252 lines
28 KiB
XML
252 lines
28 KiB
XML
<document id="CC2D2773C49041E42DB6A72F2ABB838C" ID-DOI="10.1016/j.phytochem.2020.112292" ID-ISSN="1873-3700" ID-Zenodo-Dep="8294564" IM.bibliography_approvedBy="diego" IM.illustrations_approvedBy="diego" IM.materialsCitations_approvedBy="diego" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="diego" IM.taxonomicNames_approvedBy="diego" IM.treatments_approvedBy="diego" checkinTime="1693257092145" checkinUser="felipe" docAuthor="Kang, Kyo Bin, Woo, Sunmin, Ernst, Madeleine, van der Hooft, Justin J. J., Nothias, Louis-Félix, da Silva, Ricardo R., Dorrestein, Pieter C., Sung, Sang Hyun & Lee, Mina" docDate="2020" docId="4E6E87B6FFC7B91FFC977B34FED3E4A3" docLanguage="en" docName="Phytochemistry.173.112292.pdf" docOrigin="Phytochemistry (112292) 173" docSource="http://dx.doi.org/10.1016/j.phytochem.2020.112292" docStyle="DocumentStyle:F36D69FC8B198FBE91029DF9C24697D3.6:Phytochemistry.2020-.journal_article" docStyleId="F36D69FC8B198FBE91029DF9C24697D3" docStyleName="Phytochemistry.2020-.journal_article" docStyleVersion="6" docTitle="Alnus firma" docType="treatment" docVersion="3" lastPageNumber="4" masterDocId="B257FFCEFFC5B91BFFA57C71FFE7E244" masterDocTitle="Assessing specialized metabolite diversity of Alnus species by a digitized LC-MS / MS data analysis workflow" masterLastPageNumber="10" masterPageNumber="1" pageNumber="3" updateTime="1693483351785" updateUser="diego">
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<mods:title id="B689CC24744DE60AE36B1B45096D55E3">Assessing specialized metabolite diversity of Alnus species by a digitized LC-MS / MS data analysis workflow</mods:title>
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<mods:namePart id="622813D5EF6B017AF8BD824C4489D1AD">Kang, Kyo Bin</mods:namePart>
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<mods:affiliation id="F2780C5441135EF7F0E85AC9A622FCB8">∗ & Research Institute of Pharmaceutical Sciences, College of Pharmacy, Sookmyung Women's University, Seoul, Republic of Korea & ∗ & Collaborative Mass Spectrometry Innovation Center, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California San Diego, La Jolla, CA, USA</mods:affiliation>
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<mods:namePart id="33558D1370460D5C165352E4CF77A5AC">Woo, Sunmin</mods:namePart>
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<mods:namePart id="BD796675BDB1A1E0B7F15E4560F48D12">Ernst, Madeleine</mods:namePart>
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<mods:namePart id="2F36A96937080E86A9335EEEA0D38B31">van der Hooft, Justin J. J.</mods:namePart>
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<mods:namePart id="33359588E65C80D9453A66C2C68970D6">Nothias, Louis-Félix</mods:namePart>
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<mods:namePart id="591C620C00889474EF97D6205E579879">da Silva, Ricardo R.</mods:namePart>
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<mods:namePart id="E7290BCD34A8928C1E0BCF80DDDD5467">Dorrestein, Pieter C.</mods:namePart>
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<mods:namePart id="24DAA83A9C853E7C6B4C8005E9ACB9EE">Sung, Sang Hyun</mods:namePart>
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<mods:namePart id="9E8BBD53CE0EAF4F32C7BD21CBD84987">Lee, Mina</mods:namePart>
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<mods:title id="E21C1EA08DC3B648355F77279B87F3FD">Phytochemistry</mods:title>
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<mods:date id="FB5F5D5DE15F2FBDF2009AC7303AABD3">2020</mods:date>
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<mods:title id="348ECF33A22B526BC73380E99588FC9D">112292</mods:title>
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<mods:number id="BE2FB9F62B06179007187A1D2F1CC824">2020-05-31</mods:number>
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<mods:identifier id="AB02EBBA89005D6CCDB5E3FF33D2E3B2" type="DOI">10.1016/j.phytochem.2020.112292</mods:identifier>
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<mods:identifier id="14A4B966AFA030D27E88A9D2B63D7B30" type="ISSN">1873-3700</mods:identifier>
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<treatment id="4E6E87B6FFC7B91FFC977B34FED3E4A3" LSID="urn:lsid:plazi:treatment:4E6E87B6FFC7B91FFC977B34FED3E4A3" httpUri="http://treatment.plazi.org/id/4E6E87B6FFC7B91FFC977B34FED3E4A3" lastPageId="4" lastPageNumber="4" pageId="2" pageNumber="3">
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<subSubSection id="8EDD652BFFC7B919FC977B34FA28E51C" box="[818,1487,1861,1880]" pageId="2" pageNumber="3" type="nomenclature">
