A Series of β-Carboline Alkaloids from the Seeds of Peganum harmala Show G-Quadruplex Interactions

Kai Bo Wang, Da Hong Li, Ping Hu, Wen Jing Wang, Clement Lin, Jian Wang, Bin Lin, Jiao Bai, Yue Hu Pei, Yong Kui Jing, Zhan Lin Li, Danzhou Yang, Hui Ming Hua

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

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 languageEnglish (US)
Pages (from-to)3398-3401
Number of pages4
JournalOrganic Letters
Volume18
Issue number14
DOIs
StatePublished - Jul 15 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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