Structurally Diverse Alkaloids from the Seeds of Peganum harmala

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

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

Investigation of the alkaloids from Peganum harmala seeds yielded two pairs of unique racemic pyrroloindole alkaloids, (±)-peganines A-B (1-2); two rare thiazole derivatives, peganumals A-B (3-4); six new β-carboline alkaloids, pegaharmines F-K (5-10); and 12 known analogues. Their structures, including stereochemistry, were elucidated through spectroscopic analyses, quantum chemistry calculations, and single-crystal X-ray diffraction. Notably, the incorporation of pyrrole and indole moieties in peganines A-B, thiazole fragments in peganumals A-B, and a C-1 α,β-unsaturated ester motif in pegaharmine F (5) are all rare, and their presence in the genus Peganum were demonstrated for the first time. All isolates were tested for antiproliferative activities against the HL-60, PC-3, and SGC-7901 cancer cell lines, and compounds 9, 11, 12, and 13 exhibited moderate cytotoxicity against HL-60 cancer cell lines with IC50 values in the range of 4.36-9.25 μM.

Original languageEnglish (US)
Pages (from-to)551-559
Number of pages9
JournalJournal of Natural Products
Volume80
Issue number2
DOIs
StatePublished - Feb 24 2017
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Wang, K. B., Li, D. H., Bao, Y., Cao, F., Wang, W. J., Lin, C., Bin, W., Bai, J., Pei, Y. H., Jing, Y. K., Yang, D., Li, Z. L., & Hua, H. M. (2017). Structurally Diverse Alkaloids from the Seeds of Peganum harmala. Journal of Natural Products, 80(2), 551-559. https://doi.org/10.1021/acs.jnatprod.6b01146