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<paragraph id="C67836A0FFC7B919FC977B34FA28E51C" blockId="2.[818,1487,1861,1880]" box="[818,1487,1861,1880]" pageId="2" pageNumber="3">
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<heading id="9D3081CCFFC7B919FC977B34FA28E51C" box="[818,1487,1861,1880]" centered="true" fontSize="36" level="2" pageId="2" pageNumber="3" reason="3">
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<emphasis id="F4B3EAB2FFC7B919FC977B34FA28E51C" box="[818,1487,1861,1880]" italics="true" pageId="2" pageNumber="3">
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<emphasis id="F4B3EAB2FFC7B919FC977B34FC09E51C" bold="true" box="[818,1006,1861,1880]" italics="true" pageId="2" pageNumber="3">2.3. Identification of</emphasis>
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α
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<emphasis id="F4B3EAB2FFC7B919FC5A7B34FA28E51C" bold="true" box="[1023,1487,1861,1880]" italics="true" pageId="2" pageNumber="3">
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-glucosidase inhibitory compounds from
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<taxonomicName id="01C74D23FFC7B919FAC37B34FA28E51C" ID-CoL="66962" ID-ENA="109059" box="[1382,1487,1861,1880]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="firma">Alnus firma</taxonomicName>
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</emphasis>
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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="8EDD652BFFC7B91FFCF67B0CFED3E4A3" lastPageId="4" lastPageNumber="5" pageId="2" pageNumber="3" type="description">
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<paragraph id="C67836A0FFC7B918FCF67B0CFE32E56D" blockId="2.[818,1487,1917,1992]" lastBlockId="3.[100,770,1395,1972]" lastPageId="3" lastPageNumber="4" pageId="2" pageNumber="3">
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A previous study reported that H
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<subScript id="5A4334E5FFC7B919FB317BF4FB7AE5D6" attach="both" box="[1172,1181,1925,1938]" fontSize="5" pageId="2" pageNumber="3">2</subScript>
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O or MeOH extracts of
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<taxonomicName id="01C74D23FFC7B919FA267B0CFA28E5D4" box="[1411,1487,1917,1936]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="2" pageNumber="3" phylum="Tracheophyta" rank="species" species="firma">
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<emphasis id="F4B3EAB2FFC7B919FA267B0CFA28E5D4" bold="true" box="[1411,1487,1917,1936]" italics="true" pageId="2" pageNumber="3">A. firma</emphasis>
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</taxonomicName>
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leaves exhibited inhibitory activity against α- glucosidase (
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<bibRefCitation id="A2564B51FFC7B919FAD77BE8FC85E58C" author="Yu, Y. B. & Miyashiro, H. & Nakamura, N. & Hattori, M. & Jong, C. P." pageId="2" pageNumber="3" pagination="820 - 826" refId="ref12514" refString="Yu, Y. B., Miyashiro, H., Nakamura, N., Hattori, M., Jong, C. P., 2007. Effects of triterpenoids and flavonoids isolated from Alnus firma on HIV- 1 viral enzymes. Arch. Pharm. Res. 30, 820 - 826. https: // doi. org / 10.1007 / BF 02978831." type="journal article" year="2007">Yu et al., 2007</bibRefCitation>
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). However, none of the compounds isolated in this study showed α- glucosidase inhibitory activity, and other metabolites from
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<taxonomicName id="01C74D23FFC6B918FD6A7902FCE6E7C2" box="[719,769,1395,1414]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="genus">
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<emphasis id="F4B3EAB2FFC6B918FD6A7902FCE6E7C2" bold="true" box="[719,769,1395,1414]" italics="true" pageId="3" pageNumber="4">Alnus</emphasis>
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</taxonomicName>
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have not been reported to exhibit α- glucosidase inhibition, except three cyclic diarylheptanoids isolated from
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<taxonomicName id="01C74D23FFC6B918FE6179DAFD19E7FA" authority="(Chiba et al., 2013)" baseAuthorityName="Chiba" baseAuthorityYear="2013" box="[452,766,1451,1470]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="sieboldiana">
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<emphasis id="F4B3EAB2FFC6B918FE6179DAFDA6E7FA" bold="true" box="[452,577,1451,1470]" italics="true" pageId="3" pageNumber="4">A. sieboldiana</emphasis>
