Influence of trans-cis isomerisation of coumaric acid substituents on colour variance and stabilisation in anthocyanins

被引:54
作者
George, F
Figueiredo, P
Toki, K
Tatsuzawa, F
Saito, N
Brouillard, R
机构
[1] Univ Strasbourg 1, Fac Chim, Lab Chim Polyphenols, CNRS,UMR 7509, F-67008 Strasbourg, France
[2] Univ Lusofona Humanidades & Tecnol, Dept Engn & Tecnol, P-1749024 Lisbon, Portugal
[3] Minami Kyushu Univ, Lab Floriculture, Takanabe, Japan
[4] Chiba Univ, Fac Hort, Chiba, Japan
[5] Meiji Gakuin Univ, Chem Lab, Totsuka Ku, Yokohama, Kanagawa, Japan
关键词
Petunia integrifolia; Solanaceae; Triteleia bridgesii; Liliaceae; acylated anthocyanins; coumaric acid; trans-cis isomerisation; intramolecular copigmentation; molecular modelling;
D O I
10.1016/S0031-9422(01)00105-4
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
The recently isolated pigments from Petunia integrifolia and Triteleia br brigesii present a distinct feature that sheds new light on the understanding of intramolecular copigmentation of anthocyanins. These are among the infrequent anthocyanins that naturally present a coumaric acid substituent in both cis and trans forms. As a consequence, the two isomers demonstrate substantial variations of their thermodynamic and kinetic constants and also colour properties. A possible explanation for these characteristics is presented, making use of molecular modelling and taking into account the three-dimensional structures of the pigments. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:791 / 795
页数:5
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    TOKI, K
    SAITO, N
    KAWANO, K
    LU, TS
    SHIGIHARA, A
    HONDA, T
    [J]. PHYTOCHEMISTRY, 1994, 36 (03) : 609 - 612
  • [22] (DELPHINIDIN 3-GENTIOBIOSYL) (APIGENIN 7-GLUCOSYL) MALONATE FROM THE FLOWERS OF EICHHORNIA-CRASSIPES
    TOKI, K
    SAITO, N
    IIMURA, K
    SUZUKI, T
    HONDA, T
    [J]. PHYTOCHEMISTRY, 1994, 36 (05) : 1181 - 1183
  • [23] STRUCTURE OF ANTHOCYANINS ISOLATED FROM PURPLE LEAVES OF PERILLA-OCIMOIDES L VAR CRISPA BENTH AND THEIR ISOMERIZATION BY IRRADIATION OF LIGHT
    YOSHIDA, K
    KONDO, T
    KAMEDA, K
    GOTO, T
    [J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (07): : 1745 - 1751