75 バンレイシ科植物Annona squamosaのビステトラヒドロフランアセトゲニン類の構造(ポスター発表の部)

概要

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In the course of our investigation of antitumor active substances from plant, we isolated seventeen bis-tetrahydrofuran acetogenins from pet. ether extract of the seeds of Annona squamosa (Annonaceae), collected in India. These compounds (C_<37> or C_<35>) contain an α,β-unsaturated γ-lactone, two tetrahydrofuran rings, and two to four hydroxy groups. Their structures were elucidated by means of spectral methods. In particular, FAB-MS/MS and precursor scanning technique were successfully used for determining the structures. These were classified into two types, i.e., adjacent (e.g., compound 5) and non-adjacent (e.g., compound 1) bis-tetrahydrofurans. Absolute stereochemistry at the C-36 position was established to be S by converting compound 5 into a lactic acid derivative. The C-4 stereochemistry of 4-hydroxy substituted compounds (2, 3, 13, 15) were determined as S by the application of the improved Mosher method. Relative stereochemistry at the bis-tetrahydrofuran portion was deduced from the ^1H-NMR data for the corresponding acetate derivative by the use of Hoye's method. Compound (21) was found to bear hitherto unknown threo-cis-threo-cis-threo stereo-relationship at the portion. Some compounds were examined for in vitro cytotoxic activity to L1210 cells. The ED_<50> values varied from 1.0×10^<-4> μg/ml for compound 14 to 3.3×10^<-3> for compound 17.
天然有機化合物討論会の論文
1992-09-10