Breviane Spiroditerpenoids from an Extreme-Tolerant <i>Penicillium</i> sp. Isolated from a Deep Sea Sediment Sample

Breviones F−H (1−3), three new bioactive breviane spiroditerpenoids, have been isolated from the crude extract of an extreme-tolerant Penicillium sp. obtained from a deep sea sediment sample that was collected at a depth of 5115 m. The structures of these compounds were elucidated primarily by NMR spectroscopy. The absolute configurations of 1 and 3 were assigned by application of the modified Mosher method, and 3 is further confirmed by X-ray crystallographic analysis of its S-MTPA ester. Compound 2 could be the precursor for 3, which features a previously undescribed skeleton of mixed biogenesis.