120 lines
16 KiB
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120 lines
16 KiB
XML
<document id="352FC06F01404C38C9D3546F7A08C697" ID-DOI="10.1016/j.phytochem.2015.07.010" ID-ISSN="1873-3700" ID-Zenodo-Dep="10486436" IM.bibliography_approvedBy="felipe" IM.illustrations_approvedBy="jonas" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.taxonomicNames_approvedBy="felipe" IM.treatments_approvedBy="jonas" checkinTime="1704948780941" checkinUser="felipe" docAuthor="Kurth, Caroline, Welling, Matthew & Pohnert, Georg" docDate="2015" docId="03F0B6059F15BB68137FF77EFD78C2F3" docLanguage="en" docName="Phytochemistry.117.417-423.pdf" docOrigin="Phytochemistry 117" docSource="http://dx.doi.org/10.1016/j.phytochem.2015.07.010" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Dasycladus vermicularis Krasser 1898" docType="treatment" docVersion="4" lastPageNumber="417" masterDocId="FFC9CE7D9F15BB691040F067FF9AC708" masterDocTitle="Sulfated phenolic acids from Dasycladales siphonous green algae" masterLastPageNumber="423" masterPageNumber="417" pageNumber="417" updateTime="1705588279704" updateUser="jonas">
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<mods:titleInfo id="E699BB2498C704A7978D5B59C91CC259">
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<mods:title id="4D644C22BF5769AADADBC2EFD2BCAD4F">Sulfated phenolic acids from Dasycladales siphonous green algae</mods:title>
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<mods:name id="17C31235D37BD0FC95C2BFB0D64FC7B0" type="personal">
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<mods:namePart id="EEB92CAF1D29ED0E1DE7A4459CCAEAE0">Kurth, Caroline</mods:namePart>
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<mods:namePart id="55870D6547265B881898928EB3AAB443">Welling, Matthew</mods:namePart>
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<mods:namePart id="71F13B7409E45C9C0474895D83EFFCE6">Pohnert, Georg</mods:namePart>
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<mods:title id="15135142A7DEB238C4F4065E3A048DFE">Phytochemistry</mods:title>
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<mods:part id="FE827FF048A30F4E77EE7533525CA2D1">
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<mods:date id="F92176B5596AE8CE2D9C67F61606916A">2015</mods:date>
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<mods:number id="8153554C3F100AAEEAF9ECE29FECBE1C">2015-09-30</mods:number>
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<mods:number id="B5C3A0EDD102A5F58DD82807BF14D32F">117</mods:number>
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<mods:identifier id="779FF620EACCDB251D4B8F9F453C60A5" type="DOI">10.1016/j.phytochem.2015.07.010</mods:identifier>
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<treatment id="03F0B6059F15BB68137FF77EFD78C2F3" LSID="urn:lsid:plazi:treatment:03F0B6059F15BB68137FF77EFD78C2F3" httpUri="http://treatment.plazi.org/id/03F0B6059F15BB68137FF77EFD78C2F3" lastPageId="1" lastPageNumber="417" pageId="0" pageNumber="417">
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<subSubSection id="C34354989F15BB69137FF77EFB44C025" box="[831,1246,1817,1837]" pageId="0" pageNumber="417" type="nomenclature">
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<paragraph id="8BE607139F15BB69137FF77EFB44C025" blockId="0.[831,1246,1817,1837]" box="[831,1246,1817,1837]" pageId="0" pageNumber="417">
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<heading id="D0AEB07F9F15BB69137FF77EFB44C025" box="[831,1246,1817,1837]" fontSize="36" level="2" pageId="0" pageNumber="417" reason="3">
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<emphasis id="B92DDB019F15BB69137FF77EFB44C025" box="[831,1246,1817,1837]" italics="true" pageId="0" pageNumber="417">
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2.1. Sulfated metabolites of
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<taxonomicName id="4C597C909F15BB69140CF77EFB44C025" authorityName="Krasser" authorityYear="1898" baseAuthorityName="Scopoli" box="[1100,1246,1817,1837]" class="Ulvophyceae" family="Dasycladaceae" genus="Dasycladus" kingdom="Plantae" order="Dasycladales" pageId="0" pageNumber="417" phylum="Chlorophyta" rank="species" species="vermicularis">D. vermicularis</taxonomicName>
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</emphasis>
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</heading>
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</paragraph>
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</subSubSection>
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<footnote id="E8421B1D9F15BB69103DF734FDCCC077" pageId="0" pageNumber="417">
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<paragraph id="8BE607139F15BB69103DF734FDCCC077" blockId="0.[125,598,1875,1920]" pageId="0" pageNumber="417">
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<emphasis id="B92DDB019F15BB69103DF734FF12C06C" bold="true" box="[125,136,1875,1892]" pageId="0" pageNumber="417">⇑</emphasis>
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Corresponding author.
