143 lines
16 KiB
XML
143 lines
16 KiB
XML
<document id="1CA94E58B663D1C1EF240ECBA37D95EB" ID-DOI="10.1016/j.phytochem.2018.12.010" ID-ISSN="1873-3700" ID-Zenodo-Dep="10481956" IM.bibliography_approvedBy="karina" IM.illustrations_approvedBy="karina" IM.materialsCitations_approvedBy="felipe" IM.metadata_approvedBy="felipe" IM.tables_requiresApprovalFor="GgImagineBatch,operationResults" IM.taxonomicNames_approvedBy="karina" IM.treatments_approvedBy="karina" checkinTime="1704928647344" checkinUser="felipe" docAuthor="Tatsuzawa, Fumi" docDate="2019" docId="97758935FFE6FFD9A678FC490030C914" docLanguage="en" docName="Phytochemistry.159.108-118.pdf" docOrigin="Phytochemistry 159" docSource="http://dx.doi.org/10.1016/j.phytochem.2018.12.010" docStyle="DocumentStyle:9E596C34F4E94307D29315B03ACE1007.6:Phytochemistry.2014-2019.journal_article" docStyleId="9E596C34F4E94307D29315B03ACE1007" docStyleName="Phytochemistry.2014-2019.journal_article" docStyleVersion="6" docTitle="Erysimum cheiri" docType="treatment" docVersion="5" lastPageNumber="112" masterDocId="6B4CF14DFFE2FFDDA61CFFF70446CD22" masterDocTitle="Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum × cheiri (L.) Crantz (Brassicaceae)" masterLastPageNumber="118" masterPageNumber="108" pageNumber="112" updateTime="1706405550559" updateUser="karina">
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<mods:title id="5A5672C8A711DBC9F3B951EA1320D96B">Acylated pelargonidin glycosides from the red-purple flowers of Iberis umbellata L. and the red flowers of Erysimum × cheiri (L.) Crantz (Brassicaceae)</mods:title>
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<mods:name id="C42A77CB6F7EE5CCDA087AEBA0F51EF0" type="personal">
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<mods:namePart id="464CC5BF6F1C6D1F823228F67288EECD">Tatsuzawa, Fumi</mods:namePart>
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<mods:title id="5FC41FE07089CF653C87CFA56E493B90">Phytochemistry</mods:title>
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<mods:part id="98BD794FEEC1FB0EB95994D24186B781">
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<mods:date id="4697F5B9E524338C7F49D3ADCB977EB9">2019</mods:date>
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<mods:number id="BE50A6C2FF2D22B1CE925A69D6B1920F">2019-03-31</mods:number>
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<mods:number id="9C08331D94C45C3868D32217A31E253F">159</mods:number>
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<mods:url id="E55E30F3618C7309806EAE0C37A84533">http://dx.doi.org/10.1016/j.phytochem.2018.12.010</mods:url>
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<mods:classification id="E9C54A5091C1BBD3F1EF083BA778BFCF">journal article</mods:classification>
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<mods:identifier id="39C8A46BDF83D872E9BFC6EF02DF60B1" type="DOI">10.1016/j.phytochem.2018.12.010</mods:identifier>
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<mods:identifier id="D9268949231200438A467548F930C379" type="ISSN">1873-3700</mods:identifier>
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<mods:identifier id="D40CA6472CDE1221CE7C1691A73B5A60" type="Zenodo-Dep">10481956</mods:identifier>
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<subSubSection id="57C66BA8FFE6FFD9A678FC490669CEF3" box="[100,559,958,977]" pageId="4" pageNumber="112" type="nomenclature">
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<paragraph id="1F633823FFE6FFD9A678FC490669CEF3" blockId="4.[100,559,958,977]" box="[100,559,958,977]" pageId="4" pageNumber="112">
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<heading id="442B8F4FFFE6FFD9A678FC490669CEF3" bold="true" box="[100,559,958,977]" fontSize="36" level="1" pageId="4" pageNumber="112" reason="1">
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<emphasis id="2DA8E431FFE6FFD9A678FC490669CEF3" bold="true" box="[100,559,958,977]" italics="true" pageId="4" pageNumber="112">
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2.2. Anthocyanins in the red flowers of
