498 lines
56 KiB
XML
498 lines
56 KiB
XML
<document id="F7CBC04A6861CA063164B5E8596E47C1" ID-DOI="10.1016/j.phytochem.2019.04.004" ID-ISSN="1873-3700" ID-Zenodo-Dep="10482695" IM.bibliography_approvedBy="valdenar" IM.illustrations_approvedBy="valdenar" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_approvedBy="valdenar" IM.taxonomicNames_approvedBy="valdenar" IM.treatments_approvedBy="valdenar" checkinTime="1704932088492" checkinUser="felipe" docAuthor="Li, Jie, Liu, Xiao, Gao, Yanrong, Zong, Guangning, Wang, Dandan, Liu, Meizi, Fei, Shang, Wei, Yu, Yin, Zhongping, Chen, Jiguang, Wang, Xiaoqiang & Shen, Yuequan" docDate="2019" docId="45567B47FF8D0F4BFCD06643FADAFE74" docLanguage="en" docName="Phytochemistry.163.75-88.pdf" docOrigin="Phytochemistry 163" docSource="http://dx.doi.org/10.1016/j.phytochem.2019.04.004" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Cyclocarya paliurus (Batalin) Iljinsk." docType="treatment" docVersion="2" lastPageNumber="84" masterDocId="B96F033FFF8A0F42FFE2614EFFE4FFE6" masterDocTitle="Identification of a UDP-Glucosyltransferase favouring substrate- and regiospecific biosynthesis of flavonoid glucosides in Cyclocarya paliurus" masterLastPageNumber="88" masterPageNumber="75" pageNumber="82" updateTime="1705587032784" updateUser="ExternalLinkService">
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<mods:title id="D4482901D3E2ACD5E2F1D9C5AC95E0EE">Identification of a UDP-Glucosyltransferase favouring substrate- and regiospecific biosynthesis of flavonoid glucosides in Cyclocarya paliurus</mods:title>
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<mods:namePart id="6380A06996194AFE3C9275E50D4ED1CC">Li, Jie</mods:namePart>
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<mods:affiliation id="4F95BADCFDD6A6007ECBCBD870FB4800">∗ & ∗∗ & ∗∗∗ & State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin, 300350, China & ∗ & ∗∗ & ∗∗∗ & Collaborative Innovation Center for Biotherapy and School of Medicine, Nankai University, Tianjin, 300071, China</mods:affiliation>
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<mods:namePart id="028EBD1D523AF026753D9AB037F9BF8E">Liu, Xiao</mods:namePart>
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<mods:namePart id="DF47738F30806A0DA323873EEEEFA413">Gao, Yanrong</mods:namePart>
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<mods:namePart id="01DC5F4239F1A23974F83BD38217EB72">Zong, Guangning</mods:namePart>
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<mods:namePart id="EA7CAFAD3A92518C9DC32190C7D878CE">Wang, Dandan</mods:namePart>
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<mods:namePart id="79B85D9CDAC18949468BFFEE6A8CF01D">Liu, Meizi</mods:namePart>
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<mods:namePart id="7DD40318C9DA6607DEC62951DB3F5EC6">Fei, Shang</mods:namePart>
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<mods:namePart id="5119F054E1DCC7AF0DCDB485CD76393C">Wei, Yu</mods:namePart>
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<mods:namePart id="092BFD92C4028E76454C4355BBEC2D93">Yin, Zhongping</mods:namePart>
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<mods:namePart id="B7559A106E70DCD374B6D60AF6564B1F">Chen, Jiguang</mods:namePart>
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<mods:namePart id="39E197F34ACCDE7E5DB72BFFB826FF0B">Wang, Xiaoqiang</mods:namePart>
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<mods:namePart id="1E63352F35E5946809A43121C84A65F6">Shen, Yuequan</mods:namePart>
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<mods:title id="1513E172005425B2DFEFF88121F17288">Phytochemistry</mods:title>
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<mods:date id="116BEF9D1DE83E88036FBAF82BBE266A">2019</mods:date>
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<mods:number id="7518410EE81D35AFDD98C3DB264D6913">2019-07-31</mods:number>
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<mods:url id="A9BFC4792CC3902C31158BB2D64ECCDF">http://dx.doi.org/10.1016/j.phytochem.2019.04.004</mods:url>
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<mods:classification id="A16D6F42D3B5F2B66279DEF99B79F629">journal article</mods:classification>
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<mods:identifier id="AC5DE4C2CDA38BB192B95BB0FFB60725" type="DOI">10.1016/j.phytochem.2019.04.004</mods:identifier>
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<mods:identifier id="4F6625BB8D4F16D2D9A6EE72CA22886A" type="ISSN">1873-3700</mods:identifier>
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<treatment id="45567B47FF8D0F4BFCD06643FADAFE74" ID-DOI="http://doi.org/10.5281/zenodo.10528505" ID-Zenodo-Dep="10528505" LSID="urn:lsid:plazi:treatment:45567B47FF8D0F4BFCD06643FADAFE74" httpUri="http://treatment.plazi.org/id/45567B47FF8D0F4BFCD06643FADAFE74" lastPageId="9" lastPageNumber="84" pageId="7" pageNumber="82">
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<subSubSection id="85E599DAFF8D0F45FCD06643FAC5F8C6" box="[818,1313,1805,1824]" pageId="7" pageNumber="82" type="nomenclature">
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<paragraph id="CD40CA51FF8D0F45FCD06643FAC5F8C6" blockId="7.[818,1313,1805,1824]" box="[818,1313,1805,1824]" pageId="7" pageNumber="82">
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<heading id="96087D3DFF8D0F45FCD06643FAC5F8C6" bold="true" box="[818,1313,1805,1824]" fontSize="36" level="1" pageId="7" pageNumber="82" reason="1">
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<emphasis id="FF8B1643FF8D0F45FCD06643FAC5F8C6" bold="true" box="[818,1313,1805,1824]" italics="true" pageId="7" pageNumber="82">
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2.4. N- and S-glucosylation activity of
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||
<taxonomicName id="0AFFB1D2FF8D0F45FB706643FB10F8C6" ID-CoL="32TPC" authority="(Batalin) Iljinsk." authorityName="(Batalin) Iljinsk." box="[1170,1268,1805,1824]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="7" pageNumber="82" phylum="Tracheophyta" rank="species" species="paliurus">C. paliurus</taxonomicName>
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GT1
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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="85E599DAFF8D0F4BFCB1660BFADAFE74" lastPageId="9" lastPageNumber="84" pageId="7" pageNumber="82" type="description">
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<paragraph id="CD40CA51FF8D0F4AFCB1660BFAC4FE4B" blockId="7.[818,1487,1861,1992]" lastBlockId="8.[818,1488,159,792]" lastPageId="8" lastPageNumber="83" pageId="7" pageNumber="82">
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In addition, to investigate the
|
||
<emphasis id="FF8B1643FF8D0F45FB92660BFB9BF8BE" bold="true" box="[1136,1151,1861,1880]" italics="true" pageId="7" pageNumber="82">O</emphasis>
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||
-glucosylation activity of
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||
<taxonomicName id="0AFFB1D2FF8D0F45FA8C660BFCB0F892" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="7" pageNumber="82" phylum="Tracheophyta" rank="species" species="paliurus">
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<emphasis id="FF8B1643FF8D0F45FA8C660BFA2BF8BE" bold="true" box="[1390,1487,1861,1880]" italics="true" pageId="7" pageNumber="82">C. paliurus</emphasis>
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GT
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</taxonomicName>
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1, we also explored whether
