Effects of sesquiterpenes and triterpenes from the rhizome of Alisma orientale on nitric oxide production in lipopolysaccharide-activated macrophages:: Absolute stereostructures of alismaketones-B 23-acetate and -C 23-acetate

被引:83
作者
Matsuda, H [1 ]
Kageura, T [1 ]
Toguchida, I [1 ]
Murakami, T [1 ]
Kishi, A [1 ]
Yoshikawa, M [1 ]
机构
[1] Kyoto Pharmaceut Univ, Yamashima Ku, Kyoto 6078414, Japan
关键词
D O I
10.1016/S0960-894X(99)00536-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The methanolic extract from a Chinese herbal medicine, the rhizome of Alisma orientale, was found to exhibit inhibitory activity of nitric oxide (NO) production in lipopolysaccharide (LPS)-activated macrophages. Novel triterpenes, alismaketones-B 23-acetate and -C 23-acetate, were isolated from the active extract together with eight sesquiterpenes and eighteen protostane-type triterpenes. The absolute stereostructures of new triterpenes were characterized on the basis of chemical and physicochemical evidence, which included the chemical correlations with known triterpenes. The guaiane-type sesquiterpenes (alismol, orientalols A and C) and protostane- and seco-protostane-types triterpenes (alisols C monoacetate, E-23-acetate, F, H, I, L-23-acetate, and M-23-acetate, alismaketones-B 23-acetate and -C 23-acetate, alismalactone 23-acetate, and 3-methylalismalactone 23-acetate) inhibited LPS-induced NO production (IC50 8.4-68 mu M). Other triterpenes (alisols A, A monoacetate, B, B monoacetate, E, G, K-23-acetate, and N-23-acetate and 11-deoxyalisol B) also showed the potent inhibitory activity, but they showed cytotoxic effects more than 30 mu M (MTT assay). In addition, alismol and alisol F were found to suppress iNOS induction. (C) 1999 Elsevier Science Ltd. All rights reserved.
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页码:3081 / 3086
页数:6
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