56(P-27) Solanum generaの新規Homo-cholestane Glycosides(ポスター発表の部)

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Our ongoing search for the bioactive oligoglycosides from solanaceous plants has so far resulted in the isolation of cytotoxic compounds against several tumor cell lines, antifeeding substances and the key intermediates on the biosynthesis of steroidal alkaloids. In the present study, we have investigated the constituents in the respective organs of the leaves, stems and fruits of Solanum aethiopicum to provide three novel steroidal glycosides, named aethiosides A-C (1-3). 1 was acid-hydrolyzed to afford a sapogenol, named aethiogenin a (4), C_<29>H_<42>O_2, of which structure was determined to be a homo-cholestane derivative with an aromatized ring E by spectroscopic means. 1 was characterized as 3-O-β-chacotriosyl aethiogenin a 26-O-β-D-glucopyranoside. The production of 1 was plausibly deduced as shown in Chart 2, that is, starting from the conjugation of polyhydroxycholesterol and acetyl CoA resulting in the formation of a benzene ring at E-ring. The structures of 2 and 3 were also analogously determined. In case of 3, a malonyl CoA was deduced to be impregnated into the cholesterol molecule to give a carboxyl benzene ring. These three glycosides were for the first time isolated as the steroids with a novel skeleton carrying a benzene ring at E-ring by conjugation of cholesterol derivative and acetyl CoA or malonyl CoA.
天然有機化合物討論会の論文
2003-09-01