61(P25) サボテン科植物の新規トリテルペンサポゲニンの構造と活性(ポスター発表の部)

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The triterpene sapogenins from the Cactaceae mainly Lemaireocereus were first studied by Djerassi et al. In this study, the MeOH extracts of 71 cactaceous plants belonging to 52 genera were screened for the presence of saponins and 26 plants were found to contain the saponins. We examined precisely for 13 plants and isolated 37 triterpene sapogenins including 17 new compounds (Table 1 and Figs. 1-5). Cactaceous plants were extracted with CHCl_3, and then repeatedly with MeOH. The MeOH extract was hydrolyzed with 3.5% HCl at 110℃ for 2.5 h. The CHCl_3-soluble fraction was subjected to column chromatography on silica gel and furthermore purified by HPLC over silica gel, eluted with CHCl_3-MeOH or n-hexane-acetone, resulting in the isolation of triterpenes. The structures of triterpenes were determined by two-dimentional NMR techniques and single-crystal X-ray diffraction studies. Machaerocerus eruca Br. & R. contained 13 triterpens including 5 new compounds (Table 1). Four of 5 new compounds were named machaerogenin (1), having hydroxymethyl at C-30 and formed 5-membered lactone between C-21 and C-28, 21-ketobetulinic acid (2), 16β-hydroxybetulinic acid (3), and 22β-hydroxystellatogenin (4). The last new one was determined to be 3β,19α-dihydroxygermanican-28-oic acid and named machaeroceric acid (5). The stereochemistry of H-18 for germanicanes is α-configuration in contrast with oleanane. All germanicanes known to data are characterized by a Δ^<18,19> olefinic linkage in their molecules, but machaeroceric acid (5) has no such bond. Trichocereus bridgesii Br. & R. contained 2 new compounds named bridgesigenin A (14) and B (15). Trichocereus pachanoi Br. & R. contained 2 new compounds, which have new skeleton named pachanan, named pachanol A (16) and B (17), together with 14 and 15. The methyl group at C-27 of the pachanan skeleton was combined at 15-C. Moreover, pachanol C(18) and bridgesigenin C (19), new compounds, were isolated from an enzymatic hydrolyzate of MeOH ext. of T. pachanoi. Isolatocereus dumortieri Backbg. Contained a new compound named pachanol D (20) together with dumortierigenin (21). The structure of 20 was determined by the single-crystal X-ray diffraction. Twenty triterpenes from cactaceous plants were tested for antinociceptive effects (Table 2) and inhibitiory effects of TPA-induced ^<32>Pi-incorporation into phospholipids of HeLa cells.
1998-08-31

61(P25) サボテン科植物の新規トリテルペンサポゲニンの構造と活性(ポスター発表の部)

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