90(PB3-1) Aspergillus spp.の生産する特異なEpidithiopiperazine-2,5-dione化合物 Aspirochlorineおよびその関連物質(ポスター発表の部)

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Aspirochlorine (=antibiotic A30641, C_<12>H_9N_2O_5S_2Cl, 1) was isolated as a metabolite of A. flavus which induces spherical hyphal swellings in the phytopathogenic fungus, Phytophthora sp. It was also found to be the true antimicrobial constituent of the antibiotic, oryzachlorin, produced by A. oryzae. Recently O,O-dimethyl aspirochlorine (3) crystallized as colorless single crystals. X-ray crystalographic analysis followed by CD spectroscopic analysis revised the proposed unusual structure and established the novel absolute stereostructure (1). Changing halogen composition of the culture medium of A. oryzae resulted in production of new derivatives of 1, dechloro- and bromo-derivatives (9 and 10). Addition of KI into the medium as a sole halogen source, however, did not generate any iodo-derivatives. Only 9 was produced. From the culture broth of A. oryzae two new structurally related compounds 11 and 12 were isolated. Spectroscopic analyses indicated that they are isomeric trithioderivatives of 1. Aspirochlorine (1) is the third example having a novel epidithiopiperazine-2,5-dione structure following gliovirin and antibiotic FA-2097. It is the first natural product with an N-methoxyl amide linkage. The reason for the extraordinarily high amide carbonyl IR absorption (1724 cm^<-1>) of 1 still remains to be explained, as no steric hindrance seem to be present in its ring system.
天然有機化合物討論会の論文
1987-07-25