Jordan University of Science and Technology

Waol A, trans-Dihydrowaol A, and cis-Dihydrowaol A: Polyketide-derived gamma-Lactones from a Volutella Species


Authors:  Tamam El-Elimat, Mario Figueroa, Huzefa A. Raja, Audrey F. Adcock, David J. Kroll, Steven M. Swanson, Mansukh C. Wani, Cedric J. Pearce, Nicholas H. Oberlies

Abstract:  
An organic extract of a filamentous fungus (MSX 58801), identified as a Volutella sp. (Hypocreales, Ascomycota), displayed moderate cytotoxic activity against NCI-H460 human large cell lung carcinoma. Bioactivity-directed fractionation led to the isolation of three ?-lactones having the furo[3,4-b]pyran-5-one bicyclic ring system [waol A (1), trans-dihydrowaol A (2), and cis-dihydrowaol A (3)]. The structures were elucidated using a set of spectroscopic and spectrometric techniques; the absolute configuration of 2 was established via a modified Mosher's ester method. Compounds 1 and 2 were evaluated for cytotoxicity against a human cancer cell panel.