Stemodane skeletal rearrangement: chemistry and microbial transformation.
Phytochemistry
; 66(8): 901-9, 2005 Apr.
Article
em En
| MEDLINE
| ID: mdl-15845408
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.
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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