65 イネ苗立枯病症誘起物質Rhizoxinの研究

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A phytotoxin, Rhizoxin (1), was isolated from the culture broth of Rizopus chinensis Rh-2 strain which is a potent pathogen of rice seedling blight. The compound shows; mp: 131-135°, [α]^<24>_D(c=0.8, MeOH): +201°, UV^<MeOH>_<max> nm(ε): 295(37000), 308(47800), 323(35000), similar absorptions to a all-trans tetraenic moiety, IR(CHCl_3): 3600-3400cm^<-1>(OH), 1730cm^<-1>(-O-CO-). Acetylation of 1 afforded the monoacetate 2 indicating the presence of a hydroxy group. Its molecular formula, C_<35>H_<47>NO_9 (MW=625.3250), was determined by high resolution mass spectroscopy (M^+=625.3233) and elemental analysis. The structure elucidation of Rhizoxin(1) was essentially based on the NMR spectroscopic data of 1 and of its chemical degradation products, especially by the aid of extensive decoupling experiments on 400MHz ^1H- and 100MHz ^<13>C-NMR spectrometer. The molecular structure of 1 was determined to be the new type of 16-membered macrocyclic lactone as shown in fig. 1. Rhizoxin (1) induced, at 10ng/ml of concentration, the abnormal swelling of rice seedling roots which is usually observed with the rice seedlings infected with R. chinensis as the characteristic symptom of this disease. This compound, however, caused little effect on other kinds of plant and was found to be a specific toxin to rice plant. Its anti-microbial activities were also examined. It showed potent antifungal activities, for example, it inhibited the spore germination of Pyricularia oryzae at as low as 1ng/ml of concentration. On the other hand it had only weak anti-bacterial activity.
天然有機化合物討論会の論文
1982-09-10

65 イネ苗立枯病症誘起物質Rhizoxinの研究

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