182 lines
17 KiB
XML
182 lines
17 KiB
XML
<document id="71474A3FC4DE2CC889ECED242E3B160A" ID-DOI="10.1016/j.phytochem.2018.06.008" ID-ISSN="1873-3700" ID-Zenodo-Dep="10484041" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="juliana" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.tables_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1704938836113" checkinUser="felipe" docAuthor="Milutinović, Violeta, Niketić, Marjan, Krunić, Aleksej, Nikolić, Dejan, Petković, Miloš, Ušjak, Ljuboš & Petrović, Silvana" docDate="2018" docId="90640E19FFD18D4AFFA686DBFCA74710" docLanguage="en" docName="Phytochemistry.154.19-30.pdf" docOrigin="Phytochemistry 154" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.06.008" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Hieracium L." docType="treatment" docVersion="1" lastPageNumber="29" masterDocId="6C5D7661FFDB8D40FFC2840EFFA6401D" masterDocTitle="Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance" masterLastPageNumber="30" masterPageNumber="19" pageNumber="29" updateTime="1705328458641" updateUser="juliana">
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<mods:title id="5873F76AB855FD635433F18D6C048AED">Sesquiterpene lactones from the methanol extracts of twenty-eight Hieracium species from the Balkan Peninsula and their chemosystematic significance</mods:title>
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<mods:namePart id="6157AFF03AED66867EBFA8D5249F7158">Milutinović, Violeta</mods:namePart>
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<mods:affiliation id="0415213DCFACAA735C465B4B5D0478DA">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="DD18677942CB3C5577C10C922811EFFE">Niketić, Marjan</mods:namePart>
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<mods:affiliation id="8269DF2E7223B2ACDAAC87DA546291CC">Natural History Museum, Njegoševa 51, 11000 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="4991684397776AD057BDE583A13BB190">Krunić, Aleksej</mods:namePart>
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<mods:affiliation id="E20A353682CD0A3322D8D63D2ABD195A">Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA</mods:affiliation>
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<mods:namePart id="D483EAC3F474B042B90559D0A8830E78">Nikolić, Dejan</mods:namePart>
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<mods:affiliation id="42AF291C1D165D61E25CE92313672A7A">Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois, Chicago, IL 60612, USA</mods:affiliation>
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<mods:namePart id="0CE2F86ACC7628A9FD5F804B913594B6">Petković, Miloš</mods:namePart>
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<mods:affiliation id="774308DE647B081FBC0A09BDD5131A61">Department of Organic Chemistry, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="ED9DEB59CCB26C972766E483376EE3E3">Ušjak, Ljuboš</mods:namePart>
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<mods:affiliation id="F3A8FFBDFC7CFE7095BECDF4474D89E4">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="980F04125FA37AD7031F243016A503E0">Petrović, Silvana</mods:namePart>
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<mods:affiliation id="78C6882AD467E03E4C34D48A823C90AC">Department of Pharmacognosy, University of Belgrade - Faculty of Pharmacy, Vojvode Stepe 450, 11221 Belgrade, Serbia</mods:affiliation>
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<mods:nameIdentifier id="D82FAC7651715D6AD9A5F1A57468E200" type="email">silvana.petrovic@pharmacy.bg.ac.rs</mods:nameIdentifier>
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<mods:title id="19E2EC5DF510E803EC5400E61423F6CF">Phytochemistry</mods:title>
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<mods:date id="066C704CAEC43DA881D8DDE71D02532D">2018</mods:date>
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<mods:number id="81DEC3074EA1E4F69BA97C82A7954D95">2018-10-31</mods:number>
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<mods:number id="932544C1A9B7930FEBDA6F6B4B9E2BAC">154</mods:number>
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<mods:url id="9D8898E698E5833E536235EDAF5B2CCB">http://dx.doi.org/10.1016/j.phytochem.2018.06.008</mods:url>
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<mods:classification id="DD5D4E4DD2358707E36FC93F5FB91A57">journal article</mods:classification>
