Abstract
Chemical investigation on a marine sponge, Dactylospongia elegans, yielded five new γ-oxygenated butenolide sesterterpene derivatives, dactylospenes A–E (1–5), as well as two known biosynthetically related compounds, luffariellolide (6) and furospinosulin B (7). The structures of these compounds were elucidated on the basis of their spectroscopic data, experimental and calculated electronic circular dichroism (ECD) analysis, as well as comparison of the NMR data with those of known analogs. These metabolites are the first γ-oxygenated butenolide sesterterpenes to be reported from this genus. These compounds were evaluated in antimicrobial, anti-inflammatory, and cytotoxic assays. Only compounds 1, 3, and 6 exhibited moderate cytotoxicity against DU145, SW1990, Huh7, and PANC-1 cancer cell lines with IC50 values in the range of 2.11–13.35 μM. Furthermore, compound 2, without cytotoxicity, exhibited significant inhibitory effects (inhibitory rate 77.5%) on nitric oxide production induced by lipopolysaccharide at 10 μM.
Highlights
Sesterterpenoids, mainly found in marine organisms, are a rare class of terpene that are structurally diverse and have a wide spectrum of biological activities [1,2]
As part of the ongoing bioactive natural product discovery from the organic extract of a marine sponge D. elegans, one fraction showed different LC-DAD-MS profiles to those of previously reported sesquiterpene quinones/hydroquinones based upon LC-MS analysis [6]
C25H38O3 according to the HRESIMS peak at m/z 404.3166 [M + NH4]+, requiring seven degrees of
Summary
Sesterterpenoids, mainly found in marine organisms, are a rare class of terpene that are structurally diverse and have a wide spectrum of biological activities [1,2]. Aside from a few sesterterpenoids, sponges of the genus Dactylospongia, in particular D. elegans, have been widely investigated as a rich source of sesquiterpene quinones/quinols, sesquiterpene acids, sesterterpene lactones, macrolides, and steroids [7]. These metabolites showed a spectrum of bioactivities, such as cytotoxic [8], anti-inflammatory [9], antibacterial [10], and protein kinase inhibitory activities [11]. As part of the ongoing bioactive natural product discovery from the organic extract of a marine sponge D. elegans, one fraction showed different LC-DAD-MS profiles to those of previously reported sesquiterpene quinones/hydroquinones based upon LC-MS analysis [6]. Details of the isolation, structure elucidation, and biological activity evaluation of these metabolites
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