ABSTRACT
A novel diterpenoid, sinunanolobatone A (1), featuring an unprecedented bicyclo[13.1.0]pentadecane carbon framework, along with two new casbane diterpenoids (2 and 3), and five known related ones (4-8) were isolated from the Sanya soft coral Sinularia nanolobata. The structures of the new compounds were established by detailed spectroscopic analysis, X-ray diffraction analysis, chemical reactions, or a quantum chemical computation method. A plausible biosynthetic pathway of 1 was proposed. In bioassay, the novel compound 1 showed significant inhibitory activity against lipopolysaccharide (LPS) induced inflammation in BV-2 microglial cells.
Subject(s)
Alkanes/chemistry , Anthozoa/chemistry , Anti-Inflammatory Agents/pharmacology , Diterpenes/chemistry , Lipopolysaccharides/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Crystallography, X-Ray , Microglia/drug effects , Molecular Structure , Spectrum AnalysisABSTRACT
A novel norditerpenoid, sinusiaetone A (1), featuring an uncommon bicyclo[11.3.0]hexadecane carbon skeleton, and four polyoxygenated cembranoids (2-5) were isolated from the Hainan soft coral Sinularia siaesensis. Their structures were established by spectroscopic analysis, X-ray diffraction, quantum chemical computational approaches, and/or a modified Mosher's method. A plausible biosynthetic pathway of 1 and its biogenetic relationship with 2-5 were proposed. New compounds 1-3 displayed an interesting inhibitory activity against lipopolysaccharide-induced inflammation in BV-2 microglial cells.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/pharmacology , Bridged Bicyclo Compounds/pharmacology , Diterpenes/chemistry , Lipopolysaccharides/pharmacology , Alkanes , Animals , Anti-Inflammatory Agents/chemistry , Bridged Bicyclo Compounds/chemistry , Lipopolysaccharides/chemistry , Molecular StructureABSTRACT
A detailed chemical investigation of two specimen of South China Sea sponges Halichondria sp. (No. 19-XD-47 and No. 17-XD-87) have resulted in the isolation of three new sterols, namely, halichsterols A (1), B (2) and C (3), together with seven related known ones (4-10). Their structures were determined by extensive spectroscopic analysis and by comparison with the spectral data reported in the literature. In bioassay, compound 2 displayed significantly anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated BV-2 microglial cells.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Microglia/drug effects , Porifera/chemistry , Sterols/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Cell Line , China , Mice , Molecular Structure , Pacific Ocean , Sterols/isolation & purificationABSTRACT
Six new cembrane-type diterpenoids, namely ximaoglaucumins A-F (1-6), along with fifteen known related ones (7-10 and 14-24), have been isolated from the soft coral Sarcophyton glaucum collected off the Ximao Island in the South China Sea. Their structures, including absolute stereochemistry, were elucidated by extensive spectroscopic analysis, quantum mechanical nuclear magnetic resonance (QM-NMR) methods, X-ray diffraction analysis, chemical methods, as well as comparison with the reported data in the literature. Further, detailed analysis of spectroscopic data of 7 not only clarified the confusions regarding 7, 11 (sarcophytolol) and 12/13 (sarcotrocheliol) in the literature, but also led to revise the structure of 11, which was mis-assigned due to careless/erroneous interpretation of the 2D NMR spectra, and to correct the structures of 12/13, which were both wrongly depicted. In in vitro bioassay, compounds 8 and 20 exhibited potent inhibitory effects on lipopolysaccharide (LPS)-induced inflammatory responses in BV-2 microglial cells.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Inflammation/drug therapy , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Cell Line , China , Dose-Response Relationship, Drug , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Molecular Structure , Structure-Activity RelationshipABSTRACT
The chemical investigation of the South China Sea soft coral Sinularia humilis has resulted in the isolation of a library of diverse diterpenoids, including four new cembranoids, namely, humilisins A-D (1-4), two new uncommon diterpenoids possessing a tetradecahydrocyclopenta[3',4']cyclobuta[1',2':4,5]cyclonona[1,2-b]oxirene ring system, namely, humilisins E and F (5 and 6), and eight known related compounds (7-14). Humilisin A (1) is the first cembranoid with an ether linkage between C-3 and C-7. The structures and absolute configurations of 1-8 were determined by extensive spectroscopic data analyses, chemical reactions, and a series of quantum chemical calculations including quantum mechanical-nuclear magnetic resonance (QM-NMR), time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD), and optical rotatory dispersion (ORD) methods. In bioassay, compound 6 displayed anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated BV-2 microglia cells.