ABSTRACT
Two new butanolides, lincomolide A (1), lincomolide B (2), along with seven known compounds, isolinderanolide E, sepesteonol, beta-sitosterol, beta-sitosterol-beta-glucoside, tetradecane, nonanoic acid and decanol, were isolated from the chloroform-soluble portion of the stem bark of Lindera communis. Compound 1 showed cytotoxicity against P-388, KB16 and A549, and 2 exhibited cytotoxicity against P-388 cancer cell lines. Moreover, 1 showed marginal activity against HT-29, and 2 against KB16, A549 and HT-29 cancer cell lines. The structures of these compounds were determined by spectral analyses.
Subject(s)
4-Butyrolactone/pharmacology , Antineoplastic Agents, Phytogenic/pharmacology , Lindera , Plant Bark/chemistry , 4-Butyrolactone/analogs & derivatives , 4-Butyrolactone/chemistry , 4-Butyrolactone/isolation & purification , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Cell Division/drug effects , HT29 Cells/drug effects , Humans , Tumor Cells, CulturedABSTRACT
Eight new sesquiterpenes, tubipolides A-G (1-7) and tubiporone (8) (novel carbon skeleton), and a known sesquiterpene, spirotubipolide, have been isolated from the Formosan stolonifer Tubipora musica. The structures of compounds 1-8 were determined by 1D and 2D NMR spectral analysis.
Subject(s)
Cnidaria/chemistry , Sesquiterpenes/isolation & purification , Animals , Chromatography, Thin Layer , Leukemia P388 , Leukemia, Lymphoid , Mice , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Taiwan , Tumor Cells, Cultured/drug effectsABSTRACT
A new sesquiterpenoid, junceol A(1), as well as two known diterpenoids, sclerophytin A (2) and cladiellisin (3), have been isolated from the sea pen octocoral Virgularia juncea. The structure of metabolite 1 was determined by extensive spectral analysis. Compounds 1-3 have been shown to exhibit cytotoxicity toward P-388 cancer cells.
Subject(s)
Cnidaria/chemistry , Sesquiterpenes/isolation & purification , Animals , Bridged-Ring Compounds/chemistry , Bridged-Ring Compounds/isolation & purification , Bridged-Ring Compounds/pharmacology , Chromatography, Thin Layer , Drug Screening Assays, Antitumor , Furans/chemistry , Furans/isolation & purification , Furans/pharmacology , Inhibitory Concentration 50 , Leukemia P388 , Magnetic Resonance Spectroscopy , Molecular Conformation , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Spectrophotometry, Infrared , Taiwan , Tumor Cells, Cultured/drug effectsABSTRACT
A new cytotoxic cyclopenta[b]benzofuran derivative, aglaiformosanin (1) and three known cyclopenta[b]benzofuran derivatives (2 - 4) were isolated from the stem bark of Aglaia formosana. Compounds 1 - 4 exhibited potent cytotoxicity against the P-388, KB, HT-29, HL-60, and A549 cell lines. The structure of compound 1 was determined by spectroscopic analysis.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Benzofurans/pharmacology , Magnoliopsida/chemistry , Pyrimidinones/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Benzofurans/chemistry , Benzofurans/isolation & purification , Cell Line , Cyclopentanes/chemistry , Cyclopentanes/isolation & purification , Cyclopentanes/pharmacology , Drug Screening Assays, Antitumor , Humans , Plant Stems/chemistry , Pyrimidinones/chemistry , Pyrimidinones/isolation & purification , Tumor Cells, CulturedABSTRACT
From the chloroform-soluble portion of the stem wood of Machilus obovatifolia, one new neolignan, perseal F (1), four known neolignans, perseal G (2), licarin A, licarin B, acuminatin, two butanolides, linderanolide E and isolinderanolide E, two steroids, beta-sitosterol, beta-sitosterol-beta-D-glucoside, and syringaldehyde were isolated. Perseal F (1) and G (2) are neolignans that have a C-1' formyl side chain instead of a propenyl group. Compound 2 was isolated in a mixture with acuminatin. The structure of 2 was identified by comparison with the product formed by the Lemieux-von Rudloff oxidation of licarin B. Two minor oxidative by-products, 2a and 2b, were also obtained. Linderanolide E showed cytotoxicities against P-388, KB16, A549 and HT-29, 1 against P-388, KB16 and HT-29, and isolinderanolide E against P-388, cancer cell lines, respectively. All structures were identified by means of spectroscopic analyses.
