P-45 底棲性渦鞭毛藻より単離した新規奇数員環マクロリドIriomoteolide-2aと3aの構造(ポスター発表の部)

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Marine dinoflagellates are known to produce bioactive secondary metabolites. Members of Amphidinium are among the most abundant and diverse sand-dwelling benthic dinoflagellates world-wide, and have been proven to be important sources of structurally unique polyketides. Recently, we have isolated three new 20-membered macrolides, iriomoteolides-1a〜1c, from a marine benthic Amphidinium sp. (strain HYA024). Further examination of the extract led to the isolation of two new odd-numbered macrolides, iriomoteolides-2a (1) and 3a (2). The cultured algal cells of the Amphidinium HYA024 strain were extracted with McOH/toluene. The toluene-soluble fractions of the extract were subjected to SiO_2 gel, C_<18>, and then NH_2-SiO_2 columns. Macrolide-containing fractions were separated by C_<18> HPLC to afford two new odd-numbered macrolides, iriomoteolides-2a (1) and 3a (2), together with iriomoteolides-1a〜1c. Structure elucidations of 1 and 2 were carried out using detailed analyses of 2D NMR spectra. The relative and absolute stereochemistries for 1 were assigned by combination of conformational analyses using NMR data and modified Mosher's method of 1 and its reductive product. On the other hand, those for 2 were elucidated on the basis of conformation studies of 2 and its acetonide and modified Mosher's method. Iriomoteolide-2a (1) is the first natural product possessing a 23-membered macrolactone ring consisting of a successive polyketide chain, while iriomoteolide-3a (2) is a new 15-membered macrolide having an allyl epoxide, three hydroxyl groups, and two methyl branches. Iriomoteolides-2a (1) and 3a (2) exhibited cytotoxicity against human B lymphocyte DG-75 cells (IC_<50>:0.006, and 0.08μg/mL, respectively).
天然有機化合物討論会の論文
2008-09-01

P-45 底棲性渦鞭毛藻より単離した新規奇数員環マクロリドIriomoteolide-2aと3aの構造(ポスター発表の部)

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