ACFF88FAAFFA0DF889" box="[110,1451,1359,1818]" gridcols="5" gridrows="20" pageId="4" pageNumber="84">
|
||
<tr id="368BC3197F10E3ACFF88FAAFFA0DFACE" box="[110,1451,1359,1373]" gridrow="0" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FAAFFDAAFACE" box="[110,524,1359,1373]" gridcol="0" gridrow="0" pageId="4" pageNumber="84">Compound</th>
|
||
<th id="755AAA657F10E3ACFD27FAAFFD48FACE" box="[705,750,1359,1373]" gridcol="1" gridrow="0" pageId="4" pageNumber="84">Jul12</th>
|
||
<th id="755AAA657F10E3ACFC44FAAFFC45FACE" box="[930,995,1359,1373]" gridcol="2" gridrow="0" pageId="4" pageNumber="84">Oct12</th>
|
||
<th id="755AAA657F10E3ACFB7EFAAFFB60FACE" box="[1176,1222,1359,1373]" gridcol="3" gridrow="0" pageId="4" pageNumber="84">Jan13</th>
|
||
<th id="755AAA657F10E3ACFA9CFAAFFA0DFACE" box="[1402,1451,1359,1373]" gridcol="4" gridrow="0" pageId="4" pageNumber="84">Apr13</th>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA90FA0DFAED" box="[110,1451,1392,1406]" gridrow="1" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA90FDAAFAED" box="[110,524,1392,1406]" gridcol="0" gridrow="1" pageId="4" pageNumber="84">Quinic acid</th>
|
||
<td id="755AAA657F10E3ACFD27FA90FD48FAED" box="[705,750,1392,1406]" gridcol="1" gridrow="1" pageId="4" pageNumber="84">5.38</td>
|
||
<td id="755AAA657F10E3ACFC44FA90FC45FAED" box="[930,995,1392,1406]" gridcol="2" gridrow="1" pageId="4" pageNumber="84">6.10</td>
|
||
<td id="755AAA657F10E3ACFB7EFA90FB60FAED" box="[1176,1222,1392,1406]" gridcol="3" gridrow="1" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFA9CFA90FA0DFAED" box="[1402,1451,1392,1406]" gridcol="4" gridrow="1" pageId="4" pageNumber="84">3.88</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA67FA0DFA06" box="[110,1451,1415,1429]" gridrow="2" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA67FDAAFA06" box="[110,524,1415,1429]" gridcol="0" gridrow="2" pageId="4" pageNumber="84">Stachyose</th>
|
||
<td id="755AAA657F10E3ACFD27FA67FD48FA06" box="[705,750,1415,1429]" gridcol="1" gridrow="2" pageId="4" pageNumber="84">3.97</td>
|
||
<td id="755AAA657F10E3ACFC44FA67FC45FA06" box="[930,995,1415,1429]" gridcol="2" gridrow="2" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EFA67FB60FA06" box="[1176,1222,1415,1429]" gridcol="3" gridrow="2" pageId="4" pageNumber="84">10.40</td>
|
||
<td id="755AAA657F10E3ACFA9CFA67FA0DFA06" box="[1402,1451,1415,1429]" gridcol="4" gridrow="2" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA7CFA0DFA3F" box="[110,1451,1436,1452]" gridrow="3" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA7CFDAAFA3F" box="[110,524,1436,1452]" gridcol="0" gridrow="3" pageId="4" pageNumber="84">
|
||
12-Hydroxyjasmonic acid 12-
|
||
<emphasis id="BACF1D497F101C57FEB9FA7CFECDFA3F" box="[351,363,1436,1452]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27FA7CFD48FA3F" box="[705,750,1436,1452]" gridcol="1" gridrow="3" pageId="4" pageNumber="84">1.92</td>
|
||
<td id="755AAA657F10E3ACFC44FA7CFC45FA3F" box="[930,995,1436,1452]" gridcol="2" gridrow="3" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EFA7CFB60FA3F" box="[1176,1222,1436,1452]" gridcol="3" gridrow="3" pageId="4" pageNumber="84">8.28</td>
|
||
<td id="755AAA657F10E3ACFA9CFA7CFA0DFA3F" box="[1402,1451,1436,1452]" gridcol="4" gridrow="3" pageId="4" pageNumber="84">9.51</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA53FA0DFA50" box="[110,1451,1459,1475]" gridrow="4" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA53FDAAFA50" box="[110,524,1459,1475]" gridcol="0" gridrow="4" pageId="4" pageNumber="84">
|
||
6,8-Di-
|
||
<emphasis id="BACF1D497F101C57FF40FA53FF16FA50" box="[166,176,1459,1475]" italics="true" pageId="4" pageNumber="84">C</emphasis>
|
||
-hexosylapigenin
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27FA53FD48FA50" box="[705,750,1459,1475]" gridcol="1" gridrow="4" pageId="4" pageNumber="84">3.27</td>
|
||
<td id="755AAA657F10E3ACFC44FA53FC45FA50" box="[930,995,1459,1475]" gridcol="2" gridrow="4" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EFA53FB60FA50" box="[1176,1222,1459,1475]" gridcol="3" gridrow="4" pageId="4" pageNumber="84">2.35</td>
|
||
<td id="755AAA657F10E3ACFA9CFA53FA0DFA50" box="[1402,1451,1459,1475]" gridcol="4" gridrow="4" pageId="4" pageNumber="84">4.04</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA2CFA0DFA49" box="[110,1451,1484,1498]" gridrow="5" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA2CFDAAFA49" box="[110,524,1484,1498]" gridcol="0" gridrow="5" pageId="4" pageNumber="84">Pinoresinol dihexoside</th>
|
||
<td id="755AAA657F10E3ACFD27FA2CFD48FA49" box="[705,750,1484,1498]" gridcol="1" gridrow="5" pageId="4" pageNumber="84">0.48</td>
|
||
<td id="755AAA657F10E3ACFC44FA2CFC45FA49" box="[930,995,1484,1498]" gridcol="2" gridrow="5" pageId="4" pageNumber="84">trace</td>
|
||
<td id="755AAA657F10E3ACFB7EFA2CFB60FA49" box="[1176,1222,1484,1498]" gridcol="3" gridrow="5" pageId="4" pageNumber="84">0.11</td>
|
||
<td id="755AAA657F10E3ACFA9CFA2CFA0DFA49" box="[1402,1451,1484,1498]" gridcol="4" gridrow="5" pageId="4" pageNumber="84">1.79</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA01FA0DFA62" box="[110,1451,1505,1521]" gridrow="6" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA01FDAAFA62" box="[110,524,1505,1521]" gridcol="0" gridrow="6" pageId="4" pageNumber="84">
|
||
Lariciresinol
|
||
<emphasis id="BACF1D497F101C57FF30FA01FF44FA62" box="[214,226,1505,1521]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-dihexoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27FA01FD48FA62" box="[705,750,1505,1521]" gridcol="1" gridrow="6" pageId="4" pageNumber="84">2.81</td>
|
||
<td id="755AAA657F10E3ACFC44FA01FC45FA62" box="[930,995,1505,1521]" gridcol="2" gridrow="6" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EFA01FB60FA62" box="[1176,1222,1505,1521]" gridcol="3" gridrow="6" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFA9CFA01FA0DFA62" box="[1402,1451,1505,1521]" gridcol="4" gridrow="6" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88FA18FA0DF99B" box="[110,1451,1528,1544]" gridrow="7" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88FA18FDAAF99B" box="[110,524,1528,1544]" gridcol="0" gridrow="7" pageId="4" pageNumber="84">
|
||
Quercetin-
|
||
<emphasis id="BACF1D497F101C57FF22FA18FF76F99B" box="[196,208,1528,1544]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27FA18FD48F99B" box="[705,750,1528,1544]" gridcol="1" gridrow="7" pageId="4" pageNumber="84">29.88</td>
|
||
<td id="755AAA657F10E3ACFC44FA18FC45F99B" box="[930,995,1528,1544]" gridcol="2" gridrow="7" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EFA18FB60F99B" box="[1176,1222,1528,1544]" gridcol="3" gridrow="7" pageId="4" pageNumber="84">33.28</td>
|
||
<td id="755AAA657F10E3ACFA9CFA18FA0DF99B" box="[1402,1451,1528,1544]" gridcol="4" gridrow="7" pageId="4" pageNumber="84">17.58</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F9EFFA0DF98C" box="[110,1451,1551,1567]" gridrow="8" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F9EFFDAAF98C" box="[110,524,1551,1567]" gridcol="0" gridrow="8" pageId="4" pageNumber="84">
|
||
Rosmarinic acid
|
||
<emphasis id="BACF1D497F101C57FF12F9EFFEA6F98C" box="[244,256,1551,1567]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F9EFFD48F98C" box="[705,750,1551,1567]" gridcol="1" gridrow="8" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFC44F9EFFC45F98C" box="[930,995,1551,1567]" gridcol="2" gridrow="8" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EF9EFFB60F98C" box="[1176,1222,1551,1567]" gridcol="3" gridrow="8" pageId="4" pageNumber="84">21.51</td>
|
||
<td id="755AAA657F10E3ACFA9CF9EFFA0DF98C" box="[1402,1451,1551,1567]" gridcol="4" gridrow="8" pageId="4" pageNumber="84">9.95</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F9C6FA0DF9A5" box="[110,1451,1574,1590]" gridrow="9" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F9C6FDAAF9A5" box="[110,524,1574,1590]" gridcol="0" gridrow="9" pageId="4" pageNumber="84">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F101C57FF51F9C6FF65F9A5" box="[183,195,1574,1590]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F9C6FD48F9A5" box="[705,750,1574,1590]" gridcol="1" gridrow="9" pageId="4" pageNumber="84">39.55</td>
|
||