Subject(s)
Antineoplastic Agents, Phytogenic/pharmacology , Lauraceae/chemistry , Lignans/pharmacology , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/isolation & purification , Benzofurans/chemistry , Benzofurans/isolation & purification , Benzofurans/pharmacology , Drug Screening Assays, Antitumor , Humans , Lignans/chemistry , Phytosterols/pharmacology , Plant Stems/chemistry , Tumor Cells, CulturedABSTRACT
Six new cytotoxic dolabellane diterpenes, (1R,12R)-dolabella-4(16),7,10-triene-3,13-dione (1), (1R*,7R*,8S*,12R*)-dolabella-4(16),10-diene-7,8-epoxy- 3,13-dione (2), (1R*,10R*,11S*,12R*)-dolabella-4(16),7-diene-10,11-epoxy-3,13-dione (3), (1R)-dolabella-4(16),7,11(12)-triene-3,13-dione (4), (1R*,3R*)-3-hydroxydolabella-4(16),7,11(12)-triene-3,13-dione (5), and (1R*,7R*)-7-hydroperoxydolabella-4(16),8(17),11(12)-triene-3,13-dione (6), have been isolated from the Formosan soft coral Clavularia inflata. The structures of compounds 1-6 were determined by 1D and 2D spectral analysis, and their cytotoxicity against selected cancer cells was measured in vitro.
Subject(s)
Antineoplastic Agents/isolation & purification , Cnidaria/chemistry , Diterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Carcinoma, Squamous Cell , Diterpenes/chemistry , Diterpenes/pharmacology , Humans , Leukemia P388 , Lung Neoplasms , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Molecular Structure , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Stereoisomerism , Taiwan , Tumor Cells, Cultured/drug effectsABSTRACT
Four new briarane diterpenes, briaexcavatolides K-N (1-4), along with a known diterpene, 5, have been isolated from the Taiwanese gorgonian Briareum excavatum. The structures of the new metabolites were established by extensive spectral analyses. Furthermore, the structure, including the relative configuration of briaexcavatolide K (1), was confirmed by a single-crystal X-ray analysis. Briaexcavatolides K and L (1 and 2) are the only briarane diterpenes known to possess hydroxyl groups at the C-8beta and C-17alpha positions, respectively. Cytotoxicity of these metabolites toward various cancer cell lines also is described.
Subject(s)
Cnidaria/chemistry , Diterpenes/isolation & purification , Animals , Crystallography, X-Ray , Diterpenes/chemistry , Molecular Structure , TaiwanABSTRACT
Three new cytotoxic compounds, rocagloic acid (1), elliptifoline (2), and elliptinol (3) were isolated from the leaves of Aglaia elliptifolia. The structures of compounds 1-3 were determined by spectral (NMR, MS) and chemical analysis.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Benzene Derivatives/chemistry , Benzofurans/chemistry , Diamide/chemistry , Plants, Medicinal/chemistry , Pyrroles/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Benzene Derivatives/pharmacology , Benzofurans/pharmacology , China , Chromatography, Thin Layer , Diamide/analogs & derivatives , Diamide/pharmacology , Drug Screening Assays, Antitumor , Humans , Magnetic Resonance Spectroscopy , Mass Spectrometry , Plant Leaves/chemistry , Pyrroles/pharmacology , Spectrophotometry, Infrared , Tumor Cells, CulturedABSTRACT
Six new compounds, including one nor-neolignan, dehydroxymethylailanthoidol (1), and five butanolides, litseakolide D (2), litseakolide E (3), litseakolide F (4), litseakolide G (5), and isolincomolide D (6), were isolated from the leaves of Litsea acutivena. Their structures were elucidated from spectral analyses. The butanolides (2-6) showed significant cytotoxic activity against P-388, A549, and HT-29 cell lines in vitro.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Lactones/isolation & purification , Lauraceae/chemistry , Plants, Medicinal/chemistry , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Drug Screening Assays, Antitumor , HT29 Cells/drug effects , Humans , Lactones/chemistry , Lactones/pharmacology , Leukemia P388 , Lung Neoplasms , Mass Spectrometry , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Stereoisomerism , Structure-Activity Relationship , Taiwan , Tumor Cells, Cultured/drug effectsABSTRACT
