P-39 海洋由来細菌Bacillus subtilisが生産するモルホリン骨格含有新規イソクマリンbacilosarcin類の構造(ポスター発表の部)

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There is substantial interest in discovering new lead molecules from natural products for agricultural application including plant growth regulators. In this study, the marine-derived bacterium Bacillus subtilis was found to produce two new isocoumarins, bacilosarcins A (1) and B (2) as well as three previously reported isocoumarins, amicoumacins A, B, and C. Isocoumarin-type metabolites from microorganisms are characterized by the amino-containing substituent at 3-position in the dihydrocoumarin core. There have been several such isocomarin compounds as baciphelacin and amicoumacins isolated from bacteria of the genus Bacillus. The structures of 1 and 2 were assigned on the basis of NMR analysis and chemical conversions. 1 possesses an unprecedented 3-oxa-6,9-diazabicyclo[3.3.1]nonane ring system whereas 2 has a 2-hydroxymorpholine substructure that is rare in nature. The new compounds showed plant growth inhibitory activity against barnyard millet. We herein describe the isolation, structure elucidation, absolute stereochemical assignment, and biological activity of 1 and 2.
2008-09-01