461 lines
48 KiB
XML
461 lines
48 KiB
XML
<document id="4B72784F99DB4C222129EC97EFC9C850" ID-DOI="10.1016/j.phytochem.2018.07.015" ID-ISSN="1873-3700" ID-Zenodo-Dep="10484255" IM.bibliography_approvedBy="juliana" IM.illustrations_approvedBy="felipe" IM.materialsCitations_approvedBy="juliana" IM.metadata_approvedBy="juliana" IM.taxonomicNames_approvedBy="juliana" IM.treatments_approvedBy="juliana" checkinTime="1704940056690" checkinUser="felipe" docAuthor="Matekalo, Dragana, Skorić, Marijana, Nikolić, Tijana, Novaković, Lazar, Lukić, Milana, Božunović, Jelena, Aničić, Neda, Filipović, Biljana & Mišić, Danijela" docDate="2018" docId="604887FBFFEBA144606E0C95FFCAFC6A" docLanguage="en" docName="Phytochemistry.155.69-82.pdf" docOrigin="Phytochemistry 155" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.07.015" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Centaurium erythraea subsp. methanol Rafn" docType="treatment" docVersion="4" lastPageNumber="71" masterDocId="9C71FF83FFEAA147635C0D7AFF6AFF9D" masterDocTitle="Organ-specific and genotype-dependent constitutive biosynthesis of secoiridoid glucosides in Centaurium erythraea Rafn, and its elicitation with methyl jasmonate" masterLastPageNumber="82" masterPageNumber="69" pageNumber="70" updateTime="1705338075140" updateUser="juliana">
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<mods:title id="B835D9FABABA6809C6CAACC202C30E73">Organ-specific and genotype-dependent constitutive biosynthesis of secoiridoid glucosides in Centaurium erythraea Rafn, and its elicitation with methyl jasmonate</mods:title>
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<mods:namePart id="2581F3081A1169C5C52030F757CBC64F">Matekalo, Dragana</mods:namePart>
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<mods:affiliation id="2312E6D25ABC57A14656E491ED310104">Institute for Biological Research “ Siniša Stanković ”, University of Belgrade, Bulevar despota Stefana 142, 11060 Belgrade, Serbia</mods:affiliation>
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<mods:nameIdentifier id="DACD4F4BFC412678BA47935B51A07464" type="email">dragana.bozic@ibiss.bg.ac.rs</mods:nameIdentifier>
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<mods:namePart id="8C01D0D93004721DC2E23AD4F92DB2F4">Skorić, Marijana</mods:namePart>
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<mods:namePart id="678F1AD8B5516AD68A5BDBC14AF2E70B">Nikolić, Tijana</mods:namePart>
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<mods:affiliation id="B358C713171BBB111C2B10A97925CF51">Faculty of Biology, University of Belgrade, Takovska 43, 11060 Belgrade, Serbia</mods:affiliation>
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<mods:namePart id="D3606783A3546A70ABE9249632DC270C">Novaković, Lazar</mods:namePart>
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<mods:namePart id="4EB3557CC788FB78C38E5A6C21387283">Lukić, Milana</mods:namePart>
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<mods:namePart id="65D04F64A391F48140F9B7D29023CEDA">Božunović, Jelena</mods:namePart>
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<mods:namePart id="B50A9891E36F2F9C66486B88B347DCD4">Aničić, Neda</mods:namePart>
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<mods:namePart id="161C306EF8261ED102830D384B14CEAA">Filipović, Biljana</mods:namePart>
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<mods:namePart id="B2BDE6AB69A4B558DB528A3DF2BF6AE6">Mišić, Danijela</mods:namePart>
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<mods:title id="C831CC62C19F75CFD7AF3F6D9746843D">Phytochemistry</mods:title>
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<mods:date id="F21659EC7834C2F8AC5712A4FD6245F1">2018</mods:date>
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<mods:number id="9BD882468F7B257C6B93BFE597726666">2018-11-30</mods:number>
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<mods:number id="63341E2A4BA29508FBE11C2E0CB2B029">155</mods:number>
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<mods:url id="C39F58EAD0011EC5C81057DBB48A3161">http://dx.doi.org/10.1016/j.phytochem.2018.07.015</mods:url>
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<mods:classification id="CE4C8F42AD0C6B0E381DE230BDDA5146">journal article</mods:classification>
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<mods:identifier id="A1BAAA4EBBB5BB48A09BD814F8930C88" type="DOI">10.1016/j.phytochem.2018.07.015</mods:identifier>
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<mods:identifier id="B26AD8F3827570ED7E07366FC374E279" type="ISSN">1873-3700</mods:identifier>
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<treatment id="604887FBFFEBA144606E0C95FFCAFC6A" LSID="urn:lsid:plazi:treatment:604887FBFFEBA144606E0C95FFCAFC6A" httpUri="http://treatment.plazi.org/id/604887FBFFEBA144606E0C95FFCAFC6A" lastPageId="3" lastPageNumber="71" pageId="1" pageNumber="70">
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<subSubSection id="A0FB6566FFEBA146606E0C95FC1DFD83" pageId="1" pageNumber="70" type="nomenclature">
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<paragraph id="E85E36EDFFEBA146606E0C95FC1DFD83" blockId="1.[818,1457,495,542]" pageId="1" pageNumber="70">
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<emphasis id="DA95EAFFFFEBA146606E0C95FC1DFD83" bold="true" italics="true" pageId="1" pageNumber="70">
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<heading id="B3168181FFEBA146606E0C95FADBFD9F" bold="true" box="[818,1457,495,514]" fontSize="36" level="1" pageId="1" pageNumber="70" reason="1">
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2.1. Targeted UHPLC-MS/MS analysis of SG in
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<taxonomicName id="2FE14D6EFFEBA14667B50C95FA32FD9F" ID-CoL="69GFC" authority="Rafn" authorityName="Rafn" box="[1257,1368,495,514]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="70" phylum="Tracheophyta" rank="species" species="erythraea">C. erythraea</taxonomicName>
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methanol
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</heading>
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<heading id="B3168181FFEBA146606E0F71FC1DFD83" box="[818,887,523,542]" fontSize="8" level="3" pageId="1" pageNumber="70" reason="8">extracts</heading>