Two new prenyleudesmane diterpenes, dysokusone D (1) and dysokusone E (2), were isolated from the fruits of Dysoxylum kuskusense and exhibited cytotoxicity against P-388, HT-29, and A549 cell lines. Their structures were determined by 1D and 2D NMR spectral analysis.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Diterpenes/isolation & purification , Plants, Medicinal/chemistry , Animals , Antineoplastic Agents, Phytogenic/pharmacology , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Fruit/chemistry , HT29 Cells , Humans , Leukemia P388/drug therapy , Magnetic Resonance Spectroscopy , Tumor Cells, CulturedABSTRACT
Four new cytotoxic neolignans, machilusol A (1), machilusol C (3), machilusol D (4), machilusol E (5) as well as two new inactive neolignans, machilusol B (2) and machilusol F (6), were isolated from the stem wood of Machilus obovatifolia. All structures were identified by means of spectroscopic analysis.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Lignans/isolation & purification , Plant Extracts/chemistry , Trees/chemistry , Animals , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Benzoquinones , Colorimetry , HT29 Cells , Humans , Imines , Indicators and Reagents , Lignans/chemistry , Lignans/pharmacology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Plant Stems/chemistry , Tumor Cells, Cultured , WoodABSTRACT
A new cytotoxic lobane diterpene, ineleganene (1), was isolated from the Formosan soft coral Sinularia inelegans. The structure of compound 1 was determined by 1D and 2D spectral analysis.
Subject(s)
Alkenes/isolation & purification , Antineoplastic Agents/isolation & purification , Cnidaria/chemistry , Diterpenes/isolation & purification , Alkenes/chemistry , Alkenes/pharmacology , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Leukemia P388/metabolism , Taiwan , Tumor Cells, Cultured/drug effectsABSTRACT
A new cytotoxic cembrenolide diterpene, lobocrassolide (1), and a known cytotoxic cembrenolide, lobohedleolide (2), were isolated from the Formosan soft coral Lobophytum crassum. The structure of compound 1 was determined by 1D and 2D spectral analysis.
Subject(s)
Bridged Bicyclo Compounds/isolation & purification , Cnidaria/chemistry , Cytotoxins/isolation & purification , Diterpenes/isolation & purification , Furans/isolation & purification , Animals , Bridged Bicyclo Compounds/chemistry , Bridged Bicyclo Compounds/pharmacology , Cytotoxins/chemistry , Cytotoxins/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Furans/chemistry , Furans/pharmacology , Humans , Leukemia P388/metabolism , Tumor Cells, Cultured/drug effectsABSTRACT
A new sterol, (22R,23R,24R)-5alpha,8alpha-epidioxy-22, 23-methylene-24-methylcholest-6-en-3beta-ol (1), as well as two known sterols, numersterol A (2) and pregnenolone (3), have been isolated from a soft coral Sinularia sp. The structure of metabolite 1 was determined by spectral analysis. Cytotoxicity of sterols 1-3 toward various cancer cell lines is also reported.
Subject(s)
Anthozoa/chemistry , Antineoplastic Agents/isolation & purification , Cholesterol/analogs & derivatives , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Cholesterol/chemistry , Cholesterol/isolation & purification , Cholesterol/pharmacology , Drug Screening Assays, Antitumor , Humans , Tumor Cells, CulturedABSTRACT
Five new suberosane sesquiterpenes, suberosenol A (1), suberosenol B (2), suberosanone (3), suberosenol A acetate (4), and suberosenol B acetate (5), along with the known sesquiterpene subergorgic acid (6), have been isolated from the gorgonian Isis hippuris. The structures of these metabolites were established by spectroscopic and chemical methods. Metabolites 1 and 3-5 were found to exhibit potent cytotoxicity toward P-388, A549, and HT-29 cancer cell lines.
Subject(s)
Antineoplastic Agents/isolation & purification , Cnidaria/chemistry , Sesquiterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacology , Spectrum Analysis , Tumor Cells, CulturedABSTRACT
Three new cytotoxic cembrenolide diterpenes, sarcocrassolide (1), crassolide (2), and 13-acetoxysarcocrassolide (3); a known cytotoxic cembrenolide, denticulatolide (4); and two cytotoxic steroids, (24S)-24-methylcholestane-3beta,5alpha,6beta-triol (5) and 24zeta-methylcholestane-3beta,5alpha,6beta,25-te traol-25-monoacetate (6), have been isolated from the Formosan soft coral Sarcophyton crassocaule. The structures of compounds 1-6 were determined by 1D and 2D spectral analysis.
