Bioactive saponins and glycosides. XI. Structures of new dammarane-type triterpene oligoglycosides, quinquenosides I, II, III, IV, and V, from American ginseng, the roots of Panax quinquefolium L.
Bioactive saponins and glycosides. XI. Structures of new dammarane-type triterpene oligoglycosides, quinquenosides I, II, III, IV, and V, from American ginseng, the roots of Panax quinquefolium L.
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DOI：
10.1248/cpb.46.647
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发表时间：
1998-04
影响因子：
1.7
通讯作者：
M. Yoshikawa;T. Murakami;K. Yashiro;J. Yamahara;H. Matsuda;Reiko Saijoh;O. Tanaka
中科院分区：
文献类型：
--
作者：
M. Yoshikawa;T. Murakami;K. Yashiro;J. Yamahara;H. Matsuda;Reiko Saijoh;O. Tanaka
研究发现西洋参（Panax quinquefolium L. 的根）的甲醇提取物和 1-丁醇可溶部分对 D-半乳糖胺和脂多糖引起的肝损伤具有保护作用。从 1-丁醇可溶性馏分中分离出五种新的达玛烷型三萜低聚糖苷，称为五醌苷 I、II、III、IV 和 V，以及十四种已知的达玛烷型三萜低聚糖苷，例如竹节皂苷 IVa、假人参皂苷-RC1、丙二酰人参皂苷-Rb1 和三七皂苷-A、-C 和 -K。从乙酸乙酯可溶部分中，分离出四种已知的炔属化合物和6'-O-乙酰基人参皂苷-Rg1。根据化学和物理化学证据确定五醌皂苷 I、II、III、IV 和 V 的结构为 3-O-[6-O-(E)-2-丁烯酰基-β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基]-20-O-(β-D-吡喃葡萄糖基) 20(S)-原人参二醇（五醌苷） I)、3-O-[6-O-(E)-2-辛烯酰基-β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基]-20-O-[β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]20(S)-原人参二醇(五醌苷II)， 3-O-[β-D-吡喃葡萄糖基(1-->2)-6-O-乙酰基-β-D-吡喃葡萄糖基]-20-O-(β-D-吡喃葡萄糖基)20(S)-原人参二醇(五醌苷III)， 3-O-[β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基]-20-O-β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]-3β、7β、20(S)-三羟基达玛-5,24-二烯(五醌苷IV)，和3-O-[β-D-吡喃葡萄糖基(1-->2)-β-D-吡喃葡萄糖基]-20-O-[α-D-吡喃葡萄糖基(1-->4)-β-D-吡喃葡萄糖基(1-->6)-β-D-吡喃葡萄糖基]20(S)-原人参二醇(五醌苷V)。
The methanolic extract and 1-butanol-soluble fraction of American ginseng, the roots of Panax quinquefolium L., were found to exhibit a protective effect on liver injury induced by D-galactosamine and lipopolysaccharide. Five new dammarane-type triterpene oligoglycosides called quinquenosides I, II, III, IV, and V were isolated together with fourteen known dammarane-type triterpene oligoglycosides such as chikusetsusaponin IVa, pseudo-ginsenoside-RC1, malonyl-ginsenoside-Rb1, and notoginsenosides-A,-C, and -K from the 1-butanol-soluble fraction. From the ethyl acetate-soluble fraction, four known acetylenic compounds and 6'-O-acetyl ginsenoside-Rg1 were isolated. The structures of quinquenosides I, II, III, IV, and V were determined on the basis of chemical and physicochemical evidence as 3-O-[6-O-(E)-2-butenoyl-beta-D-glucopyranosyl(1-->2)-beta-D- glucopyranosyl]-20-O-(beta-D-glucopyranosyl) 20(S)-protopanaxadiol (quinquenoside I), 3-O-[6-O-(E)-2-octenoyl-beta-D- glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-20-O-[beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosyl] 20(S)-protopanaxadiol (quinquenoside II), 3-O-[beta-D-glucopyranosyl (1-->2)-6-O-acetyl-beta-D-glucopyranosyl]-20-O-(beta-D-glucopyranosyl) 20(S)-protopanaxadiol (quinquenoside III), 3-O-[beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-20-O-beta-D- glucopyranosyl(1-->6)-beta-D-glucopyranosyl]-3 beta, 7 beta, 20(S)-trihydroxydammar-5,24-diene (quinquenoside IV), and 3-O-[beta-D-glucopyranosyl(1-->2)-beta-D-glucopyranosyl]-20-O-[alpha-D- glucopyranosyl(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranosyl ] 20(S)-protopanaxadiol (quinquenoside V).