Glaucumolides A (1) and B (2), novel biscembranes composed of an unprecedented α,β-unsaturated ε-lactone, along with the known metabolites ximaolide A (3) and isosarcophytonolide D (4), were isolated from the cultured soft coral Sarcophyton glaucum. The structures of the new metabolites were determined by extensive spectroscopic analyses. Compounds 1 and 2 were shown to exhibit cytotoxicity against a limited panel of cancer cell lines. In anti-inflammation assay, compounds 1 and 2 displayed strong inhibition of superoxide anion generation and elastase release in human neutrophils stimulated by fMLP/CB. Furthermore, both 1 and 2 were shown to significantly inhibit the accumulation of the pro-inflammatory inducible nitric oxide synthase protein, and compounds 1−3 were found to effectively reduce the expression of cyclooxygenase-2 protein, in lipopolysaccharide-stimulated RAW264.7 macrophage cells.
Nine new eunicellin-based diterpenoids, simplexins A-I (1-9), were isolated from a Dongsha Atoll soft coral, Klyxum simplex. The structures of these compounds were established by detailed spectroscopic analysis (IR, MS, 1D and 2D NMR) and by comparison with the physical and spectral data of related known compounds. The absolute configuration of 1 was determined by a modified Mosher's method. Compounds 1, 4, and 5 were found to be cytotoxic toward a limited panel of cancer cell lines. Compound 5 was shown to significantly inhibit the accumulation of the pro-inflammatory iNOS and COX-2 proteins in LPS-stimulated RAW264.7 macrophage cells.
Four new polyoxygenated briarane-type diterpenoids, briaexcavatolides O-R (1-4), have been isolated from a gorgonian octocoral Briareum excavatum. Their structures were determined using spectroscopic and chemical methods. Metabolites 1-3 were found to contain oxygenated substituents at C-2, C-3, and C-4, and the relative configurations were assigned as 2R*,3R*,4R* at these three positions. Briaranes containing this type of stereochemistry are reported for the first time. The structures of metabolites 1 and 2 were further confirmed by single-crystal X-ray analyses. Compound 2 has been shown to exhibit significant cytotoxicity toward P-388 and HT-29 cancer cells.
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