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(
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<bibRefCitation id="A2564B51FFC6B918FDEA79DAFD13E7FA" author="Chiba, K. & Ichizawa, H. & Kawai, S. & Nishida, T." box="[591,756,1451,1470]" pageId="3" pageNumber="4" pagination="44 - 51" refId="ref7424" refString="Chiba, K., Ichizawa, H., Kawai, S., Nishida, T., 2013. α- glucosidase inhibition activity by cyclic diarylheptanoids from Alnus sieboldiana. J. Wood Chem. Technol. 33, 44 - 51. https: // doi. org / 10.1080 / 02773813.2012.723778." type="journal article" year="2013">Chiba et al., 2013</bibRefCitation>
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)
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</taxonomicName>
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. We hypothesized that the chemical information derived from MS/MSbased dereplication in this study could be used to reveal which compounds contribute to the α- glucosidase inhibitory activity of
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<taxonomicName id="01C74D23FFC6B918FD15798EFD1CE456" box="[688,763,1534,1554]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="firma">
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<emphasis id="F4B3EAB2FFC6B918FD15798EFD1CE456" bold="true" box="[688,763,1534,1554]" italics="true" pageId="3" pageNumber="4">A. firma</emphasis>
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</taxonomicName>
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, and tried to associate the annotations to bioactive extracts. 15
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<taxonomicName id="01C74D23FFC6B918FD6A7A6AFF4AE40E" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="6" phylum="Tracheophyta" rank="species" species="extracts">
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<emphasis id="F4B3EAB2FFC6B918FD6A7A6AFCE6E46A" bold="true" box="[719,769,1563,1582]" italics="true" pageId="3" pageNumber="4">Alnus</emphasis>
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extracts
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</taxonomicName>
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were evaluated for their α- glucosidase inhibitory activity as shown in
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<tableCitation id="8B45031BFFC6B918FF617A22FEEBE422" box="[196,268,1619,1638]" captionStart="Table 1" captionStartId="6.[100,150,161,178]" captionTargetPageId="6" captionText="Table 1 α-Glucosidase inhibitory activity of tested Alnus extracts." pageId="3" pageNumber="4">Table 1</tableCitation>
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. As previously reported, the leaf extract of
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<taxonomicName id="01C74D23FFC6B918FD107A22FCE6E422" box="[693,769,1618,1638]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="firma">
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<emphasis id="F4B3EAB2FFC6B918FD107A22FCE6E422" bold="true" box="[693,769,1618,1638]" italics="true" pageId="3" pageNumber="4">A. firma</emphasis>
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</taxonomicName>
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exhibited potent inhibitory activity showing IC
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<subScript id="5A4334E5FFC6B918FD8F7A06FDDBE4C0" attach="left" box="[554,572,1655,1668]" fontSize="5" pageId="3" pageNumber="4">50</subScript>
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values of 12.29 μg/ mL. Extracts of
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<taxonomicName id="01C74D23FFC6B918FF5B7AFBFEAEE4D9" box="[254,329,1674,1693]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="firma">
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<emphasis id="F4B3EAB2FFC6B918FF5B7AFBFEAEE4D9" bold="true" box="[254,329,1674,1693]" italics="true" pageId="3" pageNumber="4">A. firma</emphasis>
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</taxonomicName>
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bark, twigs, and fruits, and
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<taxonomicName id="01C74D23FFC6B918FDFA7AFBFF71E4FD" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="variety" species="hirsuta" variety="sibirica">
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<emphasis id="F4B3EAB2FFC6B918FDFA7AFBFD5EE4D9" bold="true" box="[607,697,1674,1693]" italics="true" pageId="3" pageNumber="4">A. hirsuta</emphasis>
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var.
