title: Structurally Diverse Alkaloids from the Seeds of Peganum harmala.
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 IC50values in the range of 4.36-9.25 μM.
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University , West Lafayette, Indiana 47907, United States.
authors.forename: Kai-Bo
authors.initials: KB
authors.lastname: Wang
authors.forename: Da-Hong
authors.initials: DH
authors.lastname: Li
authors.forename: Yu
authors.initials: Y
authors.lastname: Bao
authors.affiliation: Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University , Baoding 071002, People's Republic of China.
authors.forename: Fei
authors.initials: F
authors.lastname: Cao
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Wang
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University , West Lafayette, Indiana 47907, United States.
authors.forename: Clement
authors.initials: C
authors.lastname: Lin
authors.forename: Wen
authors.initials: W
authors.lastname: Bin
authors.forename: Jiao
authors.initials: J
authors.lastname: Bai
authors.forename: Yue-Hu
authors.initials: YH
authors.lastname: Pei
authors.forename: Yong-Kui
authors.initials: YK
authors.lastname: Jing
authors.affiliation: Department of Medicinal Chemistry and Molecular Pharmacology, College of Pharmacy, Purdue University , West Lafayette, Indiana 47907, United States.
authors.forename: Danzhou
authors.initials: D
authors.lastname: Yang
authors.forename: Zhan-Lin
authors.initials: ZL
authors.lastname: Li
authors.forename: Hui-Ming
authors.identifier: 0000-0002-0258-3647
authors.initials: HM
authors.lastname: Hua
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002243:Carbolines / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D018922:HL-60 Cells; D006801:Humans; D026121:Indole Alkaloids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D032443:Peganum / Q000737:chemistry*; D012639:Seeds / Q000737:chemistry*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D002243:Carbolines; D004365:Drugs, Chinese Herbal; D026121:Indole Alkaloids