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<document id="DD300DEA361880EE7C14D694B8338382" 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="97758935FFE3FFDCA678FF20079DCF52" 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="Iberis umbellata" docType="treatment" docVersion="4" lastPageNumber="109" 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="109" updateTime="1706405550559" updateUser="karina">
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<mods:title id="3849DEB681B3AA940C2E1FB4DF71B087">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:namePart id="13F9375D61328ED988A900868272F283">Tatsuzawa, Fumi</mods:namePart>
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<mods:title id="077043313E61515A3C2B673736DFE3DE">Phytochemistry</mods:title>
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<mods:date id="F3A0ED3DC0CAD8582CEACF7E9A288CA8">2019</mods:date>
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<mods:number id="5E64A5E3A8122D8264DA4D715D770631">2019-03-31</mods:number>
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<mods:identifier id="357EF73B11CDA79E8367AB5AEBA18F34" type="DOI">10.1016/j.phytochem.2018.12.010</mods:identifier>
<mods:identifier id="17DB415F4E5F268CACBBF1982F62DF4F" type="ISSN">1873-3700</mods:identifier>
<mods:identifier id="2A3725673326A1A05A84363906854D83" type="Zenodo-Dep">10481956</mods:identifier>
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<subSubSection id="57C66BA8FFE3FFDCA678FF200631CDC8" box="[100,631,215,234]" pageId="1" pageNumber="109" type="nomenclature">
<paragraph id="1F633823FFE3FFDCA678FF200631CDC8" blockId="1.[100,631,215,234]" box="[100,631,215,234]" pageId="1" pageNumber="109">
<emphasis id="2DA8E431FFE3FFDCA678FF200631CDC8" bold="true" box="[100,631,215,234]" italics="true" pageId="1" pageNumber="109">
2.1. Anthocyanins in the red-purple flowers of
<taxonomicName id="D8DC43A0FFE3FFDCA410FF200631CDC8" ID-CoL="3P7D4" authority="(L.)" box="[524,631,215,234]" class="Magnoliopsida" family="Brassicaceae" genus="Iberis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="umbellata">I. umbellata</taxonomicName>
</emphasis>
</paragraph>
</subSubSection>
<subSubSection id="57C66BA8FFE3FFDCA699FEF8079DCF52" pageId="1" pageNumber="109" type="description">
<paragraph id="1F633823FFE3FFDCA699FEF804B0CED5" blockId="1.[100,771,270,1490]" pageId="1" pageNumber="109">
By HPLC analysis of an extract from the red-purple flowers of
<taxonomicName id="D8DC43A0FFE3FFDCA4C9FEF904F0CC1F" class="Magnoliopsida" family="Brassicaceae" genus="Iberis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="umbellata">
<emphasis id="2DA8E431FFE3FFDCA4C9FEF904F0CC1F" bold="true" italics="true" pageId="1" pageNumber="109">Iberis umbellata</emphasis>
</taxonomicName>
, I identified more than 20 anthocyanin peaks. Among these peaks, six major anthocyanin peaks were isolated from the flowers of ‘Candycane Red’ (