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<emphasis id="F4B3EAB2FFC6B918FD487AFBFF71E4FD" bold="true" italics="true" pageId="3" pageNumber="4">sibirica</emphasis>
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</taxonomicName>
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fruits also showed potent activity with IC
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<subScript id="5A4334E5FFC6B918FD817ADFFDD1E4FF" attach="left" box="[548,566,1710,1723]" fontSize="5" pageId="3" pageNumber="4">50</subScript>
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ranging from 6.80 to 8.48 μg/mL. Extract of
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<taxonomicName id="01C74D23FFC6B918FEEB7AB3FE51E491" box="[334,438,1730,1749]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="japonica">
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<emphasis id="F4B3EAB2FFC6B918FEEB7AB3FE51E491" bold="true" box="[334,438,1730,1749]" italics="true" pageId="3" pageNumber="4">A. japonica</emphasis>
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</taxonomicName>
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leaves and
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<taxonomicName id="01C74D23FFC6B918FD957AB3FCE5E491" box="[560,770,1730,1749]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="variety" species="hirsuta" variety="sibirica">
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<emphasis id="F4B3EAB2FFC6B918FD957AB3FD6CE491" bold="true" box="[560,651,1730,1749]" italics="true" pageId="3" pageNumber="4">A. hirsuta</emphasis>
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var.
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<emphasis id="F4B3EAB2FFC6B918FD677AB3FCE5E491" bold="true" box="[706,770,1730,1749]" italics="true" pageId="3" pageNumber="4">sibirica</emphasis>
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</taxonomicName>
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leaves exhibited moderate inhibitory activity with IC
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<subScript id="5A4334E5FFC6B918FDFC7A97FD8CE4B7" attach="left" box="[601,619,1766,1779]" fontSize="5" pageId="3" pageNumber="4">50</subScript>
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values of 23.36 and 29.84 μg/mL, while other extracts showed very weak or no inhibitory activity against α- glucosidase.
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</paragraph>
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<paragraph id="C67836A0FFC6B918FFC17970FF2BE701" blockId="3.[100,1488,1281,1349]" pageId="3" pageNumber="4">
|
||
<emphasis id="F4B3EAB2FFC6B918FFC17970FF7AE756" bold="true" box="[100,157,1281,1298]" pageId="3" pageNumber="4">Fig. 2.</emphasis>
|
||
The MS/MS spectral network of specialized metabolites contained in the bark, twigs, leaves, and fruits of
|
||
<taxonomicName id="01C74D23FFC6B918FB837970FB65E756" box="[1062,1154,1281,1298]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="japonica">
|
||
<emphasis id="F4B3EAB2FFC6B918FB837970FB65E756" bold="true" box="[1062,1154,1281,1298]" italics="true" pageId="3" pageNumber="4">A. japonica</emphasis>
|
||
</taxonomicName>
|
||
,
|
||
<taxonomicName id="01C74D23FFC6B918FB287970FB37E756" box="[1165,1232,1281,1298]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="firma">
|
||
<emphasis id="F4B3EAB2FFC6B918FB287970FB37E756" bold="true" box="[1165,1232,1281,1298]" italics="true" pageId="3" pageNumber="4">A. firma</emphasis>
|
||
</taxonomicName>
|
||
,
|
||
<taxonomicName id="01C74D23FFC6B918FB7E7970FACDE756" box="[1243,1322,1281,1298]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="species" species="hirsuta">
|
||
<emphasis id="F4B3EAB2FFC6B918FB7E7970FACDE756" bold="true" box="[1243,1322,1281,1298]" italics="true" pageId="3" pageNumber="4">A. hirsuta</emphasis>
|
||
</taxonomicName>
|
||
, and
|
||
<taxonomicName id="01C74D23FFC6B918FAFF7970FF7AE768" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="3" pageNumber="4" phylum="Tracheophyta" rank="variety" species="hirsuta" variety="sibirica">
|
||
<emphasis id="F4B3EAB2FFC6B918FAFF7970FA4EE756" bold="true" box="[1370,1449,1281,1298]" italics="true" pageId="3" pageNumber="4">A. hirsuta</emphasis>
|
||
var.