<td id="755AAA657F10E3ACFC44F9C6FC45F9A5" box="[930,995,1574,1590]" gridcol="2" gridrow="9" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EF9C6FB60F9A5" box="[1176,1222,1574,1590]" gridcol="3" gridrow="9" pageId="4" pageNumber="84">46.15</td>
|
||
<td id="755AAA657F10E3ACFA9CF9C6FA0DF9A5" box="[1402,1451,1574,1590]" gridcol="4" gridrow="9" pageId="4" pageNumber="84">51.19</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F9DCFA0DF9DF" box="[110,1451,1596,1612]" gridrow="10" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F9DCFDAAF9DF" box="[110,524,1596,1612]" gridcol="0" gridrow="10" pageId="4" pageNumber="84">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F101C57FF51F9DCFF65F9DF" box="[183,195,1596,1612]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexuronide
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F9DCFD48F9DF" box="[705,750,1596,1612]" gridcol="1" gridrow="10" pageId="4" pageNumber="84">2.21</td>
|
||
<td id="755AAA657F10E3ACFC44F9DCFC45F9DF" box="[930,995,1596,1612]" gridcol="2" gridrow="10" pageId="4" pageNumber="84">4.71</td>
|
||
<td id="755AAA657F10E3ACFB7EF9DCFB60F9DF" box="[1176,1222,1596,1612]" gridcol="3" gridrow="10" pageId="4" pageNumber="84">2.99</td>
|
||
<td id="755AAA657F10E3ACFA9CF9DCFA0DF9DF" box="[1402,1451,1596,1612]" gridcol="4" gridrow="10" pageId="4" pageNumber="84">8.12</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F9B3FA0DF9F0" box="[110,1451,1619,1635]" gridrow="11" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F9B3FDAAF9F0" box="[110,524,1619,1635]" gridcol="0" gridrow="11" pageId="4" pageNumber="84">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F101C57FF51F9B3FF65F9F0" box="[183,195,1619,1635]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-hexosylpentoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F9B3FD48F9F0" box="[705,750,1619,1635]" gridcol="1" gridrow="11" pageId="4" pageNumber="84">0.74</td>
|
||
<td id="755AAA657F10E3ACFC44F9B3FC45F9F0" box="[930,995,1619,1635]" gridcol="2" gridrow="11" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EF9B3FB60F9F0" box="[1176,1222,1619,1635]" gridcol="3" gridrow="11" pageId="4" pageNumber="84">4.64</td>
|
||
<td id="755AAA657F10E3ACFA9CF9B3FA0DF9F0" box="[1402,1451,1619,1635]" gridcol="4" gridrow="11" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F98CFA0DF9E9" box="[110,1451,1644,1658]" gridrow="12" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F98CFDAAF9E9" box="[110,524,1644,1658]" gridcol="0" gridrow="12" pageId="4" pageNumber="84">Rosmarinic acid</th>
|
||
<td id="755AAA657F10E3ACFD27F98CFD48F9E9" box="[705,750,1644,1658]" gridcol="1" gridrow="12" pageId="4" pageNumber="84">12.97</td>
|
||
<td id="755AAA657F10E3ACFC44F98CFC45F9E9" box="[930,995,1644,1658]" gridcol="2" gridrow="12" pageId="4" pageNumber="84">3029.56</td>
|
||
<td id="755AAA657F10E3ACFB7EF98CFB60F9E9" box="[1176,1222,1644,1658]" gridcol="3" gridrow="12" pageId="4" pageNumber="84">72.62</td>
|
||
<td id="755AAA657F10E3ACFA9CF98CFA0DF9E9" box="[1402,1451,1644,1658]" gridcol="4" gridrow="12" pageId="4" pageNumber="84">37.51</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F961FA0DF902" box="[110,1451,1665,1681]" gridrow="13" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F961FDAAF902" box="[110,524,1665,1681]" gridcol="0" gridrow="13" pageId="4" pageNumber="84">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F101C57FF51F961FF65F902" box="[183,195,1665,1681]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-pentoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F961FD48F902" box="[705,750,1665,1681]" gridcol="1" gridrow="13" pageId="4" pageNumber="84">5.08</td>
|
||
<td id="755AAA657F10E3ACFC44F961FC45F902" box="[930,995,1665,1681]" gridcol="2" gridrow="13" pageId="4" pageNumber="84">1.59</td>
|
||
<td id="755AAA657F10E3ACFB7EF961FB60F902" box="[1176,1222,1665,1681]" gridcol="3" gridrow="13" pageId="4" pageNumber="84">2.93</td>
|
||
<td id="755AAA657F10E3ACFA9CF961FA0DF902" box="[1402,1451,1665,1681]" gridcol="4" gridrow="13" pageId="4" pageNumber="84">3.59</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F979FA0DF93B" box="[110,1451,1689,1704]" gridrow="14" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F979FDAAF93B" box="[110,524,1689,1704]" gridcol="0" gridrow="14" pageId="4" pageNumber="84">Salvianolic acid K</th>
|
||
<td id="755AAA657F10E3ACFD27F979FD48F93B" box="[705,750,1689,1704]" gridcol="1" gridrow="14" pageId="4" pageNumber="84">19.66</td>
|
||
<td id="755AAA657F10E3ACFC44F979FC45F93B" box="[930,995,1689,1704]" gridcol="2" gridrow="14" pageId="4" pageNumber="84">15.84</td>
|
||
<td id="755AAA657F10E3ACFB7EF979FB60F93B" box="[1176,1222,1689,1704]" gridcol="3" gridrow="14" pageId="4" pageNumber="84">32.03</td>
|
||
<td id="755AAA657F10E3ACFA9CF979FA0DF93B" box="[1402,1451,1689,1704]" gridcol="4" gridrow="14" pageId="4" pageNumber="84">23.92</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F94FFA0DF92C" box="[110,1451,1711,1727]" gridrow="15" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F94FFDAAF92C" box="[110,524,1711,1727]" gridcol="0" gridrow="15" pageId="4" pageNumber="84">
|
||
Luteolin-
|
||
<emphasis id="BACF1D497F101C57FF51F94FFF65F92C" box="[183,195,1711,1727]" italics="true" pageId="4" pageNumber="84">O</emphasis>
|
||
-(acetylpentosyl)pentoside
|
||
</th>
|
||
<td id="755AAA657F10E3ACFD27F94FFD48F92C" box="[705,750,1711,1727]" gridcol="1" gridrow="15" pageId="4" pageNumber="84">10.48</td>
|
||
<td id="755AAA657F10E3ACFC44F94FFC45F92C" box="[930,995,1711,1727]" gridcol="2" gridrow="15" pageId="4" pageNumber="84">7.91</td>
|
||
<td id="755AAA657F10E3ACFB7EF94FFB60F92C" box="[1176,1222,1711,1727]" gridcol="3" gridrow="15" pageId="4" pageNumber="84">21.14</td>
|
||
<td id="755AAA657F10E3ACFA9CF94FFA0DF92C" box="[1402,1451,1711,1727]" gridcol="4" gridrow="15" pageId="4" pageNumber="84">9.42</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F927FA0DF946" box="[110,1451,1735,1749]" gridrow="16" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F927FDAAF946" box="[110,524,1735,1749]" gridcol="0" gridrow="16" pageId="4" pageNumber="84">Methylapigenin</th>
|
||
<td id="755AAA657F10E3ACFD27F927FD48F946" box="[705,750,1735,1749]" gridcol="1" gridrow="16" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFC44F927FC45F946" box="[930,995,1735,1749]" gridcol="2" gridrow="16" pageId="4" pageNumber="84">22.56</td>
|
||
<td id="755AAA657F10E3ACFB7EF927FB60F946" box="[1176,1222,1735,1749]" gridcol="3" gridrow="16" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFA9CF927FA0DF946" box="[1402,1451,1735,1749]" gridcol="4" gridrow="16" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F93BFA0DF97E" box="[110,1451,1755,1773]" gridrow="17" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F93BFDAAF97E" box="[110,524,1755,1773]" gridcol="0" gridrow="17" pageId="4" pageNumber="84">(oi- Hydroxyhydroferuloylcaffeoyl)caffeoyl hexoside</th>
|
||
<td id="755AAA657F10E3ACFD27F93BFD48F97E" box="[705,750,1755,1773]" gridcol="1" gridrow="17" pageId="4" pageNumber="84">1.59</td>
|
||
<td id="755AAA657F10E3ACFC44F93BFC45F97E" box="[930,995,1755,1773]" gridcol="2" gridrow="17" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFB7EF93BFB60F97E" box="[1176,1222,1755,1773]" gridcol="3" gridrow="17" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFA9CF93BFA0DF97E" box="[1402,1451,1755,1773]" gridcol="4" gridrow="17" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F915FA0DF890" box="[110,1451,1781,1795]" gridrow="18" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F915FDAAF890" box="[110,524,1781,1795]" gridcol="0" gridrow="18" pageId="4" pageNumber="84">Isosalvianolic acid A</th>
|
||
<td id="755AAA657F10E3ACFD27F915FD48F890" box="[705,750,1781,1795]" gridcol="1" gridrow="18" pageId="4" pageNumber="84">2.69</td>
|
||
<td id="755AAA657F10E3ACFC44F915FC45F890" box="[930,995,1781,1795]" gridcol="2" gridrow="18" pageId="4" pageNumber="84">69.28</td>
|
||
<td id="755AAA657F10E3ACFB7EF915FB60F890" box="[1176,1222,1781,1795]" gridcol="3" gridrow="18" pageId="4" pageNumber="84">20.59</td>
|
||
<td id="755AAA657F10E3ACFA9CF915FA0DF890" box="[1402,1451,1781,1795]" gridcol="4" gridrow="18" pageId="4" pageNumber="84">6.43</td>
|
||
</tr>
|
||
<tr id="368BC3197F10E3ACFF88F8EBFA0DF889" box="[110,1451,1803,1818]" gridrow="19" pageId="4" pageNumber="84">
|
||
