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Cimicifoetones A and B, Dimeric Prenylindole Alkaloids as Black Pigments of Cimicifuga foetida
Author(s) -
Zhou ChangXin,
Yu YuE,
Sheng Rong,
Mo JianXia,
Huang Min,
Ouyang Liang,
Gan LiShe
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700348
Subject(s) - stereochemistry , rhizome , chemistry , indole test , pigment , two dimensional nuclear magnetic resonance spectroscopy , prenylation , biology , botany , biochemistry , organic chemistry , enzyme
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 IC 50 values in the range of 1.36–21.09 μ m . Flow cytometric and western blot analysis revealed that compound 2 induced cell apoptosis via death receptor‐mediated extrinsic and mitochondrial‐mediated intrinsic pathways.