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<taxonomicName id="D8DC43A0FFE6FFD9A7D2FC490669CEF3" ID-CoL="3BBH8" ID-ENA="71232" authority="(L.) Crantz" box="[462,559,958,977]" class="Magnoliopsida" family="Brassicaceae" genus="Erysimum" isHybrid="true" kingdom="Plantae" order="Brassicales" pageId="4" pageNumber="112" phylum="Tracheophyta" rank="species" species="cheiri">E. × cheiri</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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<subSubSection id="57C66BA8FFE6FFD9A699FC010030C914" pageId="4" pageNumber="112" type="description">
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<paragraph id="1F633823FFE6FFD9A699FC010030C914" blockId="4.[100,770,1014,1508]" lastBlockId="4.[818,1488,808,1078]" pageId="4" pageNumber="112">
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By HPLC analysis, four major anthocyanin peaks were detected in the 5% HOAc extract from the red flowers of
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<taxonomicName id="D8DC43A0FFE6FFD9A455FBE506ECC906" box="[585,682,1041,1061]" class="Magnoliopsida" family="Brassicaceae" genus="Erysimum" isHybrid="true" kingdom="Plantae" order="Brassicales" pageId="4" pageNumber="112" phylum="Tracheophyta" rank="species" species="cheiri">
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<emphasis id="2DA8E431FFE6FFD9A455FBE5061AC907" bold="true" box="[585,604,1042,1061]" italics="true" pageId="4" pageNumber="112">E.</emphasis>
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×
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<emphasis id="2DA8E431FFE6FFD9A465FBE606ECC906" bold="true" box="[633,682,1041,1060]" italics="true" pageId="4" pageNumber="112">cheiri</emphasis>
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</taxonomicName>
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‘Aurora’ (
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<figureCitation id="87E724A6FFE6FFD9A670FBD904E5C963" box="[108,163,1070,1089]" captionStart="Fig" captionStartId="4.[977,1007,1537,1554]" captionTargetBox="[100,947,1556,1969]" captionTargetId="figure-844@4.[100,947,1536,1969]" captionTargetPageId="4" captionText="Fig. 3. HPLC profile (530 nm) and structure of acylated anthocyanins isolated from the red flowers of E.× cheiri 'Aurora'. 7: pelargonidin 3-O-[2-O-(xylosyl)-6-O-(p-coumaroyl)-glucoside]-5-O-(glucoside). 8: pelargonidin 3-O-[2- O-(xylosyl)-6-O-(feruloyl)-glucoside]-5-O-(glucoside). 9: pelargonidin 3-O-[2-O-(2-O-(p-coumaroyl)-3-O-(glucosyl)-xylosyl)-6-O-(p-coumaroyl)-glucoside]-5-O-(glucoside). 10: pelargonidin 3-O-[2-O-(2-O-(p-coumaroyl)-xylosyl)-6-O-(p- coumaroyl)-glucoside]-5-O-(glucoside)." figureDoi="http://doi.org/10.5281/zenodo.10481962" httpUri="https://zenodo.org/record/10481962/files/figure.png" pageId="4" pageNumber="112">Fig. 3</figureCitation>
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). Percentages of the total anthocyanin contents based on HPLC peak areas at
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<quantity id="D82495C6FFE6FFD9A6F5FBBE0569C97F" box="[233,303,1097,1117]" metricMagnitude="-7" metricUnit="m" metricValue="5.3" pageId="4" pageNumber="112" unit="nm" value="530.0">530 nm</quantity>
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are as follows:
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<emphasis id="2DA8E431FFE6FFD9A7DAFBBD0594C97F" bold="true" box="[454,466,1098,1117]" pageId="4" pageNumber="112">7</emphasis>
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: 52.6%,
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<emphasis id="2DA8E431FFE6FFD9A435FBBE0673C97E" bold="true" box="[553,565,1097,1116]" pageId="4" pageNumber="112">8</emphasis>
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: 7.5%,
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<emphasis id="2DA8E431FFE6FFD9A49CFBBE06CAC97E" bold="true" box="[640,652,1097,1116]" pageId="4" pageNumber="112">9</emphasis>
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: 15.7%,