<figureCitation id="87E724A6FFE3FFDCA684FE95048FCC57" box="[152,201,354,373]" captionStart="Fig" captionStartId="1.[980,1010,1538,1555]" captionTargetBox="[101,949,1559,1968]" captionTargetId="figure-1208@1.[100,950,1537,1969]" captionTargetPageId="1" captionText="Fig. 1. HPLC profile (530 nm) and structure of acylated anthocyanins isolated from the red-purple flowers of I. umbellata 'Candycane Red'. 1: pelargonidin 3-O-[2-O-(glucosyl)-6-O-(p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)- glucoside]. 2: pelargonidin 3-O-[2-O-(2-O-(sinapoyl)-glucosyl)-6-O-(4-O-(glucosyl)-p-coumaroyl)-glucoside]-5-O-[6- O-(malonyl)-glucoside]. 3: pelargonidin 3-O-[2-O-(2-O-(feruloyl)-glucosyl)-6-O-(4-O-(glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]. 4: pelargonidin 3-O- [2-O-(2-O-(sinapoyl)-glucosyl)-6-O-(4-O-(6-O-(feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]. 5: pelargonidin 3-O-[2-O-(2-O-(feruloyl)-glucosyl)-6- O-(4-O-(6-O-(feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5- O-[6-O-(malonyl)-glucoside]. 6: pelargonidin 3-O-[2-O-(2- O-(feruloyl)-glucosyl)-6-O-(4-O-(6-O-(4-O-(glucosyl)-feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]." figureDoi="http://doi.org/10.5281/zenodo.10481958" httpUri="https://zenodo.org/record/10481958/files/figure.png" pageId="1" pageNumber="109">Fig. 1</figureCitation>
) and ‘Candycane Rose’ by extraction by 5% HOAc, and purified according to the procedure described previously (
<bibRefCitation id="7B4D45D2FFE3FFDCA430FE89068CCCB3" author="Saito, N. &amp; Tatsuzawa, F. &amp; Suenaga, E. &amp; Toki, K. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[556,714,382,402]" pageId="1" pageNumber="109" 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>
). The same six pigments were found in both cultivars, but the profiles differed slightly. Percentages of total anthocyanin contents based on HPLC peak aerias at
<quantity id="D82495C6FFE3FFDCA6A4FE2504BACCC7" box="[184,252,466,485]" metricMagnitude="-7" metricUnit="m" metricValue="5.3" pageId="1" pageNumber="109" unit="nm" value="530.0">530 nm</quantity>
are as follows for the two cultivars: ‘Candycane Red’:
<emphasis id="2DA8E431FFE3FFDCA4ECFE2506BACCC7" bold="true" box="[752,764,466,485]" pageId="1" pageNumber="109">1</emphasis>
: 4.0%,
<emphasis id="2DA8E431FFE3FFDCA682FE1904ECCF23" bold="true" box="[158,170,494,513]" pageId="1" pageNumber="109">2</emphasis>
: 5.8%,
<emphasis id="2DA8E431FFE3FFDCA6ECFE1904BACF23" bold="true" box="[240,252,494,513]" pageId="1" pageNumber="109">3</emphasis>
: 8.0%,
<emphasis id="2DA8E431FFE3FFDCA75EFE190508CF23" bold="true" box="[322,334,494,513]" pageId="1" pageNumber="109">4</emphasis>
: 10.3%,
<emphasis id="2DA8E431FFE3FFDCA783FE1905EDCF23" bold="true" box="[415,427,494,513]" pageId="1" pageNumber="109">5</emphasis>
: 15.9%,
<emphasis id="2DA8E431FFE3FFDCA7E0FE19064ECF23" bold="true" box="[508,520,494,513]" pageId="1" pageNumber="109">6</emphasis>
: 7.6%; ‘Candycane Rose’
<emphasis id="2DA8E431FFE3FFDCA4ECFE1906BACF23" bold="true" box="[752,764,494,513]" pageId="1" pageNumber="109">1</emphasis>
: 5.6%,
<emphasis id="2DA8E431FFE3FFDCA682FDFD04ECCF3F" bold="true" box="[158,170,522,541]" pageId="1" pageNumber="109">2</emphasis>
: 13.4%,
<emphasis id="2DA8E431FFE3FFDCA6E7FDFD0541CF3F" bold="true" box="[251,263,522,541]" pageId="1" pageNumber="109">3</emphasis>
: 6.9%,
<emphasis id="2DA8E431FFE3FFDCA751FDFD051FCF3F" bold="true" box="[333,345,522,541]" pageId="1" pageNumber="109">4</emphasis>
: 9.6%,
<emphasis id="2DA8E431FFE3FFDCA782FDFD05ECCF3F" bold="true" box="[414,426,522,541]" pageId="1" pageNumber="109">5</emphasis>
: 6.9%,
<emphasis id="2DA8E431FFE3FFDCA7ECFDFD05BACF3F" bold="true" box="[496,508,522,541]" pageId="1" pageNumber="109">6</emphasis>
: 8.3%. The chromatographic and spectroscopic properties of these pigments are summarized in Experimental. Visible maxima (