<th id="755AAA657F10E3ACFF88F8EBFDAAF889" box="[110,524,1803,1818]" gridcol="0" gridrow="19" pageId="4" pageNumber="84">Salvianolic acid K (isomer)</th>
|
||
<td id="755AAA657F10E3ACFD27F8EBFD48F889" box="[705,750,1803,1818]" gridcol="1" gridrow="19" pageId="4" pageNumber="84">n.d.</td>
|
||
<td id="755AAA657F10E3ACFC44F8EBFC45F889" box="[930,995,1803,1818]" gridcol="2" gridrow="19" pageId="4" pageNumber="84">1.12</td>
|
||
<td id="755AAA657F10E3ACFB7EF8EBFB60F889" box="[1176,1222,1803,1818]" gridcol="3" gridrow="19" pageId="4" pageNumber="84">23.25</td>
|
||
<td id="755AAA657F10E3ACFA9CF8EBFA0DF889" box="[1402,1451,1803,1818]" gridcol="4" gridrow="19" pageId="4" pageNumber="84">n.d.</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<caption id="DCC491D37F111C56FF94FF57FC24FF61" ID-Table-UUID="DCC491D37F111C56FF94FF57FC24FF61" httpUri="http://table.plazi.org/id/DCC491D37F111C56FF94FF57FC24FF61" pageId="5" pageNumber="85" startId="5.[114,158,183,197]" targetBox="[136,1478,258,406]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="8804C15B7F111C56FF94FF57FC24FF61" blockId="5.[113,1500,183,244]" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FF94FF57FC06FF5D" bold="true" box="[114,928,183,206]" pageId="5" pageNumber="85">
|
||
Table 3
|
||
<superScript id="7FCE6C137F111C56FCDEFF27FC06FF5D" attach="left" box="[824,928,197,206]" fontSize="4" pageId="5" pageNumber="85">D+ D</superScript>
|
||
</emphasis>
|
||
+
|
||
<emphasis id="BACF1D497F111C56FB8CFF29FA7AFF40" box="[1130,1500,201,211]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FB8CFF29FA7AFF40" attach="left" box="[1130,1500,201,211]" fontSize="4" pageId="5" pageNumber="85">® ®</superScript>
|
||
</emphasis>
|
||
Antioxidant activity of
|
||
<taxonomicName id="4FBBBAD87F111C56FEC1FF2DFE13FF4F" box="[295,437,205,220]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="85" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F111C56FEC1FF2DFE13FF4F" box="[295,437,205,220]" italics="true" pageId="5" pageNumber="85">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts reported as ID
|
||
<subScript id="143FC31E7F111C56FD8BFF34FDDAFF4D" attach="left" box="[621,636,212,222]" fontSize="4" pageId="5" pageNumber="85">50</subScript>
|
||
values (µg/mL)
|
||
<emphasis id="BACF1D497F111C56FD1AFF2DFCAAFF4F" box="[764,780,205,220]" italics="true" pageId="5" pageNumber="85">vs</emphasis>
|
||
ABTS and DPPH and TEAC values (Trolox Equivalents Antioxidant Capacity, µg Trolox per g of extract) from DPPH, ABTS, FE(III)RP. ORAC values are reported as µM Trolox
|
||
<emphasis id="BACF1D497F111C56FCF7FF00FCBDFF79" box="[785,795,224,234]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FCF7FF00FCBDFF79" attach="left" box="[785,795,224,234]" fontSize="4" pageId="5" pageNumber="85">®</superScript>
|
||
</emphasis>
|
||
Equivalents.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F111C56FE65FEE4FD8BFE05" pageId="5" pageNumber="85">
|
||
<table id="FABB33FB7F11E3ACFF6EFEE2FA60FE05" box="[136,1478,258,406]" gridcols="7" gridrows="6" pageId="5" pageNumber="85">
|
||
<tr id="368BC3197F11E3ACFF6EFEE2FA60FE88" box="[136,1478,258,283]" gridrow="0" pageId="5" pageNumber="85" rowspan-0="1">
|
||
<th id="755AAA657F11E3ACFED2FEE2FE37FE88" box="[308,401,258,283]" gridcol="1" gridrow="0" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FE65FEE4FE2CFE98" bold="true" box="[387,394,260,267]" pageId="5" pageNumber="85">D</emphasis>
|
||
+ ID50 ABTS
|
||
</th>
|
||
<th id="755AAA657F11E3ACFE19FEE2FDFCFE88" box="[511,602,258,283]" gridcol="2" gridrow="0" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FDB5FEE4FDFCFE98" bold="true" box="[595,602,260,267]" pageId="5" pageNumber="85">D</emphasis>
|
||
ID50 DPPH
|
||
</th>
|
||
<th id="755AAA657F11E3ACFD2EFEE2FC88FE88" box="[712,814,258,283]" gridcol="3" gridrow="0" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FCC6FEE4FC81FE98" bold="true" box="[800,807,260,267]" pageId="5" pageNumber="85">D</emphasis>
|
||
+ TEAC ABTS
|
||
</th>
|
||
<th id="755AAA657F11E3ACFC7AFEE2FBA0FE88" box="[924,1030,258,283]" gridcol="4" gridrow="0" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FC1FFEE4FBA6FE98" bold="true" box="[1017,1024,260,267]" pageId="5" pageNumber="85">D</emphasis>
|
||
+ TEAC DPPH
|
||
</th>
|
||
<th id="755AAA657F11E3ACFB93FEE2FB4EFE88" box="[1141,1256,258,283]" gridcol="5" gridrow="0" pageId="5" pageNumber="85">TEAC Fe(III)RP</th>
|
||
<th id="755AAA657F11E3ACFAB1FEE2FA60FE88" box="[1367,1478,258,283]" gridcol="6" gridrow="0" pageId="5" pageNumber="85">
|
||
ORAC Values
|
||
<emphasis id="BACF1D497F111C56FA59FEE8FA60FE83" bold="true" box="[1471,1478,264,272]" italics="true" pageId="5" pageNumber="85">⁄</emphasis>
|
||
</th>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EFECCFA60FEA9" box="[136,1478,300,314]" gridrow="1" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EFECCFF63FEA9" box="[136,197,300,314]" gridcol="0" gridrow="1" pageId="5" pageNumber="85">Jul12</th>
|
||
<td id="755AAA657F11E3ACFED2FECCFE37FEA9" box="[308,401,300,314]" gridcol="1" gridrow="1" pageId="5" pageNumber="85">13.11</td>
|
||
<td id="755AAA657F11E3ACFE19FECCFDFCFEA9" box="[511,602,300,314]" gridcol="2" gridrow="1" pageId="5" pageNumber="85">15.72</td>
|
||
<td id="755AAA657F11E3ACFD2EFECCFC88FEA9" box="[712,814,300,314]" gridcol="3" gridrow="1" pageId="5" pageNumber="85">107.44</td>
|
||
<td id="755AAA657F11E3ACFC7AFECCFBA0FEA9" box="[924,1030,300,314]" gridcol="4" gridrow="1" pageId="5" pageNumber="85">175.15</td>
|
||
<td id="755AAA657F11E3ACFB93FECCFB4EFEA9" box="[1141,1256,300,314]" gridcol="5" gridrow="1" pageId="5" pageNumber="85">474.95</td>
|
||
<td id="755AAA657F11E3ACFAB1FECCFA60FEA9" box="[1367,1478,300,314]" gridcol="6" gridrow="1" pageId="5" pageNumber="85">524.80</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EFEA3FA60FEC2" box="[136,1478,323,337]" gridrow="2" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EFEA3FF63FEC2" box="[136,197,323,337]" gridcol="0" gridrow="2" pageId="5" pageNumber="85">Oct12</th>
|
||
<td id="755AAA657F11E3ACFED2FEA3FE37FEC2" box="[308,401,323,337]" gridcol="1" gridrow="2" pageId="5" pageNumber="85">8.91</td>
|
||
<td id="755AAA657F11E3ACFE19FEA3FDFCFEC2" box="[511,602,323,337]" gridcol="2" gridrow="2" pageId="5" pageNumber="85">9.50</td>
|
||
<td id="755AAA657F11E3ACFD2EFEA3FC88FEC2" box="[712,814,323,337]" gridcol="3" gridrow="2" pageId="5" pageNumber="85">96.52</td>
|
||
<td id="755AAA657F11E3ACFC7AFEA3FBA0FEC2" box="[924,1030,323,337]" gridcol="4" gridrow="2" pageId="5" pageNumber="85">159.15</td>
|
||
<td id="755AAA657F11E3ACFB93FEA3FB4EFEC2" box="[1141,1256,323,337]" gridcol="5" gridrow="2" pageId="5" pageNumber="85">323.24</td>
|
||
<td id="755AAA657F11E3ACFAB1FEA3FA60FEC2" box="[1367,1478,323,337]" gridcol="6" gridrow="2" pageId="5" pageNumber="85">776.54</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EFEBAFA60FEFB" box="[136,1478,346,360]" gridrow="3" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EFEBAFF63FEFB" box="[136,197,346,360]" gridcol="0" gridrow="3" pageId="5" pageNumber="85">Jan13</th>
|
||
<td id="755AAA657F11E3ACFED2FEBAFE37FEFB" box="[308,401,346,360]" gridcol="1" gridrow="3" pageId="5" pageNumber="85">15.67</td>
|
||
<td id="755AAA657F11E3ACFE19FEBAFDFCFEFB" box="[511,602,346,360]" gridcol="2" gridrow="3" pageId="5" pageNumber="85">18.89</td>
|
||
<td id="755AAA657F11E3ACFD2EFEBAFC88FEFB" box="[712,814,346,360]" gridcol="3" gridrow="3" pageId="5" pageNumber="85">112.46</td>
|
||
<td id="755AAA657F11E3ACFC7AFEBAFBA0FEFB" box="[924,1030,346,360]" gridcol="4" gridrow="3" pageId="5" pageNumber="85">180.99</td>
|
||
<td id="755AAA657F11E3ACFB93FEBAFB4EFEFB" box="[1141,1256,346,360]" gridcol="5" gridrow="3" pageId="5" pageNumber="85">290.01</td>
|
||
<td id="755AAA657F11E3ACFAB1FEBAFA60FEFB" box="[1367,1478,346,360]" gridcol="6" gridrow="3" pageId="5" pageNumber="85">519.39</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EFE91FA60FEEC" box="[136,1478,369,383]" gridrow="4" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EFE91FF63FEEC" box="[136,197,369,383]" gridcol="0" gridrow="4" pageId="5" pageNumber="85">Apr13</th>
|
||
<td id="755AAA657F11E3ACFED2FE91FE37FEEC" box="[308,401,369,383]" gridcol="1" gridrow="4" pageId="5" pageNumber="85">72.01</td>
|
||
<td id="755AAA657F11E3ACFE19FE91FDFCFEEC" box="[511,602,369,383]" gridcol="2" gridrow="4" pageId="5" pageNumber="85">64.61</td>