|
||
<emphasis id="F4B3EAB2FFC6B918FFC1796AFF7AE768" bold="true" box="[100,157,1307,1324]" italics="true" pageId="3" pageNumber="4">sibirica</emphasis>
|
||
</taxonomicName>
|
||
. Spectral nodes are colored according to the mean precursor ion intensity per different plant parts: bark, twigs, leaves, and fruits. Molecular families
|
||
<emphasis id="F4B3EAB2FFC6B918FA34796AFA48E768" bold="true" box="[1425,1455,1307,1324]" pageId="3" pageNumber="4">A–I</emphasis>
|
||
are highlighted.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="C67836A0FFC6B91FFF207B43FED3E4A3" blockId="3.[100,770,1395,1972]" lastBlockId="4.[100,770,1580,1767]" lastPageId="4" lastPageNumber="5" pageId="3" pageNumber="4">
|
||
To bridge the bioactivity and chemical information, we applied the workflow named “bioactive molecular networking”, which was developed in our previous study (
|
||
<bibRefCitation id="A2564B51FFC6B918FECA7B18FDCFE538" author="Nothias, L. F. & Nothias-Esposito, M. & da Silva, R. & Wang, M. & Protsyuk, I. & Zhang, Z. & Sarvepalli, A. & Leyssen, P. & Touboul, D. & Costa, J. & Paolini, J. & Alexandrov, T. & Litaudon, M. & Dorrestein, P. C." box="[367,552,1897,1916]" pageId="3" pageNumber="4" pagination="758 - 767" refId="ref9352" refString="Nothias, L. F., Nothias-Esposito, M., da Silva, R., Wang, M., Protsyuk, I., Zhang, Z., Sarvepalli, A., Leyssen, P., Touboul, D., Costa, J., Paolini, J., Alexandrov, T., Litaudon, M., Dorrestein, P. C., 2018. Bioactivity-based molecular networking for the discovery of drug leads in natural product bioassay-guided fractionation. J. Nat. Prod. 81, 758 - 767. https: // doi. org / 10.1021 / acs. jnatprod. 7 b 00737." type="journal article" year="2018">Nothias et al., 2018</bibRefCitation>
|
||
). In this workflow, the Pearson correlation coefficients (
|
||
<emphasis id="F4B3EAB2FFC6B918FE007BF4FE4AE5DC" bold="true" box="[421,429,1925,1944]" italics="true" pageId="3" pageNumber="4">r</emphasis>
|
||
) and their significances (
|
||
<emphasis id="F4B3EAB2FFC6B918FD0F7BF4FD53E5DC" bold="true" box="[682,692,1925,1944]" italics="true" pageId="3" pageNumber="4">p</emphasis>
|
||
values) between the semi-quantitative intensities of MS/MS features and the bioactivity value are calculated. By plotting
|
||
<emphasis id="F4B3EAB2FFC6B918FB7C7902FB06E7C2" bold="true" box="[1241,1249,1395,1414]" italics="true" pageId="3" pageNumber="4">r</emphasis>
|
||
and
|
||
<emphasis id="F4B3EAB2FFC6B918FAB77902FAFBE7C2" bold="true" box="[1298,1308,1395,1414]" italics="true" pageId="3" pageNumber="4">p</emphasis>
|
||
values on the molecular network, it was easily visualized that MS/MS spectra showing negative
|
||
<emphasis id="F4B3EAB2FFC6B918FC2979DAFC73E7FA" bold="true" box="[908,916,1451,1470]" italics="true" pageId="3" pageNumber="4">r</emphasis>
|
||
values (negative correlation with IC
|
||
<subScript id="5A4334E5FFC6B918FAA179C2FAF1E784" attach="left" box="[1284,1302,1459,1472]" fontSize="5" pageId="3" pageNumber="4">50</subScript>
|
||
; meaning possibly inhibitory against α- glucosidase) with significance (
|
||
<emphasis id="F4B3EAB2FFC6B918FA9079B6FAD8E79E" bold="true" box="[1333,1343,1479,1498]" italics="true" pageId="3" pageNumber="4">p</emphasis>
|
||
<0.05) are mainly clustered within the molecular families
|
||
<emphasis id="F4B3EAB2FFC6B918FB567992FAE6E7B2" bold="true" box="[1267,1281,1507,1526]" pageId="3" pageNumber="4">B</emphasis>
