RESUMO
One new sterol, crassarosterol A (1), and four new steroidal glycosides, crassarosterosides A-D (2-5) were isolated from the Formosan soft coral Sinularia crassa. The absolute configuration of 1 was determined using the Mosher's method. The absolute configurations for the sugar moieties of 2-5 were determined by HPLC analysis on the o-tolylthiocarbamates derived from the liberated sugar after acid hydrolysis. Compounds 2 and 4 could significantly inhibit the expression of pro-inflammatory iNOS protein at 10 µM. In contrast, 1-3 were found to stimulate the expression of COX-2 protein at this concentration. Steroids 1 and 4 also showed cytotoxicity toward the selected human liver cancer cells.
Assuntos
Antozoários/metabolismo , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Esteróis/isolamento & purificação , Esteróis/farmacologia , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/metabolismo , Antineoplásicos/química , Antineoplásicos/metabolismo , Linhagem Celular Transformada , Linhagem Celular Tumoral , Ciclo-Oxigenase 2/metabolismo , Descoberta de Drogas , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/metabolismo , Glicosídeos/farmacologia , Humanos , Concentração Inibidora 50 , Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Neoplasias/tratamento farmacológico , Óxido Nítrico Sintase Tipo II/metabolismo , Oceano Pacífico , Estereoisomerismo , Esteróis/química , Esteróis/metabolismo , TaiwanRESUMO
Six new withanolides, paraminabeolides A-F (1-6), along with five known compounds, minabeolides-1, -2, -4, -5, and -8 (7-11), were isolated from a Formosan soft coral, Paraminabea acronocephala. The structures of these compounds were elucidated by extensive spectroscopic analysis and chemical transformation. The absolute configuration of 4 was determined by the application of Mosher's method. Compounds 1 and 7 were cytotoxic toward Hep G2 cancer cells. Compounds 1-4 and 7-10 were found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein. Compounds 7-10 also could effectively reduce the expression of COX-2 protein.
Assuntos
Antozoários/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Inibidores de Ciclo-Oxigenase 2/farmacologia , Óxido Nítrico Sintase Tipo II/efeitos dos fármacos , Vitanolídeos/isolamento & purificação , Vitanolídeos/farmacologia , Animais , Anti-Inflamatórios/química , Antineoplásicos/química , Inibidores de Ciclo-Oxigenase 2/química , Ensaios de Seleção de Medicamentos Antitumorais , Células Hep G2 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Vitanolídeos/químicaRESUMO
Eight new cembranoids, crassarines A-H (1-8) were isolated from the Formosan soft coral Sinularia crassa. Compounds 1-3 represent the rare cembranoids with a 1,12-oxa-bridged tetrahydrofuran ring, while 4 and 5 are the firstly discovered 1,11-oxa-bridged tetrahydropyranocembranoids. The absolute configuration of 6 was determined using the Mosher's method. Compounds 6 and 8 were found to significantly inhibit the expression of both pro-inflammatory iNOS and COX-2 proteins at 10 µM, respectively, while compounds 4-8 were found to be non-cytotoxic toward the selected human liver cancer cells.
Assuntos
Antozoários/química , Diterpenos/isolamento & purificação , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Linhagem Celular Tumoral/efeitos dos fármacos , Inibidores de Ciclo-Oxigenase 2/química , Inibidores de Ciclo-Oxigenase 2/isolamento & purificação , Inibidores de Ciclo-Oxigenase 2/farmacologia , Citotoxinas/química , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Óxido Nítrico Sintase Tipo II/antagonistas & inibidoresRESUMO
Six norterpenes including negombatoperoxides A and B (4 and 5), the inseparable epimers negombatoperoxides C and D (6 and 7), negombatodiol (8), and negombatolactone (9), in combination with three known compounds, (+)-nuapapuin B (1), (+)-nuapapuin B methyl ester (2), and (+)-aikupikoxide C (3), were isolated from the Formosan marine sponge Negombata corticata. In addition, 6,6-dimethylundecane-2,5,10-trione (10) was isolated for the first time from a natural source. Their structures, including relative configurations, were elucidated on the basis of interpretation of spectroscopic data and by the application of the empirical rule established by Capon and MacLeod. The absolute configurations of 8 and 9 were established by the application of Mosher's method and comparison of CD data with known lactones, respectively. Cytotoxicity of these isolates against human breast carcinoma, human liver carcinoma, and human lung carcinoma cell lines was evaluated.