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Two rare 6(D)/5(E) ring-fused meroterpenoids, eupeniacetal A (1) and eupeniacetal B (2), and three new meroterpenoids, 1-methoxy-hydropreaustinoid A1 (3), hydroberkeleyone B (4), and 22-deoxy-10-oxominiolutelide B (5), as well as five known meroterpenoids, 22-deoxyminiolutelide B (6), preaustinoid A1 (7), berkeleyone C (8), berkeleyacetal A (9), and preaustinoid A3 (10), have been isolated, through the aid of LC-MS, from the sponge-derived fungus Eupenicillium sp. 6A-9. The structures of these meroterpenoids were elucidated by detailed spectroscopic analysis, comparison with literature data, and single-crystal X-ray diffraction. The absolute configurations were assigned by means of TDDFT/ECD and [a]D calculations as well as by X-ray diffraction analysis. These compounds showed inhibitory activity towards TNF-a production in the induced THP-1 cell line but were inactive against normal tumor cell lines. [ABSTRACT FROM AUTHOR]

[Display omitted] • Five new scalarane-type sesterterpenoids were isolated. • The absolute configurations of new structures were assigned by single crystal X-ray diffraction analyses. • Compounds 1 , 2 , 6 , 7 showed inhibitory activities with respective IC 50 values of 16.4, 18.5, 2.6, and 3.7 μ M, on the production of nitric oxide (NO) stimulated by lipopolysaccharide (LPS) in mouse RAW 264.7 macrophages. Dysiscalarones A-E (1 – 5), five new scalarane-type bishomoscalarane sesterterpenoids, were isolated from marine sponge Dysidea granulosa collected from the South China Sea, together with two known ones, honulactone A (6) and phyllofolactone I (7). The new structures were determined by extensive spectroscopic analysis including HR-ESI-MS and 1D and 2D NMR data, and their absolute configurations were assigned by single crystal X-ray diffraction analyses. The inhibitory activity of all the seven isolates on the production of nitric oxide (NO) stimulated by lipopolysaccharide (LPS) in mouse RAW 264.7 macrophages was evaluated. Of these metabolites, dysiscalarones A-B (1 – 2), honulactone A (6), and phyllofolactone I (7) showed inhibitory activities with respective IC 50 values of 16.4, 18.5, 2.6, and 3.7 μ M, which suggested that the γ -methylated α , β -unsaturated γ -lactone might be the functional group. In addition, all the seven metabolites showed no significant cytotoxicity against lung cancer PC9 cell line at the concentration of 20 μ M. [ABSTRACT FROM AUTHOR]