|
||
(ellagitannins) and
|
||
<emphasis id="F4B3EAB2FFC6B918FA657992FA28E7B2" bold="true" box="[1472,1487,1507,1526]" pageId="3" pageNumber="4">G</emphasis>
|
||
(gallotannins) (
|
||
<figureCitation id="5EFC2A25FFC6B918FC66798EFBE3E456" box="[963,1028,1535,1554]" captionStart="Fig" captionStartId="4.[100,130,1441,1458]" captionTargetBox="[226,1361,153,1417]" captionTargetId="figure-274@4.[225,1362,152,1418]" captionTargetPageId="4" captionText="Fig. 3. MS2LDA-driven substructural annotation of diarylheptanoids of Alnus species. Integrated with GNPS library matching and NAP in silico annotation, diarylheptanoid-related Mass2Motifs 41, 49, 72, and 81 could be characterized and correlated with specific substructures of diarylheptanoid aglycones. Scaffold diversity within diarylheptanoid molecular families A, D, and I were revealed by mapping these Mass2Motifs on the molecular network with different colors. (For interpretation of the references to color in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.8294570" httpUri="https://zenodo.org/record/8294570/files/figure.png" pageId="3" pageNumber="4">Fig. S3</figureCitation>
|
||
, Supplementary Data). In order to narrow down the candidates from chemical classes to single compounds, we filtered the candidate list using the Bonferroni correction for multiple hypothesis testing (
|
||
<bibRefCitation id="A2564B51FFC6B918FC0D7A22FB84E422" author="Nothias, L. F. & Nothias-Esposito, M. & da Silva, R. & Wang, M. & Protsyuk, I. & Zhang, Z. & Sarvepalli, A. & Leyssen, P. & Touboul, D. & Costa, J. & Paolini, J. & Alexandrov, T. & Litaudon, M. & Dorrestein, P. C." box="[936,1123,1619,1638]" pageId="3" pageNumber="4" pagination="758 - 767" refId="ref9352" refString="Nothias, L. F., Nothias-Esposito, M., da Silva, R., Wang, M., Protsyuk, I., Zhang, Z., Sarvepalli, A., Leyssen, P., Touboul, D., Costa, J., Paolini, J., Alexandrov, T., Litaudon, M., Dorrestein, P. C., 2018. Bioactivity-based molecular networking for the discovery of drug leads in natural product bioassay-guided fractionation. J. Nat. Prod. 81, 758 - 767. https: // doi. org / 10.1021 / acs. jnatprod. 7 b 00737." type="journal article" year="2018">Nothias et al., 2018</bibRefCitation>
|
||
). As a result, only one MS/MS feature (
|
||
<emphasis id="F4B3EAB2FFC6B918FC9F7A1FFCB4E4C5" bold="true" box="[826,851,1646,1665]" pageId="3" pageNumber="4">10</emphasis>
|
||
) was left as a possible contributor to the bioactivity showing an
|
||
<emphasis id="F4B3EAB2FFC6B918FA627A1FFA28E4C5" bold="true" box="[1479,1487,1646,1665]" italics="true" pageId="3" pageNumber="4">r</emphasis>
|
||
value of −0.8625 (IC
|
||
<subScript id="5A4334E5FFC6B918FBA27AE2FBFEE4E4" attach="left" box="[1031,1049,1683,1696]" fontSize="5" pageId="3" pageNumber="4">50</subScript>
|
||
values were applied as bioactivity index, so negative
|
||
<emphasis id="F4B3EAB2FFC6B918FC227AD7FC68E4FD" bold="true" box="[903,911,1702,1721]" italics="true" pageId="3" pageNumber="4">r</emphasis>
|
||
values mean higher contribution to bioactivity) and a
|
||
<emphasis id="F4B3EAB2FFC6B918FA297AD7FA71E4FD" bold="true" box="[1420,1430,1702,1721]" italics="true" pageId="3" pageNumber="4">p</emphasis>
|
||
value of 3.52 × 10
|
||
