RESUMO
Five novel iridoid glycosides, avellanedaesides A-E (1 - 5) were isolated from the H2 O extract of Tabebuia avellanedae. Their structures were determined on the basis of NMR and MS analysis. Isolated compounds suppressed inflammatory cytokine, tumor-necrosis factor-α and interleukin-1ß production in cultured human myeloma THP-1 cells co-stimulated with lipopolysaccharide (LPS). In addition, the study revealed iridoid glycosides inhibited the activity of cytochrome CYP3A4 enzyme.
Assuntos
Inibidores do Citocromo P-450 CYP3A/farmacologia , Citocromo P-450 CYP3A/metabolismo , Glicosídeos Iridoides/farmacologia , Tabebuia/química , Linhagem Celular Tumoral , Inibidores do Citocromo P-450 CYP3A/química , Inibidores do Citocromo P-450 CYP3A/isolamento & purificação , Citocinas/antagonistas & inibidores , Relação Dose-Resposta a Droga , Humanos , Glicosídeos Iridoides/química , Glicosídeos Iridoides/isolamento & purificação , Lipopolissacarídeos/farmacologia , Conformação Molecular , Relação Estrutura-AtividadeRESUMO
Three novel phenylpropanoid glycosides 2, 5, 6 were isolated from water extract of Tabebuia avellanedae, together with three known phenylpropanoid glycosides 1, 3, 4. All compounds were identified on the basis of spectroscopic analysis and chemical methods and, for known compounds, by comparison with published data. All isolated compounds showed strong antioxidant activity in the DPPH assay, and compound 5 give the highest antioxidant activity among all compounds, with an IC50 of 0.12 µM. All compounds exhibited moderate inhibitory effect on cytochrome CYP3A4 enzyme.
Assuntos
Antioxidantes/química , Antioxidantes/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Tabebuia/química , Antioxidantes/isolamento & purificação , Inibidores do Citocromo P-450 CYP3A , Sequestradores de Radicais Livres/química , Glicosídeos/isolamento & purificação , Casca de Planta/química , Extratos Vegetais/química , Propanóis/química , Propanóis/isolamento & purificaçãoRESUMO
Five novel compounds were isolated from the water extract of Tabebuia avellanedae, and their structures were established by analysis of NMR spectroscopy and mass spectrometry. Compounds 1-5 at 25µM showed strong inhibitory activity on the inflammatory cytokine, tumor-necrosis factor-α and interleukin-1ß production in cultured human myeloma THP-1 cells co-stimulated with lipopolysaccharide without any significant cytotoxicity, and their anti-allergic and antioxidant activities were evaluated.
Assuntos
Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Tabebuia/química , Compostos de Bifenilo , Linhagem Celular , Sequestradores de Radicais Livres/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-1beta/genética , Interleucina-1beta/metabolismo , Estrutura Molecular , Picratos , Fator de Necrose Tumoral alfa/genética , Fator de Necrose Tumoral alfa/metabolismo , beta-N-Acetil-Hexosaminidases/genética , beta-N-Acetil-Hexosaminidases/metabolismoRESUMO
Five new phenolic lipids, 2-(8"Z-eicosenoyl)-6-(8'Z-pentadecenyl) salicylic acid (3), 2-(9"Z-hexadecenoyl)-6-(8'Z, 11'Z-pentadecadienyl) methyl salicylate (5), 2-(10"Z, 13"Z-nonadecadienoyl)-6-(8'Z, 11'Z-pentadecadienyl) salicylic acid (6), 2-(16"Z-pentacosenoyl)-6-(8'Z-pentadecenyl) salicylic acid (7) and 2-(9"Z-octadecenoyl)-6-(8'Z, 11'Z-pentadecadienyl) methyl salicylate (8), and three known compounds, cardols (1), anacardic acid (2) and cardanols (4), were isolated from the nuts of the cashew, Anacardium occidentale L. The structures were established on the basis of detailed MS and NMR spectroscopic analyses. Compound 1 highly enhanced both Th-1 (IL-2, IFN-γ) and Th-2 (IL-4, IL-5) cytokine production, and compounds 7 and 8 highly increased cytokine IL-2 and IFN-γ production in response to concanavalin A in cultured murine Peyer's patch cells ex vivo. The isolated compounds showed moderate inhibitory activities on cytochrome CYP3A4 enzyme.
Assuntos
Anacardium/química , Inibidores do Citocromo P-450 CYP3A , Inibidores Enzimáticos/farmacologia , Lipídeos/farmacologia , Nozes/química , Nódulos Linfáticos Agregados/efeitos dos fármacos , Fenóis/farmacologia , Animais , Células Cultivadas , Concanavalina A/farmacologia , Citocromo P-450 CYP3A/metabolismo , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Interferon gama/metabolismo , Interleucina-1/metabolismo , Interleucina-4/metabolismo , Interleucina-5/metabolismo , Lipídeos/química , Lipídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Masculino , Espectrometria de Massas , Camundongos , Camundongos Endogâmicos C57BL , Estrutura Molecular , Nódulos Linfáticos Agregados/citologia , Nódulos Linfáticos Agregados/imunologia , Fenóis/química , Fenóis/isolamento & purificaçãoRESUMO
Three new steroidal saponins, Vernoniosides S1 (1), Vernoniosides S2 (2) and Vernoniosides S3 (3) were isolated from the stem of Vernonia cumingian. Their chemical structures were elucidated on the basis of MS, NMR spectroscopic and chemical analysis. Complete assignment of (1)H and (13)C NMR spectroscopic data were achieved by 1D and 2D NMR experiments (HMQC, HMBC, ROESY).
Assuntos
Colestanos/química , Glicosídeos/química , Isótopos de Carbono , Espectroscopia de Ressonância Magnética/métodosRESUMO
To search for bioactive compounds from the flower disc of Helianthus annuus L., chromatography was used to isolate and purify the chemical constituents, their structures were identified by spectral analysis, MTT method was applied to investigate their cytotoxic activities, some compounds showed moderate cytotoxic activities on SF-268, MCF-7 and HepG2 cell lines. Eleven compounds were obtained from the flower disc of H. annuus, and identified as ent-kaurane-2alpha, 16alpha-diol (1) and entkaurane-15alpha,16alpha-epoxy-17-al-19-oic acid (2), and nine known diterpenes, ent-kaurane-16P-ol (3), phyllocladan-16beta-ol (4) , ent-atisan-16a-ol (5) , grandifloric acid (6) , angeloylgrandifloric acid (7), ent-kaurane-16-en-19-oic acid (8), ent-kaurane-17-hydroxy-15-en-19-oic acid (9), ent-kaurane-16beta, 17-dihydroxy-19-oic acid (10), and ciliaric acid (11). Compounds 1 and 2 are new compounds, some compounds showed cytotoxic activities on SF-268, MCF-7 and HepG2 cell lines.
Assuntos
Diterpenos do Tipo Caurano/isolamento & purificação , Diterpenos/farmacologia , Helianthus/química , Plantas Medicinais/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cristalização , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos do Tipo Caurano/química , Flores/química , Humanos , Concentração Inibidora 50 , Conformação Molecular , Estrutura Molecular , Temperatura de TransiçãoRESUMO
Three new lignan oligosaccharide esters, rupestrin A (1), rupestrin B (2), and rupestrin C (3), were isolated from the ethanol extract of Eritrichium rupestre. Their structures were elucidated on the basis of spectroscopic and chemical evidence.
