Tabernaemontana corymbosa 中的细胞毒 Vobasinyl-Iboga 型双吲哚生物碱 Taburnaemines A-I
Taburnaemines A-I, Cytotoxic Vobasinyl-Iboga-Type Bisindole Alkaloids from Tabernaemontana corymbosa.
机构信息
State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany, Chinese Academy of Sciences , Kunming 650201 , Yunnan , People's Republic of China.
Natural Product Research Laboratories, UNC Eshelman School of Pharmacy , University of North Carolina , Chapel Hill , North Carolina 27599-7568 , United States.
出版信息
J Nat Prod. 2018 Mar 23;81(3):562-571. doi: 10.1021/acs.jnatprod.7b00949. Epub 2018 Jan 10.
Nineteen vobasinyl-ibogan-type bisindole alkaloids, including nine new compounds, taburnaemines A-I (1-9), were isolated from the twigs and leaves of Tabernaemontana corymbosa. The structures and absolute configurations of the new alkaloids were determined by a combination of MS, NMR, and ECD analyses. Alkaloids 1-5 contain a rare 1,3-oxazinane moiety in the vobasinyl unit, while 6 has an uncommon 1,3-oxazolidine moiety in the iboga unit. The absolute configurations of alkaloid 1 and the known alkaloid tabernaecorymbosine A (10) were confirmed by single-crystal X-ray diffraction analysis. All of the bisindole alkaloids, except 2 and 16'-decarbomethoxytabernaecorymbosine A (14), showed antiproliferative activity (IC 2.6-9.8 μM) against several human cancer cell lines, including A-549, MDA-MB-231, MCF-7, KB, and P-glycoprotein-overexpressing multidrug-resistant KB cells. The preliminary structure-activity relationship correlations are also discussed.
十九个 vobasinyl-ibogan 型双吲哚生物碱，包括九个新化合物，taburnaemines A-I（1-9），从 Tabernaemontana corymbosa 的嫩枝和叶子中分离出来。新生物碱的结构和绝对构型通过 MS、NMR 和 ECD 分析的组合确定。生物碱 1-5 在 vobasinyl 单元中含有罕见的 1,3-恶嗪烷部分，而 6 在 iboga 单元中含有不常见的 1,3-恶唑烷部分。生物碱 1 和已知生物碱 tabernaecorymbosine A（10）的绝对构型通过单晶 X 射线衍射分析得到证实。除了 2 和 16'-去甲氧基 tabernaecorymbosine A（14）之外，所有的双吲哚生物碱都表现出对几种人类癌细胞系的抗增殖活性（IC 2.6-9.8 μM），包括 A-549、MDA-MB-231、MCF-7、KB 和 P-糖蛋白过表达的多药耐药 KB 细胞。还讨论了初步的结构-活性关系相关性。
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