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<taxonomicName id="0AFFB1D2FF8D0F45FBB8662FFB3BF892" authority="GT" authorityName="GT" box="[1114,1247,1889,1908]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="7" pageNumber="82" phylum="Tracheophyta" rank="species" species="paliurus">
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<emphasis id="FF8B1643FF8D0F45FBB8662FFB5EF892" bold="true" box="[1114,1210,1889,1908]" italics="true" pageId="7" pageNumber="82">C. paliurus</emphasis>
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||
GT
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</taxonomicName>
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1 could catalyse
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<emphasis id="FF8B1643FF8D0F45FA95662FFA66F892" bold="true" box="[1399,1410,1889,1908]" italics="true" pageId="7" pageNumber="82">S</emphasis>
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- and/or
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<emphasis id="FF8B1643FF8D0F45FCD06633FCA5F876" bold="true" box="[818,833,1917,1936]" italics="true" pageId="7" pageNumber="82">N</emphasis>
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-glucosylation on thiol (
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<emphasis id="FF8B1643FF8D0F45FBC46633FBD5F876" bold="true" box="[1062,1073,1917,1936]" italics="true" pageId="7" pageNumber="82">S</emphasis>
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)- and amine (
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<emphasis id="FF8B1643FF8D0F45FB586633FB2DF876" bold="true" box="[1210,1225,1917,1936]" italics="true" pageId="7" pageNumber="82">N</emphasis>
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) sites of phenolic/aliphatic aglycones, with UDP-Glc as the donor substrate. Interestingly,
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<taxonomicName id="0AFFB1D2FF8D0F45FA7466D7FC74F82E" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="7" pageNumber="82" phylum="Tracheophyta" rank="species" species="paliurus">
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<emphasis id="FF8B1643FF8D0F45FA7466D7FC87F82E" bold="true" italics="true" pageId="7" pageNumber="82">C. paliurus</emphasis>
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GT
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</taxonomicName>
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1 exhibited
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<emphasis id="FF8B1643FF8D0F45FBEB66FBFBFCF82E" bold="true" box="[1033,1048,1973,1992]" italics="true" pageId="7" pageNumber="82">N</emphasis>
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- and
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<emphasis id="FF8B1643FF8D0F45FBBE66FBFB83F82E" bold="true" box="[1116,1127,1973,1992]" italics="true" pageId="7" pageNumber="82">S</emphasis>
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-glucosylation activities towards the simple aromatic molecules 3,4-dichloroaniline (DCA) and 4-chlorothiophenol (CTP), respectively, with high conversion rates (> 95%). In the HPLC analysis of CTP glucosylation catalysed by
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<taxonomicName id="0AFFB1D2FF820F4AFAD96199FA20FF0C" authority="GT" authorityName="GT" box="[1339,1476,215,234]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
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<emphasis id="FF8B1643FF820F4AFAD96199FA78FF0C" bold="true" box="[1339,1436,215,234]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
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GT
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</taxonomicName>
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1, a peak other than the monosaccharide product (CTPG) was speculated to be a disaccharide product (CTP2G), according to the molecular weight detected by LC-MS. However, no activity was observed with aliphatic molecules 4-chlorophenethylamine (CPEA) and 4-chlorobenzylmercaptan (CBM) (
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||
<figureCitation id="55C4D6D4FF820F4AFBD2602DFB82FE90" box="[1072,1126,355,374]" captionStart="Fig" captionStartId="8.[100,130,1914,1931]" captionTargetBox="[151,1437,833,1891]" captionTargetId="figure-419@8.[150,1438,832,1892]" captionTargetPageId="8" captionText="Fig. 7. NGT and SGT activities of C. paliurus GT1 with N- and S-conjugating aglycones. HPLC chromatogram and MS analyses of the enzymatic reactions with C. paliurus GT1 in vitro. The UDP-glucose (UDPG) and N- and S- phenolic/aliphatic aglycons were the sugar donor and acceptor, respectively. The substrates and corresponding products were detected using HPLC chromatogram and MS." figureDoi="http://doi.org/10.5281/zenodo.10482709" httpUri="https://zenodo.org/record/10482709/files/figure.png" pageId="8" pageNumber="83">Fig. 7</figureCitation>
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). Control reactions lacking
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<taxonomicName id="0AFFB1D2FF820F4AFA8C602DFCB6FE74" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFA8C602DFA2BFE90" bold="true" box="[1390,1487,355,374]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
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||
GT
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</taxonomicName>
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1 confirmed that the reactions were enzyme-dependent, indicating that
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<taxonomicName id="0AFFB1D2FF820F4AFCBC60D4FC03FE4B" authority="GT" authorityName="GT" box="[862,999,410,429]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFCBC60D4FC5BFE4B" bold="true" box="[862,959,410,429]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
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||
</taxonomicName>
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||
1 has broad aglycon promiscuity.
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</paragraph>
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||
<caption id="99809AD9FF820F4AFF8661EFFCE7FF2D" ID-Table-UUID="99809AD9FF820F4AFF8661EFFCE7FF2D" httpUri="http://table.plazi.org/id/99809AD9FF820F4AFF8661EFFCE7FF2D" pageId="8" pageNumber="83" startId="8.[100,150,161,178]" targetBox="[116,753,226,673]" targetIsTable="true" targetPageId="8" targetType="table">
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||
<paragraph id="CD40CA51FF820F4AFF8661EFFF4CFF54" blockId="8.[100,771,161,203]" box="[100,168,161,178]" pageId="8" pageNumber="83">
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||
<emphasis id="FF8B1643FF820F4AFF8661EFFF4CFF54" bold="true" box="[100,168,161,178]" pageId="8" pageNumber="83">Table 2</emphasis>
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</paragraph>
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<paragraph id="CD40CA51FF820F4AFF8661F4FCE7FF2D" blockId="8.[100,771,161,203]" box="[100,771,186,203]" pageId="8" pageNumber="83">
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Effects of various ions on the enzymatic activity of recombinant
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<taxonomicName id="0AFFB1D2FF820F4AFD9C61F4FD1CFF2D" authority="GT" authorityName="GT" box="[638,760,186,203]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFD9C61F4FD30FF2D" bold="true" box="[638,724,186,203]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
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GT
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||
</taxonomicName>
|
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1.
