title: Antifungal activity and biotransformation of diisophorone by Botrytis cinerea.
abstract: Diisophorone (1) was tested against two strains of the necrotrophic plant pathogen Botrytis cinerea. Fungal sensitivity varied according to the strain. B. cinera 2100 was more sensitive than B. cinereaUCA992: its mycelial growth was significantly inhibited at concentrations of 50 ppm and above. Although diisophorone (1) showed an effective control of B. cinerea, a detoxification mechanism was present. The detoxification of racemic diisophorone (1) by B. cinerea was investigated. Incubation with two strains of B. cinerea gave one and four biotransformation products (2-5), respectively. Their structures were established as the known 8beta-hydroxydiisophorone (2), 6alpha-hydroxydiisophorone (3), 6beta-hydroxydiisophorone (4) and 8beta,14beta-dihydroxydiisophorone (5) on the basis of their spectroscopic data, including two-dimensional NMR analysis [heteronuclear multiple quantum coherence (HMQC), heteronuclear multiple bond correlation (HMBC), and nuclear Overhauser enhancement spectroscopy (NOESY)] and an X-ray crystallographic study.
authors: Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado 40, 11510 Puerto Real, Cádiz, Spain.
authors: Mourad
authors: M
authors: Daoubi
authors: Athina
authors: A
authors: Deligeorgopoulou
authors: Antonio J
authors: AJ
authors: Macías-Sánchez
authors: Rosario
authors: R
authors: Hernández-Galán
authors: Peter B
authors: PB
authors: Hitchcock
authors: James R
authors: JR
authors: Hanson
authors: Isidro G
authors: IG
authors: Collado
mesh_terms: D001711:Biotransformation; D020171:Botrytis / Q000187:drug effects* / Q000254:growth & development / Q000378:metabolism*; D003512:Cyclohexanones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D005659:Fungicides, Industrial / Q000378:metabolism* / Q000494:pharmacology*; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D025282:Mycelium / Q000254:growth & development; D010944:Plants / Q000382:microbiology
chemical_list: D003512:Cyclohexanones; D005659:Fungicides, Industrial; C005940:isophorone