New Cytotoxic Manzamine Alkaloids from a Palaun Sponge

✍ Scribed by Bing-Nan Zhou; Carla Slebodnick; Randall K. Johnson; Michael R. Mattern; David G.I. Kingston

• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 102 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00534-2

✦ Synopsis

AbstractÐA crude extract of a marine sponge showed initial inhibitory bioactivities in a yeast assay for inhibitors of methionine aminopeptidase-2 (Met AP-2). Bioassay-directed fractionation indicated that the activity was concentrated in the CH 2 Cl 2 -soluble fraction, and chromatography on silica gel led to the isolation of the two new bioactive alkaloids N-methyl-epi-manzamine D 1 and epi-manzamine D 2. The structures of the epi-manzamines were assigned by 1 H and 13 C NMR, DEPT, HMQC, and HMBC spectroscopy, and by comparison with the spectra of related compounds, and the structure of 1 was con®rmed by X-ray structure analysis. Neither of the two isolated compounds showed selectivity in the yeast assay for inhibitors of Met AP-2, but both compounds were cytotoxic to HeLa and B16F10 mammalian cells, with compound 1 showing strong activity against the B16F10 cell line.