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</paragraph>
|
||
</caption>
|
||
<paragraph id="CD40CA51FF820F4AFF9661ADFD4CFD47" pageId="8" pageNumber="83">
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<th id="301EA16FFF82F0BDFF9661ACFED7FF14" box="[116,307,226,242]" gridcol="0" gridrow="0" pageId="8" pageNumber="83">Reagent</th>
|
||
<th id="301EA16FFF82F0BDFEB161ACFE59FF14" box="[339,445,226,242]" gridcol="1" gridrow="0" pageId="8" pageNumber="83">Concentration</th>
|
||
<th id="301EA16FFF82F0BDFE1261ACFD8FFF14" box="[496,619,226,242]" gridcol="2" gridrow="0" pageId="8" pageNumber="83">Relative activity</th>
|
||
<th id="301EA16FFF82F0BDFD7261ACFD15FF14" box="[656,753,226,242]" gridcol="3" gridrow="0" pageId="8" pageNumber="83">IC50 (mM)</th>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9661B7FD15FEEE" box="[116,753,249,264]" gridrow="1" pageId="8" pageNumber="83" rowspan-0="1" rowspan-3="1">
|
||
<td id="301EA16FFF82F0BDFEB161B7FE59FEEE" box="[339,445,249,264]" gridcol="1" gridrow="1" pageId="8" pageNumber="83">(mM)</td>
|
||
<td id="301EA16FFF82F0BDFE1261B7FD8FFEEE" box="[496,619,249,264]" gridcol="2" gridrow="1" pageId="8" pageNumber="83">(%)</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF96606AFD15FED2" box="[116,753,292,308]" gridrow="2" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF96606AFED7FED2" box="[116,307,292,308]" gridcol="0" gridrow="2" pageId="8" pageNumber="83">Control</th>
|
||
<td id="301EA16FFF82F0BDFEB1606AFE59FED2" box="[339,445,292,308]" gridcol="1" gridrow="2" pageId="8" pageNumber="83">–</td>
|
||
<td id="301EA16FFF82F0BDFE12606AFD8FFED2" box="[496,619,292,308]" gridcol="2" gridrow="2" pageId="8" pageNumber="83">100</td>
|
||
<td id="301EA16FFF82F0BDFD72606AFD15FED2" box="[656,753,292,308]" gridcol="3" gridrow="2" pageId="8" pageNumber="83">–</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966075FD15FEAC" box="[116,753,315,330]" gridrow="3" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF966075FED7FEAC" box="[116,307,315,330]" gridcol="0" gridrow="3" pageId="8" pageNumber="83">NaCl</th>
|
||
<td id="301EA16FFF82F0BDFEB16075FE59FEAC" box="[339,445,315,330]" gridcol="1" gridrow="3" pageId="8" pageNumber="83">500</td>
|
||
<td id="301EA16FFF82F0BDFE126075FD8FFEAC" box="[496,619,315,330]" gridcol="2" gridrow="3" pageId="8" pageNumber="83">99.35 ± 2.47</td>
|
||
<td id="301EA16FFF82F0BDFD726075FD15FEAC" box="[656,753,315,330]" gridcol="3" gridrow="3" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF96601CFD15FE85" box="[116,753,338,355]" gridrow="4" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF96601CFED7FE85" box="[116,307,338,355]" gridcol="0" gridrow="4" pageId="8" pageNumber="83">Na2SO4</th>
|
||
<td id="301EA16FFF82F0BDFEB1601CFE59FE85" box="[339,445,338,355]" gridcol="1" gridrow="4" pageId="8" pageNumber="83">500</td>
|
||
<td id="301EA16FFF82F0BDFE12601CFD8FFE85" box="[496,619,338,355]" gridcol="2" gridrow="4" pageId="8" pageNumber="83">96.77 ± 3.83</td>
|
||
<td id="301EA16FFF82F0BDFD72601CFD15FE85" box="[656,753,338,355]" gridcol="3" gridrow="4" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966027FD15FE9E" box="[116,753,361,376]" gridrow="5" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF966027FED7FE9E" box="[116,307,361,376]" gridcol="0" gridrow="5" pageId="8" pageNumber="83">KCl</th>
|
||
<td id="301EA16FFF82F0BDFEB16027FE59FE9E" box="[339,445,361,376]" gridcol="1" gridrow="5" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE126027FD8FFE9E" box="[496,619,361,376]" gridcol="2" gridrow="5" pageId="8" pageNumber="83">98.12 ± 4.11</td>
|
||
<td id="301EA16FFF82F0BDFD726027FD15FE9E" box="[656,753,361,376]" gridcol="3" gridrow="5" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9660CEFD15FE77" box="[116,753,384,401]" gridrow="6" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF9660CEFED7FE77" box="[116,307,384,401]" gridcol="0" gridrow="6" pageId="8" pageNumber="83">MgCl2</th>
|
||
<td id="301EA16FFF82F0BDFEB160CEFE59FE77" box="[339,445,384,401]" gridcol="1" gridrow="6" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE1260CEFD8FFE77" box="[496,619,384,401]" gridcol="2" gridrow="6" pageId="8" pageNumber="83">135.36 ± 2.98</td>
|
||
<td id="301EA16FFF82F0BDFD7260CEFD15FE77" box="[656,753,384,401]" gridcol="3" gridrow="6" pageId="8" pageNumber="83">–</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9660D9FD15FE41" box="[116,753,407,423]" gridrow="7" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF9660D9FED7FE41" box="[116,307,407,423]" gridcol="0" gridrow="7" pageId="8" pageNumber="83">CaCl2</th>
|
||
<td id="301EA16FFF82F0BDFEB160D9FE59FE41" box="[339,445,407,423]" gridcol="1" gridrow="7" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE1260D9FD8FFE41" box="[496,619,407,423]" gridcol="2" gridrow="7" pageId="8" pageNumber="83">62.68 ± 2.55</td>
|
||
<td id="301EA16FFF82F0BDFD7260D9FD15FE41" box="[656,753,407,423]" gridcol="3" gridrow="7" pageId="8" pageNumber="83">6.93 ± 0.31</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9660E0FD15FE58" box="[116,753,430,446]" gridrow="8" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF9660E0FED7FE58" box="[116,307,430,446]" gridcol="0" gridrow="8" pageId="8" pageNumber="83">CuSO4</th>
|
||
<td id="301EA16FFF82F0BDFEB160E0FE59FE58" box="[339,445,430,446]" gridcol="1" gridrow="8" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE1260E0FD8FFE58" box="[496,619,430,446]" gridcol="2" gridrow="8" pageId="8" pageNumber="83">9.13 ± 1.04</td>
|
||
<td id="301EA16FFF82F0BDFD7260E0FD15FE58" box="[656,753,430,446]" gridcol="3" gridrow="8" pageId="8" pageNumber="83">0.94 ± 0.04</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF96608AFD15FE33" box="[116,753,452,469]" gridrow="9" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF96608AFED7FE33" box="[116,307,452,469]" gridcol="0" gridrow="9" pageId="8" pageNumber="83">FeSO4</th>
|
||
<td id="301EA16FFF82F0BDFEB1608AFE59FE33" box="[339,445,452,469]" gridcol="1" gridrow="9" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE12608AFD8FFE33" box="[496,619,452,469]" gridcol="2" gridrow="9" pageId="8" pageNumber="83">121.15 ± 4.65</td>
