title: Biotransformation of bioactive isocaryolanes by Botrytis cinerea.
abstract: The metabolism of the fungistatic agent (8R,9R)-8-methoxyisocaryolan-9-ol (4) by the fungus Botrytis cinerea has been investigated. Biotransformation of compound 4 yielded compounds 5 and 6-9. No dihydrobotrydial is observed after 4 days of incubation of compound 4. Separate biotransformation of (8R,9R)-isocaryolane-8,9-diol (5) yielded compounds 7-11. The evaluation of the fungistatic activity against B. cinerea of compounds 4, 5, and 6 is reported. (4R,8R,9R)-8-Methoxyisocaryolane-9,15-diol (6), a major metabolite of (8R,9R)-8-methoxyisocaryolan-9-ol (4), shows a much reduced biological activity when compared with the parent compound. Isocaryolane derivatives 6-11 are described for the first time.
authors.affiliation: Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Avenida Presidente Antônio Carlos 6627, 31270-901 Belo Horizonte, MG, Brazil.
authors.forename: Jociani
authors.initials: J
authors.lastname: Ascari
authors.forename: Maria Amélia Diamantino
authors.initials: MA
authors.lastname: Boaventura
authors.forename: Jacqueline Aparecida
authors.initials: JA
authors.lastname: Takahashi
authors.forename: Rosa
authors.initials: R
authors.lastname: Durán-Patrón
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernández-Galán
authors.forename: Antonio J
authors.initials: AJ
authors.lastname: Macías-Sánchez
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
mesh_terms: D001711:Biotransformation; D020171:Botrytis / Q000187:drug effects / Q000378:metabolism*; D005659:Fungicides, Industrial / Q000378:metabolism*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
chemical_list: C561981:(8R,9R)-8-methoxyisocaryolan-9-ol; C561980:(8R,9R)-isocaryolane-8,9-diol; D005659:Fungicides, Industrial; D012717:Sesquiterpenes