2,4-cis- and trans-Venezinones: New Bioactive Ketolactone Annonaceous Acetogenins, Lacking Tetrahydrofuran Rings, from Xylopia aromatica

✍ Scribed by Trina Colman-Saizarbitoria; Dorothée Alfonso; Jerry L. McLaughlin

• Book ID: 101283473
• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 460 KB
• Volume: 7
• Category: Article
• ISSN: 0958-0344
• DOI: 10.1002/(sici)1099-1565(199611)7:6<313::aid-pca316>3.0.co;2-z

✦ Synopsis

By bioactivity-directed fractionation using lethality to brine shrimp, two new bioactive ketolactone Annonaceous acetogenins, 2,4-cis-and 2,4-trans-venezinones (1 and 2), were isolated as a mixture from the 95% ethanol extract of the bark of Xylopia aromatica (Annonaceae). Compounds 1 and 2 represent an unusual type of C-37 Annonaceous acetogenin, lacking either a tetrahydrofuran or an epoxide ring and possessing a double bond located two methylene groups distant from a vicinal diol in the hydrocarbon chain. The structures of 1 and 2 were elucidated by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry, and from simple derivatives. Both compounds showed significant cytotoxicities, one to two orders of magnitude less potent than adriamycin, against six human solid tumor cell lines.