ABSTRACT
Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.
Subject(s)
Anthozoa/chemistry , Diterpenes/pharmacology , Inflammation Mediators/pharmacology , Animals , Cyclooxygenase 2/metabolism , Diterpenes/chemistry , Diterpenes/isolation & purification , Inflammation Mediators/chemistry , Inflammation Mediators/isolation & purification , Mice , Nitric Oxide Synthase Type II/metabolism , RAW 264.7 Cells , Taiwan , X-Ray DiffractionABSTRACT
Three new 11,20-epoxybriaranes-fragilides U-W (1-3), as well as two known metabolites, junceellonoid D (4) and junceellin (5), were obtained from the octocoral Junceella fragilis. The structures of briaranes 1-3 were elucidated by spectroscopic methods and briaranes 3 and 5 displayed inhibition effects on inducible nitric oxide synthase (iNOS) release from RAW264.7.
Subject(s)
Anthozoa/physiology , Diterpenes/metabolism , Animals , Cyclooxygenase 2/metabolism , Cyclooxygenase Inhibitors/pharmacology , Diterpenes/chemistry , Diterpenes/classification , Gene Expression Regulation, Enzymologic/drug effects , Magnetic Resonance Spectroscopy , Mice , Models, Molecular , Molecular Structure , Nitric Oxide Synthase Type II/antagonists & inhibitors , Nitric Oxide Synthase Type II/metabolism , RAW 264.7 CellsABSTRACT
Two new steroids, dendronesterones D (1) and E (2), featuring with 1,4-dienone moiety, along with three known steroids, methyl 3-oxochola-4,22-diene-24-oate (3), 5α,8α-epidioxy-24(S)- methylcholesta-6,22-dien-3ß-ol (4), and 5α,8α-epidioxy-24(S)-methylcholesta-6,9(11),22-trien-3ß-ol (5), were isolated from an octocoral Dendronephthya sp. The structures of steroids 1 and 2 were elucidated by using spectroscopic methods and steroid 1 was found to exhibit significant in vitro anti-inflammatory activity in lipopolysaccharides (LPS)-induced RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/pharmacology , Steroids/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Mice , Molecular Structure , Nitric Oxide Synthase Type II/antagonists & inhibitors , RAW 264.7 Cells , Steroids/isolation & purificationABSTRACT
Three new 8-hydroxybriaranes-fragilides R-T (1-3) were obtained from a sea whip gorgonian coral Junceella fragilis. The structures of briaranes 1-3 were elucidated by using spectroscopic methods, including 1D (1H and 13C NMR), 2D (COSY, HSQC, HMBC, and NOESY experiments) NMR studies, and (+)-HRESIMS. Fragilides S and T (2 and 3) are the only briaranes known to possess 8α-hydroxy and 17ß-methyl groups, respectively. Briarane 2 exerted an inhibition effect on iNOS release from RAW264.7; a macrophage cell line that originated from a mouse monocyte macrophage, stimulated with lipopolysaccharides.