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Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived ?-lactones from a Volutella species.

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.

SUBMITTER: El-Elimat T

PROVIDER: S-EPMC3743556 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Waol A, trans-dihydrowaol A, and cis-dihydrowaol A: polyketide-derived γ-lactones from a Volutella species.

El-Elimat Tamam T Figueroa Mario M Raja Huzefa A HA Adcock Audrey F AF Kroll David J DJ Swanson Steven M SM Wani Mansukh C MC Pearce Cedric J CJ Oberlies Nicholas H NH

Tetrahedron letters 20130801 32

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 γ-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 spectro ...[more]

PMID: 23956472

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