Configurational Studies of Complexes of Various Tea Catechins and Caffeine in Crystal State

被引：15

作者：

Tsutsumi, Hiroyuki ^{[1
]}

Kinoshita, Yoshifumi ^{[1
]}

Sato, Takashi ^{[1
]}

Ishizu, Takashi ^{[1
]}

机构：

[1] Fukuyama Univ, Fac Pharm & Pharmaceut Sci, Hiroshima 7290292, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2011年 / 59卷 / 08期

关键词：

(+)-catechin; (-)-epicatechin; (-)-catechin-3-O-gallate; caffeine; intermolecular interaction; X-ray crystallographic analysis; ANTIBACTERIAL ACTIVITY; GALLOCATECHIN GALLATE; POLYPHENOLS; INHIBITION; OBESITY;

D O I：

10.1248/cpb.59.1008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Crystals of the complexes of (+)-catechin (CA) of non-galloylated catechin and (-)-catechin-3-O-gallate (Cg) of galloylated catechin with caffeine were prepared, and their stereochemical structures and intermolecular interactions were determined by X-ray crystallographic analysis. CA formed a 1:1 complex with caffeine by intermolecular hydrogen bonds, whereas Cg formed a 1: 2 complex with caffeine, which was formed by face-to-face and offset pi-pi interactions and intermolecular hydrogen bonds. A solution of two kinds of non-galloylated catechin, CA and (-)-epicatechin (EC), and caffeine (molar ratio 1 :1 : 2) in water afforded a 1 :1 : 2 complex, the crystal structure of which had two layers, one layer in which CA and caffeine formed alternate lines and an other layer in which EC and caffeine formed alternate lines. The 1 :1 : 2 complex was formed by offset pi-pi and CH-pi interactions and intermolecular hydrogen bonds.

引用

页码：1008 / 1015

页数：8

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