|
||
<td id="755AAA657F11E3ACFD2EFE91FC88FEEC" box="[712,814,369,383]" gridcol="3" gridrow="4" pageId="5" pageNumber="85">155.53</td>
|
||
<td id="755AAA657F11E3ACFC7AFE91FBA0FEEC" box="[924,1030,369,383]" gridcol="4" gridrow="4" pageId="5" pageNumber="85">220.03</td>
|
||
<td id="755AAA657F11E3ACFB93FE91FB4EFEEC" box="[1141,1256,369,383]" gridcol="5" gridrow="4" pageId="5" pageNumber="85">153.34</td>
|
||
<td id="755AAA657F11E3ACFAB1FE91FA60FEEC" box="[1367,1478,369,383]" gridcol="6" gridrow="4" pageId="5" pageNumber="85">414.14</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EFE63FA60FE05" box="[136,1478,387,406]" gridrow="5" pageId="5" pageNumber="85" rowspan-3="1" rowspan-4="1" rowspan-5="1" rowspan-6="1">
|
||
<th id="755AAA657F11E3ACFF6EFE63FF63FE05" box="[136,197,387,406]" gridcol="0" gridrow="5" pageId="5" pageNumber="85">
|
||
Trolox
|
||
<emphasis id="BACF1D497F111C56FF5DFE63FF63FE1E" box="[187,197,387,397]" italics="true" pageId="5" pageNumber="85">®</emphasis>
|
||
</th>
|
||
<td id="755AAA657F11E3ACFED2FE63FE37FE05" box="[308,401,387,406]" gridcol="1" gridrow="5" pageId="5" pageNumber="85">1.71</td>
|
||
<td id="755AAA657F11E3ACFE19FE63FDFCFE05" box="[511,602,387,406]" gridcol="2" gridrow="5" pageId="5" pageNumber="85">1.22</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<caption id="DCC491D37F111C56FCD9FE03FC70FDA5" ID-Table-UUID="DCC491D37F111C56FCD9FE03FC70FDA5" httpUri="http://table.plazi.org/id/DCC491D37F111C56FCD9FE03FC70FDA5" pageId="5" pageNumber="85" startId="5.[831,875,483,497]" targetBox="[853,1478,590,706]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="8804C15B7F111C56FCD9FE03FC70FDA5" blockId="5.[831,1502,483,566]" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FCD9FE03FCDDFE62" bold="true" box="[831,891,483,497]" pageId="5" pageNumber="85">Table 5</emphasis>
|
||
Standard scores of antioxidant capacity for each investigated extract and RACI values. These latter were calculated by averaging the standard scores from the different antioxidant assays.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F111C56FC4AFDAEFA1EFD51" pageId="5" pageNumber="85">
|
||
<table id="FABB33FB7F11E3ACFCB3FDAEFA60FD51" box="[853,1478,590,706]" gridcols="7" gridrows="5" pageId="5" pageNumber="85">
|
||
<tr id="368BC3197F11E3ACFCB3FDAEFA60FDCF" box="[853,1478,590,604]" gridrow="0" pageId="5" pageNumber="85" rowspan-0="1">
|
||
<th id="755AAA657F11E3ACFC4AFDAEFC41FDCF" box="[940,999,590,604]" gridcol="1" gridrow="0" pageId="5" pageNumber="85">DPPH</th>
|
||
<th id="755AAA657F11E3ACFBEAFDAEFBE1FDCF" box="[1036,1095,590,604]" gridcol="2" gridrow="0" pageId="5" pageNumber="85">ABTS</th>
|
||
<th id="755AAA657F11E3ACFB8AFDAEFB00FDCF" box="[1132,1190,590,604]" gridcol="3" gridrow="0" pageId="5" pageNumber="85">ORAC</th>
|
||
<th id="755AAA657F11E3ACFB2AFDAEFAA0FDCF" box="[1228,1286,590,604]" gridcol="4" gridrow="0" pageId="5" pageNumber="85">FRAP</th>
|
||
<th id="755AAA657F11E3ACFACAFDAEFAC0FDCF" box="[1324,1382,590,604]" gridcol="5" gridrow="0" pageId="5" pageNumber="85">TPC</th>
|
||
<th id="755AAA657F11E3ACFA6DFDAEFA60FDCF" box="[1419,1478,590,604]" gridcol="6" gridrow="0" pageId="5" pageNumber="85">RACI</th>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFCB3FD8FFA60FDED" box="[853,1478,623,638]" gridrow="1" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFCB3FD8FFC21FDED" box="[853,903,623,638]" gridcol="0" gridrow="1" pageId="5" pageNumber="85">Jul12</th>
|
||
<td id="755AAA657F11E3ACFC4AFD8FFC41FDED" box="[940,999,623,638]" gridcol="1" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FC4AFD90FC1FFDED" box="[940,953,624,638]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.407
|
||
</td>
|
||
<td id="755AAA657F11E3ACFBEAFD8FFBE1FDED" box="[1036,1095,623,638]" gridcol="2" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FBEAFD90FBBFFDED" box="[1036,1049,624,638]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.336
|
||
</td>
|
||
<td id="755AAA657F11E3ACFB8AFD8FFB00FDED" box="[1132,1190,623,638]" gridcol="3" gridrow="1" pageId="5" pageNumber="85">1.246</td>
|
||
<td id="755AAA657F11E3ACFB2AFD8FFAA0FDED" box="[1228,1286,623,638]" gridcol="4" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FB2AFD90FB7FFDED" box="[1228,1241,624,638]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.220
|
||
</td>
|
||
<td id="755AAA657F11E3ACFACAFD8FFAC0FDED" box="[1324,1382,623,638]" gridcol="5" gridrow="1" pageId="5" pageNumber="85">1.461</td>
|
||
<td id="755AAA657F11E3ACFA6DFD8FFA60FDED" box="[1419,1478,623,638]" gridcol="6" gridrow="1" pageId="5" pageNumber="85">0.349</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFCB3FD66FA60FD06" box="[853,1478,646,661]" gridrow="2" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFCB3FD66FC21FD06" box="[853,903,646,661]" gridcol="0" gridrow="2" pageId="5" pageNumber="85">Oct12</th>
|
||
<td id="755AAA657F11E3ACFC4AFD66FC41FD06" box="[940,999,646,661]" gridcol="1" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FC4AFD67FC1FFD06" box="[940,953,647,661]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.829
|
||
</td>
|
||
<td id="755AAA657F11E3ACFBEAFD66FBE1FD06" box="[1036,1095,646,661]" gridcol="2" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FBEAFD67FBBFFD06" box="[1036,1049,647,661]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.955
|
||
</td>
|
||
<td id="755AAA657F11E3ACFB8AFD66FB00FD06" box="[1132,1190,646,661]" gridcol="3" gridrow="2" pageId="5" pageNumber="85">0.097</td>
|
||
<td id="755AAA657F11E3ACFB2AFD66FAA0FD06" box="[1228,1286,646,661]" gridcol="4" gridrow="2" pageId="5" pageNumber="85">1.415</td>
|
||
<td id="755AAA657F11E3ACFACAFD66FAC0FD06" box="[1324,1382,646,661]" gridcol="5" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FACAFD67FA9FFD06" box="[1324,1337,647,661]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.221
|
||
</td>
|
||
<td id="755AAA657F11E3ACFA6DFD66FA60FD06" box="[1419,1478,646,661]" gridcol="6" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FA6DFD67FA3EFD06" box="[1419,1432,647,661]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.098
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFCB3FD7DFA60FD3F" box="[853,1478,669,684]" gridrow="3" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFCB3FD7DFC21FD3F" box="[853,903,669,684]" gridcol="0" gridrow="3" pageId="5" pageNumber="85">Jan13</th>
|
||
<td id="755AAA657F11E3ACFC4AFD7DFC41FD3F" box="[940,999,669,684]" gridcol="1" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FC4AFD7EFC1FFD3F" box="[940,953,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.213
|
||
</td>
|
||
<td id="755AAA657F11E3ACFBEAFD7DFBE1FD3F" box="[1036,1095,669,684]" gridcol="2" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FBEAFD7EFBBFFD3F" box="[1036,1049,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.110
|
||
</td>
|
||
<td id="755AAA657F11E3ACFB8AFD7DFB00FD3F" box="[1132,1190,669,684]" gridcol="3" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FB8AFD7EFBDFFD3F" box="[1132,1145,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.154
|
||
</td>
|
||
<td id="755AAA657F11E3ACFB2AFD7DFAA0FD3F" box="[1228,1286,669,684]" gridcol="4" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FB2AFD7EFB7FFD3F" box="[1228,1241,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.256
|
||
</td>
|
||
<td id="755AAA657F11E3ACFACAFD7DFAC0FD3F" box="[1324,1382,669,684]" gridcol="5" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FACAFD7EFA9FFD3F" box="[1324,1337,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.775
|
||
</td>
|
||
<td id="755AAA657F11E3ACFA6DFD7DFA60FD3F" box="[1419,1478,669,684]" gridcol="6" gridrow="3" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FA6DFD7EFA3EFD3F" box="[1419,1432,670,684]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.302
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFCB3FD54FA60FD51" box="[853,1478,692,706]" gridrow="4" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFCB3FD54FC21FD51" box="[853,903,692,706]" gridcol="0" gridrow="4" pageId="5" pageNumber="85">Apr13</th>
|
||
<td id="755AAA657F11E3ACFC4AFD54FC41FD51" box="[940,999,692,706]" gridcol="1" gridrow="4" pageId="5" pageNumber="85">1.450</td>
|
||