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</emphasis>
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<paragraph id="E85E36EDFFEBA146600F0F39FB83FCF0" blockId="1.[818,1489,579,1297]" pageId="1" pageNumber="70">
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<emphasis id="DA95EAFFFFEBA146600F0F39FCB1FDCB" bold="true" box="[851,987,579,598]" italics="true" pageId="1" pageNumber="70">UHPLC-qqqMS</emphasis>
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quantitative analysis of
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<taxonomicName id="2FE14D6EFFEBA146678F0F39FA2FFDCB" box="[1235,1349,579,598]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="70" phylum="Tracheophyta" rank="species" species="erythraea">
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<emphasis id="DA95EAFFFFEBA146678F0F39FA2FFDCB" bold="true" box="[1235,1349,579,598]" italics="true" pageId="1" pageNumber="70">C. erythraea</emphasis>
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</taxonomicName>
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methanol extracts was targeted towards one iridoid (loganin –
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<emphasis id="DA95EAFFFFEBA14666470F24FA4DFDEC" bold="true" box="[1307,1319,606,625]" pageId="1" pageNumber="70">1</emphasis>
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) and four secoiridoid (secologanin –
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<emphasis id="DA95EAFFFFEBA14660AE0F00FC94FD10" bold="true" box="[1010,1022,634,653]" pageId="1" pageNumber="70">2</emphasis>
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, sweroside –
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<emphasis id="DA95EAFFFFEBA14667270F00FBEDFD10" bold="true" box="[1147,1159,634,653]" pageId="1" pageNumber="70">3</emphasis>
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, swertiamarin –
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<emphasis id="DA95EAFFFFEBA14666780F00FA5AFD10" bold="true" box="[1316,1328,634,653]" pageId="1" pageNumber="70">4</emphasis>
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and gentiopicrin –
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<emphasis id="DA95EAFFFFEBA14660180FECFC3AFD34" bold="true" box="[836,848,662,681]" pageId="1" pageNumber="70">5</emphasis>
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) compounds, which were unambiguously assigned, based on their retention times, MS, MS
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, and UV spectra, and comparisons with the reference standards. Molecular ions of targeted secoiridoids were visible as adducts of acetic acid which was used as a mobile phase, as previously described in
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<bibRefCitation id="8C704B1CFFEBA14667460E7CFB98FC84" author="Banjanac, T. & S iler, B. & Bohanec, B." box="[1050,1266,774,793]" pageId="1" pageNumber="70" pagination="27 - 44" refId="ref13061" refString="Banjanac, T., Dragi c evi c, M., S iler, B., Ga s i c, U., Bohanec, B., Nestorovi c Z ivkovi c, J., Trifunovi c, S., Mi s i c, D., 2017. Chemodiversity of two closely related tetraploid Centaurium species and their hexaploid hybrid: metabolomic search for high-resolution taxonomic classifiers. Phytochemistry 140, 27 - 44. https: // doi. org / 10.1016 / j. phytochem. 2017.04.005." type="journal article" year="2017">Banjanac et al. (2017)</bibRefCitation>
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. Following PIS experiments and analysis of MS
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spectra (Table S1), two diagnostic fragments of each compound were utilized in SRM experiment for the accurate quantification of targeted compounds (
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<figureCitation id="70DA2A68FFEBA14667F90E20FBB1FCF0" box="[1189,1243,858,877]" captionStart="Fig" captionStartId="2.[100,130,919,936]" captionTargetBox="[170,1419,153,896]" captionTargetId="figure-819@2.[169,1420,152,897]" captionTargetPageId="2" captionText="Fig. 2. UHPLC-MS 2 SRM (Single Reaction Monitoring) chromatograms of targeted compounds (loganin, secologanin, sweroside, swertiamarin and gentiopicrin) in young leaves (red line), mature leaves (green line) and roots (orange line), and corresponding MS2 spectra. (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.10484259" httpUri="https://zenodo.org/record/10484259/files/figure.png" pageId="1" pageNumber="70">Fig. 2</figureCitation>
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).
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</paragraph>
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Iridoid glucoside loganin (
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), which was eluted at Rt = 3.05 min, showed a pseudomolecular ion [M +
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COOH− H]
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<superScript id="1F949BA5FFEBA14666630EF7FA25FC07" attach="left" box="[1343,1359,909,922]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
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at
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<emphasis id="DA95EAFFFFEBA146662B0EEBFAF1FC39" bold="true" box="[1399,1435,913,932]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
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449. Diagnostic MS
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fragments of
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<emphasis id="DA95EAFFFFEBA14667100ED7FB32FC5D" bold="true" box="[1100,1112,941,960]" pageId="1" pageNumber="70">1</emphasis>
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were [M− H− C
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H
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<subScript id="746534A8FFEBA146664E0ECCFA4EFC5E" attach="both" box="[1298,1316,950,963]" fontSize="5" pageId="1" pageNumber="70">10</subScript>
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O
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<subScript id="746534A8FFEBA146666F0ECCFA56FC5E" attach="left" box="[1331,1340,950,963]" fontSize="5" pageId="1" pageNumber="70">5</subScript>