<emphasis id="2DA8E431FFE3FFDCA756FDB60510CF76" bold="true" box="[330,342,577,596]" italics="true" pageId="1" pageNumber="109">λ</emphasis>
<subScript id="83583A66FFE3FFDCA749FDBC0537CF75" attach="left" box="[341,369,587,599]" fontSize="5" pageId="1" pageNumber="109">max</subScript>
) from UV–VIS spectra of
<quantity id="D82495C6FFE3FFDCA47CFDB606DACF76" box="[608,668,577,597]" metricMagnitude="-2" metricUnit="m" metricValue="8.89" metricValueMax="15.24" metricValueMin="2.54" pageId="1" pageNumber="109" unit="in" value="3.5" valueMax="6.0" valueMin="1.0">
<emphasis id="2DA8E431FFE3FFDCA47CFDB606C4CF76" bold="true" box="[608,642,577,597]" pageId="1" pageNumber="109">1–6</emphasis>
in
</quantity>
0.1% HCl-MeOH were observed at
<quantity id="D82495C6FFE3FFDCA722FDAA05F6CF53" box="[318,432,605,625]" metricMagnitude="-7" metricUnit="m" metricValue="5.135" metricValueMax="5.1899999999999995" metricValueMin="5.08" pageId="1" pageNumber="109" unit="nm" value="513.5" valueMax="519.0" valueMin="508.0">508–519 nm</quantity>
. In addition, the ratio of absorbance at
<quantity id="D82495C6FFE3FFDCA678FD8E04E1CFAF" box="[100,167,633,653]" metricMagnitude="-7" metricUnit="m" metricValue="4.4" pageId="1" pageNumber="109" unit="nm" value="440.0">440 nm</quantity>
relative to the visible maximum (
<emphasis id="2DA8E431FFE3FFDCA7ECFD8D05BDCFAF" bold="true" box="[496,507,634,653]" italics="true" pageId="1" pageNumber="109">E</emphasis>
<subScript id="83583A66FFE3FFDCA7E0FD750653CFAC" attach="right" box="[508,533,642,654]" fontSize="5" pageId="1" pageNumber="109">440</subScript>
/
<emphasis id="2DA8E431FFE3FFDCA403FD8D066CCFAF" bold="true" box="[543,554,634,653]" italics="true" pageId="1" pageNumber="109">E</emphasis>
<subScript id="83583A66FFE3FFDCA436FD75061DCFAC" attach="left" box="[554,603,642,654]" fontSize="5" pageId="1" pageNumber="109">vis.max</subScript>
) were 0.17–0.20. With the addition of AlCl
<subScript id="83583A66FFE3FFDCA753FD690511CF88" attach="left" box="[335,343,670,682]" fontSize="5" pageId="1" pageNumber="109">3</subScript>
,
<emphasis id="2DA8E431FFE3FFDCA779FD6205C1CF8A" bold="true" box="[357,391,661,681]" pageId="1" pageNumber="109">1–6</emphasis>
did not exhibit a bathochromic shift, indicating that they lacked a vicinal hydroxyl group in the B-ring. Therefore, these initial data suggest that
<emphasis id="2DA8E431FFE3FFDCA761FD3A05D9CFC2" bold="true" box="[381,415,717,736]" pageId="1" pageNumber="109">1–6</emphasis>
may have a pelargonidin 3,5-glycosyl
<typeStatus id="C0678681FFE3FFDCA678FD1E04CDCFDE" box="[100,139,745,764]" pageId="1" pageNumber="109">type</typeStatus>
structure (
<bibRefCitation id="7B4D45D2FFE3FFDCA6E5FD1E0650CFDE" author="Tatsuzawa, F. &amp; Shinoda, K." box="[249,534,745,764]" pageId="1" pageNumber="109" 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>
). This was subsequently confirmed by the NMR analysis. The ratio of
<emphasis id="2DA8E431FFE3FFDCA415FCF20652CE3A" bold="true" box="[521,532,773,792]" italics="true" pageId="1" pageNumber="109">E</emphasis>
<subScript id="83583A66FFE3FFDCA409FCF90669CE38" attach="right" box="[533,559,782,794]" fontSize="5" pageId="1" pageNumber="109">acyl</subScript>
/
<emphasis id="2DA8E431FFE3FFDCA425FCF20602CE3A" bold="true" box="[569,580,773,792]" italics="true" pageId="1" pageNumber="109">E</emphasis>
