Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i>
The bluish-purple petals of Chinese bellflower, <i>Platycodon grandiflorum</i> (kikyo in Japanese), contain platyconin (<b>1</b>) as the major anthocyanin. Platyconin (<b>1</b>) is a polyacylated anthocyanin with two caffeoyl residues at the 7-position, and its co...
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MDPI AG
2021-04-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/8/4044 |
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| author | Tadao Kondo Seiji Hagihara Yoshiaki Takaya Kumi Yoshida |
| author_facet | Tadao Kondo Seiji Hagihara Yoshiaki Takaya Kumi Yoshida |
| author_sort | Tadao Kondo |
| collection | DOAJ |
| description | The bluish-purple petals of Chinese bellflower, <i>Platycodon grandiflorum</i> (kikyo in Japanese), contain platyconin (<b>1</b>) as the major anthocyanin. Platyconin (<b>1</b>) 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 (<b>2</b>–<b>5</b>) and three new anthocyanins (<b>6</b>–<b>8</b>) were identified, which contained a delphinidin chromophore, and four of these (<b>5</b>–<b>8</b>) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-<i>O</i>-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week. |
| first_indexed | 2024-03-10T12:20:04Z |
| format | Article |
| id | doaj.art-315f93bc84a24180944579dc48b17a30 |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T12:20:04Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-315f93bc84a24180944579dc48b17a302023-11-21T15:34:23ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-04-01228404410.3390/ijms22084044Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i>Tadao Kondo0Seiji Hagihara1Yoshiaki Takaya2Kumi Yoshida3Graduate School of Informatics, Nagoya University, Chikusa, Nagoya 464-8601, JapanGraduate School of Informatics, Nagoya University, Chikusa, Nagoya 464-8601, JapanFaculty of Pharmacy, Meijo University, 150 Yagotoyama, Tenpaku, Nagoya 468-8503, JapanGraduate School of Informatics, Nagoya University, Chikusa, Nagoya 464-8601, JapanThe bluish-purple petals of Chinese bellflower, <i>Platycodon grandiflorum</i> (kikyo in Japanese), contain platyconin (<b>1</b>) as the major anthocyanin. Platyconin (<b>1</b>) 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 (<b>2</b>–<b>5</b>) and three new anthocyanins (<b>6</b>–<b>8</b>) were identified, which contained a delphinidin chromophore, and four of these (<b>5</b>–<b>8</b>) were diacylated anthocyanins, in which the acyl-glucosyl-acyl-glucosyl chain was attached at the 7-<i>O</i>-position of the delphinidin chromophore. These diacylated anthocyanins exhibited a bluish-purple color at pH 6, which was stable for more than a week.https://www.mdpi.com/1422-0067/22/8/4044bluish-purpledelphinidinintramolecular stacking<i>Platycodon grandiflorum</i>polyacylated anthocyaninstability |
| spellingShingle | Tadao Kondo Seiji Hagihara Yoshiaki Takaya Kumi Yoshida Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> International Journal of Molecular Sciences bluish-purple delphinidin intramolecular stacking <i>Platycodon grandiflorum</i> polyacylated anthocyanin stability |
| title | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> |
| title_full | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> |
| title_fullStr | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> |
| title_full_unstemmed | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> |
| title_short | Polyacylated Anthocyanins in Bluish-Purple Petals of Chinese Bellflower, <i>Platycodon grandiflorum</i> |
| title_sort | polyacylated anthocyanins in bluish purple petals of chinese bellflower i platycodon grandiflorum i |
| topic | bluish-purple delphinidin intramolecular stacking <i>Platycodon grandiflorum</i> polyacylated anthocyanin stability |
| url | https://www.mdpi.com/1422-0067/22/8/4044 |
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