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]
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<superScript id="1F949BA5FFEBA14666190ED2FA3FFC28" attach="left" box="[1349,1365,936,949]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
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at
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<emphasis id="DA95EAFFFFEBA14666250ED7FAF6FC5D" bold="true" box="[1401,1436,941,960]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
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227, resulting from the loss of glucose, and [
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F]
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at
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<emphasis id="DA95EAFFFFEBA14666520EB3FA5BFC41" bold="true" box="[1294,1329,969,988]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
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127 (
|
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<bibRefCitation id="8C704B1CFFEBA14666320EB3FC0BFC65" author="Sun, H. & Liu, M. & Lin, Z. & Jiang, H. & Niu, Y. & Wang, H. & Chen, S." pageId="1" pageNumber="70" pagination="86 - 106" refId="ref17384" refString="Sun, H., Liu, M., Lin, Z., Jiang, H., Niu, Y., Wang, H., Chen, S., 2015. Comprehensive identification of 125 multifarious constituents in Shuang-huang-lian powder injection by HPLC-DAD-ESI-IT-TOF-MS. J. Pharmaceut. Biomed. Anal. 115, 86 - 106. https: // doi. org / 10.1016 / j. jpba. 2015.06.013." type="journal article" year="2015">Sun et al., 2015</bibRefCitation>
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). According to
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<bibRefCitation id="8C704B1CFFEBA14660AB0E9FFBF3FC65" author="Sun, H. & Liu, M. & Lin, Z. & Jiang, H. & Niu, Y. & Wang, H. & Chen, S." box="[1015,1177,997,1016]" pageId="1" pageNumber="70" pagination="86 - 106" refId="ref17384" refString="Sun, H., Liu, M., Lin, Z., Jiang, H., Niu, Y., Wang, H., Chen, S., 2015. Comprehensive identification of 125 multifarious constituents in Shuang-huang-lian powder injection by HPLC-DAD-ESI-IT-TOF-MS. J. Pharmaceut. Biomed. Anal. 115, 86 - 106. https: // doi. org / 10.1016 / j. jpba. 2015.06.013." type="journal article" year="2015">Sun et al. (2015)</bibRefCitation>
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,
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F
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<superScript id="1F949BA5FFEBA14667940E9AFBB2FC70" attach="left" box="[1224,1240,992,1005]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
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ion and [3-oxoMAQ–H]
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<superScript id="1F949BA5FFEBA14666E30E9AFAA5FC70" attach="none" box="[1471,1487,992,1005]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
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ion are generated in MS
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spectrum of
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<emphasis id="DA95EAFFFFEBA14667D7097BFBFDFB89" bold="true" box="[1163,1175,1025,1044]" pageId="1" pageNumber="70">1</emphasis>
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, due to the cleavage of pyran ring stemming from isomerization of hemiacetal group. Secologanin (
|
||
<emphasis id="DA95EAFFFFEBA14666D70967FAFDFBAD" bold="true" box="[1419,1431,1053,1072]" pageId="1" pageNumber="70">2</emphasis>
|
||
) with a pseudomolecular ion [M +
|
||
<collectingCountry id="90F6767DFFEBA14667190943FB08FBD1" box="[1093,1122,1081,1100]" name="Switzerland" pageId="1" pageNumber="70">CH</collectingCountry>
|
||
<subScript id="746534A8FFEBA146673E093BFB01FBD3" attach="both" box="[1122,1131,1089,1102]" fontSize="5" pageId="1" pageNumber="70">3</subScript>
|
||
COOH− H]
|
||
<superScript id="1F949BA5FFEBA1466788094EFB8EFBDC" attach="left" box="[1236,1252,1076,1089]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA146665D0943FA4FFBD1" bold="true" box="[1281,1317,1081,1100]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
447 was eluted at Rt = 3.72 min, and it yielded daughter ions [M− C
|
||
<subScript id="746534A8FFEBA146663C0927FA03FBF7" attach="right" box="[1376,1385,1117,1130]" fontSize="5" pageId="1" pageNumber="70">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFEBA14666240927FAE0FBF7" attach="both" box="[1400,1418,1117,1130]" fontSize="5" pageId="1" pageNumber="70">10</subScript>
|
||
O
|
||
<subScript id="746534A8FFEBA14666C50927FAC8FBF7" attach="right" box="[1433,1442,1117,1130]" fontSize="5" pageId="1" pageNumber="70">5</subScript>
|
||
−H
|
||
<subScript id="746534A8FFEBA146669A0927FAA5FBF7" attach="left" box="[1478,1487,1117,1130]" fontSize="5" pageId="1" pageNumber="70">2</subScript>
|
||
O− CO−24−H]
|
||
<superScript id="1F949BA5FFEBA14660900916FCB6FBE4" attach="left" box="[972,988,1132,1145]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA1466759090BFB40FB19" bold="true" box="[1029,1066,1137,1156]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
155 via RDA cleavage, and [M− C
|
||
<subScript id="746534A8FFEBA14666D10903FAFCFB1B" attach="both" box="[1421,1430,1145,1158]" fontSize="5" pageId="1" pageNumber="70">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFEBA14666F90903FADDFB1B" attach="both" box="[1445,1463,1145,1158]" fontSize="5" pageId="1" pageNumber="70">10</subScript>
|
||
O
|
||
<subScript id="746534A8FFEBA146669A0903FAA5FB1B" attach="left" box="[1478,1487,1145,1158]" fontSize="5" pageId="1" pageNumber="70">5</subScript>
|
||
−H
|
||
<subScript id="746534A8FFEBA146600A09EFFC35FB3F" attach="both" box="[854,863,1173,1186]" fontSize="5" pageId="1" pageNumber="70">2</subScript>
|
||
O− CO− C
|
||
<subScript id="746534A8FFEBA146609E09EFFCA1FB3F" attach="both" box="[962,971,1173,1186]" fontSize="5" pageId="1" pageNumber="70">2</subScript>
|
||
O
|
||
<subScript id="746534A8FFEBA146608609EFFC89FB3F" attach="left" box="[986,995,1173,1186]" fontSize="5" pageId="1" pageNumber="70">2</subScript>
|
||
−H]
|
||
<superScript id="1F949BA5FFEBA146674C09F2FB4AFB08" attach="left" box="[1040,1056,1160,1173]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA146670309F7FBE8FB3D" bold="true" box="[1119,1154,1165,1184]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
