Formation of 2,3-seco-acids in the biotransformation of the diterpene ribenone by Gibberella fujikuroi

被引:17
作者
Fraga, BM
González, P
Hernández, MG
Suárez, S
机构
[1] CSIC, Inst Prod Nat & Agrobiol, Tenerife 38206, Canary Islands, Spain
[2] Univ La Laguna, Inst Univ Bioorgan, Tenerife, Spain
关键词
Gibberella fujikuroi; microbial reaction; diterpenes; ent-13-manoyl oxide; ribenone;
D O I
10.1016/S0040-4020(98)01190-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The biotransformation of ribenone (ent-3-oxo-13-epi-manoyl oxide) (4) by the fungus Gibberella fujikuroi led to compounds hydroxylated at C-l(alpha), C-6(beta), C-11(beta) or C-12(beta), in addition to the 2,3-seco diacids 15, 17 and 19. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1781 / 1792
页数:12
相关论文
共 23 条
[1]   TERPENIC COMPONENTS OF SPANISH LABIATAE .11. DITERPENOIDS FROM SIDERITIS-VAROI [J].
ALGARRA, J ;
GARCIAGRANADOS, A ;
DEBURUAGA, AS ;
DEBURUAGA, JMS .
PHYTOCHEMISTRY, 1983, 22 (08) :1779-1782
[2]   DITERPENOIDS OF SOLIDAGO-MISSOURIENSIS NUTT [J].
ANTHONSE.T ;
BERGLAND, G .
ACTA CHEMICA SCANDINAVICA, 1970, 24 (05) :1860-&
[3]   THE BIOSYNTHESIS OF KAURENOLIDE DITERPENOIDS BY GIBBERELLA-FUJIKUROI [J].
BEALE, MH ;
BEARDER, JR ;
DOWN, GH ;
HUTCHISON, M ;
MACMILLAN, J ;
PHINNEY, BO .
PHYTOCHEMISTRY, 1982, 21 (06) :1279-1287
[4]   FUNGAL PRODUCTS .14. METABOLIC PATHWAYS FROM ENT-KAURENOIC ACID TO FUNGAL GIBBERELLINS IN MUTANT B1-41A OF GIBBERELLA-FUJIKUROI [J].
BEARDER, JR ;
MACMILLAN, J ;
PHINNEY, BO .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (08) :721-726
[5]   6BETA, 7BETA-DIHYDROXYKAURENOIC ACID - ITS BIOLOGICAL ACTIVITY AND POSSIBLE ROLE IN BIOSYNTHESIS OF GIBBERELLIC ACID [J].
CROSS, BE ;
STEWART, JC ;
STODDART, JL .
PHYTOCHEMISTRY, 1970, 9 (05) :1065-&
[6]   NEW METABOLITES OF GIBBERELLA FUJIKUROI .2. ISOLATION OF 14 NEW METABOLITES [J].
CROSS, BE ;
GROVE, JF ;
HANSON, JR ;
MORRISON, A ;
CURTIS, PJ ;
GALT, RHB .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (MAY) :2937-&
[7]   EFFECT OF PLANT GROWTH RETARDANTS ON BIOSYNTHESIS OF DITERPENES BY GIBBERELLA FUJIKUROI [J].
CROSS, BE ;
MYERS, PL .
PHYTOCHEMISTRY, 1969, 8 (01) :79-&
[8]   AN ENZYMIC SITE OF INHIBITION OF GIBBERELLIN BIOSYNTHESIS BY AMO 1618 AND OTHER PLANT GROWTH RETARDANTS [J].
DENNIS, DT ;
UPPER, CD ;
WEST, CA .
PLANT PHYSIOLOGY, 1965, 40 (05) :948-&
[9]   The formation of an ent-11 alpha, 16 alpha-epoxykaurane of biosynthetic significance by Gibberella fujikuroi [J].
Fraga, BM ;
Gonzalez, P ;
Guillermo, R ;
Hernandez, MG .
NATURAL PRODUCT LETTERS, 1996, 8 (04) :257-262
[10]   THE BIOTRANSFORMATION OF 2 ENT-15-BETA,16-BETA-EPOXY-KAURANE DERIVATIVES BY GIBBERELLA-FUJIKUROI [J].
FRAGA, BM ;
HERNANDEZ, MG ;
GARCIATELLADO, F ;
GONZALEZ, P ;
PERALES, A .
PHYTOCHEMISTRY, 1993, 34 (01) :133-138