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<emphasis id="2DA8E431FFE6FFD9A4FFFBBE06BAC97E" bold="true" box="[739,764,1097,1116]" pageId="4" pageNumber="112">10</emphasis>
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: 14.4%. These anthocyanins (
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<emphasis id="2DA8E431FFE6FFD9A76EFB9105E4C95A" bold="true" box="[370,418,1125,1145]" pageId="4" pageNumber="112">7–10</emphasis>
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) were isolated from the dried flowers and purified according to procedures described previously (
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<bibRefCitation id="7B4D45D2FFE6FFD9A482FB75049CC992" author="Tatsuzawa, F. & Saito, N. & Shinoda, K. & Shigihara, A. & Honda, T." pageId="4" pageNumber="112" pagination="1287 - 1295" refId="ref15393" refString="Tatsuzawa, F., Saito, N., Shinoda, K., Shigihara, A., Honda, T., 2006. Acylated cyanidin 3 - sambubioside- 5 - glucosides in three garden plants of the Cruciferae. Phytochemistry 67, 1287 - 1295." type="journal article" year="2006">Tatsuzawa et al., 2006</bibRefCitation>
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). The chromatographic and spectroscopic properties of these pigments are summarized in Experimental. Visible maxima (
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<emphasis id="2DA8E431FFE6FFD9A4CCFB4E069AC9EE" bold="true" box="[720,732,1209,1228]" italics="true" pageId="4" pageNumber="112">λ</emphasis>
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<subScript id="83583A66FFE6FFD9A4C0FB3506BCC9EC" attach="left" box="[732,762,1218,1230]" fontSize="5" pageId="4" pageNumber="112">max</subScript>
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) in 0.1% HCl-MeOH were observed at
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<quantity id="D82495C6FFE6FFD9A7D3FB220601C9CB" box="[463,583,1237,1257]" metricMagnitude="-7" metricUnit="m" metricValue="5.095" metricValueMax="5.1" metricValueMin="5.09" pageId="4" pageNumber="112" unit="nm" value="509.5" valueMax="510.0" valueMin="509.0">509–510 nm</quantity>
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. In addition, (
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<emphasis id="2DA8E431FFE6FFD9A4CDFB22069BC9CA" bold="true" box="[721,733,1237,1256]" italics="true" pageId="4" pageNumber="112">E</emphasis>
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<subScript id="83583A66FFE6FFD9A4C0FB2906B1C9C8" attach="left" box="[732,759,1246,1258]" fontSize="5" pageId="4" pageNumber="112">440</subScript>
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/
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<emphasis id="2DA8E431FFE6FFD9A678FB060436C826" bold="true" box="[100,112,1265,1284]" italics="true" pageId="4" pageNumber="112">E</emphasis>
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<subScript id="83583A66FFE6FFD9A66CFB0D04E0C824" attach="left" box="[112,166,1274,1286]" fontSize="5" pageId="4" pageNumber="112">vis.max</subScript>
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) ratios were 0.22–0.23. Addition of AlCl
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<subScript id="83583A66FFE6FFD9A45FFB0D060AC824" attach="left" box="[579,588,1274,1286]" fontSize="5" pageId="4" pageNumber="112">3</subScript>
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did not exhibit a bathochromic shift, indicating that these pigments lack a vicinal hydroxyl group in the B-ring. Therefore, these data suggested that
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<emphasis id="2DA8E431FFE6FFD9A4CEFADE0744C81E" bold="true" box="[722,770,1321,1340]" pageId="4" pageNumber="112">7–10</emphasis>
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may have a pelargonidin 3,5-glycosyl
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<typeStatus id="C0678681FFE6FFD9A7C7FAB20642C87A" box="[475,516,1349,1368]" pageId="4" pageNumber="112">type</typeStatus>
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structure (