123. A pseudomolecular ion [M +
|
||
<collectingCountry id="90F6767DFFEBA146602F09D2FCFAFB26" box="[883,912,1192,1211]" name="Switzerland" pageId="1" pageNumber="70">CH</collectingCountry>
|
||
<subScript id="746534A8FFEBA14660D309CBFCF2FB23" attach="both" box="[911,920,1201,1214]" fontSize="5" pageId="1" pageNumber="70">3</subScript>
|
||
COOH− H]
|
||
<superScript id="1F949BA5FFEBA146675D09DEFB7BFB2C" attach="left" box="[1025,1041,1188,1201]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA146676F09D2FB3DFB26" bold="true" box="[1075,1111,1192,1211]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
417 visible as a peak at Rt = 3.05 min was assigned to sweroside (
|
||
<emphasis id="DA95EAFFFFEBA146673909BEFB1BFB4A" bold="true" box="[1125,1137,1220,1239]" pageId="1" pageNumber="70">3</emphasis>
|
||
), and it generated product ion [M− H− C
|
||
<subScript id="746534A8FFEBA14660C80992FCF7FB68" attach="right" box="[916,925,1256,1269]" fontSize="5" pageId="1" pageNumber="70">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFEBA14660F00992FCD4FB68" attach="both" box="[940,958,1256,1269]" fontSize="5" pageId="1" pageNumber="70">10</subScript>
|
||
O
|
||
<subScript id="746534A8FFEBA14660910992FCBCFB68" attach="right" box="[973,982,1256,1269]" fontSize="5" pageId="1" pageNumber="70">5</subScript>
|
||
]
|
||
<superScript id="1F949BA5FFEBA146608209A1FC84FB75" attach="left" box="[990,1006,1243,1256]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA1466744099AFB51FB6E" bold="true" box="[1048,1083,1248,1267]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
195 by the loss of a glucose unit, and [C
|
||
<subScript id="746534A8FFEBA1466014087EFC3BFA8C" attach="right" box="[840,849,1284,1297]" fontSize="5" pageId="1" pageNumber="70">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFEBA146603C087EFC18FA8C" attach="both" box="[864,882,1284,1297]" fontSize="5" pageId="1" pageNumber="70">12</subScript>
|
||
O
|
||
<subScript id="746534A8FFEBA14660DD087EFCE0FA8C" attach="right" box="[897,906,1284,1297]" fontSize="5" pageId="1" pageNumber="70">6</subScript>
|
||
−H]
|
||
<superScript id="1F949BA5FFEBA14660EB098DFCADFA99" attach="left" box="[951,967,1271,1284]" fontSize="5" pageId="1" pageNumber="70">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFEBA14660B30986FB79FA92" bold="true" box="[1007,1043,1276,1295]" italics="true" pageId="1" pageNumber="70">m/z</emphasis>
|
||
179, corresponding to deprotonated glucose. Swertiamarin (
|
||
<emphasis id="DA95EAFFFFE8A14563B30966FF91FBB2" bold="true" box="[239,251,1052,1071]" pageId="2" pageNumber="71">4</emphasis>
|
||
), which was eluted at Rt = 3.59 min, showed pseudomolecular ion [M +
|
||
<collectingCountry id="90F6767DFFE8A145626E0942FE25FBD6" box="[306,335,1080,1099]" name="Switzerland" pageId="2" pageNumber="71">CH</collectingCountry>
|
||
<subScript id="746534A8FFE8A1456213093AFE32FBD0" attach="both" box="[335,344,1088,1101]" fontSize="5" pageId="2" pageNumber="71">3</subScript>
|
||
COOH− H]
|
||
<superScript id="1F949BA5FFE8A145629C0949FEBAFBDD" attach="left" box="[448,464,1075,1088]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A14562AF0942FD72FBD6" bold="true" box="[499,536,1080,1099]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
433, and its main diagnostic fragments were: [C
|
||
<subScript id="746534A8FFE8A14562010926FE0CFBF4" attach="right" box="[349,358,1116,1129]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFE8A14562290926FEEDFBF4" attach="both" box="[373,391,1116,1129]" fontSize="5" pageId="2" pageNumber="71">12</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A14562CA0926FEF5FBF4" attach="left" box="[406,415,1116,1129]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
−H]
|
||
<superScript id="1F949BA5FFE8A14562900935FEB6FBC1" attach="left" box="[460,476,1103,1116]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A145615D092EFD4FFBFA" bold="true" box="[513,549,1108,1127]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
179, corresponding to deprotonated glucose, and [C
|
||
<subScript id="746534A8FFE8A14562270902FEEEFB18" attach="both" box="[379,388,1144,1157]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFE8A14562CF0902FECFFB18" attach="both" box="[403,421,1144,1157]" fontSize="5" pageId="2" pageNumber="71">12</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A14562E80902FED7FB18" attach="left" box="[436,445,1144,1157]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
−H− H
|
||
<subScript id="746534A8FFE8A145615A0902FD65FB18" attach="both" box="[518,527,1144,1157]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
O]
|
||
<superScript id="1F949BA5FFE8A145617B0911FD5DFBE5" attach="left" box="[551,567,1131,1144]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A1456105090AFD17FB1E" bold="true" box="[601,637,1136,1155]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
161 that was produced from the glycosyl ion. Gentiopicrin (
|
||
<emphasis id="DA95EAFFFFE8A145615709F1FD7DFB03" bold="true" box="[523,535,1163,1182]" pageId="2" pageNumber="71">5</emphasis>
|
||
) exhibited an acetic acidadducted ion [M +
|
||
<collectingCountry id="90F6767DFFE8A145627409D2FE2FFB26" box="[296,325,1192,1211]" name="Switzerland" pageId="2" pageNumber="71">CH</collectingCountry>
|
||
<subScript id="746534A8FFE8A145621809CAFE27FB20" attach="both" box="[324,333,1200,1213]" fontSize="5" pageId="2" pageNumber="71">3</subScript>
|
||
COOH-H]
|
||
<superScript id="1F949BA5FFE8A14562FB09D9FEDDFB2D" attach="left" box="[423,439,1187,1200]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A145628509D2FE94FB26" bold="true" box="[473,510,1192,1211]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
415 visible in UHPLC/MS
|
||
<superScript id="1F949BA5FFE8A14561A509D9FC68FB2D" attach="left" box="[761,770,1187,1200]" fontSize="5" pageId="2" pageNumber="71">2</superScript>
|
||
chromatogram as a peak at Rt = 2.59 min, and its MS
|
||
<superScript id="1F949BA5FFE8A145611009C5FD3FFB51" attach="left" box="[588,597,1215,1228]" fontSize="5" pageId="2" pageNumber="71">2</superScript>
|
||
spectrum revealed diagnostic fragments: [C
|
||