Subject(s)
Antineoplastic Agents/isolation & purification , Cnidaria/chemistry , Diterpenes/isolation & purification , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Diterpenes/chemistry , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Humans , Molecular Structure , Spectrum Analysis , Tumor Cells, CulturedABSTRACT
Two new cytotoxic cembranoid diterpenes, brassicolide (1) and brassicolide acetate (2); a new cytotoxic sesquiterpene, (-)-4alpha-O-acetyl-selin-11-en (3); and six cytotoxic terpenoids, (-)-selin-11-en-4alpha-ol (4), 2-hydroxynephthenol (5), nephthenol (6), cembrene A (7), epoxycembrene A (8), and (-)-beta-elemene (9), have been isolated from the Formosan soft coral Nephthea brassica. The structures of compounds 1-9 were determined by spectral, chemical, and X-ray crystallographic analysis.
Subject(s)
Antineoplastic Agents/isolation & purification , Cnidaria/chemistry , Heterocyclic Compounds, 2-Ring/isolation & purification , Animals , Antineoplastic Agents/pharmacology , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Heterocyclic Compounds, 2-Ring/pharmacology , Humans , KB Cells , Leukemia P388/drug therapy , Magnetic Resonance Spectroscopy , Methylene Chloride , Spectrometry, Mass, Fast Atom Bombardment , Spectrophotometry, Infrared , Taiwan , Tumor Cells, CulturedABSTRACT
A series of 9-O-acylisoaaptamine (3-14) and 4-N-acyl-dihydroaaptamine (16-19) derivatives have been prepared and evaluated for antitumor activity against murine P-388 and human tumor cells including KB16, A549, and HT-29 cell lines. All of compounds showed significant cytotoxicity against P-388 cells. Among them, compounds 9-11 showed potent activity as isoaaptamine (1). There was an apparent lack of linear relationship between cytotoxicity and carbon number of the side chain. The structure and activity relationship for these particular compounds are discussed.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Naphthyridines/chemistry , Naphthyridines/pharmacology , Animals , Drug Screening Assays, Antitumor , Humans , Mice , Molecular Structure , Porifera/chemistry , Spectrum Analysis , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
Five new sesquiterpenes, parahigginols A-D (1-4) and parahigginic acid (5), have been isolated from a Taiwanese marine sponge Parahigginsia sp. The structural assignments of the new compounds were based on their spectral data, including 1D and 2D NMR. Biological studies revealed that compounds 2-5 exhibited cytotoxicity against murine P-388 and human KB16, A549, and HT-29 tumor cells.
Subject(s)
Antineoplastic Agents/pharmacology , Sesquiterpenes/pharmacology , Animals , Antineoplastic Agents/isolation & purification , Chromatography, High Pressure Liquid , Drug Screening Assays, Antitumor , HT29 Cells , Humans , KB Cells , Leukemia P388/pathology , Magnetic Resonance Spectroscopy , Mass Spectrometry , Mice , Sesquiterpenes/isolation & purification , Spectrophotometry, Ultraviolet , Taiwan , Tumor Cells, CulturedABSTRACT
Fucosterol (1), 24xi-hydroperoxy-24-vinylcholesterol (2), 29-hydroperoxystigmasta-5,24(28)-dien-3beta-ol (3), 24-ethylcholesta-4,24(28)-dien-3-one (4), 24xi-hydroperoxy-24-ethylcholesta-4,28(29)-dien-3-one (5), 24-ethylcholesta-4,24(28)-dien-3,6-dione (6), 24xi-hydroperoxy-24-ethylcholesta-4,28(29)-dien-3,6-di one (7), 6beta-hydroxy-24-ethylcholesta-4,24(28)-dien-3-one (8), and 24xi-hydroperoxy-6beta-hydroxy-24-ethylcholesta-4,28(2 9)-dien-3-one (9) were isolated from the marine brown alga Turbinaria conoides. The structures of these compounds were established by spectral analysis. Isolated for the first time from a natural source, the oxygenated fucosterols 4-9 exhibit cytotoxicity against various cancer cell lines.