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<bibRefCitation id="7B4D45D2FFE6FFD9A46EFAB204A8C851" author="Tatsuzawa, F. & Shinoda, K." pageId="4" pageNumber="112" pagination="225 - 228" refId="ref15335" refString="Tatsuzawa, F., Shinoda, K., 2005. Comparison between identification of anthocyanin by HPLC analysis with a photodiode array detector and that using TLC combined with UV - VIS spectral analysis. Hortic. Res. (Jpn.) 4, 225 - 228 (In Japanese with English abstract)." type="journal article" year="2005">Tatsuzawa and Shinoda, 2005</bibRefCitation>
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). The
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<emphasis id="2DA8E431FFE6FFD9A731FA96057FC856" bold="true" box="[301,313,1377,1396]" italics="true" pageId="4" pageNumber="112">E</emphasis>
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<subScript id="83583A66FFE6FFD9A725FA9D0510C854" attach="left" box="[313,342,1386,1398]" fontSize="5" pageId="4" pageNumber="112">acyl</subScript>
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/
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<emphasis id="2DA8E431FFE6FFD9A77CFA96052AC856" bold="true" box="[352,364,1377,1396]" italics="true" pageId="4" pageNumber="112">E</emphasis>
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||
<subScript id="83583A66FFE6FFD9A770FA9D05E4C854" attach="left" box="[364,418,1386,1398]" fontSize="5" pageId="4" pageNumber="112">vis.max</subScript>
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ratio 0.83–1.41 suggested that
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<emphasis id="2DA8E431FFE6FFD9A4CEFA960744C851" bold="true" box="[722,770,1376,1396]" pageId="4" pageNumber="112">7–10</emphasis>
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had one or two hydroxycinnamic acid units (
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<bibRefCitation id="7B4D45D2FFE6FFD9A418FA8B06E7C8B2" author="Saito, N. & Tatsuzawa, F. & Suenaga, E. & Toki, K. & Shinoda, K. & Shigihara, A. & Honda, T." box="[516,673,1404,1424]" pageId="4" pageNumber="112" pagination="3139 - 3150" refId="ref15106" refString="Saito, N., Tatsuzawa, F., Suenaga, E., Toki, K., Shinoda, K., Shigihara, A., Honda, T., 2008. Tetra-acylated cyanidin 3 - sophoroside- 5 - glucosides from the flowers of Iberis umbellata L. (Cruciferae). Phytochemistry 69, 3139 - 3150." type="journal article" year="2008">Saito et al., 2008</bibRefCitation>
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). Alkaline hydrolysis of
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<quantity id="D82495C6FFE6FFD9A6F5FA6E0550C88E" box="[233,278,1433,1452]" metricMagnitude="-6" metricUnit="kg" metricValue="1.0" pageId="4" pageNumber="112" unit="mg" value="1.0">1 mg</quantity>
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of each pigment yielded deacyl anthocyanins and hydroxycinnamic acids. The structure of the deacyl anthocyanin of pigments
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<emphasis id="2DA8E431FFE6FFD9A6DCFA27048AC8C1" bold="true" box="[192,204,1488,1507]" pageId="4" pageNumber="112">7</emphasis>
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,
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<emphasis id="2DA8E431FFE6FFD9A6CBFA2704A5C8C1" bold="true" box="[215,227,1488,1507]" pageId="4" pageNumber="112">8</emphasis>
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, and
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<emphasis id="2DA8E431FFE6FFD9A704FA270577C8C1" bold="true" box="[280,305,1488,1507]" pageId="4" pageNumber="112">10</emphasis>
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was identified as pelargonidin 3-sambubioside-5- glucoside by direct comparison of HPLC behavior with those of authentic samples obtained from
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<taxonomicName id="D8DC43A0FFE6FFD9A27AFCB40730CE51" authority="(Tatsuzawa et al., 2010 a)" baseAuthorityName="Tatsuzawa" baseAuthorityYear="2010" class="Magnoliopsida" family="Brassicaceae" genus="Lobularia" kingdom="Plantae" order="Brassicales" pageId="4" pageNumber="112" phylum="Tracheophyta" rank="species" species="maritima">
