56(P-23) Enterolobium contortisiliquumより単離された新規トリテルペン配糖体の構造とそれらのマクロファージに対する細胞毒性活性(ポスター発表の部)

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Enterolobium contortisiliquum (Vell.) Morong is a Leguminosae plant indigenous to South America and has been used as a folk medicine in Brazil for the treatment of helminthiasis and blennorrhea. Although a few triterpenes and triterpene glycosides were isolated from E. contortisiliquum, no systematic chemical examination has been carried out with the plant up to the present. We made a phytochmical screening of the pericarps of E. contortisiliquum paying particular attention to the polar triterpene glycoside constituents, and isolated eight novel bisdesmosidic triterpene saponins (1-8) based upon 3β,21β-dihydroxyolean-12-en-28-oic acid. The chemical structures of 1-8 were determined by analysis of their NMR spectroscopic data (^1H-^1H COSY, selective TOCSY, 2D TOCSY, HSQC-TOCSY, HMQC, and HMBC), as well as acid hydrolysis followed by chromatographic and spectroscopic studies. Compounds 7 and 8 are especially unique in structure having 2-N-acetyl-D-glucosamine as one of the monosaccharides constituting their oligosaccharide units. The cytotoxic activities of 1-8 against BAC1.2F5 mouse macrophages, EL-4 mouse lymphoma cells, and L-929 mouse fibroblasts, were examined. Compounds 2 and 7, which have a cinnamoyloxy group at C-21 of the aglycon and slightly differ from the other saponins in the monosaccharides composed of the sugar moieties, exhibited a selective cytotoxicity against macrophages with an LD_<50> value of about 5μg/mL. The morphology of the died cells, whose cytosol occurred in vacuolation, showed that the cell death was neither necrotic nor due to induction of apoptosis. The biological mechanism of the selective and unusual macrophage death induced by 2 and 7 is under investigation.
天然有機化合物討論会の論文
2002-09-01

56(P-23) Enterolobium contortisiliquumより単離された新規トリテルペン配糖体の構造とそれらのマクロファージに対する細胞毒性活性(ポスター発表の部)

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