RESUMO
Three previously undescribed polyoxygenated cyclohexene derivatives named cherrevenol M (1), cherrevenol N (2), and cherrevenone (3), together with nine related known analogues 4-12 were isolated from the ethyl acetate fraction partitioned from the methanol extract of the aerial parts of Uvaria cherrevensis (Annonaceae). The determination of the structures and their relative configurations of the isolated compounds were established by spectroscopic techniques, electronic circular dichroism (ECD) analysis as well as comparison with the literature data. For cherrevenone (3), the relative and absolute configurations were also confirmed by using X-ray diffraction and ECD techniques, respectively. Compounds isolated except for compounds 8 and 10 were evaluated for their cytotoxic activity and cherrevenone (3) showed moderate cytotoxic activity against all cancerous cell lines except for ASK cell line with ED50 values ranging from 1.04⯱â¯0.13 to 10.09⯱â¯4.31⯵M.
Assuntos
Antineoplásicos Fitogênicos/farmacocinética , Cicloexenos/farmacologia , Uvaria/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cicloexenos/isolamento & purificação , Humanos , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Ratos , TailândiaRESUMO
Eleven previously undescribed compounds, including four benzophenones (garciosones A-D), four xanthones (garciosones E-H) and three biphenyls (garciosines A-C), along with eighteen known compounds were isolated from the stems, leaves and twigs of Garcinia speciosa Wall. (Clusiaceae). Their structures were established by extensive spectroscopic analysis. For garciosines A-C, the structures were confirmed by single crystal X-ray diffraction analysis. Most of the isolated compounds were evaluated for their cytotoxic activity and anti-HIV-1 activity using the syncytium inhibition assay and HIV-1 reverse transcriptase (RT) assay. The known compounds, 4,6,3',4'-tetrahydroxy-2-methoxybenzophenone and macluraxanthone, displayed significant cytotoxic activity with the ED50 in the range of 1.85-11.76 µM. 1,5-Dihydroxyxanthone exhibited the most potent anti-HIV activity against syncytium formation with EC50 < 17.13 µM (SI > 25.28) and 2-(3,3-dimethylallyl)-1,3,7-trihydroxyxanthone was the most active compound in the HIV-1 reverse transcriptase assay with IC50 value of 58.24 µM. Structure-activity relationship of some isolated compounds were also discussed.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Benzofenonas/farmacologia , Compostos de Bifenilo/farmacologia , Garcinia/química , HIV-1/efeitos dos fármacos , Xantonas/farmacologia , Animais , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Benzofenonas/química , Benzofenonas/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Infecções por HIV/tratamento farmacológico , Humanos , Camundongos , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Ratos , Relação Estrutura-Atividade , Xantonas/química , Xantonas/isolamento & purificaçãoRESUMO
Seven previously undescribed compounds, including three polycyclic polyprenylated acylphloroglucinols (garcinuntins A-C), three biphenyl derivatives (garcinuntabiphenyls A-C) and a lanostane triterpene (garcinuntine), along with thirteen known compounds were isolated from the root of Garcinia nuntasaenii Ngerns. & Suddee. Their structures were elucidated on the basis of spectroscopic techniques. For garcinuntins A-C, the absolute configurations were confirmed by the combination of single X-ray crystallography and ECD calculations. Anti-HIV activity using anti-HIV-1 reverse transcriptase and syncytium inhibition assays, and cytotoxic activity against a panel of cultured mammalian cancer cell lines of isolated compounds were investigated.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Compostos de Bifenilo/farmacologia , Garcinia/química , Transcriptase Reversa do HIV/antagonistas & inibidores , HIV-1/efeitos dos fármacos , Floroglucinol/farmacologia , Fármacos Anti-HIV/química , Fármacos Anti-HIV/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Compostos de Bifenilo/química , Compostos de Bifenilo/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HEK293 , Transcriptase Reversa do HIV/metabolismo , Humanos , Modelos Moleculares , Estrutura Molecular , Floroglucinol/análogos & derivados , Floroglucinol/isolamento & purificação , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
Five new lanostanes, wallichinanes A-E (1-5) together with a known lanostane derivative 6 were isolated from the cytotoxic hexanes extract of fruits of Garcinia wallichii Choisy (Guttiferae). The structures of the isolated compounds were established by analysis of spectroscopic data, X-ray diffraction technique as well as comparison with the literature data. The cytotoxicity of all isolated compounds against a panel of cultured cancer cell lines was evaluated. Compound 4 exhibited good cytotoxicity with ED50 values ranging from 3.91 to 7.63µM.
Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Garcinia/química , Lanosterol/análogos & derivados , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Frutas/química , Humanos , Lanosterol/química , Lanosterol/isolamento & purificação , Lanosterol/farmacologia , Modelos Moleculares , Neoplasias/tratamento farmacológico , Difração de Raios XRESUMO
Six new naturally occurring polyoxygenated cyclohexene derivatives together with eight related known derivatives, two known alkaloids, and two known flavonoid derivatives were isolated from bioassay-guided fractionation of the ethyl acetate extract of the leaves and twigs of Dasymaschalon sootepense. The structure elucidation and determination of absolute configurations were established by various spectroscopic methods, X-ray diffraction techniques as well as comparison with the literature data. Several isolated compounds were evaluated for their cytotoxic, anti-HIV-1 RT and anti-inflammatory activities.
Assuntos
Alcaloides/química , Annonaceae/química , Fármacos Anti-HIV/química , Anti-Inflamatórios/química , Cicloexenos/química , Alcaloides/isolamento & purificação , Animais , Fármacos Anti-HIV/isolamento & purificação , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Cicloexenos/isolamento & purificação , HIV-1/efeitos dos fármacos , Humanos , Masculino , Camundongos , Estrutura Molecular , Folhas de Planta/química , Ratos , Ratos Sprague-Dawley , Inibidores da Transcriptase Reversa/química , Inibidores da Transcriptase Reversa/isolamento & purificaçãoRESUMO
Bioassay-guided fractionation of the cytotoxic ethyl acetate fraction of the sequential methanol extract from the leaves and twigs of Dasymaschalon sootepense led to the isolation of a new 7-hydroxy aporphine alkaloid, 6a,7-dehydrodasymachaline (1) along with the five known compounds (-)-nordicentrine (2), dicentrinone (3), (-)-sinactine (4), aristolactam AII (5) and epiberberine (6). Their structures were elucidated by spectroscopic methods. This is the first report of alkaloids 1-2 and 5-6 from the genus Dasymaschalon. Compounds 1 and 5 showed cytotoxicity against a panel of cancer cell lines.
Assuntos
Alcaloides/química , Alcaloides/farmacologia , Annonaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Animais , Linhagem Celular Tumoral , Humanos , Estrutura MolecularRESUMO
Three new caged xanthones, 7-methoxydesoxymorellin (1), 2-isoprenylforbesione (2) and 8,8a-epoxymorellic acid (3), together with nine known caged xanthones were isolated from the EtOAc extracts of resin and fruits of Garcinia hanburyi. The structures were determined by spectroscopic methods. Most of the isolated compounds showed significant cytotoxicities against a panel of mammalian cancer cell lines. Compound 3, together with the known compounds desoxymorellin, morellic acid, gambogic acid, hanburin, forbesione and dihydroisomorellin, exhibited anti-HIV-1 activity in the reverse transcriptase (RT) assay while the known compounds desoxygambogenin and dihydroisomorellin were found moderately active in the syncytium assay. This work represents the first report on the anti-HIV-1 activities of caged xanthones.
Assuntos
Fármacos Anti-HIV/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Garcinia , HIV-1/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Animais , Fármacos Anti-HIV/administração & dosagem , Fármacos Anti-HIV/uso terapêutico , Antineoplásicos Fitogênicos/administração & dosagem , Antineoplásicos Fitogênicos/uso terapêutico , Frutas , Transcriptase Reversa do HIV/efeitos dos fármacos , HIV-1/genética , Humanos , Camundongos , Extratos Vegetais/administração & dosagem , Extratos Vegetais/uso terapêutico , RNA Viral/análise , Ratos , Resinas Vegetais , Reação em Cadeia da Polimerase Via Transcriptase Reversa , Xantonas/administração & dosagem , Xantonas/farmacologia , Xantonas/uso terapêuticoRESUMO
Two new naturally occurring coumarins, isomesuol (1) and mammearin A (2), together with nine known Mammea coumarins 3-11 were isolated from the EtOAc extract of the leaves and twigs of Mammea harmandii. Coumarins 1, 3 and 4 showed cytotoxicity against a panel of mammalian cancer cell lines. Their structures were determined by spectroscopic methods. The assignments of 13C-NMR signals of isomesuol (1), which was isolated for the first time as a natural product, have been revised.