title: Cytotoxic Alangium alkaloids from Alangium longiflorum.
abstract: Seven alkaloids (1-7) were isolated from the stem bark of Alangium longiflorum. Compound 1, (-)-10-O-demethylisocephaeline, was isolated for the first time as a naturally occurring product from a plant source. All structures were elucidated by detailed spectroscopic analysis. Biological evaluation showed that 2, 10-O-demethylcephaeline, exhibited potent cytotoxic activity against human lung carcinoma (A549) and breast adenocarcinoma (MCF-7) with ED(50) values of 0.013 and 0.062 microM, respectively. The stereoisomer 1 was less potent than 2, and related compounds with different hydroxy/methoxy substitution patterns were also less potent or inactive. Thus, compound 2 merits attention as a cytotoxic lead for further study.
authors.affiliation: Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill, 27599, USA.
authors.forename: Nobuko
authors.initials: N
authors.lastname: Sakurai
authors.forename: Kyoko
authors.initials: K
authors.lastname: Nakagawa-Goto
authors.forename: Junko
authors.initials: J
authors.lastname: Ito
authors.forename: Yojiro
authors.initials: Y
authors.lastname: Sakurai
authors.forename: Yuka
authors.initials: Y
authors.lastname: Nakanishi
authors.forename: Kenneth F
authors.initials: KF
authors.lastname: Bastow
authors.forename: Gordon
authors.initials: G
authors.lastname: Cragg
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
mesh_terms: D032604:Alangiaceae / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D001943:Breast Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008175:Lung Neoplasms / Q000188:drug therapy; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: C512479:10-O-demethylcephaeline; D000470:Alkaloids; D013729:Terpenes; D044005:Tetrahydroisoquinolines; C502716:isocephaeline