New triterpenic acids from Uncaria rhynchophylla: Chemistry, NO-inhibitory activity, and tandem mass spectrometric analysis

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• 作者：Yi-bei Zhang¹ ; Wen-zhi Yang¹ ; Chang-liang Yao ; Rui-hong Feng ; Min Yang ; De-an Guo ; Wan-ying Wu ; ^{wanyingwu@simm.ac.cn" class="auth_mail}
• 关键词：Uncaria rhynchophylla ; Uncarinic acid ; NO-inhibitory effect ; Tandem mass spectrometric fragmentation
• 刊名：Fitoterapia
• 出版年：July 2014
• 年：2014
• 卷：96
• 期：Complete
• 页码：39-47
• 全文大小：893 K

文摘

Five new oleanane and ursane type triterpenes, namely uncarinic acids F–J (1–5), together with six known triterpenic acids (6–11) were isolated from the stems and hooks of Uncaria rhynchophylla. Structure elucidation of 1–5 was based on the integrated analyses of high-resolution MS data, 1D (¹H NMR, ¹³C NMR, DEPT) and 2D (HSQC, HMBC, ROESY) NMR spectra. Compounds 4, 10, and 11 exhibited weak inhibitory effects on LPS-induced NO production in RAW264.7 cells (with IC₅₀ 1.48, 7.01, and 1.89 渭M, respectively) with dexamethasone (IC₅₀ 0.04 渭M) and quercetin (IC₅₀ 0.86 渭M) as the positive controls. 19-OH substituted oleanane triterpenic acids (1, 2, 5, 8) were prone to eliminate CH₂O₃, whereas those ursane-type encompassing 19-OH (3, 6, 7, 9, 4) were featured by preferred cleavage of H₂O while performing the negative collision-induced MS/MS fragmentation on an LTQ/Orbitrap mass spectrometer.