77(P-71) Securidaca inappendiculataより単離されたマクロファージ細胞死誘導活性物質の構造(ポスター発表の部)

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In order to develop new anti-inflammatory agents with new modes of action, we have evaluated the cytotoxic activity of more than 60 Chinese crude drugs, which are used for the treatment of inflammation, against M-CSF-stimulated macrophages from C3H/He male mice. As a result, we have found that the hot H_2O extract of Securidaca inappendiculata (Polygalaceae) showed a selective cytotoxic activity against macrophages at a sample concentration of 2.5μg/mL. The H_2O infusion was successively extracted with Et_2O and then with n-BuOH. The cytotoxic activity was observed only in the n-BuOH phase with an IC_<50> value of less than 0.63μg/mL. By bioassay-guided fractionation of the n-BuOH-soluble phase, two new acylated triterpene saponins (1, 2) were isolated as the active constituents responsible for the macrophages cytostasis. The structures of 1 and 2 were determined mainly by 2D NMR spectral data interpretation, along with the results of acid- and alkaline-catalyzed hydrolysis to be 3-O-β-D-glucopyranosyl presenegenin 28-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-O-[6-O-acetyl-β-D-gluco-pyranosyl-(1→3)]-4-O-(E)-3,4-dimethoxycinnamoyl-β-D-fucopyranosyl ester (1), and 3-O-β-D-glucopyranosyl presenegenin 28-O-α-L-arabinopyranosyl-(1→3)-O-[β-D-galactopyranosyl-(→4)]-O-β-D-xylopyranosyl-(1→4)-O-α-L-rhamnopyranosyl-(1→2)-4-O-(E)-3,4-dimethoxycinnamoyi-β-D-fucopyranosyl ester (2). Compounds 1 and 2 exhibited potent cytotoxic activities against macrophages with an IC_<50> value of about 0.5μg/mL, while the corresponding deacyl derivatives (1a, 2a), soyasaponins, glycyrrhizin, and some cinnamic acid derivatives were not cytotoxic themselves. This indicates that the acyl group(s) attached at the glycoside moiety are essential for the appearance of the activity. It is also noteworthy that 1 and 2 showed more than 10-fold higher cytotoxic activities against macrophages than against bone-marrow cells and lymphocytes.
天然有機化合物討論会の論文
2000-10-01

77(P-71) Securidaca inappendiculataより単離されたマクロファージ細胞死誘導活性物質の構造(ポスター発表の部)

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