<subScript id="83583A66FFE3FFDCA458FCF90630CE38" attach="left" box="[580,630,782,794]" fontSize="5" pageId="1" pageNumber="109">vis.max</subScript>
was 0.90–1.63 suggesting that they had one, two or three hydroxycinnamic acid units (
<bibRefCitation id="7B4D45D2FFE3FFDCA670FCCA0556CE72" author="Saito, N. &amp; Tatsuzawa, F. &amp; Suenaga, E. &amp; Toki, K. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[108,272,829,848]" pageId="1" pageNumber="109" 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>
) which was also confirmed in the subsequent NMR analysis. Pigment
<emphasis id="2DA8E431FFE3FFDCA71BFCAF0555CE49" bold="true" box="[263,275,856,875]" pageId="1" pageNumber="109">1</emphasis>
was identified by HR-FAB MS (calc. for C
<subScript id="83583A66FFE3FFDCA48EFC9606E5CE4F" attach="both" box="[658,675,865,877]" fontSize="5" pageId="1" pageNumber="109">45</subScript>
H
<subScript id="83583A66FFE3FFDCA4AEFC950685CE4C" attach="both" box="[690,707,866,878]" fontSize="5" pageId="1" pageNumber="109">49</subScript>
O
<subScript id="83583A66FFE3FFDCA4CEFC9606A5CE4F" attach="left" box="[722,739,865,877]" fontSize="5" pageId="1" pageNumber="109">25</subScript>
requires: 989.2563. Found: 989.2556) and comparison of HPLC, TLC, and UV–Vis data (see section 4.3.1) with pelargonidin 3-
<emphasis id="2DA8E431FFE3FFDCA44DFC670619CE81" bold="true" box="[593,607,912,931]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-[2-
<emphasis id="2DA8E431FFE3FFDCA463FC6706CBCE81" bold="true" box="[639,653,912,931]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-(β-glucopyranosyl)-6-
<emphasis id="2DA8E431FFE3FFDCA6A0FC5B048CCE9D" bold="true" box="[188,202,940,959]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-(
<emphasis id="2DA8E431FFE3FFDCA6C4FC5B0554CE9D" bold="true" box="[216,274,940,960]" italics="true" pageId="1" pageNumber="109">trans -p</emphasis>
-coumaroyl)-β-glucopyranoside]-5-
<emphasis id="2DA8E431FFE3FFDCA45BFC5B0613CE9D" bold="true" box="[583,597,940,959]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-[6-
<emphasis id="2DA8E431FFE3FFDCA469FC5B06C5CE9D" bold="true" box="[629,643,940,959]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-(malonyl)-β-glucopyranoside] obtained from
<taxonomicName id="D8DC43A0FFE3FFDCA794FC3F0744CEF9" authority="(Tatsuzawa et al., 2008 b)" baseAuthorityName="Tatsuzawa" baseAuthorityYear="2008" box="[392,770,968,987]" class="Magnoliopsida" family="Brassicaceae" genus="Raphanus" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="sativus">
<emphasis id="2DA8E431FFE3FFDCA794FC3F065FCEF9" bold="true" box="[392,537,968,987]" italics="true" pageId="1" pageNumber="109">Raphanus sativus</emphasis>
(
<bibRefCitation id="7B4D45D2FFE3FFDCA43AFC3F06BCCEF9" author="Tatsuzawa, F. &amp; Toki, K. &amp; Saito, N. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[550,762,968,987]" pageId="1" pageNumber="109" refId="ref15560" refString="Tatsuzawa, F., Toki, K., Saito, N., Shinoda, K., Shigihara, A., Honda, T., 2008 b." type="book" year="2008">Tatsuzawa et al., 2008b</bibRefCitation>
)
</taxonomicName>
(