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<mods:identifier id="5F5B3565BFF1A46A481CEDEB569B5FFA" type="DOI">10.1016/j.phytochem.2018.06.008</mods:identifier>
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<mods:identifier id="8A3B769F712AF0339827AB72C4A09654" type="ISSN">1873-3700</mods:identifier>
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<treatment id="90640E19FFD18D4AFFA686DBFCA74710" LSID="urn:lsid:plazi:treatment:90640E19FFD18D4AFFA686DBFCA74710" httpUri="http://treatment.plazi.org/id/90640E19FFD18D4AFFA686DBFCA74710" lastPageNumber="29" pageId="10" pageNumber="29">
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<subSubSection id="50D7EC84FFD18D4AFFA686DBFEA54319" pageId="10" pageNumber="29" type="nomenclature">
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<paragraph id="1872BF0FFFD18D4AFFA686DBFEA54319" blockId="10.[100,766,725,772]" pageId="10" pageNumber="29">
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<heading id="433A0863FFD18D4AFFA686DBFD5842F5" bold="true" box="[100,766,725,744]" centered="true" fontSize="36" level="1" pageId="10" pageNumber="29" reason="1">
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<emphasis id="2AB9631DFFD18D4AFFA686DBFD5842F5" bold="true" box="[100,766,725,744]" italics="true" pageId="10" pageNumber="29">4.4. LC-MS analysis of dry MeOH extracts of flowering aerial parts of 28</emphasis>
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</heading>
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<heading id="433A0863FFD18D4AFFA686FFFEA54319" box="[100,259,753,772]" fontSize="8" level="3" pageId="10" pageNumber="29" reason="8">
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<emphasis id="2AB9631DFFD18D4AFFA686FFFEA54319" bold="true" box="[100,259,753,772]" italics="true" pageId="10" pageNumber="29">
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<taxonomicName id="DFCDC48CFFD18D4AFFA686FFFF664319" ID-CoL="4X5R" authority="L." authorityName="L." box="[100,192,753,772]" class="Magnoliopsida" family="Asteraceae" genus="Hieracium" kingdom="Plantae" order="Asterales" pageId="10" pageNumber="29" phylum="Tracheophyta" rank="genus">Hieracium</taxonomicName>
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species
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<subSubSection id="50D7EC84FFD18D4AFF478727FCA74710" pageId="10" pageNumber="29" type="description">
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<paragraph id="1872BF0FFFD18D4AFF478727FF5446A5" blockId="10.[100,770,808,1720]" pageId="10" pageNumber="29">
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Dried and powdered flowering aerial parts of 28
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<taxonomicName id="DFCDC48CFFD18D4AFD9F8727FD1F4321" box="[605,697,809,828]" pageId="10" pageNumber="29">
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<emphasis id="2AB9631DFFD18D4AFD9F8727FD1F4321" bold="true" box="[605,697,809,828]" italics="true" pageId="10" pageNumber="29">Hieracium</emphasis>
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</taxonomicName>
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species were pre-extracted with
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<collectingCountry id="60DAFF9FFFD18D4AFE90874AFEC9434A" box="[338,367,836,855]" name="Switzerland" pageId="10" pageNumber="29">CH</collectingCountry>
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<subScript id="8449BD4AFFD18D4AFEB28743FEDF4347" attach="right" box="[368,377,845,858]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
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Cl
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<subScript id="8449BD4AFFD18D4AFE4E8743FE334347" attach="left" box="[396,405,845,858]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
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and then bimacerated with MeOH in the same manner as in the case of the flowering heads of
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<taxonomicName id="DFCDC48CFFD18D4AFDB7876EFD5A436E" box="[629,764,864,883]" class="Magnoliopsida" family="Asteraceae" genus="Hieracium" kingdom="Plantae" order="Asterales" pageId="10" pageNumber="29" phylum="Tracheophyta" rank="species" species="calophyllum">
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<emphasis id="2AB9631DFFD18D4AFDB7876EFD22436E" bold="true" box="[629,644,864,883]" italics="true" pageId="10" pageNumber="29">H</emphasis>
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.
