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
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.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/pharmacology , Diterpenes/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Diterpenes/chemistry , Diterpenes/isolation & purification , Mice , Molecular Structure , Nitric Oxide Synthase Type II/antagonists & inhibitors , Nitric Oxide Synthase Type II/metabolism , Proton Magnetic Resonance Spectroscopy , RAW 264.7 Cells , Structure-Activity RelationshipABSTRACT
Two new 11,20-epoxybriaranes, fragilides P (1) and Q (2), as well as two known analogues, robustolide F (3) and juncin Z (4), were obtained from the gorgonian coral Junceella fragilis. The structures, including the absolute configurations of briaranes 1 and 2, were elucidated by using spectroscopic methods and comparing the spectroscopic and rotation data with those of known related analogues. Briarane 4 decreased the generation of superoxide anions by human neutrophils. The propionate group in 1 is rarely found.
Subject(s)
Anthozoa/chemistry , Diterpenes/chemistry , Plant Proteins/chemistry , Animals , Diterpenes/isolation & purification , Diterpenes/pharmacology , Models, Molecular , Molecular Conformation , Molecular Structure , Plant Proteins/isolation & purification , Plant Proteins/pharmacology , Spectrum AnalysisABSTRACT
Two new briarane metabolitesfragilides K (1) and L (2)along with five known analoguesgemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (3â»7)were extracted and purified from Junceella fragilis, a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes 1 and 2 were determined and the cyclohexane rings in 1 and 2 were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes 2, 3, and 6 inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes 3 and 7 suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.