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Cimicifoetones A and B, Dimeric Prenylindole Alkaloids as Black Pigments of Cimicifuga foetida.

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机构： [1]College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058 (China) E-mail: lsgan@zju.edu.cn [2]Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203 (China) [3]State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, 1# Keyuan 4th Road, High-tech Zone, Chengdu 610041 (China)

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关键词： alkaloids apoptosis cimicifoetones cytotoxicity natural products structure elucidation

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Two dimeric prenylindole alkaloids with a unique indole-benzoindolequinone skeleton, cimicifoetones A (1) and B (2), were isolated as black pigments from the rhizomes of Cimicifuga foetida. The structures were elucidated by spectroscopic methods including HRMS and 2D NMR, as well as single-crystal X-ray diffraction and computational chemical modeling techniques. Cimicifoetones A and B represented the first examples of dimeric indole alkaloids generated through [4+2] Diels-Alder cycloaddition between the prenyl side chain in one 3-prenylindole and the aromatic ring in another. The two compounds showed promising anti-proliferative activity on seven tumor cell lines with IC50 values in the range of 1.36-21.09 μm. Flow cytometric and western blot analysis revealed that compound 2 induced cell apoptosis via death receptor-mediated extrinsic and mitochondrial-mediated intrinsic pathways. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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出版当年[2017]版：

大类 | 2 区化学

小类 | 3 区化学综合

最新[2023]版：

大类 | 3 区化学

小类 | 4 区化学：综合

第一作者：

第一作者机构： [1]College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058 (China) E-mail: lsgan@zju.edu.cn

通讯作者：

通讯机构： [1]College of Pharmaceutical Sciences, Zhejiang University, 866 Yuhangtang Road, Hangzhou 310058 (China) E-mail: lsgan@zju.edu.cn

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