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<emphasis id="B92DDB019F15BB6910D1F716FE93C088" box="[145,265,1905,1920]" italics="true" pageId="0" pageNumber="417">E-mail address:</emphasis>
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georg.pohnert@uni-jena.de (G. Pohnert).
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</paragraph>
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</footnote>
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<subSubSection id="C34354989F15BB68131EF735FD78C2F3" lastPageId="1" lastPageNumber="418" pageId="0" pageNumber="417" type="biology_ecology">
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<paragraph id="8BE607139F15BB68131EF735FD78C2F3" blockId="0.[831,1501,1874,1922]" lastBlockId="1.[87,758,758,1531]" lastPageId="1" lastPageNumber="418" pageId="0" pageNumber="417">
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Three candidate molecules for which sulfatation was indicated by the presence of a fragment of [M–H–80]
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<superScript id="7C2CAA5B9F15BB6914B4F70EFA9AC07F" attach="left" box="[1268,1280,1897,1911]" fontSize="5" pageId="0" pageNumber="417">–</superScript>
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in the mass spectrum were detected by UPLC–MS/MS measurements in extracts of
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<taxonomicName id="4C597C909F14BB681017F376FF70C42D" authorityName="Krasser" authorityYear="1898" baseAuthorityName="Scopoli" box="[87,234,785,805]" class="Ulvophyceae" family="Dasycladaceae" genus="Dasycladus" kingdom="Plantae" order="Dasycladales" pageId="1" pageNumber="418" phylum="Chlorophyta" rank="species" species="vermicularis">
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<emphasis id="B92DDB019F14BB681017F376FF70C42D" box="[87,234,785,805]" italics="true" pageId="1" pageNumber="418">D. vermicularis</emphasis>
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</taxonomicName>
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. The metabolite with a mass of 273 [M–H]
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<superScript id="7C2CAA5B9F14BB6812E8F36AFD2EC413" attach="left" box="[680,692,781,795]" fontSize="5" pageId="1" pageNumber="418">–</superScript>
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and a fragment with
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<emphasis id="B92DDB019F14BB6810B2F34AFE9FC449" box="[242,261,813,833]" italics="true" pageId="1" pageNumber="418">m</emphasis>
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/
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<emphasis id="B92DDB019F14BB68114DF34AFE8DC449" box="[269,279,813,833]" italics="true" pageId="1" pageNumber="418">z</emphasis>
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= 193 could readily be assigned to dihydroxycoumarin sulfate (
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<figureCitation id="13621B969F14BB68114EF32DFED8C455" box="[270,322,842,861]" captionStart="Fig" captionStartId="1.[395,421,701,715]" captionTargetBox="[231,1328,181,671]" captionTargetId="figure-882@1.[231,1328,181,671]" captionTargetPageId="1" captionText="Fig. 1. Structures and transformation of the sulfated aromatic metabolites from Dascycladales." figureDoi="http://doi.org/10.5281/zenodo.10486438" httpUri="https://zenodo.org/record/10486438/files/figure.png" pageId="1" pageNumber="418">Fig. 1</figureCitation>
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) based on previous results and co-injection with a synthetic standard (
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<bibRefCitation id="EFC87AE29F14BB68112CF301FDA8C471" author="Welling, M. & Pohnert, G. & Kupper, F. C. & Ross, C." box="[364,562,870,889]" pageId="1" pageNumber="418" pagination="825 - 838" refId="ref5947" refString="Welling, M., Pohnert, G., Kupper, F. C., Ross, C., 2009. Rapid biopolymerisation during wound plug formation in green algae. J. Adhes. 85, 825 - 838." type="journal article" year="2009">Welling et al., 2009</bibRefCitation>
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). For identification of the two unknown potentially sulfated metabolites (
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<emphasis id="B92DDB019F14BB6812D4F3E6FD3DC49D" box="[660,679,897,917]" italics="true" pageId="1" pageNumber="418">m</emphasis>
