Stemodane skeletal rearrangement: chemistry and microbial transformation.

Martin, Glenroy D A; Reynolds, William F; Reese, Paul B

Martin, Glenroy D A; Reynolds, William F; Reese, Paul B.

Afiliação

Martin GD; Department of Chemistry, University of the West Indies, Mona, Kingston 7, Jamaica.

Phytochemistry ; 66(8): 901-9, 2005 Apr.

Article em En | MEDLINE | ID: mdl-15845408

RESUMO

Solvolytic rearrangement of the C/D ring system of the tetracyclic diterpenoid stemodinone (2) afforded the compounds 15(13-->12)abeo-13beta-hydroxystemaran-2-one (5) and 15(8-->9)abeo-8beta(H)-12beta-hydroxystachan-2-one (10). Terpene 5 possesses a novel diterpene skeleton. Oxidation of these compounds yielded their respective diketones. Bioconversion of 5 by Rhizopus oryzae yielded 15(13-->12)abeo-7beta,13beta-dihydroxystemaran-2-one (18) while microbial transformation of 10 provided 15(8-->9)abeo-8beta(H)-6alpha,12beta-dihydroxystachan-2-one (19), 15(8-->9)abeo-8beta(H)-7beta,12beta-dihydroxystachan-2-one (20) and 15(8-->9)abeo-8beta(H)-6alpha,12beta,14beta-trihydroxystachan-2-one (21). A rationale for the formation of the rearranged compounds is proposed.

Assuntos

Diterpenos/química; Diterpenos/metabolismo; Rhizopus/metabolismo; Scrophulariaceae/química; Biotransformação; Estrutura Molecular

Buscar no Google

Adicionar na Minha BVS

Imprimir

XML

PubMed Links

Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Rhizopus / Scrophulariaceae / Diterpenos Idioma: En Revista: Phytochemistry Ano de publicação: 2005 Tipo de documento: Article País de afiliação: Jamaica País de publicação: Reino Unido

Buscar no Google

Adicionar na Minha BVS

Imprimir

XML

PubMed Links