RESUMO
Four new cytochalasin derivatives (1-4), together with cytochalasin B (5), were isolated from the fungus Phoma sp. obtained from the giant jellyfish Nemopilema nomurai. The planar structure and relative stereochemistry were established by analysis of 1D and 2D NMR data. The absolute configuration was defined by the modified Mosher's method. The compounds showed significant cytotoxicity against a small panel of human solid tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF 498, and HCT15) with IC(50) values in the range of 0.5-30 µM. The cytochalasin B (5) showed obvious cytotoxicity with IC(50) of 7.9 µM against HeLa human cervical carcinoma cells.
Assuntos
Ascomicetos/química , Citocalasinas/farmacologia , Cifozoários/microbiologia , Animais , Antineoplásicos/química , Morte Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Citocalasinas/química , Relação Dose-Resposta a Droga , Detecção Precoce de Câncer , Humanos , Concentração Inibidora 50 , Estrutura MolecularRESUMO
A new butenolide (1) was isolated, along with a known acyclic polyhalogenated monoterpene (2), from the brittle star Ophiomastix mixta. The structures were defined by analysis and comparision of the spectral data with those in the literature. The 2,3-dimethyl butenolide (1) is uncommon and first encountered in a marine organism. The compounds were tested for cytotoxicity against a panel of five human solid tumor cell lines and displayed mild to significant activity.
Assuntos
4-Butirolactona/análogos & derivados , 4-Butirolactona/química , Equinodermos/química , Equinodermos/metabolismo , 4-Butirolactona/metabolismo , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Linhagem Celular Tumoral , Humanos , Estrutura MolecularRESUMO
Two new sulfated saponins designated as certonardosides P2 and I3 (1 and 2) were isolated from the brine shrimp active fraction of the MeOH extract of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis. Compounds 1 and 2 were tested for cytotoxicity against five human tumor cell lines (A549, SK-OV-3, SK-MEL-2, XF498, and HCT15), and compound 1 displayed significant cytotoxicity against the SK-MEL-2 skin cancer cell.
Assuntos
Antineoplásicos/isolamento & purificação , Saponinas/isolamento & purificação , Estrelas-do-Mar/química , Ácidos Sulfônicos/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Humanos , Saponinas/química , Saponinas/farmacologia , Ácidos Sulfônicos/química , Ácidos Sulfônicos/farmacologia , Células Tumorais CultivadasRESUMO
Twelve new (1-7, 9-13) polyhydroxysterols and two new saponins (14 and 15) were isolated from the starfish Certonardoa semiregularis by activity-guided fractionation. Compounds 1-7 are rare examples of 15-keto steroids from starfish. The side chain of compound 11 was also unprecedented in nature. The structures were determined by combined spectroscopic methods and chemical derivatization. These compounds were evaluated for cytotoxicity against a small panel of human solid tumor cell lines, and most of them exhibited considerable activity. One of the 15-keto sterols (6) displayed the highest potency, which is comparable to that of doxorubicin.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Saponinas/isolamento & purificação , Estrelas-do-Mar/química , Esteróis/isolamento & purificação , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Estrutura Molecular , Oceanos e Mares , Saponinas/química , Saponinas/farmacologia , Estereoisomerismo , Esteróis/química , Esteróis/farmacologia , Células Tumorais CultivadasRESUMO
Eleven new polyhydroxysterols (1-11) and eight new saponins (12-19) were isolated from the brine shrimp active fraction of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical derivatization. The structural variations of these compounds are due to the hydroxylation pattern of the sterol nucleus, the functionalization of the side chain, or the nature and location of the saccharide moiety. These compounds displayed considerable cytotoxicity against a small panel of human solid tumor cell lines.
Assuntos
Antineoplásicos/isolamento & purificação , Saponinas/isolamento & purificação , Estrelas-do-Mar/química , Esteróis/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Coreia (Geográfico) , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Oceanos e Mares , Saponinas/química , Saponinas/farmacologia , Estereoisomerismo , Esteróis/química , Esteróis/farmacologia , Células Tumorais CultivadasRESUMO
Four new saponins, designated as certonardosides K-N (1-3, 5), were isolated, along with culcitoside C(6) (4), from the brine shrimp active fraction of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical derivatization. These compounds were evaluated for cytotoxicity and antibacterial activity.
Assuntos
Saponinas/química , Saponinas/isolamento & purificação , Estrelas-do-Mar , Animais , Avaliação Pré-Clínica de Medicamentos/métodos , Humanos , Saponinas/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Thirteen new polyhydroxysterols (1-5, 7-12, 14, 15) and two known polyhydroxysterols (6, 13) were isolated from the brine shrimp active fraction of the starfish Certonardoa semiregularis. The structures were determined on the basis of spectral analysis and chemical derivatization. These compounds displayed considerable cytotoxicity against a small panel of human solid tumor cell lines. These compounds were also evaluated for antibacterial activity against 20 clinically isolated strains. Most of the compounds showed weak antibacterial activity against Streptococcus pyogenes 308A, Pseudomonas aeruginosa 1771, and Pseudomonas aeruginosa 1771M.
Assuntos
Antibacterianos/isolamento & purificação , Antineoplásicos/isolamento & purificação , Artemia/química , Estrelas-do-Mar/química , Esteróis/isolamento & purificação , Animais , Antibacterianos/química , Antibacterianos/farmacologia , Antineoplásicos/química , Antineoplásicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Coreia (Geográfico) , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Pseudomonas aeruginosa/efeitos dos fármacos , Estereoisomerismo , Esteróis/química , Esteróis/farmacologia , Streptococcus pyogenes/efeitos dos fármacos , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Two new sphingosine 4-sulfates (1 and 2) have been isolated from the sponge Spirastrella abata as cytotoxic constituents. The gross structures of 1 and 2 were determined by spectroscopic analysis, and their stereochemistry was established by chemical conversion. The compounds exhibited significant cytotoxicity against a small panel of five human tumor cell lines.
Assuntos
Antineoplásicos/isolamento & purificação , Poríferos/química , Esfingosina , Sulfatos/isolamento & purificação , Animais , Antineoplásicos/química , Antineoplásicos/farmacologia , Cromatografia Líquida de Alta Pressão , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Coreia (Geográfico) , Neoplasias Pulmonares , Estrutura Molecular , Neoplasias do Sistema Nervoso , Ressonância Magnética Nuclear Biomolecular , Neoplasias Ovarianas , Esfingosina/análogos & derivados , Esfingosina/química , Esfingosina/isolamento & purificação , Esfingosina/farmacologia , Estereoisomerismo , Sulfatos/química , Sulfatos/farmacologia , Células Tumorais Cultivadas/efeitos dos fármacosRESUMO
Three new diacetylenes (1, 4, 6) have been isolated as cytotoxic constituents from the methanolic extract of the stony coral Montipora sp. The structures have been elucidated on the basis of spectroscopic evidence. The compounds were evaluated for cytotoxicity against a small panel of human tumor cell lines and showed moderate to significant activity.