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
Ten briarane-type diterpenoids (1-10), including one new stereoisomer 17-epi-junceellolide B (1), were isolated from the MeOH extract of the Vietnamese gorgonian Junceella fragilis. Their structures were elucidated by spectroscopic experiments including 1D and 2D NMR, and HR-QTOF-MS. In addition, the in vitro cytotoxic activity against eight human cancer cell lines (LNCaP, HepG2, KB, MCF-7, SK-Mel2, HL-60, LU-1 and SW480) of all isolated compounds was evaluated by SRB assays.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/isolation & purification , Diterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Cytotoxins/chemistry , Cytotoxins/isolation & purification , Cytotoxins/pharmacology , Diterpenes/chemistry , Humans , Molecular Structure , Spectrum Analysis/methods , VietnamABSTRACT
The chemical constituents of gorgonian Junceella fragilis Ridley, collected from Ximao Island, the South China Sea, were investigated. A new briarane-type diterpenoid, named fragilide Y (1), together with five known compounds (2–6), namely fragilide D (2), cholesterol (3), ergosterol peroxide (4), 2'-deoxythymidine (5) and cis-thyminenol (6), were isolated from the acetone extract of J. fragilis. The structure of the new compound 1 was elucidated by extensive spectroscopic analysis, while the known compounds were identified by comparison with the reported data. In bioassay, none of these compounds displayed obvious anti-inflammatory and cytotoxic effects.
ABSTRACT
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.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/chemistry , Diterpenes/chemistry , Gene Expression/drug effects , Animals , Anthozoa/metabolism , Anti-Inflammatory Agents/isolation & purification , Anti-Inflammatory Agents/pharmacology , Carbohydrate Conformation , Cell Survival/drug effects , Cyclooxygenase 2/genetics , Cyclooxygenase 2/metabolism , Diterpenes/isolation & purification , Diterpenes/pharmacology , Heterocyclic Compounds, 4 or More Rings/chemistry , Heterocyclic Compounds, 4 or More Rings/isolation & purification , Heterocyclic Compounds, 4 or More Rings/pharmacology , Lactones/chemistry , Lactones/isolation & purification , Lactones/pharmacology , Lipopolysaccharides/antagonists & inhibitors , Lipopolysaccharides/pharmacology , Mice , Nitric Oxide Synthase Type II/antagonists & inhibitors , Nitric Oxide Synthase Type II/genetics , Nitric Oxide Synthase Type II/metabolism , Plant Proteins/chemistry , Plant Proteins/isolation & purification , Plant Proteins/pharmacology , RAW 264.7 CellsABSTRACT
Chemical examination of the gorgonian coral Junceella fragilis resulted in the isolation of four pairs of acetyl isomers belonging to briarane diterpenoids, including five new compounds. Their structures were determined on the basis of extensive spectroscopic (IR, MS, NMR, and single-crystal X-ray diffraction) analysis in association with the chemical conversion. Each pair of isomers featured by dynamical interconversion through as acetyl migration in 1,2-diol, which was postulated to be generated under the formation of a cyclic orthoacetate intermediate. All compounds exerted the inhibitory activities against the nitric oxide production in RAW264.7 macrophage cells.
Subject(s)
Anthozoa/chemistry , Diterpenes/chemistry , Animals , Diterpenes/pharmacology , Halogenation , Isomerism , Macrophages/metabolism , Mice , Molecular Structure , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , RAW 264.7 CellsABSTRACT
In this article, the complete mitogenome of the Octocorallia, zooxanthellate, Junceella fragilis has been amplified and sequenced. This mitochondrial genome consists of 18,724 bp, with 14 protein-coding genes, 2 ribosomal RNA genes, 1 transfer RNA genes, no intron was observed. It has been observed that a mitochondrial mismatch repair (mtMutS) gene was present in all octocorals. The overall base composition of the heavy strand was A, 29.1%; G, 20.4%; C, 33.0%; and T, 17.5%, with a slight AT bias of 62.1%. The complete mitogenomic data may provide more informative for phylogenetic approach for soft corals phylogeny especially for octocorallian species.
Subject(s)
Anthozoa/genetics , DNA, Mitochondrial/genetics , Genome, Mitochondrial/genetics , Mitochondria/genetics , Animals , Base Composition/genetics , Base Sequence , DNA Mismatch Repair/genetics , Genome Size/genetics , Polymerase Chain Reaction , RNA, Ribosomal/genetics , RNA, Transfer/genetics , Sequence Analysis, DNAABSTRACT
Four new 8-hydroxybriarane diterpenoids, frajunolides L-O (1-4), were isolated from the Taiwanese gorgonian Junceella fragilis. The structures of compounds 1-4 were elucidated based on spectroscopic analysis, especially 2D NMR ((1)H-(1)H COSY, HSQC, HMBC and NOESY) and HRMS. Compounds 1 and 4 showed weak anti-inflammatory activity as tested by superoxide anion generation and elastase release by human neutrophil in response to fMLP/CB. Compound 3 showed selective inhibition on elastase release in vitro.