<td id="755AAA657F11E3ACFBEAFD54FBE1FD51" box="[1036,1095,692,706]" gridcol="2" gridrow="4" pageId="5" pageNumber="85">1.401</td>
|
||
<td id="755AAA657F11E3ACFB8AFD54FB00FD51" box="[1132,1190,692,706]" gridcol="3" gridrow="4" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FB8AFD54FBDFFD51" box="[1132,1145,692,706]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
1.189
|
||
</td>
|
||
<td id="755AAA657F11E3ACFB2AFD54FAA0FD51" box="[1228,1286,692,706]" gridcol="4" gridrow="4" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FB2AFD54FB7FFD51" box="[1228,1241,692,706]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.939
|
||
</td>
|
||
<td id="755AAA657F11E3ACFACAFD54FAC0FD51" box="[1324,1382,692,706]" gridcol="5" gridrow="4" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FACAFD54FA9FFD51" box="[1324,1337,692,706]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.465
|
||
</td>
|
||
<td id="755AAA657F11E3ACFA6DFD54FA60FD51" box="[1419,1478,692,706]" gridcol="6" gridrow="4" pageId="5" pageNumber="85">0.051</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF77FD3BFDE5FC22" blockId="5.[113,784,480,1252]" pageId="5" pageNumber="85">
|
||
When ORAC assay was performed, all the extracts massively scavenged ROO
|
||
<emphasis id="BACF1D497F111C56FEEDFD13FEB5FD6C" box="[267,275,755,767]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FEEDFD13FEB5FD6C" attach="left" box="[267,275,755,767]" fontSize="5" pageId="5" pageNumber="85">•</superScript>
|
||
</emphasis>
|
||
radicals at the highest doses tested and no fluorescein decay could be observed. Thus ORAC values were determined by calculating the net area under the curve (AUC) of the samples at the lowest tested dose (0.781 µg/mL). Oct12 was able to exert the strongest antiradical efficacy (776.54 µM Trolox
|
||
<emphasis id="BACF1D497F111C56FDB7FC82FDF8FCFC" box="[593,606,866,879]" italics="true" pageId="5" pageNumber="85">
|
||
<superScript id="7FCE6C137F111C56FDB7FC82FDF8FCFC" attach="left" box="[593,606,866,879]" fontSize="5" pageId="5" pageNumber="85">®</superScript>
|
||
</emphasis>
|
||
Equivalents). The activity of Oct12 sample was about 1.48, 1.49, and 1.87-fold that of Jul12, Jan13, and Apr13 extracts, respectively.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF77FC5AFE06FB77" blockId="5.[113,784,480,1252]" pageId="5" pageNumber="85">
|
||
Data from ABTS, DPPH, ORAC, Fe
|
||
<superScript id="7FCE6C137F111C56FE35FC56FE43FC51" attach="left" box="[467,485,950,962]" fontSize="5" pageId="5" pageNumber="85">3+</superScript>
|
||
RP, and TPC assays were used to calculate RACI (Relative Antioxidant Capacity Index) value for each extract. RACI index allows the comparison of phytocomplexes antioxidant capacity derived from different chemical methods and provides a more comprehensive assessment of the whole antioxidant capacity. The ranking of antioxidant capacity of investigated extracts differed between methods. In particular, it was observed that ABTS and DPPH data had significant correlation (
|
||
<tableCitation id="C539F4E07F111C56FD63FB9DFD6BFB02" box="[645,717,1149,1169]" captionStart="Table 4" captionStartId="5.[114,158,1774,1788]" captionTargetPageId="5" captionText="Table 4 Correlation coefficients between the different applied methods for analyzing antioxidant capacity." httpUri="http://table.plazi.org/id/DCC491D37F111C56FF94F90EFF41F8B9" pageId="5" pageNumber="85" tableUuid="DCC491D37F111C56FF94F90EFF41F8B9">Table 4</tableCitation>
|
||
). RACI values highlighted that the four extracts were able to exert a similar antioxidant capability. Jul12 sample was slightly more active than the other ones (
|
||
<tableCitation id="C539F4E07F111C56FEAFFB31FE35FB77" box="[329,403,1233,1252]" captionStart="Table 5" captionStartId="5.[831,875,483,497]" captionTargetPageId="5" captionText="Table 5 Standard scores of antioxidant capacity for each investigated extract and RACI values. These latter were calculated by averaging the standard scores from the different antioxidant assays." httpUri="http://table.plazi.org/id/DCC491D37F111C56FCD9FE03FC70FDA5" pageId="5" pageNumber="85" tableUuid="DCC491D37F111C56FCD9FE03FC70FDA5">Table 5</tableCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF94FAF5FD94FABA" blockId="5.[114,562,1301,1321]" box="[114,562,1301,1321]" pageId="5" pageNumber="85">
|
||
<heading id="D34C76377F111C56FF94FAF5FD94FABA" box="[114,562,1301,1321]" fontSize="36" level="2" pageId="5" pageNumber="85" reason="3">
|
||
<emphasis id="BACF1D497F111C56FF94FAF5FD94FABA" box="[114,562,1301,1321]" italics="true" pageId="5" pageNumber="85">
|
||
2.4. Cytotoxicity of extracts from
|
||
<taxonomicName id="4FBBBAD87F111C56FE52FAF5FD94FABA" ID-CoL="56R5N" authorityName="C. Presl" box="[436,562,1301,1321]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="85" phylum="Tracheophyta" rank="species" species="longicaulis">T. longicaulis</taxonomicName>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF77FAAEFDADFA42" blockId="5.[113,783,1358,1740]" pageId="5" pageNumber="85">
|
||
The evaluation of cytotoxicity was carried out by application of the XTT test that allows to estimate the number of metabolically active cells present in culture and then to evaluate the effect of treatment with an exogenously added agent on the viability of the cell population (
|
||
<bibRefCitation id="EC2ABCAA7F111C56FEA6FA5DFE58FA42" author="Roehm, N. W. & Rodgers, G. H. & Hatfield, S. M. & Glasebrook, A. L." box="[320,510,1469,1489]" pageId="5" pageNumber="85" pagination="257 - 265" refId="ref13546" refString="Roehm, N. W., Rodgers, G. H., Hatfield, S. M., Glasebrook, A. L., 1991. An improved colorimetric assay for cell proliferation and viability utilizing the tetrazolium salt XTT. J. Immunol. Methods 142, 257 - 265." type="journal article" year="1991">Roehm et al., 1991</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF77FA39FD97F9EB" blockId="5.[113,783,1358,1740]" pageId="5" pageNumber="85">The test is based on the ability of the compound XTT tetrazolium (yellow colored) to be metabolized by the mitochondrial dehydrogenases, active in living cells, in a water-soluble formazan derivative of (bright orange colored). The viable cells, unlike those of non-viable, reduce XTT and the amount of formazan product is proportional to the number of present cells.</paragraph>
|
||
<paragraph id="8804C15B7F111C56FF77F961FA7AFBE8" blockId="5.[113,783,1358,1740]" lastBlockId="5.[831,1501,765,1147]" pageId="5" pageNumber="85">
|
||
In order to obtain a cytotoxic profile of the investigated extracts and to fit out non toxic and safe preparations, each extract was tested in a wide dose level range (10–250 µg/mL;
|
||
<figureCitation id="1080DDDE7F111C56FD60F959FD19F95F" box="[646,703,1721,1740]" captionStart="Fig" captionStartId="6.[87,113,1483,1497]" captionTargetBox="[147,1404,190,1450]" captionTargetId="graphics-834@6.[429,1342,692,891]" captionTargetPageId="6" captionText="Fig. 3. Cell viability (%) of Thymus longicaulis extracts (Jul12, Oct12, Jan13, Apr13) towards HCT-116, MDA-MB-231, U-251, CCRF-CEM and MRC-5 cell lines. Values are the mean ± SD of measurements were carried out on 3 samples (n = 3) analyzed twelve times." figureDoi="http://doi.org/10.5281/zenodo.10491174" httpUri="https://zenodo.org/record/10491174/files/figure.png" pageId="5" pageNumber="85">Fig. 3</figureCitation>
|
||
). Jul12, Oct12, Jan13 and Apr13 extracts showed dissimilar behaviors towards the different cell lines (HCT-116, MDA-MB-231, U-251, CCRF-CEM and MRC-5). In HCT-116 colon carcinoma cells Jul12 extract at the highest doses (50.0, 100.0 and 250.0 µg/mL) elicited a potent cytotoxic response after 48 and 72 h exposure times. The same extract defined a decrease of cell viability of MDA-MB-23 breast cancer cells, at a dose of 250 µg/mL. All the extracts did not affect the growth of U251 glioblastoma cells, while they exercised proliferative effects on CCRF-CEM lymphoblastic cells. Jul12 and Jan13 extracts exerted antiproliferative effects at the highest dose level tested even on MRC-5 cells, suggesting the potential cytotoxicity of both these extracts. Furthermore, the evidenced cytotoxic effects were due to an extract dose far higher than those chosen for testing antioxidant and anti-inflammatory capabilities.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FCD9FB41FA29FB26" blockId="5.[831,1423,1185,1205]" box="[831,1423,1185,1205]" pageId="5" pageNumber="85">
