Cucurbitane Glucosides from the Root of Machilus yaoshansis

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• 作者：Maoluo Gan ; Mingtao Liu ; Bo Liu ; Sheng Lin ; Yanling Zhang ; Jiachen Zi ; Weixia Song ; Fei Ye ; Xiaoguang Chen ; Jiangong Shi
• 刊名：Journal of Natural Products
• 出版年：2011
• 出版时间：November 28, 2011
• 年：2011
• 卷：74
• 期：11
• 页码：2431-2437
• 全文大小：273K
• 年卷期：v.74,no.11(November 28, 2011)
• ISSN：1520-6025

文摘

Seven new cucurbitane triterpene glucosides (1鈥?b>5, 8, and 9) and five known analogues (6, 7, 10, cucurbitacin I 2-O-尾-d-glucopyranoside, and khekadaengoside K) have been isolated from an ethanol extract of roots of Machilus yaoshansis. Compounds 1 and 2 have an unusual 16,23:22,25-diepoxy unit, 4 is an uncommon cucurbitane 25-carbamate with the carbamoyl amino group attached at C-24 to form an oxazolidinone ring in the side chain, and 8 is the first example of a trinorcucurbitane derivative. The configurations in several pairs of C-24 epimeric cucurbitacins with 24,25-dihydroxy-22-one side chains were assigned, and the validity of J_23a,24 and J_23b,24 values to differentiate the configuration at C-24 in these cucurbitane derivatives is discussed. Compounds 2鈥?b>4 showed in vitro activity against protein tyrosine phosphatase 1B with IC₅₀ values of 8.63, 2.81, and 4.26 渭M, respectively. Cucurbitacin E 2-O-尾-d-glucopyranoside (10) showed selective cytotoxicity against BGC-823 and A549 cancer cells with IC₅₀ values of 4.98 and 3.20 渭M, respectively.