|
||
<td id="301EA16FFF82F0BDFD72608AFD15FE33" box="[656,753,452,469]" gridcol="3" gridrow="9" pageId="8" pageNumber="83">–</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966095FD15FE0A" box="[116,753,475,492]" gridrow="10" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF966095FED7FE0A" box="[116,307,475,492]" gridcol="0" gridrow="10" pageId="8" pageNumber="83">FeCl3</th>
|
||
<td id="301EA16FFF82F0BDFEB16095FE59FE0A" box="[339,445,475,492]" gridcol="1" gridrow="10" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE126095FD8FFE0A" box="[496,619,475,492]" gridcol="2" gridrow="10" pageId="8" pageNumber="83">50.14 ± 2.42</td>
|
||
<td id="301EA16FFF82F0BDFD726095FD15FE0A" box="[656,753,475,492]" gridcol="3" gridrow="10" pageId="8" pageNumber="83">5.50 ± 0.83</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9660BCFD15FDE5" box="[116,753,498,515]" gridrow="11" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF9660BCFED7FDE5" box="[116,307,498,515]" gridcol="0" gridrow="11" pageId="8" pageNumber="83">ZnCl2</th>
|
||
<td id="301EA16FFF82F0BDFEB160BCFE59FDE5" box="[339,445,498,515]" gridcol="1" gridrow="11" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE1260BCFD8FFDE5" box="[496,619,498,515]" gridcol="2" gridrow="11" pageId="8" pageNumber="83">72.33 ± 2.90</td>
|
||
<td id="301EA16FFF82F0BDFD7260BCFD15FDE5" box="[656,753,498,515]" gridcol="3" gridrow="11" pageId="8" pageNumber="83">8.00 ± 0.50</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966347FD15FDFC" box="[116,753,521,538]" gridrow="12" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF966347FED7FDFC" box="[116,307,521,538]" gridcol="0" gridrow="12" pageId="8" pageNumber="83">NiCl2</th>
|
||
<td id="301EA16FFF82F0BDFEB16347FE59FDFC" box="[339,445,521,538]" gridcol="1" gridrow="12" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE126347FD8FFDFC" box="[496,619,521,538]" gridcol="2" gridrow="12" pageId="8" pageNumber="83">97.98 ± 4.52</td>
|
||
<td id="301EA16FFF82F0BDFD726347FD15FDFC" box="[656,753,521,538]" gridcol="3" gridrow="12" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF96636EFD15FDC9" box="[116,753,544,559]" gridrow="13" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF96636EFED7FDC9" box="[116,307,544,559]" gridcol="0" gridrow="13" pageId="8" pageNumber="83">Dimethyl sulphoxide（ v/</th>
|
||
<td id="301EA16FFF82F0BDFEB1636EFE59FDC9" box="[339,445,544,559]" gridcol="1" gridrow="13" pageId="8" pageNumber="83">20</td>
|
||
<td id="301EA16FFF82F0BDFE12636EFD8FFDC9" box="[496,619,544,559]" gridcol="2" gridrow="13" pageId="8" pageNumber="83">98.98 ± 3.67</td>
|
||
<td id="301EA16FFF82F0BDFD72636EFD15FDC9" box="[656,753,544,559]" gridcol="3" gridrow="13" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966379FD15FDA0" box="[116,753,567,582]" gridrow="14" pageId="8" pageNumber="83" rowspan-1="1" rowspan-2="1" rowspan-3="1">
|
||
<th id="301EA16FFF82F0BDFF966379FED7FDA0" box="[116,307,567,582]" gridcol="0" gridrow="14" pageId="8" pageNumber="83">v， %）</th>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966303FD15FDBB" box="[116,753,589,605]" gridrow="15" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF966303FED7FDBB" box="[116,307,589,605]" gridcol="0" gridrow="15" pageId="8" pageNumber="83">Methanol （ v/v， %）</th>
|
||
<td id="301EA16FFF82F0BDFEB16303FE59FDBB" box="[339,445,589,605]" gridcol="1" gridrow="15" pageId="8" pageNumber="83">20</td>
|
||
<td id="301EA16FFF82F0BDFE126303FD8FFDBB" box="[496,619,589,605]" gridcol="2" gridrow="15" pageId="8" pageNumber="83">96.22 ± 2.47</td>
|
||
<td id="301EA16FFF82F0BDFD726303FD15FDBB" box="[656,753,589,605]" gridcol="3" gridrow="15" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF96632AFD15FD95" box="[116,753,612,627]" gridrow="16" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF96632AFED7FD95" box="[116,307,612,627]" gridcol="0" gridrow="16" pageId="8" pageNumber="83">β- mercaptoethanol (β-</th>
|
||
<td id="301EA16FFF82F0BDFEB1632AFE59FD95" box="[339,445,612,627]" gridcol="1" gridrow="16" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE12632AFD8FFD95" box="[496,619,612,627]" gridcol="2" gridrow="16" pageId="8" pageNumber="83">98.41 ± 3.30</td>
|
||
<td id="301EA16FFF82F0BDFD72632AFD15FD95" box="[656,753,612,627]" gridcol="3" gridrow="16" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF966335FD15FD6C" box="[116,753,635,650]" gridrow="17" pageId="8" pageNumber="83" rowspan-1="1" rowspan-2="1" rowspan-3="1">
|
||
<th id="301EA16FFF82F0BDFF966335FED7FD6C" box="[116,307,635,650]" gridcol="0" gridrow="17" pageId="8" pageNumber="83">ME)</th>
|
||
</tr>
|
||
<tr id="73CFC813FF82F0BDFF9663DCFD15FD47" box="[116,753,658,673]" gridrow="18" pageId="8" pageNumber="83">
|
||
<th id="301EA16FFF82F0BDFF9663DCFED7FD47" box="[116,307,658,673]" gridcol="0" gridrow="18" pageId="8" pageNumber="83">Dithiothreitol (DTT)</th>
|
||
<td id="301EA16FFF82F0BDFEB163DCFE59FD47" box="[339,445,658,673]" gridcol="1" gridrow="18" pageId="8" pageNumber="83">5</td>
|
||
<td id="301EA16FFF82F0BDFE1263DCFD8FFD47" box="[496,619,658,673]" gridcol="2" gridrow="18" pageId="8" pageNumber="83">93.75 ± 4.13</td>
|
||
<td id="301EA16FFF82F0BDFD7263DCFD15FD47" box="[656,753,658,673]" gridcol="3" gridrow="18" pageId="8" pageNumber="83">ND</td>
|
||
</tr>
|
||
</table>
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF820F4BFCB160F8FDA7FE2F" blockId="8.[818,1488,159,792]" lastBlockId="9.[100,770,159,457]" lastPageId="9" lastPageNumber="84" pageId="8" pageNumber="83">
|
||
Thus far, only a few
|
||
<emphasis id="FF8B1643FF820F4AFBD060F8FBA5FE2F" bold="true" box="[1074,1089,438,457]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
- and
|
||
<emphasis id="FF8B1643FF820F4AFB6160F8FB6AFE2F" bold="true" box="[1155,1166,438,457]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
-UGTs have been reported, e.g.,
|
||
<taxonomicName id="0AFFB1D2FF820F4AFCD0609CFC33FE03" authority="UGT" authorityName="UGT" box="[818,983,466,485]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="genus">
|
||
