ABSTRACT
A formerly unpublicized briarane diterpenoid, briastecholide M (1), and its established analogue, brianodin B (2), were purified from Briareum stechei, an octocoral collected from Okinawan waters. Using spectroscopic methods, the structure of 1 was established. Functional study showed that 1 can reducing the release of inducible nitric oxide synthase (iNOS) but enhancing cyclooxygenase-2 (COX-2) protein expression.
Subject(s)
Anthozoa , Diterpenes , Animals , Anthozoa/chemistry , Anthozoa/metabolism , Diterpenes/pharmacology , Diterpenes/chemistry , Nitric Oxide Synthase Type II/metabolism , Cyclooxygenase 2/metabolismABSTRACT
The chemical screening of a cultured soft coral, Briareum violaceum, led to the isolation of eight natural, briarane-related diterpenoids, including three unreported metabolites, briavioids E-G (1-3), and five known briaranes, briacavatolides B (4) and C (5), briaexcavatin L (6), briaexcavatolide U (7) and briarenol K (8). The structures of briaranes 1-8 were established using spectroscopic methods. The absolute configuration of briavioid A (9), obtained in a previous study, was reported for the first time in this study by a single-crystal X-ray diffraction analysis using a copper radiation source. The anti-inflammatory activity of briaranes 1 and 2 and briaranes 4-8 was evaluated by screening their inhibitory ability against the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins in lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells.
Subject(s)
Anthozoa , Diterpenes , Animals , Mice , Anti-Inflammatory Agents/pharmacology , RAW 264.7 Cells , Macrophages/metabolism , Diterpenes/pharmacology , Anthozoa/chemistry , Nitric Oxide Synthase Type II/metabolism , Cyclooxygenase 2/metabolismABSTRACT
A known polyoxygenated briarane, briaexcavatolide P (1), was isolated from a Formosan octocoral Briareum stechei. Moreover, the same species B. stechei, collected from Okinawan waters, yielded three chlorine-containing briaranes, including two new compounds, briastecholides B (2) and C (3) as well as a known analogue, briarenol R (4). The structures of 1-4 were established using spectroscopic methods. In addition, briarane 1 demonstrated anti-inflammatory activity in lipo-polysaccharide-induced RAW 264.7 mouse macrophage cells by suppressing the expression of inducible nitric oxide synthase (iNOS) protein.
Subject(s)
Anthozoa/chemistry , Diterpenes/chemistry , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Diterpenes/pharmacology , Mice , Nitric Oxide Synthase Type II/antagonists & inhibitors , Nitric Oxide Synthase Type II/metabolism , RAW 264.7 CellsABSTRACT
Chemical investigation of the octocoral Briareum stechei, collected in the Ie Island, Okinawa, Japan, resulted in the isolation of a new briarane-type diterpenoid, briastecholide A (1), as well as the previously reported metabolites, solenolide C (2) and briarenolide S (3). The structures of briaranes 1-3 were characterized through spectroscopic analysis, and the absolute configuration of 2 was corroborated by a single-crystal X-ray diffraction analysis. Briarane 3 exhibited bioactivity against the protein expression of inducible nitric oxide synthase (iNOS).
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/isolation & purification , Diterpenes/isolation & purification , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Gene Expression Regulation, Enzymologic/drug effects , Japan , Mice , Nitric Oxide Synthase Type II/genetics , RAW 264.7 Cells , X-Ray DiffractionABSTRACT
In this review, 170 natural substances, including steroid, diterpenoid, sesquiterpenoid, peptide, prostaglandin, base, chlorolipid, bicyclolactone, amide, piperazine, polyketide, glycerol, benzoic acid, glycyrrhetyl amino acid, hexitol, pentanoic acid, aminoethyl ester, octadecanone, alkaloid, and a 53-kD allergenic component from octocorals belonging to genus Dendronephthya, were listed. Some of these compounds displayed potential bioactivities.
Subject(s)
Anthozoa/metabolism , Biological Products/chemistry , Allergens/chemistry , Allergens/metabolism , Amino Acids/chemistry , Amino Acids/metabolism , Animals , Biological Products/metabolism , Prostaglandins/chemistry , Prostaglandins/metabolism , Steroids/chemistry , Steroids/metabolism , Terpenes/chemistry , Terpenes/metabolismABSTRACT
Five 8,17-epoxybriaranes, including three new compounds-briarenols I-K (1-3), along with two known analogues, briaexcavatolide P (4) and briaexcavatin P (5), were isolated from the octocoral Briareum excavatum. The structures of briaranes 1-3 were elucidated by spectroscopic methods, including 1D and 2D NMR studies and (+)-HRESIMS. Briarane 4 exerted inhibition effects on inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/pharmacology , Cyclooxygenase 2/metabolism , Diterpenes/pharmacology , Nitric Oxide Synthase Type II/metabolism , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Diterpenes/chemistry , Diterpenes/isolation & purification , Down-Regulation , Gene Expression Regulation, Enzymologic/drug effects , Mice , Molecular Structure , 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 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.
