P-53 海洋糸状菌代謝物の絶対配置に関する研究(ポスター発表の部)

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Marine microorganisms are recognized as important sources of pharmacologically active metabolites, and a growing number of marine fungi have been reported to produce novel bioactive secondary metabolites. We report chemical investigation of the metabolites obtained from the extracts of two sorts of marine fungi culture filtrates. We previously reported three antibacterial chlorine-containing components of Aspergillus ostianus strain 01F313 that had been isolated from an unidentified marine sponge collected at Pohnpei. The chlorine must have originated from cultivation medium composed of natural seawater. Expecting that bromine-containing compounds might be obtained by the use of a medium, in which a bromide solution replaces seawater, we cultivated the same strain in a brominemodified 1/2PD medium. Actually, we were able to isolate the brominated compounds, and found, at the same time, that the metabolites were considerably different from those obtained from the strain cultured in seawater medium. We also succeeded in isolating several benzodiazepine alkaloids that are not produced in seawater medium. The structures of compounds 1 and 2 were revised from the previously-reported betaine structures to unique oxepin ones by X-ray crystallography. Concomitant known alkaloids, compounds 3, 4, and 5, and a new compound, compound 6, have a common circumdatin framework. Penicillium sp. is known as sources of hybrid polyketides such as berkeleytrione and berkeleydione. We detected cytotoxic activity against A549 cells (IC_<50> 500μg/mL) in an acetone extract of the marine-derived fungus, Penicillium minioluteum 03HE3-1, which had been isolated from sea mud of Heita Bay, Kamaishi, Japan. The fungus was cultured in a 1/2PD medium containing 50% seawater. Four novel hybrid polyketide-terpenoid metabolites were obtained from the culture filtrate. Their structures were determined by NMR spectroscopic analyses and X-ray crystallography. The biosynthetic pathway of four meroterpenes from farnesyl pyrophosphate and 3,5-dimethylorsellinic acid is proposed.
天然有機化合物討論会の論文
2008-09-01

P-53 海洋糸状菌代謝物の絶対配置に関する研究(ポスター発表の部)

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