BIOTRANSFORMATION OF 2 ENT-15-BETA-HYDROXY-KAUR-16-ENE DERIVATIVES BY GIBBERELLA-FUJIKUROI

被引：19

作者：

FRAGA, BM ^{[1
]}

HERNANDEZ, MG ^{[1
]}

GONZALEZ, P ^{[1
]}

机构：

[1] UNIV LA LAGUNA,DEPT QUIM,LA LAGUNA,SPAIN

来源：

PHYTOCHEMISTRY | 1992年 / 31卷 / 11期

关键词：

GIBBERELLA-FUJIKUROI; DITERPENES; ENT-15-BETA-HYDROXY-KAUR-16-ENE; CANDIDIOL; MICROBIOLOGICAL TRANSFORMATIONS;

D O I：

10.1016/S0031-9422(00)97539-3

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：

Incubation of the fungus Gibberella fujikuroi with ent-15beta-hydroxy-kaur-16-ene gave ent-11alpha,15beta-dihydroxy-kaur-16-ene, ent-7beta,11alpha,15beta-trihydroxy-kaur-16-ene,ent-11alpha,13,15beta-trihydroxy-kaur-16-ene,ent-11alpha,15beta,19-trihydroxy-kaur-16-ene, and ent-11alpha,14alpha,15beta-trihydroxy-kaur-16-ene, and a mixture of products, which was resolved by acetylation to give ent-11alpha,14alpha,15beta-triacetoxy-kaur-16-ene and ent-7beta,15beta,17-triacetoxy-11alpha,16alpha-epoxy-kaur-16-ene. The addition of candidiol (ent-15beta,18-dihydroxy-kaur-16-ene)gave ent-11alpha,15beta,18-trihydroxy-kaur-16-ene, and a mixture of substances, which was resolved by acetylation to give ent-11beta,15beta,18-triacetoxy-kaur-16-ene, ent-7beta,11alpha,15beta,18-tetraacetoxy-kaur-16-ene and ent-15beta,17,18-triacetoxy-11alpha,16alpha-epoxykaurane. These results confirm that the presence in ent-kaur-16-ene derivatives of a 15alpha-hydroxyl group inhibits oxidation at C-19 to the acid level. The biotransformation of these compounds may be useful for the synthesis of natural 11beta-hydroxy-ent-kaurene analogues.

引用

页码：3845 / 3849

页数：5

共 17 条

[1] TERPENES .245. ENT-KAURENE DITERPENOIDS FROM LIVERWORT JUNGERMANNIA-SPHAEROCARPA HOOK [J].