New monoterpenoid oxindole alkaloid derivatives from the stems of Uncaria hirsuta Havil. and their cytotoxicity and tandem mass spectrometric fragmentation

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• 作者：Hui-qin Pan^a ; ^b ; ¹ ; Wen-zhi Yang^a ; ¹ ; Dan Zhao^c ; Cheng Luo^c ; Chang-liang Yao^a ; ^b ; Xiao-jian Shi^a ; Yi-bei Zhang^a ; Shi-you Li^d ; Ying Bi^d ; Zhen Wang^d ; Shuai Yao^a ; Wan-ying Wu^a ; ^{wanyingwu@simm.ac.cn} ; De-an Guo^a ; ^{daguo@simm.ac.cn}
• 关键词：Uncaria hirsuta ; Monoterpenoid oxindole alkaloid ; MDA-MB-231 ; Collision-induced dissociation
• 刊名：Fitoterapia
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：116
• 期：Complete
• 页码：85-92
• 全文大小：947 K
• 卷排序：116

文摘

Four new alkaloids, comprising three 3-oxo-3,7-seco-oxindole alkaloids (hirsutanine D–F, 1–3) and one oxindole alkaloid N-oxide (uncarine B N-oxide, 4), together with four known heteroyohimbine-type oxindole alkaloids, were isolated from the stems of Uncaria hirsuta Havil. Structures of 1–4 were elucidated by extensive NMR and HR-ESIMS data analyses. Compound 3 is the first 3-oxo-3,7-seco-oxindole alkaloid with ring B opened and degraded isolated from the Uncaria genus. Compounds 1–3 exhibited slight inhibition effect on the proliferation of the breast cancer cell MDA-MB-231. The positive mode collision-induced dissociation of the 3-oxo-3,7-seco-oxindole alkaloids (1–3) was featured by the β-cleavage and α-cleavage of the amido bond, while the N-oxide (4) showed characteristic neutral eliminations of ·OH and H2O.