<emphasis id="FF8B1643FF820F4AFCD0609CFC7DFE03" bold="true" box="[818,921,466,485]" italics="true" pageId="8" pageNumber="83">Arabidopsis</emphasis>
|
||
UGT
|
||
</taxonomicName>
|
||
72B1 with both
|
||
<emphasis id="FF8B1643FF820F4AFB66609CFB77FE03" bold="true" box="[1156,1171,466,485]" italics="true" pageId="8" pageNumber="83">O</emphasis>
|
||
- and N-glycosylation activities (
|
||
<bibRefCitation id="A96EB7A0FF820F4AFCD860A0FBD1FDE7" author="Brazier-Hicks, M. & Offen, W. A. & Gershater, M. C. & Revett, T. J. & Lim, E. K. & Bowles, D. J. & Davies, G. J. & Edwards, R." box="[826,1077,494,513]" pageId="8" pageNumber="83" pagination="20238 - 20243" refId="ref11700" refString="Brazier-Hicks, M., Offen, W. A., Gershater, M. C., Revett, T. J., Lim, E. K., Bowles, D. J., Davies, G. J., Edwards, R., 2007. Characterization and engineering of the bifunctional N- and O-glucosyltransferase involved in xenobiotic metabolism in plants. Proc. Natl. Acad. Sci. U. S. A. 104, 20238 - 20243." type="journal article" year="2007">Brazier-Hicks et al., 2007</bibRefCitation>
|
||
), UGT74B1 with S-glycosylation function (
|
||
<bibRefCitation id="A96EB7A0FF820F4AFCD86344FC0DFDFB" author="Grubb, C. D. & Zipp, B. J. & Kopycki, J. & Schubert, M. & Quint, M. & Lim, E. K. & Bowles, D. J. & Pedras, M. S. C. & Abel, S." box="[826,1001,522,541]" pageId="8" pageNumber="83" pagination="92 - 105" refId="ref12137" refString="Grubb, C. D., Zipp, B. J., Kopycki, J., Schubert, M., Quint, M., Lim, E. K., Bowles, D. J., Pedras, M. S. C., Abel, S., 2014. Comparative analysis of Arabidopsis UGT 74 glucosyltransferases reveals a special role of UGT 74 C 1 in glucosinolate biosynthesis. Plant J. 79, 92 - 105." type="journal article" year="2014">Grubb et al., 2014</bibRefCitation>
|
||
), and
|
||
<taxonomicName id="0AFFB1D2FF820F4AFBCA6344FB0EFDFB" authority="BcGT" authorityName="BcGT" box="[1064,1258,522,541]" class="Insecta" family="Bacillidae" genus="Bacillus" kingdom="Animalia" order="Phasmida" pageId="8" pageNumber="83" phylum="Arthropoda" rank="species" species="cereus">
|
||
<emphasis id="FF8B1643FF820F4AFBCA6344FB4FFDFB" bold="true" box="[1064,1195,522,541]" italics="true" pageId="8" pageNumber="83">Bacillus cereus</emphasis>
|
||
BcGT
|
||
</taxonomicName>
|
||
1 with
|
||
<emphasis id="FF8B1643FF820F4AFACB6344FADCFDFB" bold="true" box="[1321,1336,522,541]" italics="true" pageId="8" pageNumber="83">O</emphasis>
|
||
-,
|
||
<emphasis id="FF8B1643FF820F4AFAAE6344FAB3FDFB" bold="true" box="[1356,1367,522,541]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
-, and
|
||
<emphasis id="FF8B1643FF820F4AFA776344FA40FDFB" bold="true" box="[1429,1444,522,541]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
-glucosidation (
|
||
<bibRefCitation id="A96EB7A0FF820F4AFC436368FBA7FDDF" author="Chiu, H. H. & Shen, M. Y. & Liu, Y. T. & Fu, Y. L. & Chiu, Y. A. & Chen, Y. H. & Huang, C. P. & Li, Y. K." box="[929,1091,550,569]" pageId="8" pageNumber="83" pagination="4459 - 4471" refId="ref11790" refString="Chiu, H. H., Shen, M. Y., Liu, Y. T., Fu, Y. L., Chiu, Y. A., Chen, Y. H., Huang, C. P., Li, Y. K., 2016. Diversity of sugar acceptor of glycosyltransferase 1 from Bacillus cereus and its application for glucoside synthesis. Appl. Microbiol. Biotechnol. 100, 4459 - 4471." type="journal article" year="2016">Chiu et al., 2016</bibRefCitation>
|
||
). Remarkably,
|
||
<taxonomicName id="0AFFB1D2FF820F4AFB346368FA84FDDF" authority="GT" authorityName="GT" box="[1238,1376,550,569]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFB346368FADCFDDF" bold="true" box="[1238,1336,550,569]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 showed
|
||
<emphasis id="FF8B1643FF820F4AFA5F6368FA2CFDDF" bold="true" box="[1469,1480,550,569]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
- and
|
||
<emphasis id="FF8B1643FF820F4AFCBF630CFC88FDB3" bold="true" box="[861,876,578,597]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
-glucosylation activities to catalyse the attachment of sugars to the aromatic amine or thiophenol groups, leading to the generation of
|
||
<emphasis id="FF8B1643FF820F4AFCD06334FCA5FD6B" bold="true" box="[818,833,634,653]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
- or
|
||
<emphasis id="FF8B1643FF820F4AFC886334FC91FD6B" bold="true" box="[874,885,634,653]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
-glucosides. However,
|
||
<taxonomicName id="0AFFB1D2FF820F4AFBA96334FB37FD6B" authority="GT" authorityName="GT" box="[1099,1235,634,653]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFBA96334FB48FD6B" bold="true" box="[1099,1196,634,653]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 could not catalyse glucosylation on the amino or thiol group of the aliphatic chain towards formation of the corresponding glucosides. We hypothesize that
|
||
<taxonomicName id="0AFFB1D2FF820F4AFA7A63FFFC6FFD06" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFA7A63FFFC87FD06" bold="true" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 catalyses
|
||
<emphasis id="FF8B1643FF820F4AFC146383FBE1FD06" bold="true" box="[1014,1029,717,736]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
- or
|
||
<emphasis id="FF8B1643FF820F4AFBCD6383FBDEFD06" bold="true" box="[1071,1082,717,736]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
-glucosylation by utilizing a SN2-like reaction mechanism similar to its
|
||
<emphasis id="FF8B1643FF820F4AFBB363A7FB84FD1A" bold="true" box="[1105,1120,745,764]" italics="true" pageId="8" pageNumber="83">O</emphasis>
|
||
-glucosylation and that it also has certain selectivity and energy requirements (
|
||
<bibRefCitation id="A96EB7A0FF820F4AFB3E624BFA75FCFE" author="Hans, J. & Brandt, W. & Vogt, T." box="[1244,1425,773,792]" pageId="8" pageNumber="83" pagination="319 - 333" refId="ref12225" refString="Hans, J., Brandt, W., Vogt, T., 2004. Site-directed mutagenesis and protein 3 D-homology modelling suggest a catalytic mechanism for UDP-glucose-dependent betanidin 5 - Oglucosyltransferase from Dorotheanthus bellidiformis. Plant J.: Cell Cult. Methods Mol. Cell Biol. 39, 319 - 333." type="journal article" year="2004">Hans et al., 2004</bibRefCitation>
