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ID: ALA4033607

Journal: J Nat Prod

Title: Structurally Diverse Alkaloids from the Seeds of Peganum harmala.

Authors: Wang KB, Li DH, Bao Y, Cao F, Wang WJ, Lin C, Bin W, Bai J, Pei YH, Jing YK, Yang D, Li ZL, Hua HM.

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.

CiteXplore: 28128938

DOI: 10.1021/acs.jnatprod.6b01146