ABSTRACT
Three new cembranoids crassocolides N-P (1-3), was isolated from the organic extract of a Formosan soft coral Sarcophyton crassocaule. These structures were elucidated on the basis of spectroscopic analyses and by comparison with those previously reported in literature. The cytotoxicity of these compounds toward various cancer cell lines has also been determined.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/chemistry , Diterpenes/chemistry , Animals , Antineoplastic Agents/pharmacology , Cell Survival/drug effects , HeLa Cells , Humans , Inhibitory Concentration 50 , Magnetic Resonance Spectroscopy , Molecular Structure , TaiwanABSTRACT
Six new sesquiterpenoids, paralemnolins J-O (1-6), along with one novel norsesquiterpenoid, paralemnolin P (7), have been isolated from the soft coral Paralemnalia thyrsoides. The structures of metabolites 1-7 were established on the basis of extensive NMR study and chemical methods. The structure of 5 was further confirmed by a single-crystal X-ray analysis. Cytotoxicity of these metabolites toward a limited panel of cancer cell lines also is described.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/analysis , Antineoplastic Agents/pharmacology , Sesquiterpenes/analysis , Sesquiterpenes/pharmacology , Animals , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Cell Survival/drug effects , Crystallography, X-Ray , Humans , Models, Molecular , Molecular StructureABSTRACT
Two new polychlorolipids, namely, (2R,3S,4R,5S,6S,7R)-2,3,5,6,7-pentachloropentadec-14-en-4-yl hydrogen sulfate (2) and (2R,3S,4R,5S,6S,7R)-2,3,5,6,7-pentachloropentadec-14-en-4-ol (4), along with a known chlorosulfolipid (1), were isolated from the octocoral Dendronephthya griffini. (2R,3S,4R,5S,6S,7R,E)-2,3,5,6,7,15-Hexachloropentadec-14-en-4-ol (3) was isolated for the first time from a natural source. The structures of these compounds were elucidated by extensive spectroscopic analysis and by comparison of the NMR data with those of known compound 1. This type of compound was isolated for the first time from the soft corals.
Subject(s)
Alcohols/chemistry , Anthozoa/chemistry , Hydrocarbons, Chlorinated/chemistry , Lipids/chemistry , Animals , Hydrocarbons, Chlorinated/isolation & purification , Lipids/isolation & purification , Magnetic Resonance Spectroscopy , Molecular Conformation , StereoisomerismABSTRACT
Seven new polyoxygenated cembranoids possessing an alpha-methylene-gamma-lactone group, crassocolides G-M (1-7, resp.), have been isolated from the AcOEt extract of the Formosan soft coral Sarcophyton crassocaule. The structures of compounds 1-7 were established by detailed spectroscopic analyses, including 2D-NMR spectroscopy ((1)H,(1)H-COSY, HMQC, HMBC, and NOESY), while the absolute configuration of 1 was determined using a modified reaction of Mosher's method. The cytotoxicity of compounds 1-7 against a limited panel of cancer cell lines was also determined.
Subject(s)
Anthozoa/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Lactones/isolation & purification , Animals , Antineoplastic Agents/pharmacology , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/pharmacology , Cell Line, Tumor , Drug Screening Assays, Antitumor , Humans , Inhibitory Concentration 50 , Lactones/chemistry , Lactones/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Five new steroids, namely griffinisterones F-I (1-4) and griffinipregnone (5) have been isolated from the octocoral Dendronephthya griffini. The structures of these compounds were elucidated by extensive spectroscopic analysis. Compounds 1-3 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells at 10 microM. At the same concentrations 2 also could significantly inhibit the accumulation of the pro-inflammatory COX-2 protein.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/isolation & purification , Glucocorticoids/isolation & purification , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Cells, Cultured , Cyclooxygenase 2/metabolism , Glucocorticoids/chemistry , Glucocorticoids/pharmacology , Lipopolysaccharides/pharmacology , Macrophages/drug effects , Macrophages/metabolism , Magnetic Resonance Spectroscopy , Mice , Molecular Structure , Nitric Oxide Synthase Type II/metabolismABSTRACT
Three glycolipids (1--3), possessing a sugar moiety at C-2 of glycerol ether, have been isolated from the Formosan soft coral Lobophytum crassum. Their structures were elucidated by spectroscopic methods, particularly in 1D- and 2D-NMR experiments. The absolute configurations on the sugar portion and lipid aglycon of 1--3 were determined by methanolysis, chemical transformation and the application of Mosher's method on 1 and 3. Compounds 1--3 exhibited weak cytotoxic activities.
Subject(s)
Anthozoa/chemistry , Glycolipids/chemistry , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Cell Line, Tumor , Chromatography, Thin Layer , Drug Screening Assays, Antitumor , Glycolipids/isolation & purification , Glycolipids/pharmacology , Humans , Hydrolysis , Indicators and Reagents , Mass Spectrometry , TaiwanABSTRACT
Six new sesquiterpenoids, paralemnolins D-I (1-6), have been isolated from the EtOAc extract of the soft coral Paralemnalia thyrsoides. The structures of these metabolites were determined by extensive spectroscopic analysis and by comparison of their spectral data with those of related metabolites. The absolute stereochemistry of these metabolites was established by application of the Mosher's method on 1 and on the basis of the absolute structures of other related compounds previously isolated from the soft corals of the genera Paralemnalia and Lemnalia. Cytotoxicity of these metabolites toward a limited panel of cancer cell lines also is reported.
Subject(s)
Anthozoa/chemistry , Sesquiterpenes/isolation & purification , Animals , Magnetic Resonance Spectroscopy , Models, Molecular , Sesquiterpenes/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
Six new polyoxygenated cembrane-based diterpenoids possessing a trans-fused alpha-methylene-gamma-lactone, crassocolides A-F (1-6), have been isolated along with the known compound 7 from the ethyl acetate extract of a Taiwanese soft coral, Sarcophyton crassocaule. The structures of 1-6 have been established by detailed spectroscopic analysis, including 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY) spectroscopy, while their absolute configurations were determined using a modified Mosher's method for 1. The structure of 5 was further proven by X-ray diffraction analysis. The full assignment of NMR data of 7 is reported herein for the first time. The cytotoxicity of crassocolides 1-4, 6, and 7 against a limited panel of cancer cells was also determined.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/isolation & purification , Diterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , StereoisomerismABSTRACT
Six new polyoxygenated steroids, hippuristerones J-L (1-3), hippuristerols E-F (4, 5), and a novel gorgosteroid, 1alpha,3beta,5beta,11alpha-tetrahydroxygorgostan-6-one (6), were isolated from the gorgonian Isis hippuris. The structures of these metabolites were elucidated by extensive spectroscopic analyses and comparison of the NMR data with those of related steroids.