Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata
Flabellipparicine, a Flabelliformide-Apparicine-Type Bisindole Alkaloid from Tabernaemontana divaricata
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DOI：
10.1021/acs.jnatprod.8b00191
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发表时间：
2018-09-01
影响因子：
5.1
通讯作者：
Yang, Sheng-Ping
中科院分区：
文献类型：
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作者：
Cai, You-Sheng;Sarotti, Ariel M.;Yang, Sheng-Ping
从苋菜茎中分离得到 4 种新的单萜双吲哚生物碱：flabellipparicine (1)、19,20-二氢伏巴辛 (2)、10'-demethoxy-19,20-diHydrovobatensine D (3) 和 3'-(2-oxopropyl)ervahanine A (4)，以及 10 种已知的单萜吲哚生物碱。 Tabernaemontana divaricata。所有结构均基于光谱方法进行阐明，并使用构象分析和所选立体异构体的TDDFT-ECD计算建立了1的绝对构型。化合物1代表第一个flabelliformide-apparicine型双吲哚生物碱，其中flabelliformide样单元通过C-3-C-22'键和N-1-C-16'键与apparicine样单元连接，在两个单体之间形成不常见的五元环。评估了所有生物碱对两种人类癌细胞系 MCF-7 和 A-549 的细胞毒性。化合物 2、4 和 14 对 MCF-7 和 A-549 表现出细胞毒性，IC50 值在 2 nM 至 8 muM 范围内。
Four new monoterpenoid bisindole alkaloids, flabellipparicine (1), 19,20-dihydrovobparicine (2), 10'-demethoxy-19,20-dihydrovobatensine D (3), and 3'-(2-oxopropyl)ervahanine A (4), and 10 known monoterpenoid indole alkaloids were isolated from the stems of Tabernaemontana divaricata. All structures were elucidated based on spectroscopic methods, and the absolute configuration of 1 was established using conformational analysis and TDDFT-ECD calculation of selected stereoisomers. Compound 1 represents the first flabelliformide-apparicine-type bisindole alkaloid, in which the flabelliformide-like unit connects to the apparicine-like unit with a C-3-C-22' bond and an N-1-C-16' bond to form an uncommon five-membered ring between the two monomers. All alkaloids were evaluated for their cytotoxicity against two human cancer cell lines, MCF-7 and A-549. Compounds 2, 4, and 14 exhibited cytotoxicity against MCF-7 and A-549 with IC50 values in the range of 2 nM to 8 mu M.