|
||
<heading id="D34C76377F111C56FCD9FB41FA29FB26" box="[831,1423,1185,1205]" fontSize="36" level="2" pageId="5" pageNumber="85" reason="3">
|
||
<emphasis id="BACF1D497F111C56FCD9FB41FA29FB26" box="[831,1423,1185,1205]" italics="true" pageId="5" pageNumber="85">
|
||
2.5. Anti-inflammatory activity of extracts from
|
||
<taxonomicName id="4FBBBAD87F111C56FAF7FB41FA29FB26" box="[1297,1423,1185,1205]" pageId="5" pageNumber="85">T. longicaulis</taxonomicName>
|
||
</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FCB8FB3BFC79FACE" blockId="5.[831,1501,1241,2015]" pageId="5" pageNumber="85">
|
||
Extracts of
|
||
<taxonomicName id="4FBBBAD87F111C56FC02FB39FBCDFB7E" box="[996,1131,1241,1261]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="85" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F111C56FC02FB39FBCDFB7E" box="[996,1131,1241,1261]" italics="true" pageId="5" pageNumber="85">T. longicaulis</emphasis>
|
||
</taxonomicName>
|
||
collected from different seasons exhibited a varying COX-2 gene expression inhibition in THP-1 macrophages whereas extract from October showed a significant COX-2 inhibition at 41.9 ± 6.6% compared to materials from other seasons (
|
||
<figureCitation id="1080DDDE7F111C56FC7DFAAAFC74FACE" box="[923,978,1354,1373]" captionStart="Fig" captionStartId="7.[113,139,852,866]" captionTargetBox="[149,751,185,822]" captionTargetId="graphics-901@7.[213,670,192,581]" captionText="Fig. 4. Effects of Thymus longicaulis extracts collected during 4 different seasons on COX-2 gene expression on human leukemia cell line THP-1. All extracts (Jul12, Oct12, Jan13, Apr13) were tested at 50 µg/ml. Dexamethasone (Dex) 2.5 nM served as positive control. The graph depicts compiled data (% inhibition) of 2 independent experiments (mean ± SD). The numbers below the graph show % inhibition of COX- 2 gene expression." figureDoi="http://doi.org/10.5281/zenodo.10570163" httpUri="https://zenodo.org/record/10570163/files/figure.png" pageId="5" pageNumber="85">Fig. 4</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F111C56FCB8FA86FA0BFA22" blockId="5.[831,1501,1241,2015]" pageId="5" pageNumber="85">The phenophase in which the leaves were collected makes significance difference concerning phenolic composition of the extracts therefrom and consequently their biological activity.</paragraph>
|
||
<paragraph id="8804C15B7F111C56FCB8FA59FA7AF84C" blockId="5.[831,1501,1241,2015]" pageId="5" pageNumber="85">
|
||
Wild plants of
|
||
<taxonomicName id="4FBBBAD87F111C56FC16FA58FBCDFA5F" box="[1008,1131,1464,1484]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="5" pageNumber="85" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F111C56FC16FA58FBCDFA5F" box="[1008,1131,1464,1484]" italics="true" pageId="5" pageNumber="85">T. longicaulis</emphasis>
|
||
</taxonomicName>
|
||
were collected in Durazzano, a small center in the Southern
|
||
<collectingCountry id="F0AC81CB7F111C56FBA5FA35FBD6FA7B" box="[1091,1136,1493,1512]" name="Italy" pageId="5" pageNumber="85">Italy</collectingCountry>
|
||
(altitude
|
||
<quantity id="4F436CBE7F111C56FB07FA35FA87FA7A" box="[1249,1313,1493,1513]" metricMagnitude="2" metricUnit="m" metricValue="2.86" pageId="5" pageNumber="85" unit="m" value="286.0">286 m</quantity>
|
||
above sea level) characterized by a mild Mediterranean climate, identified as Csa climate on the basis of Köppen and Geiger classification. Four collection times, between 2012 and 2013 years, were considered, each of them represented the first month of season. Data from ISPRA (Istituto Superiore per la Protezione e la Ricerca Ambientale) reports show that 2012, as well as 2013, was a year warmer than the climatological mean, both globally and in
|
||
<collectingCountry id="F0AC81CB7F111C56FAF0F979FAE5F93F" box="[1302,1347,1689,1708]" name="Italy" pageId="5" pageNumber="85">Italy</collectingCountry>
|
||
(
|
||
<bibRefCitation id="EC2ABCAA7F111C56FAB4F979FCD5F95B" author="Desiato, F. & Fioravanti, G. & Fraschetti, P. & Perconti, W. & Piervitali, E. & Pavan, V." pageId="5" pageNumber="85" refId="ref12481" refString="Desiato, F., Fioravanti, G., Fraschetti, P., Perconti, W., Piervitali, E., Pavan, V., 2013. Gli indicatori del clima in Italia nel 2012 Anno VIII. ISPRA Ed., Rome." type="book" year="2013">Desiato et al., 2013</bibRefCitation>
|
||
,
|
||
<bibRefCitation id="EC2ABCAA7F111C56FC99F955FC14F95B" author="Desiato, F. & Fioravanti, G. & Fraschetti, P. & Perconti, W. & Piervitali, E. & Pavan, V." box="[895,946,1717,1736]" pageId="5" pageNumber="85" refId="ref12530" refString="Desiato, F., Fioravanti, G., Fraschetti, P., Perconti, W., Piervitali, E., Pavan, V., 2014. Gli indicatori del clima in Italia nel 2013 Anno IX. ISPRA Ed., Rome." type="book" year="2014">2014</bibRefCitation>
|
||
). The summer of 2012 was characterized by a strong lack of rainfall and strong positive thermal anomalies that have made it one of the hottest summers of the last fifty years. In the first July decade the average temperature in Durazzano was equal to 25.5
|
||
<emphasis id="BACF1D497F111C56FC6CF8C4FC35F8A4" box="[906,915,1828,1847]" italics="true" pageId="5" pageNumber="85">°</emphasis>
|
||
<collectionCode id="EEAA599E7F111C56FC74F8C4FC39F8A4" box="[914,927,1828,1847]" country="Denmark" name="University of Copenhagen" pageId="5" pageNumber="85" type="Herbarium">C</collectionCode>
|
||
with an average relative humidity of 59.4%. On 10th July the maximum temperature was 34.8
|
||
<emphasis id="BACF1D497F111C56FB54F8A0FB1DF8C0" box="[1202,1211,1856,1875]" italics="true" pageId="5" pageNumber="85">°</emphasis>
|
||
<collectionCode id="EEAA599E7F111C56FB5DF8A0FB6DF8C0" box="[1211,1227,1856,1875]" country="Denmark" name="University of Copenhagen" pageId="5" pageNumber="85" type="Herbarium">C</collectionCode>
|
||
. The drought condition and the absence of precipitations define a strong decrease of rosmarinic acid amount. The content of the other compounds, among those identified, was also negatively affected, with the exception of metabolites
|
||
<emphasis id="BACF1D497F111C56FC5BF84FFC6CF851" bold="true" box="[957,970,1967,1986]" pageId="5" pageNumber="85">6</emphasis>
|
||
and
|
||
<emphasis id="BACF1D497F111C56FC1BF84FFBB0F851" bold="true" box="[1021,1046,1967,1986]" pageId="5" pageNumber="85">17</emphasis>
|
||
, present only in the summer sample, and of compound
|
||
<emphasis id="BACF1D497F111C56FC55F82BFC6AF84D" bold="true" box="[947,972,1995,2014]" pageId="5" pageNumber="85">13</emphasis>
|
||
which was 3.19, 1.73 and 1.41-fold that of Oct12,
|
||
</paragraph>
|
||
<caption id="DCC491D37F111C56FF94F90EFF41F8B9" ID-Table-UUID="DCC491D37F111C56FF94F90EFF41F8B9" httpUri="http://table.plazi.org/id/DCC491D37F111C56FF94F90EFF41F8B9" pageId="5" pageNumber="85" startId="5.[114,158,1774,1788]" targetBox="[136,761,1858,1997]" targetIsTable="true" targetPageId="5" targetType="table">
|
||
<paragraph id="8804C15B7F111C56FF94F90EFF41F8B9" blockId="5.[113,782,1774,1834]" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FF94F90EFF08F96F" bold="true" box="[114,174,1774,1788]" pageId="5" pageNumber="85">Table 4</emphasis>
|
||
Correlation coefficients between the different applied methods for analyzing antioxidant capacity.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F111C56FF6EF8A2FD6EF85E" pageId="5" pageNumber="85">
|
||
<table id="FABB33FB7F11E3ACFF6EF8A2FD5FF85E" box="[136,761,1858,1997]" gridcols="6" gridrows="6" pageId="5" pageNumber="85">
|
||
<tr id="368BC3197F11E3ACFF6EF8A2FD5FF8C2" box="[136,761,1858,1873]" gridrow="0" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EF8A2FF61F8C2" box="[136,199,1858,1873]" gridcol="0" gridrow="0" pageId="5" pageNumber="85">Method</th>
|
||
<th id="755AAA657F11E3ACFEE7F8A2FE8CF8C2" box="[257,298,1858,1873]" gridcol="1" gridrow="0" pageId="5" pageNumber="85">ABTS</th>
|
||
<th id="755AAA657F11E3ACFE82F8A2FE37F8C2" box="[356,401,1858,1873]" gridcol="2" gridrow="0" pageId="5" pageNumber="85">DPPH</th>
|
||
<th id="755AAA657F11E3ACFE2AF8A2FDA9F8C2" box="[460,527,1858,1873]" gridcol="3" gridrow="0" pageId="5" pageNumber="85">Fe(III)RP</th>
|
||
<th id="755AAA657F11E3ACFDACF8A2FD22F8C2" box="[586,644,1858,1873]" gridcol="4" gridrow="0" pageId="5" pageNumber="85">ORAC</th>
|
||