<subScript id="746534A8FFE8A145621B0992FE3AFB68" attach="both" box="[327,336,1256,1269]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFE8A145623C0992FE18FB68" attach="both" box="[352,370,1256,1269]" fontSize="5" pageId="2" pageNumber="71">12</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A14562DD0992FEE0FB68" attach="right" box="[385,394,1256,1269]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
−H]
|
||
<superScript id="1F949BA5FFE8A14562EB09A0FEADFB7A" attach="left" box="[439,455,1242,1255]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A14562BA09A5FD61FB6F" bold="true" box="[486,523,1247,1266]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
179, corresponding to deprotonated glucose, and [M− C
|
||
<subScript id="746534A8FFE8A14562D0087EFEFFFA8C" attach="right" box="[396,405,1284,1297]" fontSize="5" pageId="2" pageNumber="71">6</subScript>
|
||
H
|
||
<subScript id="746534A8FFE8A14562F8087EFEDCFA8C" attach="both" box="[420,438,1284,1297]" fontSize="5" pageId="2" pageNumber="71">10</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A1456299087EFEA4FA8C" attach="left" box="[453,462,1284,1297]" fontSize="5" pageId="2" pageNumber="71">5</subScript>
|
||
−H
|
||
<subScript id="746534A8FFE8A14562AE087EFE91FA8C" attach="both" box="[498,507,1284,1297]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
O− C
|
||
<subScript id="746534A8FFE8A1456170087EFD5FFA8C" attach="both" box="[556,565,1284,1297]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A1456119087EFD24FA8C" attach="right" box="[581,590,1284,1297]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
−H]
|
||
<superScript id="1F949BA5FFE8A1456127098CFDE1FA9E" attach="left" box="[635,651,1270,1283]" fontSize="5" pageId="2" pageNumber="71">−</superScript>
|
||
at
|
||
<emphasis id="DA95EAFFFFE8A14561F10981FDBAFA93" bold="true" box="[685,720,1275,1294]" italics="true" pageId="2" pageNumber="71">m/z</emphasis>
|
||
119, resulting from the loss of glucose, H
|
||
<subScript id="746534A8FFE8A14562ED0865FED0FAB1" attach="both" box="[433,442,1311,1324]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
O and C
|
||
<subScript id="746534A8FFE8A14561590865FD64FAB1" attach="both" box="[517,526,1311,1324]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
O
|
||
<subScript id="746534A8FFE8A14561420865FD4DFAB1" attach="left" box="[542,551,1311,1324]" fontSize="5" pageId="2" pageNumber="71">2</subScript>
|
||
moieties. Identification of targeted compounds in samples was additionally confirmed by UHPLC/DAD analysis, by comparing the UV spectra with those of the reference standards. UHPLC/DAD data, including Rt and
|
||
<emphasis id="DA95EAFFFFE8A14561290810FDEBFAE0" bold="true" box="[629,641,1386,1405]" pageId="2" pageNumber="71">λ</emphasis>
|
||
<subScript id="746534A8FFE8A14561DD0809FDF4FA1D" attach="left" box="[641,670,1395,1408]" fontSize="5" pageId="2" pageNumber="71">max</subScript>
|
||
values are presented in Table S1. The average UHPLC-MS chromatogram as well as the UHPLC-UV chromatogram of
|
||
<taxonomicName id="2FE14D6EFFE8A14562EC08D9FD48FA2B" box="[432,546,1443,1462]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="erythraea">
|
||
<emphasis id="DA95EAFFFFE8A14562EC08D9FD48FA2B" bold="true" box="[432,546,1443,1462]" italics="true" pageId="2" pageNumber="71">C. erythraea</emphasis>
|
||
</taxonomicName>
|
||
methanolic extracts is characterized by a predominant peak attributed to the presence of
|
||
<emphasis id="DA95EAFFFFE8A145619008C4FDB2FA4C" bold="true" box="[716,728,1470,1489]" pageId="2" pageNumber="71">4</emphasis>
|
||
, the main component of the leaves (chromatograms not presented). Compounds
|
||
<emphasis id="DA95EAFFFFE8A14563F1088CFFD3F994" bold="true" box="[173,185,1526,1545]" pageId="2" pageNumber="71">3</emphasis>
|
||
and
|
||
<emphasis id="DA95EAFFFFE8A14563BB088CFF99F994" bold="true" box="[231,243,1526,1545]" pageId="2" pageNumber="71">5</emphasis>
|
||
are less abundant. These findings are in accordance with some previous studies (
|
||
<bibRefCitation id="8C704B1CFFE8A145621B0B68FD7EF9B8" author="Banjanac, T. & S iler, B. & Bohanec, B." box="[327,532,1554,1573]" pageId="2" pageNumber="71" pagination="27 - 44" refId="ref13061" refString="Banjanac, T., Dragi c evi c, M., S iler, B., Ga s i c, U., Bohanec, B., Nestorovi c Z ivkovi c, J., Trifunovi c, S., Mi s i c, D., 2017. Chemodiversity of two closely related tetraploid Centaurium species and their hexaploid hybrid: metabolomic search for high-resolution taxonomic classifiers. Phytochemistry 140, 27 - 44. https: // doi. org / 10.1016 / j. phytochem. 2017.04.005." type="journal article" year="2017">Banjanac et al., 2017</bibRefCitation>
|
||
; Bo
|
||
<emphasis id="DA95EAFFFFE8A14561670B68FD2FF9B8" bold="true" box="[571,581,1554,1573]" pageId="2" pageNumber="71">ž</emphasis>
|
||
unovi
|
||
<emphasis id="DA95EAFFFFE8A14561250B68FDE9F9B8" bold="true" box="[633,643,1554,1573]" pageId="2" pageNumber="71">ć</emphasis>
|
||
et al., 2018;
|
||
<emphasis id="DA95EAFFFFE8A14563380B54FF19F9DC" bold="true" box="[100,115,1582,1601]" pageId="2" pageNumber="71">Đ</emphasis>
|
||
or
|
||
<emphasis id="DA95EAFFFFE8A14563DA0B54FFF8F9DC" bold="true" box="[134,146,1582,1601]" pageId="2" pageNumber="71">đ</emphasis>
|
||
evi
|
||
<emphasis id="DA95EAFFFFE8A14563F20B54FFD2F9DC" bold="true" box="[174,184,1582,1601]" pageId="2" pageNumber="71">ć</emphasis>
|
||
et al., 2017;
|
||
<bibRefCitation id="8C704B1CFFE8A145626B0B54FEB9F9DC" author="S iler, B. & Banjanac, T." box="[311,467,1582,1601]" pageId="2" pageNumber="71" pagination="367 - 376" refId="ref17003" refString="S iler, B., Z ivkovi c, S., Banjanac, T., Cvetkovi c, J., Nestorovi c Z ivkovi c, J., C iri c, A., Sokovi c, M., Mi s i c, D., 2014. Centauries as underestimated food additives: antioxidant and antimicrobial potential. Food Chem. 147, 367 - 376. https: // doi. org / 10. 1016 / j. foodchem. 2013.10.007." type="journal article" year="2014">
|
||
<emphasis id="DA95EAFFFFE8A145626B0B54FE28F9DC" bold="true" box="[311,322,1582,1601]" pageId="2" pageNumber="71">Š</emphasis>
|
||
iler et al., 2014
|
||
</bibRefCitation>
|
||
,
|
||