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/
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<emphasis id="B92DDB019F14BB6812EEF3E6FD22C49D" box="[686,696,897,917]" italics="true" pageId="1" pageNumber="418">z</emphasis>
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= 217 [M–H]
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<superScript id="7C2CAA5B9F14BB6810DDF3FEFF33C4AF" attach="left" box="[157,169,921,935]" fontSize="5" pageId="1" pageNumber="418">–</superScript>
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and 231 [M–H]
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<superScript id="7C2CAA5B9F14BB681112F3FEFEC4C4AF" attach="none" box="[338,350,921,935]" fontSize="5" pageId="1" pageNumber="418">–</superScript>
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, respectively) synthetic standards were prepared. Based on mass spectra and polarity in UPLC–MS (
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<figureCitation id="13621B969F14BB68101FF3B2FE99C4E1" box="[95,259,981,1001]" captionStart="Fig" captionStartId="2.[113,139,1569,1583]" captionTargetBox="[333,1278,181,1539]" captionTargetId="figure-237@2.[333,1278,181,1539]" captionTargetPageId="2" captionText="Fig. 2. LC/MS chromatograms (base peak intensity, BPI) of (A) a D. vermicularis extract. The labeled peak indicates dihydroxycoumarin sulfate (DHyCS). (B) MS/MS of DHyCS in ESI-negative ionization mode. (C) Co-injection with 4-(sulfooxy)benzoic acid (SBA). (D) MS/MS of SBA in ESI-negative ionization mode. (E) Co-injection with 4-(sulfooxy)phenylacetic acid (SPA). (F) MS/MS of SPA in ESI-negative ionization mode." figureDoi="http://doi.org/10.5281/zenodo.10486440" httpUri="https://zenodo.org/record/10486440/files/figure.png" pageId="1" pageNumber="418">Fig. 2A, D and F</figureCitation>
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) we selected 4-(sulfooxy)benzoic acid (SBA) and 4-(sulfooxy)phenylacetic acid (SPA) as likely candidates. After estimation of the content of the metabolites in the algal extract, co-injection experiments with algal extract and the synthetic standards were performed (
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<figureCitation id="13621B969F14BB681150F422FE3AC350" box="[272,416,1093,1112]" captionStart="Fig" captionStartId="2.[113,139,1569,1583]" captionTargetBox="[333,1278,181,1539]" captionTargetId="figure-237@2.[333,1278,181,1539]" captionTargetPageId="2" captionText="Fig. 2. LC/MS chromatograms (base peak intensity, BPI) of (A) a D. vermicularis extract. The labeled peak indicates dihydroxycoumarin sulfate (DHyCS). (B) MS/MS of DHyCS in ESI-negative ionization mode. (C) Co-injection with 4-(sulfooxy)benzoic acid (SBA). (D) MS/MS of SBA in ESI-negative ionization mode. (E) Co-injection with 4-(sulfooxy)phenylacetic acid (SPA). (F) MS/MS of SPA in ESI-negative ionization mode." figureDoi="http://doi.org/10.5281/zenodo.10486440" httpUri="https://zenodo.org/record/10486440/files/figure.png" pageId="1" pageNumber="418">Fig. 2C and E</figureCitation>
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). Peak symmetry was important since the short retention times and strong solvent effects of the samples required a rigorous quality control of co-eluting peaks. SBA showed the same retention time and mass spectrum to the first sulfated metabolite in the
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<taxonomicName id="4C597C909F14BB6811CEF4D4FD85C3CF" authorityName="Krasser" authorityYear="1898" baseAuthorityName="Scopoli" box="[398,543,1203,1223]" class="Ulvophyceae" family="Dasycladaceae" genus="Dasycladus" kingdom="Plantae" order="Dasycladales" pageId="1" pageNumber="418" phylum="Chlorophyta" rank="species" species="vermicularis">
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<emphasis id="B92DDB019F14BB6811CEF4D4FD85C3CF" box="[398,543,1203,1223]" italics="true" pageId="1" pageNumber="418">D. vermicularis</emphasis>
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</taxonomicName>
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extract. When added in co-injection experiments, an increase of intensity of the first signal was observed (
