Contribution of each caffeoyl residue of the pigment molecule of gentiodelphin to blue color development

被引：55

作者：

Yoshida, K ^{[2
]}

Toyama, Y

Kameda, K

Kondo, T

机构：

[1] Sugiyama Jogakuen Univ, Sch Life Sci, Nagoya, Aichi 4648662, Japan

[2] Nagoya Univ, Grad Sch Human Informat, Nagoya, Aichi 4648601, Japan

[3] Nagoya Univ, Chem Instrument Ctr, Nagoya, Aichi 4648602, Japan

来源：

PHYTOCHEMISTRY | 2000年 / 54卷 / 01期

关键词：

Gentiana makinoi; gentiodelphin; acylated anthocyanin; intramolecular stacking; flower color development; conformational analysis;

D O I：

10.1016/S0031-9422(00)00049-2

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

To clarify the function of each caffeoyl residue in the diacylated anthocyanin gentiodelphin, a pigment from the blue flower of Gentiana makinoi, two mono-deacyl derivatives were compared for both color development and stability. In neutral solution, 3.5-di-O-beta-D-glucopyranosyl-3'-O-(6-O-caffeoyl-beta-D-glucopyranosyl)delphinidin was both bluer and more stable than 3,3'-di-0-8D-glucopyrannsyl-5-O-(6-O-caffeoyl-beta-D-glucopyranosyl)delphinidin. Conformational analysis of each derivative under acidic conditions revealed only the 3'-O-caffeoylglucopyranosyl derivative to demonstrate intramolecular stacking. Additionally, the acyl residue in the B-ring contributed more to blue color development than that in the A-ring. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：85 / 92

页数：8

共 23 条

[1]

[Anonymous], 1994, FLAVONOIDS ADV RES 1

[2] MECHANISM OF STRUCTURAL TRANSFORMATIONS OF ANTHOCYANINS IN ACIDIC MEDIA [J].

BROUILLARD, R ;

DUBOIS, JE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (05) :1359-1364

[3] CHEMISTRY OF ANTHOCYANIN PIGMENTS .2. KINETIC AND THERMODYNAMIC STUDY OF PROTON-TRANSFER, HYDRATION, AND TAUTOMERIC REACTIONS OF MALVIDIN 3-GLUCOSIDE [J].

BROUILLARD, R ;

DELAPORTE, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (26) :8461-8468

[4] THE CHEMISTRY OF ANTHOCYANIN PIGMENTS .7. ORIGIN OF THE EXCEPTIONAL COLOR STABILITY OF THE ZEBRINA ANTHOCYANIN [J].

BROUILLARD, R .

PHYTOCHEMISTRY, 1981, 20 (01) :143-145

[5]

Brouillard R., 1982, Chemical structure of anthocyanins, V1, DOI DOI 10.1016/B978-0-12-472550-8.50005-6

[6]

Brouillard R., 1988, The Flavonoids, P525, DOI DOI 10.1007/978-1-4899-2913-6_16

[7]

BRUYN AD, 1976, CARBOHYD RES, V47, P311

[8] KINETIC AND THERMODYNAMIC CONTROL OF FLAVYLIUM HYDRATION IN THE PELARGONIDIN CINNAMIC ACID COMPLEXATION - ORIGIN OF THE EXTRAORDINARY FLOWER COLOR DIVERSITY OF PHARBITIS-NIL [J].

DANGLES, O ;

SAITO, N ;

BROUILLARD, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (08) :3125-3132

[9] New aspects of anthocyanin complexation. Intramolecular copigmentation as a means for colour loss? [J].

Figueiredo, P ;

Elhabiri, M ;

Toki, K ;

Saito, N ;

Dangles, O ;

Brouillard, R .

PHYTOCHEMISTRY, 1996, 41 (01) :301-308

[10] STRUCTURE OF GENTIODELPHIN, AN ACYLATED ANTHOCYANIN ISOLATED FROM GENTIANA-MAKINOI, THAT IS STABLE IN DILUTE AQUEOUS-SOLUTION [J].

GOTO, T ;

KONDO, T ;

TAMURA, H ;

IMAGAWA, H ;

IINO, A ;

TAKEDA, K .

TETRAHEDRON LETTERS, 1982, 23 (36) :3695-3698

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