<bibRefCitation id="8C704B1CFFE8A14562BC0B54FD65F9DC" author="S iler, B. & Avramov, S. & Banjanac, T." box="[480,527,1582,1601]" pageId="2" pageNumber="71" pagination="336 - 344" refId="ref16905" refString="S iler, B., Avramov, S., Banjanac, T., Cvetkovi c, J., Nestorovi c Z ivkovi c, J., Patenkovi c, A., Mi s i c, D., 2012. Secoiridoid glycosides as a marker system in chemical variability estimation and chemotype assignment of Centaurium erythraea Rafn from the Balkan Peninsula. Ind. Crop. Prod. 40, 336 - 344. https: // doi. org / 10.1016 / j. indcrop. 2012.03. 026." type="journal article" year="2012">2012</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="8C704B1CFFE8A14561400B54FDB9F9DC" author="Stefkov, G. & Miova, B. & Dinevska-Kjovkarovska, S. & Stanoeva, J. P. & Stefova, M. & Petrusevska, G. & Kulevanova, S." box="[540,723,1582,1601]" pageId="2" pageNumber="71" pagination="71 - 77" refId="ref17230" refString="Stefkov, G., Miova, B., Dinevska-Kjovkarovska, S., Stanoeva, J. P., Stefova, M., Petrusevska, G., Kulevanova, S., 2014. Chemical characterization of Centaurium erythrea L. and its effects on carbohydrate and lipid metabolism in experimental diabetes. J. Ethnopharmacol. 152, 71 - 77. https: // doi. org / 10.1016 / j. jep. 2013.11.047." type="journal article" year="2014">Stefkov et al., 2014</bibRefCitation>
|
||
;
|
||
<bibRefCitation id="8C704B1CFFE8A14561BC0B54FF99F9C0" author="van der Sluis, W. G." pageId="2" pageNumber="71" pagination="253 - 286" refId="ref17752" refString="van der Sluis, W. G., 1985. Chemotaxonomical investigations of the genera Blackstonia and Centaurium (Gentianaceae). Plant Syst. Evol. 149, 253 - 286. https: // doi. org / 10.1007 / BF 00983311." type="journal article" year="1985">van der Sluis, 1985</bibRefCitation>
|
||
). Loganin has also been previously reported for
|
||
<taxonomicName id="2FE14D6EFFE8A14561990B30FFF6F9E4" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="erythraea">
|
||
<emphasis id="DA95EAFFFFE8A14561990B30FFF6F9E4" bold="true" italics="true" pageId="2" pageNumber="71">C. erythraea</emphasis>
|
||
</taxonomicName>
|
||
(
|
||
<emphasis id="DA95EAFFFFE8A14563F00B1CFFD1F9E4" bold="true" box="[172,187,1638,1657]" pageId="2" pageNumber="71">Đ</emphasis>
|
||
or
|
||
<emphasis id="DA95EAFFFFE8A14563920B1CFFB0F9E4" bold="true" box="[206,218,1638,1657]" pageId="2" pageNumber="71">đ</emphasis>
|
||
evi
|
||
<emphasis id="DA95EAFFFFE8A14563AA0B1CFE6AF9E4" bold="true" box="[246,256,1638,1657]" pageId="2" pageNumber="71">ć</emphasis>
|
||
et al., 2017), as well as secologanin (
|
||
<emphasis id="DA95EAFFFFE8A145612C0B1CFD15F9E4" bold="true" box="[624,639,1638,1657]" pageId="2" pageNumber="71">Đ</emphasis>
|
||
or
|
||
<emphasis id="DA95EAFFFFE8A14561CE0B1CFDF4F9E4" bold="true" box="[658,670,1638,1657]" pageId="2" pageNumber="71">đ</emphasis>
|
||
evi
|
||
<emphasis id="DA95EAFFFFE8A14561E50B1CFDA9F9E4" bold="true" box="[697,707,1638,1657]" pageId="2" pageNumber="71">ć</emphasis>
|
||
et al., 2017;
|
||
<bibRefCitation id="8C704B1CFFE8A14563FC0BF8FEFAF908" author="Takagi, S. & Yamaki, M." box="[160,400,1666,1685]" pageId="2" pageNumber="71" pagination="546 - 548" refId="ref17463" refString="Takagi, S., Yamaki, M., 1982. Studies on the constituents of Erythraea centaurium (Linne) Persoon. III. Isolation and structure of xanthones. Yakugaku Zasshi 102, 546 - 548. https: // doi. org / 10.1248 / yakushi 1947.102.6 _ 546." type="journal article" year="1982">Takagi and Yamaki, 1982</bibRefCitation>
|
||
).
|
||
</paragraph>
|
||
<caption id="BC9E6665FFEBA14663380A3DFEBFF823" ID-DOI="http://doi.org/10.5281/zenodo.10484257" ID-Zenodo-Dep="10484257" httpUri="https://zenodo.org/record/10484257/files/figure.png" pageId="1" pageNumber="70" startId="1.[100,130,1863,1880]" targetBox="[271,1315,1346,1838]" targetPageId="1" targetType="figure">
|
||
<paragraph id="E85E36EDFFEBA14663380A3DFEBFF823" blockId="1.[100,1487,1863,1982]" pageId="1" pageNumber="70">
|
||
<emphasis id="DA95EAFFFFEBA14663380A3DFFF6F8C5" bold="true" box="[100,156,1863,1880]" pageId="1" pageNumber="70">Fig. 1.</emphasis>
|
||
The presumed biosynthetic pathway of secoiridoid glucosides in
|
||
<taxonomicName id="2FE14D6EFFEBA14661980A3DFC4CF8C5" box="[708,806,1863,1880]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="1" pageNumber="70" phylum="Tracheophyta" rank="species" species="erythraea">
|
||
<emphasis id="DA95EAFFFFEBA14661980A3DFC4CF8C5" bold="true" box="[708,806,1863,1880]" italics="true" pageId="1" pageNumber="70">C. erythraea</emphasis>
|
||
</taxonomicName>
|
||
. GPPS – geranyl diphosphate synthase, GES – geraniol synthase, G8O – geraniol- 8-oxidase, 8HGO-8-hydrohygeraniol oxidoreductase, IS – iridoid synthase, IO – iridoid oxidase, 7DLGT – 7-deoxyloganetic acid glucosyltransferase, 7DLH1 and 7DLH2 – 7-deoxyloganic acid hydrolase, LAMT – loganic acid O-methyltransferase, SLS – secologanin synthase. Cytochrome P450 enzymes, which require cytochrome P450 reductase (CPR) for their reactions, are indicated with red rectangles. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)
|
||
</paragraph>
|
||
</caption>
|
||
<caption id="BC9E6665FFE8A14563380EEDFDE1FC41" ID-DOI="http://doi.org/10.5281/zenodo.10484259" ID-Zenodo-Dep="10484259" httpUri="https://zenodo.org/record/10484259/files/figure.png" pageId="2" pageNumber="71" startId="2.[100,130,919,936]" targetBox="[170,1419,153,896]" targetPageId="2" targetType="figure">
|
||
<paragraph id="E85E36EDFFE8A14563380EEDFDE1FC41" blockId="2.[100,1487,915,988]" pageId="2" pageNumber="71">
|
||
<emphasis id="DA95EAFFFFE8A14563380EEDFFF4FC34" bold="true" box="[100,158,919,937]" pageId="2" pageNumber="71">Fig. 2.</emphasis>
|
||
UHPLC-MS
|
||
<superScript id="1F949BA5FFE8A145625E0EE9FE60FC03" attach="left" box="[258,266,915,926]" fontSize="5" pageId="2" pageNumber="71">2</superScript>
|
||
SRM (Single Reaction Monitoring) chromatograms of targeted compounds (loganin, secologanin, sweroside, swertiamarin and gentiopicrin) in young leaves (red line), mature leaves (green line) and roots (orange line), and corresponding MS
|
||
<superScript id="1F949BA5FFE8A14560CE0ED7FCF0FC25" attach="left" box="[914,922,941,952]" fontSize="5" pageId="2" pageNumber="71">2</superScript>
|
||
spectra. (For interpretation of the references to colour in this figure legend, the reader is referred to the Web version of this article.)
