Antifungal activity and biotransformation of diisophorone by Botrytis cinerea.
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.
Daoubi
Mourad
M
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado 40, 11510 Puerto Real, Cádiz, Spain.
Deligeorgopoulou
Athina
A
Macías-Sánchez
Antonio J
AJ
Hernández-Galán
Rosario
R
Hitchcock
Peter B
PB
Hanson
James R
JR
Collado
Isidro G
IG
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
D003512:Cyclohexanones; D005659:Fungicides, Industrial; C005940:isophorone