|
||
). The oxygen atom of the phenolic, the sulphur atom of the thiophenol, and the nitrogen atom of the aromatic amine all contained a lone-pair of electrons and were activated by the aromatic group. Thereby the hydrogen atoms on the heteroatom were easily deprotonated by His-16 through direct and orientated nucleophilic attack compared with the corresponding atoms on an aliphatic chain. There is currently no additional evidence on
|
||
<taxonomicName id="0AFFB1D2FF830F4BFED66009FE24FEBC" authority="GT" authorityName="GT" box="[308,448,327,346]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFED66009FE7CFEBC" bold="true" box="[308,408,327,346]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1-mediated glucosylation towards the disaccharide product of
|
||
<emphasis id="FF8B1643FF830F4BFE89602DFE92FE90" bold="true" box="[363,374,355,374]" italics="true" pageId="9" pageNumber="84">S</emphasis>
|
||
-glucoside, or whether
|
||
<taxonomicName id="0AFFB1D2FF830F4BFDAC602DFD30FE90" authority="GT" authorityName="GT" box="[590,724,355,374]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFDAC602DFD4AFE90" bold="true" box="[590,686,355,374]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 can catalyse the formation of sugar chains. Further biochemical and mechanistic studies are needed to understand its multiple functions, especially the
|
||
<emphasis id="FF8B1643FF830F4BFF0E60F8FF1FFE2F" bold="true" box="[236,251,438,457]" italics="true" pageId="9" pageNumber="84">N</emphasis>
|
||
- and
|
||
<emphasis id="FF8B1643FF830F4BFED660F8FEDBFE2F" bold="true" box="[308,319,438,457]" italics="true" pageId="9" pageNumber="84">S</emphasis>
|
||
-glucosylation mechanisms.
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF820F4AFF86638EFDD2FD37" blockId="8.[100,566,704,721]" box="[100,566,704,721]" pageId="8" pageNumber="83">
|
||
<tableNote id="3019CBDFFF820F4AFF86638EFDD2FD37" box="[100,566,704,721]" pageId="8" pageNumber="83" targetBox="[116,753,226,673]" targetPageId="8">ND: no effects detected at the selected concentrations.</tableNote>
|
||
</paragraph>
|
||
<caption id="99809AD9FF820F4AFF866634FD00F858" ID-DOI="http://doi.org/10.5281/zenodo.10482709" ID-Zenodo-Dep="10482709" httpUri="https://zenodo.org/record/10482709/files/figure.png" pageId="8" pageNumber="83" startId="8.[100,130,1914,1931]" targetBox="[151,1437,833,1891]" targetPageId="8" targetType="figure">
|
||
<paragraph id="CD40CA51FF820F4AFF866634FD00F858" blockId="8.[100,1488,1914,1982]" pageId="8" pageNumber="83">
|
||
<emphasis id="FF8B1643FF820F4AFF866634FF7AF86D" bold="true" box="[100,158,1914,1931]" pageId="8" pageNumber="83">Fig. 7.</emphasis>
|
||
NGT and SGT activities of
|
||
<taxonomicName id="0AFFB1D2FF820F4AFE696634FDE3F86D" authority="GT" authorityName="GT" box="[395,519,1914,1931]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFE696634FE07F86D" bold="true" box="[395,483,1914,1931]" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 with
|
||
<emphasis id="FF8B1643FF820F4AFDA36634FDABF86D" bold="true" box="[577,591,1914,1931]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
- and
|
||
<emphasis id="FF8B1643FF820F4AFD636634FD6FF86D" bold="true" box="[641,651,1914,1931]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
-conjugating aglycones. HPLC chromatogram and MS analyses of the enzymatic reactions with
|
||
<taxonomicName id="0AFFB1D2FF820F4AFA5C6634FF2DF843" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="8" pageNumber="83" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF820F4AFA5C6634FF40F843" bold="true" italics="true" pageId="8" pageNumber="83">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1
|
||
<emphasis id="FF8B1643FF820F4AFF3566DAFEF6F843" bold="true" box="[215,274,1940,1957]" italics="true" pageId="8" pageNumber="83">in vitro</emphasis>
|
||
. The UDP-glucose (UDPG) and
|
||
<emphasis id="FF8B1643FF820F4AFDC966DAFDDDF843" bold="true" box="[555,569,1940,1957]" italics="true" pageId="8" pageNumber="83">N</emphasis>
|
||
- and
|
||
<emphasis id="FF8B1643FF820F4AFD8C66DAFD9CF843" bold="true" box="[622,632,1940,1957]" italics="true" pageId="8" pageNumber="83">S</emphasis>
|
||
- phenolic/aliphatic aglycons were the sugar donor and acceptor, respectively. The substrates and corresponding products were detected using HPLC chromatogram and MS.
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="CD40CA51FF830F4BFF8660BFFD0FFDE2" blockId="9.[100,747,497,516]" box="[100,747,497,516]" pageId="9" pageNumber="84">
|
||
<emphasis id="FF8B1643FF830F4BFF8660BFFD0FFDE2" bold="true" box="[100,747,497,516]" italics="true" pageId="9" pageNumber="84">
|
||
2.5. Homology modelling and molecular docking of the
|
||
<taxonomicName id="0AFFB1D2FF830F4BFDBE60BFFD07FDE2" ID-CoL="32TPC" authority="GT" authorityName="GT" box="[604,739,497,516]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">C. paliurus GT</taxonomicName>
|
||
1
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF830F4BFF676367FF24FC88" blockId="9.[100,771,553,1992]" pageId="9" pageNumber="84">
|
||
Due to the high degree of sequence similarity between
|
||
<taxonomicName id="0AFFB1D2FF830F4BFD7D6367FF60FDBE" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFD7D6367FCE6FDDA" bold="true" box="[671,770,553,572]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 and UGT71G1 and the significant difference in the catalytic activity of glucosylation, it is necessary to understand the structural differences between the two proteins and to identify the key amino acid residue responsible for their differences. The homology-based structural model of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFF2B63FAFEBFFD21" authority="GT" authorityName="GT" box="[201,347,692,711]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFF2B63FAFECBFD21" bold="true" box="[201,303,692,711]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 was constructed with the SWISS-MODEL server (https://swissmodel.expasy.org), using the crystal structure of UGT71G1 (PDB ID: 2ACW) as a template to predict the key amino acids involved in glucosylation.