|
||
</paragraph>
|
||
</caption>
|
||
<paragraph id="E85E36EDFFE8A14563380BC3FC68F951" blockId="2.[100,770,1721,1768]" box="[100,770,1721,1740]" pageId="2" pageNumber="71">
|
||
<emphasis id="DA95EAFFFFE8A14563380BC3FC68F951" box="[100,770,1721,1740]" italics="true" pageId="2" pageNumber="71">
|
||
<emphasis id="DA95EAFFFFE8A14563380BC3FFAEF951" bold="true" box="[100,196,1721,1740]" italics="true" pageId="2" pageNumber="71">2.2. Identi</emphasis>
|
||
fi
|
||
<emphasis id="DA95EAFFFFE8A145638D0BC3FC68F951" bold="true" box="[209,770,1721,1740]" italics="true" pageId="2" pageNumber="71">cation of SG biosynthetic pathway genes in the transcriptome of</emphasis>
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="E85E36EDFFE8A14563380BAFFE2AF975" blockId="2.[100,770,1721,1768]" box="[100,320,1749,1768]" pageId="2" pageNumber="71">
|
||
<emphasis id="DA95EAFFFFE8A14563380BAFFE2AF975" bold="true" box="[100,320,1749,1768]" italics="true" pageId="2" pageNumber="71">
|
||
<taxonomicName id="2FE14D6EFFE8A14563380BAFFFB9F975" box="[100,211,1749,1768]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="erythraea">C. erythraea</taxonomicName>
|
||
aerial parts
|
||
</emphasis>
|
||
</paragraph>
|
||
<paragraph id="E85E36EDFFE8A14463D90A77FFCAFC6A" blockId="2.[100,770,1805,1992]" lastBlockId="3.[100,770,968,1015]" lastPageId="3" lastPageNumber="72" pageId="2" pageNumber="71">
|
||
For the purpose of elucidating the biosynthetic pathway responsible for the synthesis of SG, we have taken advantage of the transcriptome resource available for the aerial parts of
|
||
<taxonomicName id="2FE14D6EFFE8A14562AB0A3FFD02F8C5" box="[503,616,1861,1880]" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="erythraea">
|
||
<emphasis id="DA95EAFFFFE8A14562AB0A3FFD02F8C5" bold="true" box="[503,616,1861,1880]" italics="true" pageId="2" pageNumber="71">C. erythraea</emphasis>
|
||
</taxonomicName>
|
||
. Previously unknown candidates for all genes potentially responsible for the synthesis of secologanin have been identified by screening this transcriptome database for candidate genes by performing a BLAST search with already characterized MIA pathway genes from
|
||
<taxonomicName id="2FE14D6EFFE8A145611C0ACFFD96F855" box="[576,764,1973,1992]" class="Magnoliopsida" family="Apocynaceae" genus="Catharanthus" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="roseus">
|
||
<emphasis id="DA95EAFFFFE8A145611C0ACFFD96F855" bold="true" box="[576,764,1973,1992]" italics="true" pageId="2" pageNumber="71">Catharanthus roseus</emphasis>
|
||
</taxonomicName>
|
||
. These included geranyl diphosphate synthase (
|
||
<emphasis id="DA95EAFFFFE8A14567BB0966FA73FBB2" bold="true" box="[1255,1305,1052,1071]" italics="true" pageId="2" pageNumber="71">GPPS</emphasis>
|
||
), geraniol synthase (
|
||
<emphasis id="DA95EAFFFFE8A14560660942FC35FBD6" bold="true" box="[826,863,1080,1099]" italics="true" pageId="2" pageNumber="71">GES</emphasis>
|
||
), geraniol-8-oxidase (
|
||
<emphasis id="DA95EAFFFFE8A14567630942FB02FBD6" bold="true" box="[1087,1128,1080,1099]" italics="true" pageId="2" pageNumber="71">G8O</emphasis>
|
||
), 8-hydrohygeraniol oxidoreductase (
|
||
<emphasis id="DA95EAFFFFE8A1456066092EFC19FBFA" bold="true" box="[826,883,1108,1127]" italics="true" pageId="2" pageNumber="71">8HGO</emphasis>
|
||
), iridoid synthase (
|
||
<emphasis id="DA95EAFFFFE8A145676A092EFB22FBFA" bold="true" box="[1078,1096,1108,1127]" italics="true" pageId="2" pageNumber="71">IS</emphasis>
|
||
), iridoid oxidase (
|
||
<emphasis id="DA95EAFFFFE8A145665D092EFA7DFBFA" bold="true" box="[1281,1303,1108,1127]" italics="true" pageId="2" pageNumber="71">IO</emphasis>
|
||
), 7-deoxyloganetic acid glucosyltransferase (
|
||
<emphasis id="DA95EAFFFFE8A1456774090AFB02FB1E" bold="true" box="[1064,1128,1136,1155]" italics="true" pageId="2" pageNumber="71">7DLGT</emphasis>
|
||
), two candidates for 7-deoxyloganic acid hydrolase (
|
||
<emphasis id="DA95EAFFFFE8A145609009F6FB67FB02" bold="true" box="[972,1037,1164,1183]" italics="true" pageId="2" pageNumber="71">7DLH1</emphasis>
|
||
and
|
||
<emphasis id="DA95EAFFFFE8A145676309F6FBEAFB02" bold="true" box="[1087,1152,1164,1183]" italics="true" pageId="2" pageNumber="71">7DLH2</emphasis>
|
||
), loganic acid O-methyltransferase (
|
||
<emphasis id="DA95EAFFFFE8A145606609D2FC18FB26" bold="true" box="[826,882,1192,1211]" italics="true" pageId="2" pageNumber="71">LAMT</emphasis>
|
||
), and secologanin synthase (
|
||
<emphasis id="DA95EAFFFFE8A14567D909D2FBCCFB26" bold="true" box="[1157,1190,1192,1211]" italics="true" pageId="2" pageNumber="71">SLS</emphasis>
|
||
). All of the selected candidates have shown very high similarity (above 70%) to the corresponding MIA biosynthetic genes present in the NCBI database. Additionally, two candidate
|
||
<emphasis id="DA95EAFFFFE8A14560CB0981FCD4FA93" bold="true" box="[919,958,1275,1294]" italics="true" pageId="2" pageNumber="71">CPR</emphasis>
