62(P-41) 沖縄近海産Strongylophora属海綿の新規ジインジオールstrongylodiols A-Gの構造および鏡像異性体存在比(ポスター発表の部)

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During our continuous investigation directing the discovery of new bioactive constituents from the Okinawan marine invertebrates, seven new cytotoxic acetylenic alcohols, strongylodiols A-G, were obtained from the marine sponge belonging to the genus Storongylophora. Strongylodiols A-G were isolated from the AcOEt soluble part of the MeOH extract of the sponge by chromatographic separation using normal (silica gel, hexane/AcOEt) and reverse (ODS silica gel, CH_3CN) phase LCC and HPLC. Their gross structures were elucidated based on spectroscopic analysis. The positions of the central double or triple bond were effectively determined by the negative FAB MS/MS spectra. During the process for determination of the absolute stereochemistry at C-6 using the modified Mosher's method, strongylodiols A-G were found to be each enantiomeric mixture with a different ratio. The R configuration for each major enantiomer was established by the modified Mosher's method. To determine the enatiomeric ratio, the (S)-MTPA esters of strongylodiols A-C were prepared. These diastereomers were separated and quantified by normal phase HPLC (silica gel, hexane/AcOET) with a chromatographic data processor. The enantiomeric ratio was found to be 91:9 for strongylodiol A, 97:3 for strongylodiol B and 84:16 for strongylodiol C. Each enantiomer was obtained as a pure form and fully characterized. The enantiomeric ratios of strongylodiols D-G are now being studied. Strongylodiols A, B, C and D showed cytotoxic activity toward human T lymphocyte leukemia (MOLT-4) cells.
天然有機化合物討論会の論文
2000-10-01

62(P-41) 沖縄近海産Strongylophora属海綿の新規ジインジオールstrongylodiols A-Gの構造および鏡像異性体存在比(ポスター発表の部)

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