46 放線菌の生産するpiericidin類縁化合物

概要

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Piericidin A (I) and B (II), metabolites of Streptomyces mobaraensis, show strong inhibitory effects on electron transport system in mitochondoria as well as strong insecticidal activities. In the screening project to find out new natural insecticides among metabolites of microorganisms, an unidentified Streptomyces was found to produce several piericidin-like substances. From its culture filtrate and mycellia, thirteen new active principles, besides piericidins A and B, were isolated. Based on PMR and mass spectroscopy, the structures III-XV were assigned to these new metabolites. These members of piericidin homologues are considered to be formed by some of the following structural modifications for the basic structure of piericidin A. 1) The introduction of a methyl group at C_5. 2) The replacement of the methyl group at C_<12> by an isopropyl group. 3) The epoxydation of the terminal double bond (C_<11>-C_<12>). 4) O-methylation of the C_<10> hydroxyl. Theoretically the combination of such modifications may result in the formation of sixteen homologues. Present experimental results indicate that fifteen of them were characterized. The sixteenth homologue could not be isolated, but its occurrence has been indicated. These substances showed very strong inhibitory effects on electron transport system in rat liver mitochondoria at the same order as that of piericidin A. Their antimicrobial and insecticidal activities are also discussed.
1974-10-01