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||
<emphasis id="2AB9631DFFD18D4AFD52876EFD5A436E" bold="true" box="[656,764,864,883]" italics="true" pageId="10" pageNumber="29">calophyllum</emphasis>
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</taxonomicName>
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||
. The number of individual plants from each species used for the extraction, the total masses of plant material, the masses of the obtained methanol extracts, and extraction yields are presented in
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<tableCitation id="554F8AB4FFD18D4AFD4887BAFD7743DA" box="[650,721,948,967]" captionStart="Table 4" captionStartId="9.[100,150,161,178]" captionTargetPageId="9" captionText="Table 4 Collection dates and localities, voucher numbers, numbers of individual plants (n) used for extraction, dried plant material and obtained dried methanol extracts masses (mpm and mme), and extraction yields (yldex) of investigated Hieracium species." pageId="10" pageNumber="29">Table 4</tableCitation>
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. The obtained dried MeOH extracts were dissolved in MeOH (
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<quantity id="DF3512EAFFD18D4AFD5387DEFD7343FE" box="[657,725,976,995]" metricMagnitude="-6" metricUnit="kg" metricValue="8.5" pageId="10" pageNumber="29" unit="mg" value="8.5">8.5 mg</quantity>
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/ml), filtered through a membrane filter (0.22 μm) and subjected to qualitative and quantitative LC/SQ-MS analysis. For this purpose, Zorbax SBAq column (150 × 3.0 mm; 3.5 μm particle size, Agilent Technologies), operating at 25 ̊C, was used. The mobile phases consisted of 5 mM HCO
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<subScript id="8449BD4AFFD18D4AFF53806AFF3C446C" attach="both" box="[145,154,1124,1137]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
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NH
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<quantity id="DF3512EAFFD18D4AFF7B806AFF7B4472" box="[185,221,1116,1137]" metricMagnitude="-1" metricUnit="m" metricValue="1.016" pageId="10" pageNumber="29" unit="in" value="4.0">
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<subScript id="8449BD4AFFD18D4AFF7B806AFF64446C" attach="left" box="[185,194,1124,1137]" fontSize="5" pageId="10" pageNumber="29">4</subScript>
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in
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</quantity>
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H
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<subScript id="8449BD4AFFD18D4AFF35806AFEA6446C" attach="both" box="[247,256,1124,1137]" fontSize="5" pageId="10" pageNumber="29">2</subScript>
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O (A), and MeOH (B). The gradient program was as follows: 5–10% B (8 min), 10–30% B (5 min), isocratic 30% B (2 min), 30-20% B (2 min), isocratic 20% B (2 min), 20–30% B (4 min), 30–40% B (5 min), 40–95% B (2 min), with the total run of 30 min, post run of 5 min, flow rate of 0.3 ml/min, and
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<subScript id="8449BD4AFFD18D4AFE7C80C5FE7944FD" attach="left" box="[446,479,1227,1248]" fontSize="5" pageId="10" pageNumber="29">Vinj</subScript>
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of 3 μl. DAD was operating at 210 and
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<quantity id="DF3512EAFFD18D4AFF7C80E9FEA044E7" box="[190,262,1255,1274]" metricMagnitude="-7" metricUnit="m" metricValue="2.54" pageId="10" pageNumber="29" unit="nm" value="254.0">254 nm</quantity>
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, while MSD data were acquired in the positive ion mode: in the full-scan mode in the range of
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<emphasis id="2AB9631DFFD18D4AFDD8810DFD99450B" bold="true" box="[538,575,1283,1302]" italics="true" pageId="10" pageNumber="29">m/z</emphasis>
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80–700, and in the Selected Ion Monitoring (SIM) mode at
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<emphasis id="2AB9631DFFD18D4AFE208111FDA1452F" bold="true" box="[482,519,1311,1330]" italics="true" pageId="10" pageNumber="29">m/z</emphasis>
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540.20 (
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<emphasis id="2AB9631DFFD18D4AFDA28111FDCA452F" bold="true" box="[608,620,1311,1330]" pageId="10" pageNumber="29">1</emphasis>
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and
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<emphasis id="2AB9631DFFD18D4AFD5C8111FD0C452F" bold="true" box="[670,682,1311,1330]" pageId="10" pageNumber="29">3</emphasis>
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), 378.10 (
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<emphasis id="2AB9631DFFD18D4AFFAE8135FFDE4553" bold="true" box="[108,120,1339,1358]" pageId="10" pageNumber="29">2</emphasis>
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) of [M+H]
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<superScript id="EFB81247FFD18D4AFF288138FF5C455E" attach="right" box="[234,250,1334,1347]" fontSize="5" pageId="10" pageNumber="29">+</superScript>