<figureCitation id="87E724A6FFE3FFDCA670FC1304D8CED5" box="[108,158,996,1015]" captionStart="Fig" captionStartId="2.[158,188,596,613]" captionTargetBox="[345,1243,158,569]" captionTargetId="figure-1084@2.[340,1247,152,573]" captionTargetPageId="2" captionText="Fig. 2. Acylated anthocyanins from the red-purple flowers of Iberis umbellata. Observed main NOEs of pigments 2, 4, and 6 are indicated by arrows." figureDoi="http://doi.org/10.5281/zenodo.10481960" httpUri="https://zenodo.org/record/10481960/files/figure.png" pageId="1" pageNumber="109">Fig. 2</figureCitation>
,
<figureCitation id="87E724A6FFE3FFDCA6B7FC1304AECED5" box="[171,232,996,1015]" captionStart="Fig" captionStartId="1.[980,1010,1538,1555]" captionTargetBox="[101,949,1559,1968]" captionTargetId="figure-1208@1.[100,950,1537,1969]" captionTargetPageId="1" captionText="Fig. 1. HPLC profile (530 nm) and structure of acylated anthocyanins isolated from the red-purple flowers of I. umbellata 'Candycane Red'. 1: pelargonidin 3-O-[2-O-(glucosyl)-6-O-(p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)- glucoside]. 2: pelargonidin 3-O-[2-O-(2-O-(sinapoyl)-glucosyl)-6-O-(4-O-(glucosyl)-p-coumaroyl)-glucoside]-5-O-[6- O-(malonyl)-glucoside]. 3: pelargonidin 3-O-[2-O-(2-O-(feruloyl)-glucosyl)-6-O-(4-O-(glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]. 4: pelargonidin 3-O- [2-O-(2-O-(sinapoyl)-glucosyl)-6-O-(4-O-(6-O-(feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]. 5: pelargonidin 3-O-[2-O-(2-O-(feruloyl)-glucosyl)-6- O-(4-O-(6-O-(feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5- O-[6-O-(malonyl)-glucoside]. 6: pelargonidin 3-O-[2-O-(2- O-(feruloyl)-glucosyl)-6-O-(4-O-(6-O-(4-O-(glucosyl)-feruloyl)-glucosyl)-p-coumaroyl)-glucoside]-5-O-[6-O-(malonyl)-glucoside]." figureDoi="http://doi.org/10.5281/zenodo.10481958" httpUri="https://zenodo.org/record/10481958/files/figure.png" pageId="1" pageNumber="109">Fig. S1</figureCitation>
).
</paragraph>
<paragraph id="1F633823FFE3FFDCA69AFBF706B5C840" blockId="1.[100,771,270,1490]" pageId="1" pageNumber="109">
From all pigments
<emphasis id="2DA8E431FFE3FFDCA72FFBF70510C931" bold="true" box="[307,342,1024,1043]" pageId="1" pageNumber="109">2–6</emphasis>
(
<emphasis id="2DA8E431FFE3FFDCA778FBF7053EC931" bold="true" box="[356,376,1024,1043]" italics="true" pageId="1" pageNumber="109">ca</emphasis>
.
<quantity id="D82495C6FFE3FFDCA79FFBF705F6C931" box="[387,432,1024,1043]" metricMagnitude="-6" metricUnit="kg" metricValue="1.0" pageId="1" pageNumber="109" unit="mg" value="1.0">1 mg</quantity>
each), the same deacyl anthocyanin was obtained from the alkaline hydrolysis (see section 4.4.). These were identified to be pelargonidin 3-sophoroside-5-glucoside by direct comparison of HPLC behavior with those of authentic samples obtained from
<taxonomicName id="D8DC43A0FFE3FFDCA686FB98067AC9A1" authority="(Tatsuzawa et al., 2008 b)" baseAuthorityName="Tatsuzawa" baseAuthorityYear="2008" box="[154,572,1135,1155]" class="Magnoliopsida" family="Brassicaceae" genus="Raphanus" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="sativus">
<emphasis id="2DA8E431FFE3FFDCA686FB980571C9A0" bold="true" box="[154,311,1135,1154]" italics="true" pageId="1" pageNumber="109">Raphanus sativus</emphasis>
(
<bibRefCitation id="7B4D45D2FFE3FFDCA754FB870674C9A0" author="Tatsuzawa, F. &amp; Toki, K. &amp; Saito, N. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[328,562,1135,1155]" pageId="1" pageNumber="109" refId="ref15560" refString="Tatsuzawa, F., Toki, K., Saito, N., Shinoda, K., Shigihara, A., Honda, T., 2008 b." type="book" year="2008">Tatsuzawa et al., 2008b</bibRefCitation>
)
</taxonomicName>
. 4-
<emphasis id="2DA8E431FFE3FFDCA440FB98062DC9A0" bold="true" box="[604,619,1135,1154]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-glucosyl-ferulic acid, 4-
<emphasis id="2DA8E431FFE3FFDCA6B6FB7C04FFC9BC" bold="true" box="[170,185,1163,1182]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-glucosyl-
<emphasis id="2DA8E431FFE3FFDCA708FB7B0558C9BD" bold="true" box="[276,286,1164,1183]" italics="true" pageId="1" pageNumber="109">p</emphasis>
-coumaric acid, and ferulic acid (
<bibRefCitation id="7B4D45D2FFE3FFDCA449FB7C06B2C9BC" author="Saito, N. &amp; Tatsuzawa, F. &amp; Suenaga, E. &amp; Toki, K. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[597,756,1163,1183]" pageId="1" pageNumber="109" 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>
), 4-
<emphasis id="2DA8E431FFE3FFDCA66BFB5004C0C998" bold="true" box="[119,134,1191,1210]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-glucosyl-
<emphasis id="2DA8E431FFE3FFDCA6FDFB5F04ADC999" bold="true" box="[225,235,1192,1211]" italics="true" pageId="1" pageNumber="109">p</emphasis>
-coumaric acid and ferulic acid, 4-
<emphasis id="2DA8E431FFE3FFDCA42CFB500679C998" bold="true" box="[560,575,1191,1210]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-glucosyl-
<emphasis id="2DA8E431FFE3FFDCA485FB5F06E5C999" bold="true" box="[665,675,1192,1211]" italics="true" pageId="1" pageNumber="109">p</emphasis>
-coumaric acid and sinapic acid, and 4-
<emphasis id="2DA8E431FFE3FFDCA763FB3405C8C9F4" bold="true" box="[383,398,1219,1238]" italics="true" pageId="1" pageNumber="109">O</emphasis>
-glucosyl-
<emphasis id="2DA8E431FFE3FFDCA7F5FB3405B5C9F4" bold="true" box="[489,499,1219,1238]" italics="true" pageId="1" pageNumber="109">p</emphasis>
-coumaric acid, ferulic acid, and sinapic acid were obtained from the alkaline hydrolysate of pigment
<emphasis id="2DA8E431FFE3FFDCA686FB0C04E0C82C" bold="true" box="[154,166,1275,1294]" pageId="1" pageNumber="109">6</emphasis>
, pigments
<emphasis id="2DA8E431FFE3FFDCA712FB0C055CC82C" bold="true" box="[270,282,1275,1294]" pageId="1" pageNumber="109">3</emphasis>
and
<emphasis id="2DA8E431FFE3FFDCA756FB0C0510C82C" bold="true" box="[330,342,1275,1294]" pageId="1" pageNumber="109">5</emphasis>
, pigment
<emphasis id="2DA8E431FFE3FFDCA7AAFB0C0584C82C" bold="true" box="[438,450,1275,1294]" pageId="1" pageNumber="109">2</emphasis>
, and pigment
<emphasis id="2DA8E431FFE3FFDCA456FB0C0610C82C" bold="true" box="[586,598,1275,1294]" pageId="1" pageNumber="109">4</emphasis>
, respectively, and they were identified by comparison of HPLC behavior with those of authentic samples obtained from a purple-violet cultivar of
<taxonomicName id="D8DC43A0FFE3FFDCA484FAC40744C867" box="[664,770,1330,1350]" class="Magnoliopsida" family="Brassicaceae" genus="Iberis" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="umbellata">
<emphasis id="2DA8E431FFE3FFDCA484FAC40744C867" bold="true" box="[664,770,1330,1350]" italics="true" pageId="1" pageNumber="109">I. umbellata</emphasis>
</taxonomicName>
using the same process as for alkaline hydrolysis (
<bibRefCitation id="7B4D45D2FFE3FFDCA45FFAB806A0C840" author="Saito, N. &amp; Tatsuzawa, F. &amp; Suenaga, E. &amp; Toki, K. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[579,742,1359,1378]" pageId="1" pageNumber="109" 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>
).
