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

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• 作者：Matsuda ; Hisashi ; Kageura ; Tadashi ; Toguchida ; Iwao ; Murakami ; Toshiyuki ; Kishi ; Akinobu ; Yoshikawa ; Masayuki
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：1999
• 出版时间：November 1, 1999
• 年：1999
• 卷：9
• 期：21
• 页码：3081-3086
• 全文大小：353 K

文摘

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 μM). 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 μM (MTT assay). In addition, alismol and alisol F were found to suppress iNOS induction.