<superScript id="31B29BE8FFC6B918FC097ACFFC22E48E" attach="none" box="[940,965,1725,1738]" fontSize="5" pageId="3" pageNumber="4">−5</superScript>
|
||
. The MS/MS feature
|
||
<emphasis id="F4B3EAB2FFC6B918FB287AB3FB41E491" bold="true" box="[1165,1190,1730,1749]" pageId="3" pageNumber="4">10</emphasis>
|
||
was annotated as gallic acid by spectral matching, and the identification was confirmed by standard compound injection. We inspected the MS/MS feature table and confirmed that active extracts (Af-B, Af-T, Af-L, Af-F, Aj-L, Ahv-L, and AhvF; ion intensity for
|
||
<emphasis id="F4B3EAB2FFC6B918FC497B43FBE2E501" bold="true" box="[1004,1029,1842,1861]" pageId="3" pageNumber="4">10</emphasis>
|
||
ranging from 49,854 to 96,211) show a higher intensity of the gallic acid ion than inactive extracts (Aj-B, Aj-T, Aj-F, Ah-L, Ah-F, Ah-B, and Ahv-T; ion intensity for
|
||
<emphasis id="F4B3EAB2FFC6B918FB4A7B18FAEFE538" bold="true" box="[1263,1288,1897,1916]" pageId="3" pageNumber="4">10</emphasis>
|
||
ranging from 520 to 11,358) as shown in
|
||
<figureCitation id="5EFC2A25FFC6B918FC597BF4FBA9E5DC" box="[1020,1102,1925,1944]" captionStart="Fig" captionStartId="6.[100,130,1965,1982]" captionTargetBox="[302,1286,986,1941]" captionTargetId="figure-367@6.[301,1287,984,1942]" captionTargetPageId="6" captionText="Fig. 5. A boxplot showing the ion intensities of MS/MS feature 10 (gallic acid) in extracts which were active (IC50 <30 μg/mL) and inactive against α-glucosidase." figureDoi="http://doi.org/10.5281/zenodo.8294574" httpUri="https://zenodo.org/record/8294574/files/figure.png" pageId="3" pageNumber="4">Fig. 5. A</figureCitation>
|
||
previous study reported gallic acid as a potent α- glucosidase inhibitor (
|
||
<bibRefCitation id="A2564B51FFC6B918FBC97BD0FAC0E5F0" author="Wansi, J. D. & Lallemand, M. C. & Chiozem, D. D. & Toze, F. A. A. & Mbaze, L. M. & Naharkhan, S. & Iqbal, M. C. & Tillequin, F. & Wandji, J. & Fomum, Z. T." box="[1132,1319,1953,1972]" pageId="3" pageNumber="4" pagination="2096 - 2100" refId="ref12102" refString="Wansi, J. D., Lallemand, M. C., Chiozem, D. D., Toze, F. A. A., Mbaze, L. M., Naharkhan, S., Iqbal, M. C., Tillequin, F., Wandji, J., Fomum, Z. T., 2007. α- Glucosidase inhibitory constituents from stem bark of Terminalia superba (Combretaceae). Phytochemistry 68, 2096 - 2100. https: // doi. org / 10.1016 / j. phytochem. 2007.02.020." type="journal article" year="2007">Wansi et al., 2007</bibRefCitation>
|
||
), so it could be hypothesized that gallic acid is the main contributor of α- glucosidase inhibition of these
|
||
<taxonomicName id="01C74D23FFC1B91FFEB17A39FE70E41F" box="[276,407,1608,1627]" class="Magnoliopsida" family="Betulaceae" genus="Alnus" kingdom="Plantae" order="Fagales" pageId="4" pageNumber="6" phylum="Tracheophyta" rank="species" species="extracts">
|
||
<emphasis id="F4B3EAB2FFC1B91FFEB17A39FEA1E41F" bold="true" box="[276,326,1608,1627]" italics="true" pageId="4" pageNumber="5">Alnus</emphasis>
|
||
extracts
|
||
</taxonomicName>
|
||
. Although this result did not provoke a discovery of a previously unknown bioactive compound, it demonstrated that the digitized MS/MS-based dereplication strategy can reveal bioactive components from complex phytochemical extracts and reduce the unnecessary effort spent in re-isolation of previously known bioactive compounds.
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |