Loading…
Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum
The bluish-purple petals of Chinese bellflower, (kikyo in Japanese), contain platyconin ( ) as the major anthocyanin. Platyconin ( ) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its color is stable in a diluted, weakly acidic aqueous solutions. HPLC analysis of the...
Saved in:
| Published in: | International journal of molecular sciences 2021-04, Vol.22 (8), p.4044 |
|---|---|
| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3 |
| container_end_page | |
| container_issue | 8 |
| container_start_page | 4044 |
| container_title | International journal of molecular sciences |
| container_volume | 22 |
| creator | Kondo, Tadao Hagihara, Seiji Takaya, Yoshiaki Yoshida, Kumi |
| description | The bluish-purple petals of Chinese bellflower,
(kikyo in Japanese), contain platyconin (
) as the major anthocyanin. Platyconin (
) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its color is stable in a diluted, weakly acidic aqueous solutions. HPLC analysis of the fresh petal extract showed the presence of several minor pigments. Photo-diode array detection of minor pigments suggested that some of these were polyacylated anthocyanins. To establish the relationship between structure and stability of the acylated anthocyanins and to obtain information on their biosynthetic pathways, minor pigments were isolated from the petals, and their structures were determined by MS and NMR analyses. Four known (
-
) and three new anthocyanins (
-
) were identified, which contained a delphinidin chromophore, and four of these (
-
) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-
-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week. |
| doi_str_mv | 10.3390/ijms22084044 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_315f93bc84a24180944579dc48b17a30</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_315f93bc84a24180944579dc48b17a30</doaj_id><sourcerecordid>2548644926</sourcerecordid><originalsourceid>FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3</originalsourceid><addsrcrecordid>eNpdkktv1DAQgCMEoqVw44wiceHQgB_jxL4gtSselSp1D3A2ju3seuXYi52A8u9xu6Xa9mTL881ne2aq6i1GHykV6JPbjZkQxAEBPKtOMRDSINR2z4_2J9WrnHcIEUqYeFmdlEQsBEKn1a919IvSi1eTNfVFmLZRLyq4kGsX6ks_u7xt1nPae1uv7aR8ruNQr7Yu2GzrS-v94ONfm87rdVEsOpoY6k1SwbgSSPP4unoxlCz75n49q35-_fJj9b25vvl2tbq4bjQDmJoeoWEAiwlXPe6w4dC2PQXSCdoKqlnPBAFjLNMDbsEg0grGCFM9azHHWNGz6urgNVHt5D65UaVFRuXk3UFMG6nS5LS3kmI2CNprDooA5kgAsE4YDbxcrSgqrs8H137uR2u0DVNS_pH0cSS4rdzEP5KjDgnCi-DDvSDF37PNkxxd1qVYKtg4Z0lYaVgHGENB3z9Bd3FOoZSqUMBbAEHaQp0fKJ1izskOD4_BSN6OgTweg4K_O_7AA_y_7_QfSr2tWA</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2548644926</pqid></control><display><type>article</type><title>Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum</title><source>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</source><source>PubMed Central (Open access)</source><creator>Kondo, Tadao ; Hagihara, Seiji ; Takaya, Yoshiaki ; Yoshida, Kumi</creator><creatorcontrib>Kondo, Tadao ; Hagihara, Seiji ; Takaya, Yoshiaki ; Yoshida, Kumi</creatorcontrib><description>The bluish-purple petals of Chinese bellflower,
(kikyo in Japanese), contain platyconin (
) as the major anthocyanin. Platyconin (
) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its color is stable in a diluted, weakly acidic aqueous solutions. HPLC analysis of the fresh petal extract showed the presence of several minor pigments. Photo-diode array detection of minor pigments suggested that some of these were polyacylated anthocyanins. To establish the relationship between structure and stability of the acylated anthocyanins and to obtain information on their biosynthetic pathways, minor pigments were isolated from the petals, and their structures were determined by MS and NMR analyses. Four known (
-
) and three new anthocyanins (
-
) were identified, which contained a delphinidin chromophore, and four of these (
-
) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-
-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week.</description><identifier>ISSN: 1422-0067</identifier><identifier>ISSN: 1661-6596</identifier><identifier>EISSN: 1422-0067</identifier><identifier>DOI: 10.3390/ijms22084044</identifier><identifier>PMID: 33919900</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acylation ; Anthocyanins ; Anthocyanins - chemistry ; Anthocyanins - genetics ; Aqueous solutions ; Biosynthetic Pathways - genetics ; bluish-purple ; Chromatography ; Chromophores ; Color ; delphinidin ; Flowers - anatomy & histology ; Flowers - chemistry ; Flowers - genetics ; High-performance liquid chromatography ; intramolecular stacking ; NMR ; Nuclear magnetic resonance ; Petals ; Pigmentation ; Pigments ; Platycodon - anatomy & histology ; Platycodon - chemistry ; Platycodon - genetics ; Platycodon grandiflorum ; polyacylated anthocyanin ; stability ; Structural stability</subject><ispartof>International journal of molecular sciences, 2021-04, Vol.22 (8), p.4044</ispartof><rights>2021 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3</citedby><cites>FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3</cites><orcidid>0000-0002-1238-6348</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2548644926/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2548644926?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33919900$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kondo, Tadao</creatorcontrib><creatorcontrib>Hagihara, Seiji</creatorcontrib><creatorcontrib>Takaya, Yoshiaki</creatorcontrib><creatorcontrib>Yoshida, Kumi</creatorcontrib><title>Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum</title><title>International journal of molecular sciences</title><addtitle>Int J Mol Sci</addtitle><description>The bluish-purple petals of Chinese bellflower,
(kikyo in Japanese), contain platyconin (
) as the major anthocyanin. Platyconin (
) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its color is stable in a diluted, weakly acidic aqueous solutions. HPLC analysis of the fresh petal extract showed the presence of several minor pigments. Photo-diode array detection of minor pigments suggested that some of these were polyacylated anthocyanins. To establish the relationship between structure and stability of the acylated anthocyanins and to obtain information on their biosynthetic pathways, minor pigments were isolated from the petals, and their structures were determined by MS and NMR analyses. Four known (
-
) and three new anthocyanins (
-
) were identified, which contained a delphinidin chromophore, and four of these (
-
) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-
-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week.</description><subject>Acylation</subject><subject>Anthocyanins</subject><subject>Anthocyanins - chemistry</subject><subject>Anthocyanins - genetics</subject><subject>Aqueous solutions</subject><subject>Biosynthetic Pathways - genetics</subject><subject>bluish-purple</subject><subject>Chromatography</subject><subject>Chromophores</subject><subject>Color</subject><subject>delphinidin</subject><subject>Flowers - anatomy & histology</subject><subject>Flowers - chemistry</subject><subject>Flowers - genetics</subject><subject>High-performance liquid chromatography</subject><subject>intramolecular stacking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Petals</subject><subject>Pigmentation</subject><subject>Pigments</subject><subject>Platycodon - anatomy & histology</subject><subject>Platycodon - chemistry</subject><subject>Platycodon - genetics</subject><subject>Platycodon grandiflorum</subject><subject>polyacylated anthocyanin</subject><subject>stability</subject><subject>Structural stability</subject><issn>1422-0067</issn><issn>1661-6596</issn><issn>1422-0067</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdkktv1DAQgCMEoqVw44wiceHQgB_jxL4gtSselSp1D3A2ju3seuXYi52A8u9xu6Xa9mTL881ne2aq6i1GHykV6JPbjZkQxAEBPKtOMRDSINR2z4_2J9WrnHcIEUqYeFmdlEQsBEKn1a919IvSi1eTNfVFmLZRLyq4kGsX6ks_u7xt1nPae1uv7aR8ruNQr7Yu2GzrS-v94ONfm87rdVEsOpoY6k1SwbgSSPP4unoxlCz75n49q35-_fJj9b25vvl2tbq4bjQDmJoeoWEAiwlXPe6w4dC2PQXSCdoKqlnPBAFjLNMDbsEg0grGCFM9azHHWNGz6urgNVHt5D65UaVFRuXk3UFMG6nS5LS3kmI2CNprDooA5kgAsE4YDbxcrSgqrs8H137uR2u0DVNS_pH0cSS4rdzEP5KjDgnCi-DDvSDF37PNkxxd1qVYKtg4Z0lYaVgHGENB3z9Bd3FOoZSqUMBbAEHaQp0fKJ1izskOD4_BSN6OgTweg4K_O_7AA_y_7_QfSr2tWA</recordid><startdate>20210414</startdate><enddate>20210414</enddate><creator>Kondo, Tadao</creator><creator>Hagihara, Seiji</creator><creator>Takaya, Yoshiaki</creator><creator>Yoshida, Kumi</creator><general>MDPI AG</general><general>MDPI</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>8G5</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>GUQSH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>M2O</scope><scope>MBDVC</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-1238-6348</orcidid></search><sort><creationdate>20210414</creationdate><title>Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum</title><author>Kondo, Tadao ; Hagihara, Seiji ; Takaya, Yoshiaki ; Yoshida, Kumi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acylation</topic><topic>Anthocyanins</topic><topic>Anthocyanins - chemistry</topic><topic>Anthocyanins - genetics</topic><topic>Aqueous solutions</topic><topic>Biosynthetic Pathways - genetics</topic><topic>bluish-purple</topic><topic>Chromatography</topic><topic>Chromophores</topic><topic>Color</topic><topic>delphinidin</topic><topic>Flowers - anatomy & histology</topic><topic>Flowers - chemistry</topic><topic>Flowers - genetics</topic><topic>High-performance liquid chromatography</topic><topic>intramolecular stacking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Petals</topic><topic>Pigmentation</topic><topic>Pigments</topic><topic>Platycodon - anatomy & histology</topic><topic>Platycodon - chemistry</topic><topic>Platycodon - genetics</topic><topic>Platycodon grandiflorum</topic><topic>polyacylated anthocyanin</topic><topic>stability</topic><topic>Structural stability</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kondo, Tadao</creatorcontrib><creatorcontrib>Hagihara, Seiji</creatorcontrib><creatorcontrib>Takaya, Yoshiaki</creatorcontrib><creatorcontrib>Yoshida, Kumi</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest_Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>Research Library (Alumni Edition)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>Research Library Prep</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>ProQuest_Research Library</collection><collection>Research Library (Corporate)</collection><collection>Publicly Available Content Database (Proquest) (PQ_SDU_P3)</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>International journal of molecular sciences</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kondo, Tadao</au><au>Hagihara, Seiji</au><au>Takaya, Yoshiaki</au><au>Yoshida, Kumi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum</atitle><jtitle>International journal of molecular sciences</jtitle><addtitle>Int J Mol Sci</addtitle><date>2021-04-14</date><risdate>2021</risdate><volume>22</volume><issue>8</issue><spage>4044</spage><pages>4044-</pages><issn>1422-0067</issn><issn>1661-6596</issn><eissn>1422-0067</eissn><abstract>The bluish-purple petals of Chinese bellflower,
(kikyo in Japanese), contain platyconin (
) as the major anthocyanin. Platyconin (
) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its color is stable in a diluted, weakly acidic aqueous solutions. HPLC analysis of the fresh petal extract showed the presence of several minor pigments. Photo-diode array detection of minor pigments suggested that some of these were polyacylated anthocyanins. To establish the relationship between structure and stability of the acylated anthocyanins and to obtain information on their biosynthetic pathways, minor pigments were isolated from the petals, and their structures were determined by MS and NMR analyses. Four known (
-
) and three new anthocyanins (
-
) were identified, which contained a delphinidin chromophore, and four of these (
-
) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-
-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>33919900</pmid><doi>10.3390/ijms22084044</doi><orcidid>https://orcid.org/0000-0002-1238-6348</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1422-0067 |
| ispartof | International journal of molecular sciences, 2021-04, Vol.22 (8), p.4044 |
| issn | 1422-0067 1661-6596 1422-0067 |
| language | eng |
| recordid | cdi_doaj_primary_oai_doaj_org_article_315f93bc84a24180944579dc48b17a30 |
| source | Publicly Available Content Database (Proquest) (PQ_SDU_P3); PubMed Central (Open access) |
| subjects | Acylation Anthocyanins Anthocyanins - chemistry Anthocyanins - genetics Aqueous solutions Biosynthetic Pathways - genetics bluish-purple Chromatography Chromophores Color delphinidin Flowers - anatomy & histology Flowers - chemistry Flowers - genetics High-performance liquid chromatography intramolecular stacking NMR Nuclear magnetic resonance Petals Pigmentation Pigments Platycodon - anatomy & histology Platycodon - chemistry Platycodon - genetics Platycodon grandiflorum polyacylated anthocyanin stability Structural stability |
| title | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, Platycodon grandiflorum |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T08%3A35%3A18IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Polyacylated%20Anthocyanins%20in%20Bluish-Purple%20Petals%20of%20Chinese%20Bellflower,%20Platycodon%20grandiflorum&rft.jtitle=International%20journal%20of%20molecular%20sciences&rft.au=Kondo,%20Tadao&rft.date=2021-04-14&rft.volume=22&rft.issue=8&rft.spage=4044&rft.pages=4044-&rft.issn=1422-0067&rft.eissn=1422-0067&rft_id=info:doi/10.3390/ijms22084044&rft_dat=%3Cproquest_doaj_%3E2548644926%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c544t-b00ff4e128ab171d8466b342793693c5b5924dde5cf164d02695525ab561811a3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2548644926&rft_id=info:pmid/33919900&rfr_iscdi=true |