title: Phytotoxic activity and metabolism of Botrytis cinerea and structure-activity relationships of isocaryolane derivatives.
abstract: Research has been conducted on the biotransformation of (8S,9R)-isocaryolan-9-ol (4a) and (1S,2S,5R,8S)-8-methylene-1,4,4-trimethyltricyclo[6.2.1.0(2,5)]undecan-12-ol (5a) by the fungal phytopathogen Botrytis cinerea. The biotransformation of compound 4a yielded compounds 6-9, while the biotransformation of compound 5a yielded compounds 10-13. The activity of compounds 4a and 5a against B. cinerea has been evaluated. (8R,9R)-Isocaryolane-8,9-diol (6), a major metabolite of compound 4a, shows activity compared to its parent compound 4a, which is inactive. The effect of isocaryolanes 3, 4a, and 5a, together with their biotransformation products 6-8, 10, and 14-17, on the germination and radicle and shoot growth of Lactuca sativa (lettuce) has also been determined. Compounds 7-13 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: D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D001711:Biotransformation; D020171:Botrytis / Q000378:metabolism*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry / Q000378:metabolism; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology*; D018545:Lactuca / Q000254:growth & development / Q000502:physiology; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C561980:(8R,9R)-isocaryolane-8,9-diol; D000447:Aldehydes; D001643:Bridged Bicyclo Compounds; D005659:Fungicides, Industrial; D012717:Sesquiterpenes; C432873:botrydial