Daoubi Mourad, Deligeorgopoulou Athina, Macías-Sánchez Antonio J, Hernández-Galán Rosario, Hitchcock Peter B, Hanson James R, Collado Isidro G
Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado 40, 11510 Puerto Real, Cádiz, Spain.
J Agric Food Chem. 2005 Jul 27;53(15):6035-9. doi: 10.1021/jf050600n.
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.
异佛尔酮（1）针对两种坏死型植物病原菌灰葡萄孢菌的菌株进行了测试。真菌的敏感性因菌株而异。灰葡萄孢菌2100比灰葡萄孢菌UCA992更敏感：在50 ppm及以上的浓度下，其菌丝体生长受到显著抑制。尽管异佛尔酮（1）对灰葡萄孢菌显示出有效的防治效果，但存在一种解毒机制。对消旋异佛尔酮（1）被灰葡萄孢菌解毒的情况进行了研究。用两株灰葡萄孢菌进行培养，分别得到了一种和四种生物转化产物（2 - 5）。根据它们的光谱数据，包括二维核磁共振分析[异核多量子相干（HMQC）、异核多键相关（HMBC）和核Overhauser增强光谱（NOESY）]以及X射线晶体学研究，确定了它们的结构分别为已知的8β - 羟基异佛尔酮（2）、6α - 羟基异佛尔酮（3）、6β - 羟基异佛尔酮（4）和8β,14β - 二羟基异佛尔酮（5）。
