Flavan-3-ols and prodelphinidins from Stryphnodendron adstringens

被引:81
作者
deMello, JP [1 ]
Petereit, F [1 ]
Nahrstedt, A [1 ]
机构
[1] UNIV MUNSTER, INST PHARMAZEUT BIOL & PHYTOCHEM, D-48149 MUNSTER, GERMANY
关键词
Stryphnodendron adstringens; Mimosaceae; stem bark; tannins; proanthocyanidins; flavan-3-ols; prodelphinidins;
D O I
10.1016/0031-9422(95)00686-9
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
Six flavan-3-ols and eight proanthocyanidins have been isolated from the stem bark of Stryphnodendron adstringens, which is traditionally used in Brazil against various diseases. Two new flavan-3-ols were isolated as epigallocatechin 3-0-(3,5-dimethyl)-gallate and epigallocatechin 3-0-(3-methoxy-4-hydroxybenzoate). Isolation and elucidation of four new proanthocyanidins gave epigallocatechin-(4 beta --> 8)-epigallocatechin 3-O-(4-hydroxy)benzoate epigallocatechin-(4 beta --> 6)-epigallocatechin, gallocatechin-(4 alpha --> 8)-epigallocatechin 3-O-gallate and gallocatechin(4 alpha --> 8)-epigallocatechin 3-O-(4-hydroxy)benzoate. So the bark of S. adstringens is a rich source of proanthocyanidins with biologically active pyrogallol units.
引用
收藏
页码:807 / 813
页数:7
相关论文
共 31 条
[1]   PLANT PROANTHOCYANIDINS .6. CHIROPTICAL STUDIES .95. CIRCULAR-DICHROISM OF PROCYANIDINS [J].
BARRETT, MW ;
KLYNE, W ;
SCOPES, PM ;
FLETCHER, AC ;
PORTER, LJ ;
HASLAM, E .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10) :2375-2377
[2]   SYNTHESIS OF CONDENSED TANNINS .1. STEREOSELECTIVE AND STEREOSPECIFIC SYNTHESES OF OPTICALLY PURE 4-ARYLFLAVAN-3-OLS, AND ASSESSMENT OF THEIR ABSOLUTE STEREOCHEMISTRY AT C-4 BY MEANS OF CIRCULAR-DICHROISM [J].
BOTHA, JJ ;
YOUNG, DA ;
FERREIRA, D ;
ROUX, DG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (04) :1213-1219
[3]   PROANTHOCYANIDINS FROM CISTUS-INCANUS [J].
DANNE, A ;
PETEREIT, F ;
NAHRSTEDT, A .
PHYTOCHEMISTRY, 1993, 34 (04) :1129-1133
[4]   FLAVAN-3-OLS, PRODELPHINIDINS AND FURTHER POLYPHENOLS FROM CISTUS-SALVIFOLIUS [J].
DANNE, A ;
PETEREIT, F ;
NAHRSTEDT, A .
PHYTOCHEMISTRY, 1994, 37 (02) :533-538
[5]  
DESIQUEIRA JC, 1982, SPECTRUM J BRAS CI, V2, P41
[6]   FLAVANOIDS AND TRITERPENOIDS FROM CASSINE-PAPILLOSA AND THE ABSOLUTE-CONFIGURATION OF 11,11-DIMETHYL-1,3,8,10-TETRA-HYDROXY-9-METHOXYPELTOGYNAN [J].
DREWES, SE ;
MASHIMBYE, MJ .
PHYTOCHEMISTRY, 1993, 32 (04) :1041-1044
[7]  
FIELD JA, 1992, BASIC LIFE SCI, V59, P673
[8]   PLANT PROANTHOCYANIDINS .3. CONFORMATIONAL AND CONFIGURATIONAL STUDIES OF NATURAL PROCYANIDINS [J].
FLETCHER, AC ;
PORTER, LJ ;
HASLAM, E ;
GUPTA, RK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (14) :1628-1637
[9]   PRODELPHINIDIN POLYMERS - DEFINITION OF STRUCTURAL UNITS [J].
FOO, LY ;
PORTER, LJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (10) :1186-1190
[10]   STUDIES IN STRYPHNODENDRON (LEGUMINOSAE-MIMOSOIDEAE) INCLUDING 2 NEW TAXA [J].
FORERO, E .
BRITTONIA, 1972, 24 (02) :143-&