|
||
<emphasis id="FF8B1643FF830F4BFEBE6246FE0DFCFD" bold="true" box="[348,489,776,795]" italics="true" pageId="9" pageNumber="84">
|
||
<taxonomicName id="0AFFB1D2FF830F4BFEBE6246FE04FCFD" authority="GT" authorityName="GT" box="[348,480,776,795]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">C. paliurus GT</taxonomicName>
|
||
1
|
||
</emphasis>
|
||
consisted of similar N- and Cterminal domains with an α/β/α fold, and the sugar donor and acceptor binding pockets are located in a cleft between these two domains (
|
||
<figureCitation id="55C4D6D4FF830F4BFF8E6215FF50FC88" box="[108,180,859,878]" captionStart="Fig" captionStartId="10.[1041,1071,152,169]" captionTargetBox="[101,1009,153,1395]" captionTargetId="figure-220@10.[100,1010,151,1396]" captionTargetPageId="10" captionText="Fig. 8. Comparison of the binding pattern of UDP- Glc (yellow sticks) and acceptor quercetin (black sticks) in C. paliurus GT1 (left) or UGT71G1 (right). (A) Homology model of C. paliurus GT1 or crystal structure of UGT71G1 docked with UDP-Glc and quercetin. (B) The substrate binding pocket in C. paliurus GT1 or UGT71G1 with the docked quercetin and the surrounding residues. (C) Molecular surfaces of C. paliurus GT1 or UGT71G1 showing their substrate binding pockets and entrance of the pockets. Residue W283 in C. paliurus GT1 or M286 in UGT71G1 is shown in red; residues V309 to D320 of the cap region in C. paliurus GT1 or the corresponding site (N313 to A315) in UGT71G1 are shown in green, respectively. White circles mark the entrance to the substrate binding pocket. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10482711" httpUri="https://zenodo.org/record/10482711/files/figure.png" pageId="9" pageNumber="84">Fig. 8A</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF830F4BFF676239FDD0FAF7" blockId="9.[100,771,553,1992]" pageId="9" pageNumber="84">
|
||
Recent studies have revealed important correlations between the amino acids around the binding pocket and its catalytic activity and selectivity, based on the crystal structural studies of some UGTs (
|
||
<bibRefCitation id="A96EB7A0FF830F4BFD3D62E1FF32FC38" author="Fan, B. & Dong, W. X. & Chen, T. Y. & Chu, J. L. & He, B. F." pageId="9" pageNumber="84" pagination="2464 - 2469" refId="ref12074" refString="Fan, B., Dong, W. X., Chen, T. Y., Chu, J. L., He, B. F., 2018. Switching glycosyltransferase UGT (BL) 1 regioselectivity toward polydatin synthesis using a semi-rational design. Org. Biomol. Chem. 16, 2464 - 2469." type="journal article" year="2018">Fan et al., 2018</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="A96EB7A0FF830F4BFF076285FE56FC38" author="Modolo, L. V. & Escamilla-Trevino, L. L. & Dixon, R. A. & Wang, X." box="[229,434,971,990]" pageId="9" pageNumber="84" pagination="2131 - 2135" refId="ref12790" refString="Modolo, L. V., Escamilla-Trevino, L. L., Dixon, R. A., Wang, X., 2009 a. Single amino acid mutations of Medicago glycosyltransferase UGT 85 H 2 enhance activity and impart reversibility. FEBS Lett. 583, 2131 - 2135." type="journal article" year="2009">Modolo et al., 2009a</bibRefCitation>
|
||
,
|
||
<bibRefCitation id="A96EB7A0FF830F4BFE236285FE19FC38" author="Modolo, L. V. & Li, L. & Pan, H. & Blount, J. W. & Dixon, R. A. & Wang, X." box="[449,509,971,990]" pageId="9" pageNumber="84" pagination="1292 - 1302" refId="ref12845" refString="Modolo, L. V., Li, L., Pan, H., Blount, J. W., Dixon, R. A., Wang, X., 2009 b. Crystal structures of glycosyltransferase UGT 78 G 1 reveal the molecular basis for glycosylation and deglycosylation of (iso) flavonoids. J. Mol. Biol. 392, 1292 - 1302." type="journal article" year="2009">2009b</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="A96EB7A0FF830F4BFDEE6285FD23FC38" author="Wilson, A. E. & Wu, S. & Tian, L." box="[524,711,971,990]" pageId="9" pageNumber="84" pagination="184 - 193" refId="ref13542" refString="Wilson, A. E., Wu, S., Tian, L., 2018. PgUGT 95 B 2 preferentially metabolizes flavones / flavonols and has evolved independently from flavone / flavonol UGTs identified in Arabidopsis thaliana. Phytochemistry 157, 184 - 193." type="journal article" year="2018">Wilson et al., 2018</bibRefCitation>
|
||
). The homology-based structural modelling and docking studies provide some insights into the catalytic properties of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFE1A654DFD69FBF0" authority="GT" authorityName="GT" box="[504,653,1027,1046]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFE1A654DFDBAFBF0" bold="true" box="[504,606,1027,1046]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1. Molecular docking was performed to investigate the binding mode between quercetin and the enzymes. The docking results showed that the substrate binding pockets of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFEB96519FE01FB8C" authority="GT" authorityName="GT" box="[347,485,1111,1130]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFEB96519FE59FB8C" bold="true" box="[347,445,1111,1130]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 and UGT71G1 were similar; however, there were certain differences between
|
||
<taxonomicName id="0AFFB1D2FF830F4BFDA1653CFD2BFB63" authority="GT" authorityName="GT" box="[579,719,1138,1157]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFDA1653CFD42FB63" bold="true" box="[579,678,1138,1157]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 and UGT71G
|
||
<quantity id="0A0767B4FF830F4BFF5965C0FF3AFB47" box="[187,222,1166,1185]" metricMagnitude="-2" metricUnit="m" metricValue="2.54" pageId="9" pageNumber="84" unit="in" value="1.0">1 in</quantity>
|
||
the binding site, which might be responsible for their differences in catalytic selectivity and activity. There are twenty key residues in the acceptor substrate quercetin binding pocket of the
|
||
<taxonomicName id="0AFFB1D2FF830F4BFD0C6588FF35FB13" authority="GT" authorityName="GT" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFD0C6588FF4FFB13" bold="true" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 structural model, six of which are conserved in UGT71G1; the rest differ from those in UGT71G1 (
|
||
<tableCitation id="807DFFEAFF830F4BFE0265B0FDC3FAF7" box="[480,551,1278,1297]" captionStart="Table 3" captionStartId="10.[100,150,1457,1474]" captionTargetPageId="10" captionText="Table 3 Conserved and different residues between C. paliurus GT1 and UGT71G1 in the substrate binding site." httpUri="http://table.plazi.org/id/99809AD9FF800F48FF8664FFFEC6FA10" pageId="9" pageNumber="84" tableUuid="99809AD9FF800F48FF8664FFFEC6FA10">Table 3</tableCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF830F4BFF676454FE07F84A" blockId="9.[100,771,553,1992]" pageId="9" pageNumber="84">
|
||
