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: Nobuko Sakurai, Kyoko Nakagawa-Goto, Junko Ito, Yojiro Sakurai, Yuka Nakanishi, Kenneth F Bastow, Gordon Cragg, Kuo-Hsiung Lee
• Journal: Phytochemistry (Phytochemistry) Vol. 67 Issue 9 Pg. 894-7 (May 2006) ISSN: 0031-9422 [Print] England
• PMID: 16530796 (Publication Type: Journal Article, Research Support, N.I.H., Extramural)

Chemical References

• 10-O-demethylcephaeline
• Alkaloids
• Terpenes
• Tetrahydroisoquinolines
• isocephaeline

Topics

• Alangiaceae (chemistry)
• Alkaloids (chemistry, pharmacology)
• Breast Neoplasms (drug therapy)
• Cell Line, Tumor
• Drug Screening Assays, Antitumor
• Humans
• Lung Neoplasms (drug therapy)
• Molecular Structure
• Plant Bark (chemistry)
• Stereoisomerism
• Terpenes (chemical synthesis, pharmacology)
• Tetrahydroisoquinolines (chemical synthesis, pharmacology)