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...

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Bibliographic Details
Published in:International journal of molecular sciences 2021-04, Vol.22 (8), p.4044
Main Authors: Kondo, Tadao, Hagihara, Seiji, Takaya, Yoshiaki, Yoshida, Kumi
Format: Article
Language:English
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
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Summary: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.
ISSN:1422-0067
1661-6596
1422-0067
DOI:10.3390/ijms22084044