Peganumine A, a β‑Carboline Dimer with a New Octacyclic Scaffold from Peganum harmala

Peganumine A (1), a new dimeric β-carboline alkaloid characterized by a unique 3,9-diaza­tetra­cyclo­[6.5.2.01,9.03,8]­pentadec-2-one scaffold, was isolated from the seeds of Peganum harmala. The structure including the absolute configuration was determined by spectroscopic data, X-ray crystallograp...

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Bibliographic Details
Published in:Organic letters 2014-08, Vol.16 (15), p.4028-4031
Main Authors: Wang, Kai-Bo, Di, Ying-Tong, Bao, Yu, Yuan, Chun-Mao, Chen, Gang, Li, Da-Hong, Bai, Jiao, He, Hong-Ping, Hao, Xiao-Jiang, Pei, Yue-Hu, Jing, Yong-Kui, Li, Zhan-Lin, Hua, Hui-Ming
Format: Article
Language:English
Subjects:
Alkaloids - chemistry
Alkaloids - isolation & purification
Alkaloids - pharmacology
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Carbolines - chemistry
Carbolines - isolation & purification
Carbolines - pharmacology
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Hep G2 Cells
HL-60 Cells
Humans
Inhibitory Concentration 50
Molecular Conformation
Molecular Structure
Peganum - chemistry
Seeds - chemistry
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Summary:Peganumine A (1), a new dimeric β-carboline alkaloid characterized by a unique 3,9-diaza­tetra­cyclo­[6.5.2.01,9.03,8]­pentadec-2-one scaffold, was isolated from the seeds of Peganum harmala. The structure including the absolute configuration was determined by spectroscopic data, X-ray crystallography, ECD calculation, and CD exciton chirality approaches. Compound 1 showed moderate cytotoxic activity against MCF-7, PC-3, and HepG2 cells and selective effects on HL-60 cells with an IC50 value of 5.8 μM.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol501856v