Cytotoxic Alangium alkaloids from Alangium longiflorum.
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.
Sakurai
Nobuko
N
Natural Products Laboratory, School of Pharmacy, University of North Carolina, Chapel Hill, 27599, USA.
Nakagawa-Goto
Kyoko
K
Ito
Junko
J
Sakurai
Yojiro
Y
Nakanishi
Yuka
Y
Bastow
Kenneth F
KF
Cragg
Gordon
G
Lee
Kuo-Hsiung
KH
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*
C512479:10-O-demethylcephaeline; D000470:Alkaloids; D013729:Terpenes; D044005:Tetrahydroisoquinolines; C502716:isocephaeline