In the docking model, UDP-glucose was almost completely buried in a long and narrow channel formed mainly by the PSPG motif in the Cterminal domain of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFEFC641FFE42FA82" authority="GT" authorityName="GT" box="[286,422,1361,1380]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFEFC641FFE99FA82" bold="true" box="[286,381,1361,1380]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1. The 3’-, 4′- and 6′-OH groups of the glucose moiety formed hydrogen bonds with the OE2 atom of Q387, the N atom of W366, and the OG1 atom of T142 to further stabilize the transition states. These interactions were similar to the binding pattern of UGT71G1. Quercetin adopted a compact conformation to bind in the active site of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFF3C6493FE82FA16" authority="GT" authorityName="GT" box="[222,358,1501,1520]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFF3C6493FEDAFA16" bold="true" box="[222,318,1501,1520]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1. The phenyl B ring of quercetin was located at the hydrophobic pocket, surrounded by residues M121, F122, F147, F190, and A386, forming strong hydrophobic binding. A detailed analysis showed that the phenyl B ring of quercetin formed anion-π and π- π interactions with the side chains of residues E85 and F122, respectively. Importantly, the hydroxyl group at the 3′-position of the quercetin was close to the glucose moiety and C1′ atom of UDP-Glc, facilitating nucleophilic attack. All these interactions facilitated the anchoring of 3′- OH of quercetin in the active site and provided the best fitness score. UGT71G1 is capable of transferring glucose to each of the five hydroxyl groups on the quercetin molecule since all of them can dock close to the catalytic residue H22 within approximately 3 Å. We found that only the hydroxyl groups at the 3′- and 3-position could contact the corresponding catalytic residue H16 within approximately 3 Å. An acidic residue D120 was identified that may form an electron transfer chain with H16 to help deprotonate acceptor molecules, which is highly conserved in most plant UGTs (
|
||
<figureCitation id="55C4D6D4FF830F4BFE7366D7FE33F84A" box="[401,471,1945,1964]" captionStart="Fig" captionStartId="10.[1041,1071,152,169]" captionTargetBox="[101,1009,153,1395]" captionTargetId="figure-220@10.[100,1010,151,1396]" captionTargetPageId="10" captionText="Fig. 8. Comparison of the binding pattern of UDP- Glc (yellow sticks) and acceptor quercetin (black sticks) in C. paliurus GT1 (left) or UGT71G1 (right). (A) Homology model of C. paliurus GT1 or crystal structure of UGT71G1 docked with UDP-Glc and quercetin. (B) The substrate binding pocket in C. paliurus GT1 or UGT71G1 with the docked quercetin and the surrounding residues. (C) Molecular surfaces of C. paliurus GT1 or UGT71G1 showing their substrate binding pockets and entrance of the pockets. Residue W283 in C. paliurus GT1 or M286 in UGT71G1 is shown in red; residues V309 to D320 of the cap region in C. paliurus GT1 or the corresponding site (N313 to A315) in UGT71G1 are shown in green, respectively. White circles mark the entrance to the substrate binding pocket. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10482711" httpUri="https://zenodo.org/record/10482711/files/figure.png" pageId="9" pageNumber="84">Fig. 8B</figureCitation>
|
||
).
|
||
</paragraph>
|
||
<paragraph id="CD40CA51FF830F4BFF6766FBFADAFE74" blockId="9.[100,771,553,1992]" lastBlockId="9.[818,1487,159,402]" pageId="9" pageNumber="84">
|
||
The molecular surfaces of the two UGTs also exhibit differences. The W283 residue of the
|
||
<taxonomicName id="0AFFB1D2FF830F4BFC1D61D1FB6EFF54" authority="GT" authorityName="GT" box="[1023,1162,159,178]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFC1D61D1FB86FF54" bold="true" box="[1023,1122,159,178]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 may serve as a guard at the entrance of the substrate binding pocket. The large indole ring of W283 has strong hydrophobicity and steric hindrance compared with the corresponding residue M
|
||
<quantity id="0A0767B4FF830F4BFBC361BDFBBAFEE0" box="[1057,1118,243,262]" metricMagnitude="0" metricUnit="m" metricValue="7.2644" pageId="9" pageNumber="84" unit="in" value="286.0">286 in</quantity>
|
||
UGT71G1, and it may intercept large sugar acceptors, e.g., triterpenes. Moreover, compared with UGT71G1, an extra β- sheet (V309 to D320) in
|
||
<taxonomicName id="0AFFB1D2FF830F4BFB6B6065FAF6FED8" authority="GT" authorityName="GT" box="[1161,1298,299,318]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFB6B6065FB0FFED8" bold="true" box="[1161,1259,299,318]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
GT
|
||
</taxonomicName>
|
||
1 forms a cap at the entrance of the substrate binding pocket, further reducing the size of the entrance. This modelling study provides some insights into the strict selectivity of
|
||
<taxonomicName id="0AFFB1D2FF830F4BFC506031FBF7FE74" box="[946,1043,383,402]" class="Magnoliopsida" family="Juglandaceae" genus="Cyclocarya" kingdom="Plantae" order="Fagales" pageId="9" pageNumber="84" phylum="Tracheophyta" rank="species" species="paliurus">
|
||
<emphasis id="FF8B1643FF830F4BFC506031FBF7FE74" bold="true" box="[946,1043,383,402]" italics="true" pageId="9" pageNumber="84">C. paliurus</emphasis>
|
||
</taxonomicName>
|
||
of GTI for substrates (
|
||
<figureCitation id="55C4D6D4FF830F4BFB0E6031FAD7FE74" box="[1260,1331,383,402]" captionStart="Fig" captionStartId="10.[1041,1071,152,169]" captionTargetBox="[101,1009,153,1395]" captionTargetId="figure-220@10.[100,1010,151,1396]" captionTargetPageId="10" captionText="Fig. 8. Comparison of the binding pattern of UDP- Glc (yellow sticks) and acceptor quercetin (black sticks) in C. paliurus GT1 (left) or UGT71G1 (right). (A) Homology model of C. paliurus GT1 or crystal structure of UGT71G1 docked with UDP-Glc and quercetin. (B) The substrate binding pocket in C. paliurus GT1 or UGT71G1 with the docked quercetin and the surrounding residues. (C) Molecular surfaces of C. paliurus GT1 or UGT71G1 showing their substrate binding pockets and entrance of the pockets. Residue W283 in C. paliurus GT1 or M286 in UGT71G1 is shown in red; residues V309 to D320 of the cap region in C. paliurus GT1 or the corresponding site (N313 to A315) in UGT71G1 are shown in green, respectively. White circles mark the entrance to the substrate binding pocket. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)" figureDoi="http://doi.org/10.5281/zenodo.10482711" httpUri="https://zenodo.org/record/10482711/files/figure.png" pageId="9" pageNumber="84">Fig. 8C</figureCitation>
|
||
).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |