Biotransformation of the fungistatic sesquiterpenoid ginsenol by Botrytis cinerea

被引:31
作者
Aleu, J
Hernández-Galán, R
Hanson, JR
Hitchcock, PB
Collado, IG
机构
[1] Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain
[2] Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 06期
关键词
D O I
10.1039/a808044e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The antifungal properties of ginsenol (1) have been determined. The biotransformation of this fungistatic sesquiterpenoid by the plant pathogen Botrytis cinerea gave the 8- and 9-hydroxy derivatives (5 and 3) as the major metabolites and the 6 alpha- and 10 beta-hydroxy (8 and 7) and 8- and 9-oxo derivatives (6 and 4) as minor metabolites. The structure and stereochemistry of the major compound 3 were established by X-ray crystallography.
引用
收藏
页码:727 / 730
页数:4
相关论文
共 11 条
[1]  
COLLADO IG, 1994, J NAT PRODUCTS, V59, P738
[2]   BOTRYDIAL, A SESQUITERPENE ANTIBIOTIC FROM CULTURE SOLUTION OF FUNGUS BOTRYTIS-CINEREA [J].
FEHLHABER, HW ;
GEIPEL, R ;
MERCKER, HJ ;
TSCHESCHE, R ;
WELMAR, K ;
SCHONBECK, F .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (05) :1720-1730
[3]   THE BIOSYNTHESIS OF SOME SESQUITERPENOIDS [J].
HANSON, JR .
PURE AND APPLIED CHEMISTRY, 1981, 53 (06) :1155-1162
[4]  
IWABUCHI H, 1988, CHEM PHARM BULL, V36, P2447, DOI 10.1248/cpb.36.2447
[5]  
Provalis research, 2020, WEIB 5 SOFTW VERS 5
[6]   The phytotoxic activity of some metabolites of Botrytis cinerea [J].
Rebordinos, L ;
Cantoral, JM ;
Prieto, MV ;
Hanson, JR ;
Collado, IG .
PHYTOCHEMISTRY, 1996, 42 (02) :383-387
[7]  
SHELDRICK GM, 1985, SHELXS 86 PROGRAM SO
[8]  
SHLEDRICK GM, 1993, SHELXL 93 PROGRAM CR
[9]  
SMITH JRC, 1980, BIOL BOTRYTIS, P153