|
||
genes necessary for the activity of cytochrome P450s were retrieved. The gene-specific primers were successfully designed for the expression analysis of the selected genes, which was confirmed by regular PCR and dissociation curve analysis after the real-time PCR run. The identity of the retrieved candidates was confirmed by sequencing PCR products acquired by amplification using primers designed for qPCR analysis. Herewith reported for the first time for
|
||
<taxonomicName id="2FE14D6EFFE8A14566E008D9FCECFA4F" class="Magnoliopsida" family="Gentianaceae" genus="Centaurium" kingdom="Plantae" order="Gentianales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="erythraea">
|
||
<emphasis id="DA95EAFFFFE8A14566E008D9FCECFA4F" bold="true" italics="true" pageId="2" pageNumber="71">C. erythraea</emphasis>
|
||
</taxonomicName>
|
||
, these newly identified genes encoding probable rate-influencing enzymes in the SG biosynthetic pathway improve the knowledge of the molecular mechanisms underlying the SG biosynthesis and chemical diversity found in this species. Understanding the biogenetic pathways in plants is the first step towards achieving improved production of specialized metabolites. The only way to overcome the rate limiting steps of a targeted pathway is to elucidate their intrinsic regulation. Two distinctive attempts at upregulation have been performed, that can be described as “push” and “pull” strategies. The two strategies are focused on overexpressing either the starting steps of a pathway or the terminal ones. Both strategies were shown to have their own advantages and disadvantages, depending on the specific pathway that has been investigated. Pathways leading to the production of various specialized metabolites have been elucidated in plants so far using biochemical and genetics approaches. Good examples are tropane biosynthetic pathway in
|
||
<taxonomicName id="2FE14D6EFFE8A145675C0A1BFA02F8E9" authority="(Zhang et al., 2004)" baseAuthorityName="Zhang" baseAuthorityYear="2004" box="[1024,1384,1889,1908]" class="Magnoliopsida" family="Solanaceae" genus="Hyoscyamus" kingdom="Plantae" order="Solanales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="niger">
|
||
<emphasis id="DA95EAFFFFE8A145675C0A1BFBCBF8E9" bold="true" box="[1024,1185,1889,1908]" italics="true" pageId="2" pageNumber="71">Hyoscyamus niger</emphasis>
|
||
(
|
||
<bibRefCitation id="8C704B1CFFE8A14567EC0A1BFA35F8E9" author="Zhang, L. & Ding, R. & Chai, Y. & Bonfill, M. & Moyano, E. & Oksman-Caldentey, K. - M. & Xu, T. & Pi, Y. & Wang, Z. & Zhang, H. & Kai, G. & Liao, Z. & Sun, X. & Tang, K." box="[1200,1375,1889,1908]" pageId="2" pageNumber="71" pagination="6786 - 6791" refId="ref18272" refString="Zhang, L., Ding, R., Chai, Y., Bonfill, M., Moyano, E., Oksman-Caldentey, K. - M., Xu, T., Pi, Y., Wang, Z., Zhang, H., Kai, G., Liao, Z., Sun, X., Tang, K., 2004. Engineering tropane biosynthetic pathway in Hyoscyamus Niger hairy root cultures. Proc. Natl. Acad. Sci. U. S. A. 101, 6786 - 6791. https: // doi. org / 10.1073 / pnas. 0401391101." type="journal article" year="2004">Zhang et al., 2004</bibRefCitation>
|
||
)
|
||
</taxonomicName>
|
||
, investigation of the factors that regulate carotenoid biosynthesis in tomato fruits (
|
||
<bibRefCitation id="8C704B1CFFE8A14560660AE3FCA5F831" author="Liu, L. & Shao, Z. & Zhang, M. & Wang, Q." box="[826,975,1945,1964]" pageId="2" pageNumber="71" pagination="28 - 39" refId="ref15284" refString="Liu, L., Shao, Z., Zhang, M., Wang, Q., 2015. Regulation of carotenoid metabolism in omato. Mol. Plant 8, 28 - 39. https: // doi. org / 10.1016 / j. molp. 2014.11.006." type="journal article" year="2015">Liu et al., 2015</bibRefCitation>
|
||
) and flavonoid biosynthesis in both the model plant
|
||
<taxonomicName id="2FE14D6EFFE8A145606E0ACFFC87F855" box="[818,1005,1973,1992]" class="Magnoliopsida" family="Brassicaceae" genus="Arabidopsis" kingdom="Plantae" order="Brassicales" pageId="2" pageNumber="71" phylum="Tracheophyta" rank="species" species="thaliana">
|
||
<emphasis id="DA95EAFFFFE8A145606E0ACFFC87F855" bold="true" box="[818,1005,1973,1992]" italics="true" pageId="2" pageNumber="71">Arabidopsis thaliana</emphasis>
|
||
</taxonomicName>
|
||
and a range of crop species, including tomato, maize, rice, and bean (See
|
||
<bibRefCitation id="8C704B1CFFE9A144622C0EB2FD4FFC46" author="Tohge, T. & De Souza, L. P. & Fernie, A. R." box="[368,549,968,987]" pageId="3" pageNumber="72" pagination="4013 - 4028" refId="ref17517" refString="Tohge, T., De Souza, L. P., Fernie, A. R., 2017. Current understanding of the pathways of flavonoid biosynthesis in model and crop plants. J. Exp. Bot. 68, 4013 - 4028. https: // doi. org / 10.1093 / jxb / erx 177." type="journal article" year="2017">Tohge et al., 2017</bibRefCitation>
|
||
for comprehensive review).
|
||
</paragraph>
|
||
</subSubSection>
|
||
</treatment>
|
||
</document> |