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||
, and 442.20 (
|
||
<emphasis id="2AB9631DFFD18D4AFEBD8135FE2D4553" bold="true" box="[383,395,1339,1358]" pageId="10" pageNumber="29">4</emphasis>
|
||
) of [M+NH
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||
<subScript id="8449BD4AFFD18D4AFDC1814DFDAA454D" attach="left" box="[515,524,1347,1360]" fontSize="5" pageId="10" pageNumber="29">4</subScript>
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]
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<superScript id="EFB81247FFD18D4AFDD78138FD83455E" attach="none" box="[533,549,1334,1347]" fontSize="5" pageId="10" pageNumber="29">+</superScript>
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. Ion source parameters were the same as for the preparative LC-MS analysis. The MSD (in SIM mode) peak areas were used for the quantitative analysis by the external standard method. Isolated compounds (
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<emphasis id="2AB9631DFFD18D4AFDE58180FDEC45BC" bold="true" box="[551,586,1422,1441]" pageId="10" pageNumber="29">1–4</emphasis>
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) were used as the reference substances and dissolved in MeOH to obtain stock solutions (
|
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<quantity id="DF3512EAFFD18D4AFFA981C8FF0945C4" box="[107,175,1478,1497]" metricMagnitude="-7" metricUnit="kg" metricValue="2.0" pageId="10" pageNumber="29" unit="mg" value="0.2">0.2 mg</quantity>
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/ml). The calibration curves were constructed using ten different concentrations of
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<emphasis id="2AB9631DFFD18D4AFE9481ECFEDF45E8" bold="true" box="[342,377,1506,1525]" pageId="10" pageNumber="29">1–4</emphasis>
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. For each concentration, the data were recorded three times. Linearity, linear ranges, LODs and LOQs of the compounds were determined according to International Conference on Harmonization guidelines (ICH, 2005). Resulting regression equations were used to test the linearity by calculating the correlation coefficients (
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<emphasis id="2AB9631DFFD18D4AFFAE8263FFDB466B" bold="true" box="[108,125,1641,1664]" italics="true" pageId="10" pageNumber="29">
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r
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<superScript id="EFB81247FFD18D4AFFB68267FFDB466B" attach="left" box="[116,125,1641,1654]" fontSize="5" pageId="10" pageNumber="29">2</superScript>
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</emphasis>
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), as well as to determine LODs and LOQs using the standard deviations of the response (
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<emphasis id="2AB9631DFFD18D4AFE968287FEF94681" box="[340,351,1673,1692]" italics="true" pageId="10" pageNumber="29">σ</emphasis>
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) and the calibration curve slopes (
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<emphasis id="2AB9631DFFD18D4AFD698287FD104681" bold="true" box="[683,694,1673,1692]" italics="true" pageId="10" pageNumber="29">a</emphasis>
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), in the following way:
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</paragraph>
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LOD=3.3 ×
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<emphasis id="2AB9631DFFD18D4AFF1682C3FF7946FD" box="[212,223,1741,1760]" italics="true" pageId="10" pageNumber="29">σ</emphasis>
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/
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<emphasis id="2AB9631DFFD18D4AFF3382C3FF5A46C2" box="[241,252,1741,1759]" italics="true" pageId="10" pageNumber="29">a</emphasis>
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</paragraph>
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<paragraph id="1872BF0FFFD18D4AFFA182F4FF524710" blockId="10.[99,244,1786,1805]" box="[99,244,1786,1805]" pageId="10" pageNumber="29">
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LOQ =10 ×
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<emphasis id="2AB9631DFFD18D4AFF1182F4FF784710" box="[211,222,1786,1805]" italics="true" pageId="10" pageNumber="29">σ</emphasis>
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/
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<emphasis id="2AB9631DFFD18D4AFF2B82F4FF524710" box="[233,244,1786,1805]" italics="true" pageId="10" pageNumber="29">a</emphasis>
|
||
</paragraph>
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<paragraph id="1872BF0FFFD18D4AFD2482C5FCA446C3" blockId="10.[742,770,1739,1758]" box="[742,770,1739,1758]" pageId="10" pageNumber="29">(1)</paragraph>
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<paragraph id="1872BF0FFFD18D4AFD2482F4FCA74710" blockId="10.[742,769,1786,1805]" box="[742,769,1786,1805]" pageId="10" pageNumber="29">(2)</paragraph>
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</subSubSection>
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</treatment>
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</document> |