ABSTRACT
Four new sesterterpenes, named as hippotulosas A-D (1-4), and a known sesterterpene furospinulosin-1 (5) were isolated from the marine sponge Hippospongia fistulosa by various chromatographic methods. Their structures were established by extensive spectroscopic analyses (IR, HR-ESI-MS, 1D and 2D NMR) and by comparison of the spectral data with those reported in the literature.[Formula: see text].
Subject(s)
Porifera , Sesterterpenes , Animals , Magnetic Resonance Spectroscopy , Molecular Structure , Porifera/chemistry , Sesterterpenes/chemistryABSTRACT
Using various chromatographic methods, five new sesquiterpene derivatives named smenohaimiens A-E (1-5) and five known, 19-hydroxy-polyfibrospongol B (6), ilimaquinone (7), dictyoceratin C (8), polyfibrospongol A (9), and polyfibrospongol B (10) were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were assigned by 1D, 2D NMR spectroscopic analysis, HR ESI MS, and calculations of the electron circular dichroism spectra. All compounds were evaluated for the inhibitory activity against NO production in lipopolysaccharide-stimulated in BV2 microglia cells. As the results, compound 7 significantly inhibited NO production with the IC50 value of 10.40±1.28µM. The remaining compounds showed moderate inhibitory NO production activities with IC50 values ranging from 24.37 to 30.43µM.
Subject(s)
Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Porifera/chemistry , Sesquiterpenes/pharmacology , Animals , Anti-Inflammatory Agents, Non-Steroidal/chemistry , Anti-Inflammatory Agents, Non-Steroidal/isolation & purification , Cell Line , Circular Dichroism , Magnetic Resonance Spectroscopy , Mice , Nitric Oxide/antagonists & inhibitors , Nitric Oxide/biosynthesis , Quinones/chemistry , Quinones/isolation & purification , Quinones/pharmacology , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Stereoisomerism , omega-N-Methylarginine/pharmacologyABSTRACT
Using various chromatographic methods, one new sesquiterpene quinone named smenohaimien F (1) and five known, neodactyloquinone (2), dactyloquinone C (3), dactyloquinone D (4), isoamijiol (5), and amijiol (6), were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were elucidated by ID-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and by comparing with the NMR data reported in the literature. The cytotoxic activities of the all compounds were evaluated on five human cancer cell lines, LU-1, HL-60, SK-Mel-2, HepG-2, and MCF-7. Compound 4 was found to exhibit significant cytotoxic activities on all tested human cancer cell lines with IC50 values ranging from 0.7 to 1.6 µg/mL.
Subject(s)
Diterpenes/chemistry , Diterpenes/toxicity , Porifera/chemistry , Quinones/chemistry , Quinones/toxicity , Sesquiterpenes/chemistry , Sesquiterpenes/toxicity , Animals , Cell Line, Tumor , Cell Survival/drug effects , Diterpenes/isolation & purification , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Quinones/isolation & purification , Sesquiterpenes/isolation & purificationABSTRACT
The rhizomes of Hedychium coronarium have been used for the treatment of inflammation, skin diseases, headache, and sharp pain due to rheumatism in traditional medicine. From this plant, two new labdanes, 15-methoxylabda-8(17),11E,13-trien-16,15-olide (1) and 16-methoxylabda-8(17),11E,13-trien-15,16-olide (3), named hedycoronens A and B, as well as four known, labda-8(17),11,13-trien-16,15-olide (2), 16-hydroxylabda-8(17),11,13-trien-15,16-olide (4), coronarin A (5), and corronarin E (6) were isolated. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance (NMR) spectroscopy. They were evaluated for inhibitory effects on the lipopolysaccharide (LPS)-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Among of them, compounds 1-3 were potent inhibitors of LPS-stimulated interleukin-6 (IL-6) and IL-12 p40, with IC(50) ranging from 4.1±0.2 to 9.1±0.3 µM. Compounds 1 and 3 showed moderate inhibitory activity on the tumor necrosis factor-α (TNF-α) production with IC(50) values of 46.0±1.3 and 12.7±0.3 µM. The remains of compounds showed inactivity. These results warrant further studies concerning the potential anti-inflammatory benefits of labdane-diterpenes from H. coronarium.
Subject(s)
Cytokines/metabolism , Dendritic Cells/drug effects , Diterpenes/pharmacology , Down-Regulation/drug effects , Lipopolysaccharides , Rhizome/chemistry , Zingiberaceae/chemistry , Animals , Bone Marrow Cells/cytology , Bone Marrow Cells/drug effects , Dendritic Cells/cytology , Diterpenes/chemistry , Inflammation , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Mice , Mice, Inbred C57BL , Molecular StructureABSTRACT
The rhizomes of Hedychium coronarium have been used for the treatment of inflammation, skin diseases, headache, and sharp pain due to rheumatism in traditional medicine. From this plant, three new labdane-type diterpenes 1-3, named coronarins G-I as well as seven known 4-10, coronarin D, coronarin D methyl ether, hedyforrestin C, (E)-nerolidol, ß-sitosterol, daucosterol, and stigmasterol were isolated. Their chemical structures were elucidated by mass, 1D- and 2D-nuclear magnetic resonance spectroscopy. They were evaluated for inhibitory effects on lipopolysaccharide-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells. Among of them, compounds 1, 2, and 6 were significant inhibitors of LPS-stimulated TNF-α, IL-6, and IL-12 p40 productions with IC(50) ranging from 0.19±0.11 to 10.38±2.34 µM. The remains of compounds showed inactivity or due to cytotoxicity. These results warrant further studies concerning the potential anti-inflammatory benefits of labdane-type diterpenes from H. coronarium.