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<emphasis id="2DA8E431FFE6FFD9A27AFCB40150CE75" bold="true" box="[1126,1302,835,855]" italics="true" pageId="4" pageNumber="112">Lobularia maritima</emphasis>
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(Tatsuzawa et al., 2010a)
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</taxonomicName>
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. The structure of the deacyl anthocyanin of pigment
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<emphasis id="2DA8E431FFE6FFD9A36EFC970138CE51" bold="true" box="[1394,1406,864,883]" pageId="4" pageNumber="112">9</emphasis>
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was not identified at this stage.
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<emphasis id="2DA8E431FFE6FFD9A212FC8B005ECEAD" bold="true" box="[1038,1048,892,911]" italics="true" pageId="4" pageNumber="112">p</emphasis>
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-Coumaric acid was obtained from the alkaline hydrolysate of pigments
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<emphasis id="2DA8E431FFE6FFD9A238FC6F0076CE89" bold="true" box="[1060,1072,920,939]" pageId="4" pageNumber="112">7</emphasis>
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,
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<emphasis id="2DA8E431FFE6FFD9A25CFC60000ACE88" bold="true" box="[1088,1100,919,938]" pageId="4" pageNumber="112">9</emphasis>
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, and
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<emphasis id="2DA8E431FFE6FFD9A294FC6000E7CE88" bold="true" box="[1160,1185,919,938]" pageId="4" pageNumber="112">10</emphasis>
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, but ferulic acid was obtained from the alkaline hydrolysate of pigment
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<emphasis id="2DA8E431FFE6FFD9A2D3FC44009DCEE4" bold="true" box="[1231,1243,947,966]" pageId="4" pageNumber="112">8</emphasis>
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based on comparison to authentic samples (Wako Pure chemical Industries. Ltd.,
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<collectingRegion id="DD18F6C1FFE6FFD9A359FC3801C7CEC0" box="[1349,1409,975,994]" country="Japan" name="Osaka" pageId="4" pageNumber="112">Osaka</collectingRegion>
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,
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<collectingCountry id="67CB78B3FFE6FFD9A395FC270183CEC1" box="[1417,1477,976,995]" name="Japan" pageId="4" pageNumber="112">Japan</collectingCountry>
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). The structures of
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<emphasis id="2DA8E431FFE6FFD9A5F9FC1C0050CEDC" bold="true" box="[997,1046,1003,1023]" pageId="4" pageNumber="112">7–10</emphasis>
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were elucidated further as described below based on analysis of their NMR spectra in CF
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<subScript id="83583A66FFE6FFD9A2ECFBE700BFC93E" attach="both" box="[1264,1273,1040,1052]" fontSize="5" pageId="4" pageNumber="112">3</subScript>
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COOD-DMSO‑
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<emphasis id="2DA8E431FFE6FFD9A362FBF001CFC938" bold="true" box="[1406,1417,1031,1050]" italics="true" pageId="4" pageNumber="112">d</emphasis>
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<subScript id="83583A66FFE6FFD9A395FBE701D4C93E" attach="left" box="[1417,1426,1040,1052]" fontSize="5" pageId="4" pageNumber="112">6</subScript>
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(1:9), with TMS as an internal standard.
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</paragraph>
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</subSubSection>
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</treatment>
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</document> |