Abstract
In this study, we screened 17 medicinal plants for binding activity to G-quadruplex d(TTGGGTT)4 by 1H NMR spectroscopy and found that the crude extract of Peganum harmala L. seeds showed the most potential binding activity. Subsequently, 1H NMR- and bioassay-guided isolation of the extract of P. harmala L. was performed to obtain four pairs of partially racemized β-carboline alkaloids, pegaharmines A-D (1-4). Their structures and absolute configurations were determined by extensive NMR analyses, X-ray crystallography, ECD calculations, and CD exciton chirality approaches. Interestingly, pegaharmine D (4), which showed the strongest G-quadruplex interaction, exhibited significant cytotoxic activity against three cancer cell lines. This work contributed a practical strategy for the discovery of novel G-quadruplex ligands from natural products and provided potential insights for using β-carboline alkaloids as anticancer lead compounds specifically targeting G-quadruplexes.
Original language | English (US) |
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Pages (from-to) | 3398-3401 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 18 |
Issue number | 14 |
DOIs | |
State | Published - Jul 15 2016 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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CCDC 1476718: Experimental Crystal Structure Determination
Wang, K. (Creator), Li, D. (Creator), Hu, P. (Creator), Wang, W. (Creator), Lin, C. (Creator), Wang, J. (Creator), Lin, B. (Creator), Bai, J. (Creator), Pei, Y. (Creator), Jing, Y. (Creator), Li, Z. (Creator), Yang, D. (Creator) & Hua, H. (Creator), Cambridge Crystallographic Data Centre, 2016
DOI: 10.5517/ccdc.csd.cc1lkn2w, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1lkn2w&sid=DataCite
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