</paragraph>
<paragraph id="1F633823FFE3FFDCA69AFA9D079DCF52" blockId="1.[100,771,270,1490]" lastBlockId="1.[818,1488,159,624]" pageId="1" pageNumber="109">
Elemental components of
<emphasis id="2DA8E431FFE3FFDCA79DFA9D05E2C85F" bold="true" box="[385,420,1386,1406]" pageId="1" pageNumber="109">2–6</emphasis>
were confirmed by measuring their high resolution FAB mass spectra (HR-FAB MS) (LMS-700, JEOL Ltd.). To obtain information on the linkages among the aglycone, sugars, and/ or acids as well as to investigate the structural similarity of these pigments, partial hydrolysis (see section 4.5.) of
<emphasis id="2DA8E431FFE3FFDCA2E5FF68015ACD90" bold="true" box="[1273,1308,159,179]" pageId="1" pageNumber="109">1–6</emphasis>
was carried with a procedure described previously (
<bibRefCitation id="7B4D45D2FFE3FFDCA276FF4C014BCDEC" author="Saito, N. &amp; Tatsuzawa, F. &amp; Suenaga, E. &amp; Toki, K. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[1130,1293,187,206]" pageId="1" pageNumber="109" 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>
). Pelargonidin 3-sophoroside-5-glucoside was detected in the hydrolysates as intermediary pigment products. The intermediate was confirmed by comparing HPLC results to those of authentic deacylated anthocyanin obtained from
<taxonomicName id="D8DC43A0FFE3FFDCA52EFEDD0088CC1C" authority="(Tatsuzawa et al., 2008 b)" baseAuthorityName="Tatsuzawa" baseAuthorityYear="2008" box="[818,1230,298,318]" class="Magnoliopsida" family="Brassicaceae" genus="Raphanus" kingdom="Plantae" order="Brassicales" pageId="1" pageNumber="109" phylum="Tracheophyta" rank="species" species="sativus">
<emphasis id="2DA8E431FFE3FFDCA52EFEDD078BCC1F" bold="true" box="[818,973,298,317]" italics="true" pageId="1" pageNumber="109">Raphanus sativus</emphasis>
(
<bibRefCitation id="7B4D45D2FFE3FFDCA5C1FEDC0082CC1C" author="Tatsuzawa, F. &amp; Toki, K. &amp; Saito, N. &amp; Shinoda, K. &amp; Shigihara, A. &amp; Honda, T." box="[989,1220,299,318]" pageId="1" pageNumber="109" refId="ref15560" refString="Tatsuzawa, F., Toki, K., Saito, N., Shinoda, K., Shigihara, A., Honda, T., 2008 b." type="book" year="2008">Tatsuzawa et al., 2008b</bibRefCitation>
)
</taxonomicName>
. Pigment
<emphasis id="2DA8E431FFE3FFDCA32CFEDD017ACC1F" bold="true" box="[1328,1340,298,317]" pageId="1" pageNumber="109">1</emphasis>
was in the hydrolysate as one of the intermediary pigment products from pigments
<emphasis id="2DA8E431FFE3FFDCA52EFE950713CC57" bold="true" box="[818,853,354,374]" pageId="1" pageNumber="109">2–6</emphasis>
. The pigments
<emphasis id="2DA8E431FFE3FFDCA5FBFE9507B5CC57" bold="true" box="[999,1011,354,373]" pageId="1" pageNumber="109">1</emphasis>
,
<emphasis id="2DA8E431FFE3FFDCA21CFE95004ACC57" bold="true" box="[1024,1036,354,373]" pageId="1" pageNumber="109">3</emphasis>
, and
<emphasis id="2DA8E431FFE3FFDCA25EFE950008CC57" bold="true" box="[1090,1102,354,373]" pageId="1" pageNumber="109">5</emphasis>
were detected in the hydrolysate of
<emphasis id="2DA8E431FFE3FFDCA3B5FE9501F3CC57" bold="true" box="[1449,1461,354,373]" pageId="1" pageNumber="109">6</emphasis>
as intermediary pigment products. Similarly,
<emphasis id="2DA8E431FFE3FFDCA2DEFE890088CCB3" bold="true" box="[1218,1230,382,401]" pageId="1" pageNumber="109">1</emphasis>
and
<emphasis id="2DA8E431FFE3FFDCA2E1FE89014FCCB3" bold="true" box="[1277,1289,382,401]" pageId="1" pageNumber="109">3</emphasis>
were detected in the hydrolysate of