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<figureCitation id="13621B969F14BB68110AF48BFE02C3F7" box="[330,408,1260,1279]" captionStart="Fig" captionStartId="2.[113,139,1569,1583]" captionTargetBox="[333,1278,181,1539]" captionTargetId="figure-237@2.[333,1278,181,1539]" captionTargetPageId="2" captionText="Fig. 2. LC/MS chromatograms (base peak intensity, BPI) of (A) a D. vermicularis extract. The labeled peak indicates dihydroxycoumarin sulfate (DHyCS). (B) MS/MS of DHyCS in ESI-negative ionization mode. (C) Co-injection with 4-(sulfooxy)benzoic acid (SBA). (D) MS/MS of SBA in ESI-negative ionization mode. (E) Co-injection with 4-(sulfooxy)phenylacetic acid (SPA). (F) MS/MS of SPA in ESI-negative ionization mode." figureDoi="http://doi.org/10.5281/zenodo.10486440" httpUri="https://zenodo.org/record/10486440/files/figure.png" pageId="1" pageNumber="418">Fig. 2C</figureCitation>
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). The mass spectrum remained unaffected by the co-injection. The
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<emphasis id="B92DDB019F14BB681195F560FD93C213" box="[469,521,1287,1307]" italics="true" pageId="1" pageNumber="418">ortho</emphasis>
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- and
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<emphasis id="B92DDB019F14BB68120EF560FDE5C213" box="[590,639,1287,1307]" italics="true" pageId="1" pageNumber="418">meta</emphasis>
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-isomers of (sulfooxy)benzoic acid eluted at different retention times (data not shown). The same procedure was applied for co-injection of SPA (
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<figureCitation id="13621B969F14BB6810D4F53BFF79C267" box="[148,227,1372,1391]" captionStart="Fig" captionStartId="2.[113,139,1569,1583]" captionTargetBox="[333,1278,181,1539]" captionTargetId="figure-237@2.[333,1278,181,1539]" captionTargetPageId="2" captionText="Fig. 2. LC/MS chromatograms (base peak intensity, BPI) of (A) a D. vermicularis extract. The labeled peak indicates dihydroxycoumarin sulfate (DHyCS). (B) MS/MS of DHyCS in ESI-negative ionization mode. (C) Co-injection with 4-(sulfooxy)benzoic acid (SBA). (D) MS/MS of SBA in ESI-negative ionization mode. (E) Co-injection with 4-(sulfooxy)phenylacetic acid (SPA). (F) MS/MS of SPA in ESI-negative ionization mode." figureDoi="http://doi.org/10.5281/zenodo.10486440" httpUri="https://zenodo.org/record/10486440/files/figure.png" pageId="1" pageNumber="418">Fig. 2E</figureCitation>
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). No significant change in peak symmetry was observed upon addition of SBA or SPA, which unambiguously confirms the identity of the natural and synthetic products. Besides the occurrence as catabolic products in mouse urine, these metabolites have to our knowledge not been reported as natural products before (
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<bibRefCitation id="EFC87AE29F14BB681146F58FFE5CC2F3" author="Manna, S. K. & Patterson, A. D. & Yang, Q. & Krausz, K. W. & Idle, J. R. & Fornace, A. J. & Gonzalez, F. J." box="[262,454,1511,1531]" pageId="1" pageNumber="418" pagination="4120 - 4133" refId="ref5357" refString="Manna, S. K., Patterson, A. D., Yang, Q., Krausz, K. W., Idle, J. R., Fornace, A. J., Gonzalez, F. J., 2011. UPLC - MS-based urine metabolomics reveals indole- 3 - lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. J. Proteome Res. 10, 4120 - 4133." type="journal article" year="2011">Manna et al., 2011</bibRefCitation>
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;
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<bibRefCitation id="EFC87AE29F14BB681191F58FFD4FC2F3" author="van der Hooft, J. J. J. & de Vos, R. C. H. & Mihaleva, V. & Bino, R. J. & Ridder, L. & de Roo, N. & Jacobs, D. M. & van Duynhoven, J. P. M. & Vervoort, J." box="[465,725,1511,1531]" pageId="1" pageNumber="418" pagination="7263 - 7271" refId="ref5718" refString="van der Hooft, J. J. J., de Vos, R. C. H., Mihaleva, V., Bino, R. J., Ridder, L., de Roo, N., Jacobs, D. M., van Duynhoven, J. P. M., Vervoort, J., 2012. Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal. Chem. 84, 7263 - 7271." type="journal article" year="2012">van der Hooft et al., 2012</bibRefCitation>
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).
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</paragraph>
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</subSubSection>
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</treatment>
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</document> |