<th id="755AAA657F11E3ACFD58F8A2FD5FF8C2" box="[702,761,1858,1873]" gridcol="5" gridrow="0" pageId="5" pageNumber="85">TPC</th>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EF884FD5FF8E1" box="[136,761,1892,1906]" gridrow="1" pageId="5" pageNumber="85">
|
||
<th id="755AAA657F11E3ACFF6EF884FF61F8E1" box="[136,199,1892,1906]" gridcol="0" gridrow="1" pageId="5" pageNumber="85">ABTS</th>
|
||
<td id="755AAA657F11E3ACFEE7F884FE8CF8E1" box="[257,298,1892,1906]" gridcol="1" gridrow="1" pageId="5" pageNumber="85">1</td>
|
||
<td id="755AAA657F11E3ACFE82F884FE37F8E1" box="[356,401,1892,1906]" gridcol="2" gridrow="1" pageId="5" pageNumber="85">0.994</td>
|
||
<td id="755AAA657F11E3ACFE2AF884FDA9F8E1" box="[460,527,1892,1906]" gridcol="3" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FE2AF884FE7FF8E1" box="[460,473,1892,1906]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.760
|
||
</td>
|
||
<td id="755AAA657F11E3ACFDACF884FD22F8E1" box="[586,644,1892,1906]" gridcol="4" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FDACF884FDF1F8E1" box="[586,599,1892,1906]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.797
|
||
</td>
|
||
<td id="755AAA657F11E3ACFD58F884FD5FF8E1" box="[702,761,1892,1906]" gridcol="5" gridrow="1" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FD58F884FD6DF8E1" box="[702,715,1892,1906]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.307
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EF89BFD5FF81A" box="[136,761,1915,1929]" gridrow="2" pageId="5" pageNumber="85" rowspan-1="1">
|
||
<th id="755AAA657F11E3ACFF6EF89BFF61F81A" box="[136,199,1915,1929]" gridcol="0" gridrow="2" pageId="5" pageNumber="85">DPPH</th>
|
||
<td id="755AAA657F11E3ACFE82F89BFE37F81A" box="[356,401,1915,1929]" gridcol="2" gridrow="2" pageId="5" pageNumber="85">1</td>
|
||
<td id="755AAA657F11E3ACFE2AF89BFDA9F81A" box="[460,527,1915,1929]" gridcol="3" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FE2AF89BFE7FF81A" box="[460,473,1915,1929]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.720
|
||
</td>
|
||
<td id="755AAA657F11E3ACFDACF89BFD22F81A" box="[586,644,1915,1929]" gridcol="4" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FDACF89BFDF1F81A" box="[586,599,1915,1929]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.855
|
||
</td>
|
||
<td id="755AAA657F11E3ACFD58F89BFD5FF81A" box="[702,761,1915,1929]" gridcol="5" gridrow="2" pageId="5" pageNumber="85">
|
||
<emphasis id="BACF1D497F111C56FD58F89BFD6DF81A" box="[702,715,1915,1929]" italics="true" pageId="5" pageNumber="85">—</emphasis>
|
||
0.282
|
||
</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EF872FD5FF833" box="[136,761,1938,1952]" gridrow="3" pageId="5" pageNumber="85" rowspan-1="1" rowspan-2="1">
|
||
<th id="755AAA657F11E3ACFF6EF872FF61F833" box="[136,199,1938,1952]" gridcol="0" gridrow="3" pageId="5" pageNumber="85">FRAP</th>
|
||
<td id="755AAA657F11E3ACFE2AF872FDA9F833" box="[460,527,1938,1952]" gridcol="3" gridrow="3" pageId="5" pageNumber="85">1</td>
|
||
<td id="755AAA657F11E3ACFDACF872FD22F833" box="[586,644,1938,1952]" gridcol="4" gridrow="3" pageId="5" pageNumber="85">0.340</td>
|
||
<td id="755AAA657F11E3ACFD58F872FD5FF833" box="[702,761,1938,1952]" gridcol="5" gridrow="3" pageId="5" pageNumber="85">0.824</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EF849FD5FF824" box="[136,761,1961,1975]" gridrow="4" pageId="5" pageNumber="85" rowspan-1="1" rowspan-2="1" rowspan-3="1">
|
||
<th id="755AAA657F11E3ACFF6EF849FF61F824" box="[136,199,1961,1975]" gridcol="0" gridrow="4" pageId="5" pageNumber="85">ORAC</th>
|
||
<td id="755AAA657F11E3ACFDACF849FD22F824" box="[586,644,1961,1975]" gridcol="4" gridrow="4" pageId="5" pageNumber="85">1</td>
|
||
<td id="755AAA657F11E3ACFD58F849FD5FF824" box="[702,761,1961,1975]" gridcol="5" gridrow="4" pageId="5" pageNumber="85">0</td>
|
||
</tr>
|
||
<tr id="368BC3197F11E3ACFF6EF85FFD5FF85E" box="[136,761,1983,1997]" gridrow="5" pageId="5" pageNumber="85" rowspan-1="1" rowspan-2="1" rowspan-3="1" rowspan-4="1">
|
||
<th id="755AAA657F11E3ACFF6EF85FFF61F85E" box="[136,199,1983,1997]" gridcol="0" gridrow="5" pageId="5" pageNumber="85">TPC</th>
|
||
<td id="755AAA657F11E3ACFD58F85FFD5FF85E" box="[702,761,1983,1997]" gridcol="5" gridrow="5" pageId="5" pageNumber="85">1</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<caption id="DCC491D37F121C55FFB1FA2BFC90FA63" ID-DOI="http://doi.org/10.5281/zenodo.10491174" ID-Zenodo-Dep="10491174" httpUri="https://zenodo.org/record/10491174/files/figure.png" pageId="6" pageNumber="86" startId="6.[87,113,1483,1497]" targetBox="[147,1404,190,1450]" targetPageId="6" targetType="figure">
|
||
<paragraph id="8804C15B7F121C55FFB1FA2BFC90FA63" blockId="6.[87,1474,1482,1520]" pageId="6" pageNumber="86">
|
||
<emphasis id="BACF1D497F121C55FFB1FA2BFF2FFA4A" bold="true" box="[87,137,1483,1497]" pageId="6" pageNumber="86">Fig. 3.</emphasis>
|
||
Cell viability (%) of
|
||
<taxonomicName id="4FBBBAD87F121C55FED6FA2AFE65FA4A" box="[304,451,1482,1497]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="6" pageNumber="86" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F121C55FED6FA2AFE65FA4A" box="[304,451,1482,1497]" italics="true" pageId="6" pageNumber="86">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts (Jul12, Oct12, Jan13, Apr13) towards HCT-116, MDA-MB-231, U-251, CCRF-CEM and MRC-5 cell lines. Values are the mean ± SD of measurements were carried out on 3 samples (
|
||
<emphasis id="BACF1D497F121C55FDAEFA01FDF4FA63" box="[584,594,1505,1520]" italics="true" pageId="6" pageNumber="86">n</emphasis>
|
||
= 3) analyzed twelve times.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F121C55FFB1F9C6FA64F84F" blockId="6.[87,758,1574,2012]" lastBlockId="6.[805,1474,1574,2012]" pageId="6" pageNumber="86">
|
||
Jan13, and Apr13 extracts, respectively. The deleterious effect of heat stress on rosmarinic acid accumulation was previously reported by
|
||
<bibRefCitation id="EC2ABCAA7F121C55FF04F9BEFE6FF9E2" author="Fletcher, R. S. & Slimmon, T. & McAuley, C. Y. & Kott, L. S." box="[226,457,1630,1650]" pageId="6" pageNumber="86" pagination="2429 - 2436" refId="ref11969" refString="Fletcher, R. S., Slimmon, T., McAuley, C. Y., Kott, L. S., 2005. Heat stress reduces the accumulation of rosmarinic acid and the total antioxidant capacity in spearmint (Mentha spicata L). J. Sci. Food Agric. 85, 2429 - 2436." type="journal article" year="2005">Fletcher et al. (2005)</bibRefCitation>
|
||
, who hypothesize that the decrease of rosmarinic acid levels during continuous heat stress conditions could be due to a competing reaction. In fact the high demand for prenylquinones biosynthesis in plant tissues under stress conditions, reduces the availability of 4-hydroxyphenylpyruvate (common precursor) for rosmarinic acid production. The long drought period characterizing the summer of 2012 ended on September and in
|
||
<date id="FC05E79B7F121C55FF09F8C1FEDFF8A7" box="[239,377,1825,1844]" pageId="6" pageNumber="86" value="2012-10">October 2012</date>
|
||
, our second collection time, typically autumnal conditions were present. The temperatures were slightly above the normal with a monthly average of 16.7
|
||
<emphasis id="BACF1D497F121C55FDBBF8B9FDC0F8FF" box="[605,614,1881,1900]" italics="true" pageId="6" pageNumber="86">°</emphasis>
|
||
<collectionCode id="EEAA599E7F121C55FD83F8B9FDD2F8FF" box="[613,628,1881,1900]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="86" type="Herbarium">C</collectionCode>
|
||
, and rainfall was in line with the normal values (
|
||
<quantity id="4F436CBE7F121C55FE2FF895FDBBF81B" box="[457,541,1909,1928]" metricMagnitude="-1" metricUnit="m" metricValue="1.7" pageId="6" pageNumber="86" unit="mm" value="170.0">170 mm</quantity>
|
||
in 24 h). These environmental conditions, together with an average relative humidity equal to 76.2%, promoted a rosmarinic acid overproduction. Isosalvianolic acid
|
||
<collectionCode id="EEAA599E7F121C55FEC1F829FE93F84F" box="[295,309,1993,2012]" country="USA" lsid="urn:lsid:biocol.org:col:15406" name="Harvard University - Arnold Arboretum" pageId="6" pageNumber="86" type="Herbarium">A</collectionCode>
|
||