<emphasis id="2DA8E431FFE3FFDCA5A2FE6D078CCC8F" bold="true" box="[958,970,410,429]" pageId="1" pageNumber="109">5</emphasis>
. Pigments
<emphasis id="2DA8E431FFE3FFDCA22FFE6D0079CC8F" bold="true" box="[1075,1087,410,429]" pageId="1" pageNumber="109">1</emphasis>
and
<emphasis id="2DA8E431FFE3FFDCA273FE6D003DCC8F" bold="true" box="[1135,1147,410,429]" pageId="1" pageNumber="109">2</emphasis>
were detected in the hydrolysate of
<emphasis id="2DA8E431FFE3FFDCA52EFE410778CCEB" bold="true" box="[818,830,438,457]" pageId="1" pageNumber="109">4</emphasis>
. Moreover, pigment
<emphasis id="2DA8E431FFE3FFDCA210FE41005ECCEB" bold="true" box="[1036,1048,438,457]" pageId="1" pageNumber="109">1</emphasis>
was detected in the hydrolysate of
<emphasis id="2DA8E431FFE3FFDCA360FE4101CECCEB" bold="true" box="[1404,1416,438,457]" pageId="1" pageNumber="109">2</emphasis>
and
<emphasis id="2DA8E431FFE3FFDCA3A1FE41018FCCEB" bold="true" box="[1469,1481,438,457]" pageId="1" pageNumber="109">3</emphasis>
. From these results, the structures of
<emphasis id="2DA8E431FFE3FFDCA294FE2500EDCCC7" bold="true" box="[1160,1195,466,485]" pageId="1" pageNumber="109">2–6</emphasis>
were presumed to be based on pigment
<emphasis id="2DA8E431FFE3FFDCA595FE1907D3CF23" bold="true" box="[905,917,494,513]" pageId="1" pageNumber="109">1</emphasis>
. The structures of
<emphasis id="2DA8E431FFE3FFDCA245FE19003ACF23" bold="true" box="[1113,1148,494,513]" pageId="1" pageNumber="109">2–6</emphasis>
were elucidated further based on analyses of their
<superScript id="E8A9956BFFE3FFDCA5CEFDF1079DCF30" attach="right" box="[978,987,518,530]" fontSize="5" pageId="1" pageNumber="109">1</superScript>
H (400 MHz),
<superScript id="E8A9956BFFE3FFDCA27EFDF10032CF30" attach="right" box="[1122,1140,518,530]" fontSize="5" pageId="1" pageNumber="109">13</superScript>
C (100 MHz) and 2D (COSY, NOESY,
<superScript id="E8A9956BFFE3FFDCA52EFDD5077DCF0C" attach="right" box="[818,827,546,558]" fontSize="5" pageId="1" pageNumber="109">1</superScript>
H-
<superScript id="E8A9956BFFE3FFDCA54DFDD50725CF0C" attach="both" box="[849,867,546,558]" fontSize="5" pageId="1" pageNumber="109">13</superScript>
C HMQC, and
<superScript id="E8A9956BFFE3FFDCA5E0FDD50043CF0C" attach="right" box="[1020,1029,546,558]" fontSize="5" pageId="1" pageNumber="109">1</superScript>
H-
<superScript id="E8A9956BFFE3FFDCA207FDD5006BCF0C" attach="both" box="[1051,1069,546,558]" fontSize="5" pageId="1" pageNumber="109">13</superScript>
C HMBC) NMR (JNM AL-400, JEOL Ltd.,
<collectingRegion id="DD18F6C1FFE3FFDCA52EFDB60729CF76" box="[818,879,577,596]" country="Japan" name="Tokyo" pageId="1" pageNumber="109">Tokyo</collectingRegion>
,
<collectingCountry id="67CB78B3FFE3FFDCA561FDB507F0CF77" box="[893,950,578,597]" name="Japan" pageId="1" pageNumber="109">Japan</collectingCountry>
) spectra in CF
<subScript id="83583A66FFE3FFDCA257FDBC0012CF75" attach="both" box="[1099,1108,587,599]" fontSize="5" pageId="1" pageNumber="109">3</subScript>
COOD-DMSO‑
<emphasis id="2DA8E431FFE3FFDCA2C5FDB600A2CF76" bold="true" box="[1241,1252,577,596]" italics="true" pageId="1" pageNumber="109">d</emphasis>
<subScript id="83583A66FFE3FFDCA2F8FDBC00ABCF75" attach="left" box="[1252,1261,587,599]" fontSize="5" pageId="1" pageNumber="109">6</subScript>
(1:9) with TMS as an internal standard.
</paragraph>
</subSubSection>
</treatment>
</document>
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