INTRAMOLECULAR STACKING CONFORMATION OF GENTIODELPHIN, A DIACYLATED ANTHOCYANIN FROM GENTIANA-MAKINOI

被引:63
作者
YOSHIDA, K
KONDO, T
GOTO, T
机构
[1] NAGOYA UNIV,FAC AGR,CTR CHEM INSTRUMENT,NAGOYA 46401,JAPAN
[2] NAGOYA UNIV,FAC AGR,ORGAN CHEM LAB,NAGOYA 46401,JAPAN
关键词
GENTIODELPHIN; POLYACYLATED ANTHOCYANIN; SANDWICH-TYPE STACKING; CONFORMATIONAL ANALYSIS;
D O I
10.1016/S0040-4020(01)80442-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gentiodelphin from Gentiana makinoi is unusually stable in neutral aqueous solutions and may be stabilized by intramolecular sandwich-type stacking of two caffeic acids. Although in acidic methanol solution, evidence for intramolecular stacking of gentiodelphin was obtained from electronic spectra and H-1 NMR analysis. Using computer-assisted conformational analysis with NOE constraints and bond angle constraints, we first established the intramolecular stacking conformation of aromatic acid to the anthocyanidin nucleus. Under acidic conditions, one caffeic acid attached at the glucose of the 2-position of the B-ring was stacked to the delphinidin nucleus but the other acid attached at the glucose of the 5-position was not stacked.
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页码:4313 / 4326
页数:14
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