were also abundantly present, whereas methylapigenin was for the first time identified. It was evident that Oct12 extract lacks a good portion of flavonoid glycosides component. This latter was again present in Jan13 sample and underwent a further increase in Apr13 sample. In the first half of
|
||
<date id="FC05E79B7F121C55FADFF99AFA18F91E" box="[1337,1470,1658,1677]" pageId="6" pageNumber="86" value="2013-01">January 2013</date>
|
||
, the permanence of a high pressure area brought relatively mild temperatures over a large part of the Italian regions. In collection area the monthly average in terms of temperature, relative humidity and rainfall were 7.6
|
||
<emphasis id="BACF1D497F121C55FBD3F90AFB98F96E" box="[1077,1086,1770,1789]" italics="true" pageId="6" pageNumber="86">°</emphasis>
|
||
<collectionCode id="EEAA599E7F121C55FBD8F90AFBEBF96E" box="[1086,1101,1770,1789]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="86" type="Herbarium">C</collectionCode>
|
||
, 77.3%, and
|
||
<quantity id="4F436CBE7F121C55FB3CF90AFA8FF96E" box="[1242,1321,1770,1789]" metricMagnitude="-3" metricUnit="m" metricValue="6.4" pageId="6" pageNumber="86" unit="mm" value="6.4">6.4 mm</quantity>
|
||
. Although the advent of the spring season was marked by low temperatures, mild climatic conditions characterized the
|
||
<date id="FC05E79B7F121C55FB46F8C1FAADF8A7" box="[1184,1291,1825,1844]" pageId="6" pageNumber="86" value="2013-04">April 2013</date>
|
||
month with average temperature and rainfall of 15.0
|
||
<emphasis id="BACF1D497F121C55FB71F8DEFB06F8C2" box="[1175,1184,1854,1873]" italics="true" pageId="6" pageNumber="86">°</emphasis>
|
||
<collectionCode id="EEAA599E7F121C55FB46F8DDFB0BF8C3" box="[1184,1197,1853,1872]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="86" type="Herbarium">C</collectionCode>
|
||
and
|
||
<quantity id="4F436CBE7F121C55FB06F8DDFA89F8C2" box="[1248,1327,1853,1873]" metricMagnitude="-3" metricUnit="m" metricValue="2.5" pageId="6" pageNumber="86" unit="mm" value="2.5">2.5 mm</quantity>
|
||
. On 10th April average temperature and relative humidity equal to 13.7
|
||
<emphasis id="BACF1D497F121C55FA9BF8B9FA20F8FF" box="[1405,1414,1881,1900]" italics="true" pageId="6" pageNumber="86">°</emphasis>
|
||
<collectionCode id="EEAA599E7F121C55FA60F8B9FA35F8FF" box="[1414,1427,1881,1900]" country="Denmark" name="University of Copenhagen" pageId="6" pageNumber="86" type="Herbarium">C</collectionCode>
|
||
and 70.0% were recorded. Common factors affecting the presence of flavonoid glycosides were the low precipitation rate and the high drought conditions that characterized the different considered collection times. Considering climate data, it is clear that Oct12
|
||
</paragraph>
|
||
<caption id="DCC491D37F131C54FF97FCB4FEAFFC47" ID-DOI="http://doi.org/10.5281/zenodo.10570163" ID-Zenodo-Dep="10570163" httpUri="https://zenodo.org/record/10570163/files/figure.png" pageId="7" pageNumber="87" startId="7.[113,139,852,866]" targetBox="[149,751,185,822]" targetPageId="7" targetType="figure">
|
||
<paragraph id="8804C15B7F131C54FF97FCB4FEAFFC47" blockId="7.[113,784,851,980]" pageId="7" pageNumber="87">
|
||
<emphasis id="BACF1D497F131C54FF97FCB4FF05FCF1" bold="true" box="[113,163,852,866]" pageId="7" pageNumber="87">Fig. 4.</emphasis>
|
||
Effects of
|
||
<taxonomicName id="4FBBBAD87F131C54FF1CFCB3FE2BFCF1" box="[250,397,851,866]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="7" pageNumber="87" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F131C54FF1CFCB3FE2BFCF1" box="[250,397,851,866]" italics="true" pageId="7" pageNumber="87">Thymus longicaulis</emphasis>
|
||
</taxonomicName>
|
||
extracts collected during 4 different seasons on COX-2 gene expression on human leukemia cell line THP-1. All extracts (Jul12, Oct12, Jan13, Apr13) were tested at 50 µg/ml. Dexamethasone (Dex) 2.5 nM served as positive control. The graph depicts compiled data (% inhibition) of 2 independent experiments (mean ± SD). The numbers below the graph show % inhibition of COX- 2 gene expression.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="8804C15B7F131C54FF97FC11FCA9FB1C" blockId="7.[113,783,1008,1167]" pageId="7" pageNumber="87">
|
||
was a positive exception. Abiotic stresses resulting from water deficit led to reduction in photosynthesis, transpiration and other biochemical processes associated with plant growth and development (
|
||
<bibRefCitation id="EC2ABCAA7F131C54FF51FBA4FD8BFBC4" author="Ramakrishna, A. & Ravishankar, G. A." box="[183,557,1092,1111]" pageId="7" pageNumber="87" pagination="1720 - 1731" refId="ref13322" refString="Ramakrishna, A., Ravishankar, G. A., 2011. Influence of abiotic stress signals on secondary metabolites in plants. Plant Signal Behav. 6, 1720 - 1731." type="journal article" year="2011">Ramakrishna and Ravishankar, 2011</bibRefCitation>
|
||
). Furthermore abiotic stress leads to oxidative stress which was counteracted by the biosynthesis of phenol compounds (
|
||
<bibRefCitation id="EC2ABCAA7F131C54FE5BFB9CFCA7FB1C" author="Nascimento, N. C. & Fett-Neto, A. G." box="[445,769,1148,1167]" pageId="7" pageNumber="87" pagination="1 - 13" refId="ref12952" refString="Nascimento, N. C., Fett-Neto, A. G., 2010. Plant secondary metabolism and challenges in modifying its operation: an overview. Methods Mol. Biol. 643, 1 - 13." type="journal article" year="2010">Nascimento and Fett-Neto, 2010</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
<subSubSection id="C0A192D07F131C54FF94FB59FDBCF885" pageId="7" pageNumber="87" type="discussion">
|
||
<paragraph id="8804C15B7F131C54FF94FB59FEACFB5F" blockId="7.[114,266,1209,1228]" box="[114,266,1209,1228]" pageId="7" pageNumber="87">
|
||
<heading id="D34C76377F131C54FF94FB59FEACFB5F" bold="true" box="[114,266,1209,1228]" fontSize="36" level="1" pageId="7" pageNumber="87" reason="1">
|
||
<emphasis id="BACF1D497F131C54FF94FB59FEACFB5F" bold="true" box="[114,266,1209,1228]" pageId="7" pageNumber="87">3. Conclusions</emphasis>
|
||
</heading>
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F131C54FF77FB10FDB5F9FD" blockId="7.[113,784,1264,1814]" pageId="7" pageNumber="87">
|
||
<taxonomicName id="4FBBBAD87F131C54FF77FB10FEF9FA97" authority="C. Presl." authorityName="C. Presl." box="[145,351,1264,1284]" class="Magnoliopsida" family="Lamiaceae" genus="Thymus" kingdom="Plantae" order="Lamiales" pageId="7" pageNumber="87" phylum="Tracheophyta" rank="species" species="longicaulis">
|
||
<emphasis id="BACF1D497F131C54FF77FB10FEAAFA97" box="[145,268,1264,1284]" italics="true" pageId="7" pageNumber="87">T. longicaulis</emphasis>
|
||
C. Presl.
|
||
</taxonomicName>
|
||
is a small aromatic plant abundant in Mediterranean macchia with traditional medicinal use. The plant, known for the antimicrobial properties of its essential oils, is a rich source of polyphenol compounds. LC–
|
||
<collectionCode id="EEAA599E7F131C54FE13FAA5FDB5FACB" box="[501,531,1349,1368]" country="Italy" lsid="urn:lsid:biocol.org:col:14396" name="Herbarium Messanaensis, Università di Messina" pageId="7" pageNumber="87" type="Herbarium">MS</collectionCode>
|
||
<superScript id="7FCE6C137F131C54FDF5FAA1FDBBFADE" attach="left" box="[531,541,1345,1357]" fontSize="5" pageId="7" pageNumber="87">n</superScript>
|
||
based metabolic profiling analyses showed marked qualitative and quantitative variations in the plant phytochemical constitution during its life cycle. Plants collected in July showed radical scavenging activity comparable to that exerted from autumnal extract, which consisted almost exclusively of rosmarinic acid. Jul12 extract was capable of exerting cytotoxic effects on colon and breast cancer cell lines comparable to or higher than those observed for vinblastine, a known anti-cancer agent. Oct12 extract, which was particularly rich in rosmarinic acid and methylapigenin, showed a marked antioxidant and anti-inflammatory potential.
|
||
</paragraph>
|
||
<paragraph id="8804C15B7F131C54FF77F997FDBBF885" blockId="7.[113,784,1264,1814]" pageId="7" pageNumber="87">Furthermore, the study shows that the effectiveness of a plant can go far beyond its balsamic period reaching optimal values in a period in which the organism in order to cope with unfavorable environmental conditions (e.g. high temperature, dryness of the soil) activates secondary metabolic pathways useful for the biosynthesis of polyphenolic antioxidants.</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |