Brocaenols A-C: novel polyketides from a marine derived Penicillium brocae |
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Authors: | Bugni Tim S Bernan Valerie S Greenstein Michael Janso Jeffrey E Maiese William M Mayne Charles L Ireland Chris M |
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Institution: | Department of Medicinal Chemistry, University of Utah, Salt Lake City, Utah 84112, USA. |
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Abstract: | Chemical investigation of a Penicillium brocae, obtained from a tissue sample of a Fijian Zyzyya sp. sponge, yielded two known diketopiperazines and three novel cytotoxic polyketides, brocaenols A-C. The brocaenols contain an unusual enolized oxepine lactone ring system that to the best of our knowledge is unprecedented in the literature. The structures were elucidated by using 2D-NMR methods including an INADEQUATE experiment. The absolute stereochemistry of brocaenol A was established by using a modified Mosher method. The taxonomy of the producing fungus was elucidated by using both morphological and rDNA sequence analysis. |
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