RESUMO
Three new orcinol (3-hydroxy-5-methylphenol)-conjugated hydrolysable tannins, together with two known compounds were isolated from the leaves of Cleyera japonica (CJ), and have been tentatively named cleyeratannin A (1), cleyeratannin B (2) and cleyeratannin C (3). The chemical structures of these compounds were elucidated using 1 dimensional (1D)/2D NMR and high resolution FAB-MS, and the absolute configuration was confirmed by circular dichroism (CD). To evaluate their anti-oxidative activities, 1,1-diphenyl-2-picrylhydrazyl (DPPH)/free radical scavenging activity and nitroblue tetrazolium (NBT)/superoxide anion scavenging activity were determined.
Assuntos
Antioxidantes/química , Sequestradores de Radicais Livres/química , Taninos Hidrolisáveis/química , Extratos Vegetais/química , Resorcinóis/química , Theaceae/química , Nitroazul de Tetrazólio/química , Superóxidos/químicaRESUMO
Fifteen phenolic compounds, including three caffeoyl derivatives, four gallotannins, three ellagitannins and five flavonoids, were isolated from an 80% MeOH extract of the leaves of Corylopsis coreana Uyeki (Korean winter hazel; CL). The anti-oxidative activities [1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and xanthine oxidase superoxide scavenging activities (NBT)] and the anti-proliferative activity on human prostate cancer cell lines (DU145 and LNCaP) were also evaluated.
Assuntos
Antineoplásicos Fitogênicos , Antioxidantes , Proliferação de Células/efeitos dos fármacos , Hamamelidaceae/química , Extratos Vegetais , Folhas de Planta/química , Neoplasias da Próstata/tratamento farmacológico , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Masculino , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Neoplasias da Próstata/metabolismo , Neoplasias da Próstata/patologiaRESUMO
BACKGROUND AND PURPOSE: Microbial product lipopolysaccharide (LPS) has been shown to be involved in the pathogenesis of inflammatory skin diseases. Caffeoyl derivatives have demonstrated anti-inflammatory and antioxidant effects. However, the effect of 3,4,5-tricaffeoylquinic acid (3,4,5-triCQA) on the production of microbial product-induced inflammatory mediators in keratinocytes has not yet been studied. EXPERIMENTAL APPROACH: Using human keratinocytes, we investigated the effect of 3,4,5-triCQA on the LPS-stimulated production of inflammatory mediators in relation to the nuclear factor (NF)-ĸB, Akt and ERK pathways. RESULTS: 3,4,5-triCQA inhibited the LPS-induced expression of Toll-like receptor 4, and the production of cytokines and chemokines in keratinocytes. 3,4,5-triCQA, Bay 11-7085, Aĸt inhibitor and ERK inhibitor each attenuated the LPS-induced production of inflammatory mediators by inhibiting the NF-ĸB, Akt and ERK pathways. CONCLUSIONS AND IMPLICATIONS: 3,4,5-triCQA may attenuate the LPS-stimulated production of inflammatory mediators in keratinocytes by suppressing the Toll-like receptor 4 expression-mediated activation of the Akt, ERK and NF-ĸB pathways. 3,4,5-triCQA may exert a preventive effect against microbial product-induced inflammatory skin diseases.
Assuntos
Ácido Clorogênico/análogos & derivados , Mediadores da Inflamação/metabolismo , Queratinócitos/metabolismo , Lipopolissacarídeos/antagonistas & inibidores , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Ácido Clorogênico/farmacologia , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Humanos , NF-kappa B/metabolismo , Proteínas Proto-Oncogênicas c-akt/metabolismo , Ácido Quínico/análogos & derivadosRESUMO
Isolation of compounds from the root of Rhodiola sachalinensis (RRS) yielded tyrosol (1), salidroside (2), multiflorin B (3), kaempferol-3,4'-di-O-ß-D-glucopyranoside (4), afzelin (5), kaempferol (6), rhodionin (7), and rhodiosin (8). Quantification of these compounds was performed by high-performance liquid chromatography (HPLC). To investigate the antioxidant and anti-inflammatory effects of the compounds, DPPH radical scavenging, NBT superoxide scavenging and nitric oxide production inhibitory activities were examined in LPS-stimulated Raw 264.7 cells. We suggest that the major active components of RRS are herbacetin glycosides, exhibiting antioxidant activity, and kaempferol, exhibiting anti-inflammatory activity.
Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Fenóis/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Rhodiola/química , Compostos de Bifenilo/antagonistas & inibidores , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Humanos , Óxido Nítrico/biossíntese , Picratos/antagonistas & inibidores , Superóxidos/antagonistas & inibidoresRESUMO
FlexPro MD® (FP-MD), a novel multi-ingredient dietary supplement formulation, has been demonstrated to relieve knee joint pain in humans. However, the mechanisms of action responsible for the activity of FP-MD have not been elucidated. In this study, we show the anti-inflammatory effects of FP-MD in RAW264.7 macrophage cells and mice challenged with lipopolysaccharide (LPS). FP-MD significantly inhibited the mRNA levels of pro-inflammatory cytokines, including interleukin-6 (IL-6), tumor necrosis factor-α (TNF-α), and IL-1ß. In contrast, it elevated the mRNA levels of anti-inflammatory cytokine IL-10 in LPS-stimulated RAW264.7 cells. FP-MD markedly reduced LPS-induced phosphorylation levels of nuclear factor-κB (NF-κB) p65 and inhibitor of κB-α (IκB-α). Importantly, the anti-inflammatory effects of FP-MD were demonstrated in mice with LPS-induced inflammatory arthritis in which FP-MD significantly reduced the expression levels of pro-inflammatory cytokines and inflammatory markers. Thus, this study suggests that FP-MD has anti-inflammatory effects by inhibiting NF-κB that may offer a molecular basis for its pain relief property.
Assuntos
Anti-Inflamatórios/farmacologia , Euphausiacea/química , Ácido Hialurônico/administração & dosagem , NF-kappa B/antagonistas & inibidores , Óleos/administração & dosagem , Analgésicos , Animais , Artrite Experimental/induzido quimicamente , Artrite Experimental/tratamento farmacológico , Ciclo-Oxigenase 2/genética , Citocinas/biossíntese , Citocinas/genética , Suplementos Nutricionais , Expressão Gênica/efeitos dos fármacos , Inflamação/induzido quimicamente , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Lipopolissacarídeos/farmacologia , Macrófagos/química , Macrófagos/metabolismo , Masculino , Metaloproteinase 1 da Matriz/genética , Metaloproteinase 2 da Matriz/genética , Camundongos , Camundongos Endogâmicos C57BL , Óxido Nítrico Sintase Tipo II/genética , Dor/tratamento farmacológico , Células RAW 264.7 , RNA Mensageiro/análise , Xantofilas/administração & dosagemRESUMO
Two new phenolic compounds, 4-O-glucopyranosyl-5-O-caffeoylshikimic acid (1) and 2,3-digalloyl oregonin (2), were isolated along with eight known phenolic compounds (3-10) from an 80% acetone extract of Alnus sibirica leaves. The chemical structures of these compounds were elucidated using 1D/2D nuclear magnetic resonance and high resolution-MS. The anti-oxidative activities of these compounds were determined by assaying their 1,1-diphenyl-2-picrylhydrazyl radical and nitroblue tetrazolium superoxide anion scavenging activity. All of the isolated phenolic compounds (1-10) exhibited potent anti-oxidative activities. In particular, 2 and 4, which are diarylheptanoids, and 10 which is ellagitannin exhibited excellent anti-oxidative activities with almost the same potency as that of the positive controls L-ascorbic acid and allopurinol.
Assuntos
Alnus/química , Antioxidantes/química , Antioxidantes/farmacologia , Diarileptanoides/química , Ácido Gálico/análogos & derivados , Glucosídeos/química , Folhas de Planta/química , Ácido Chiquímico/análogos & derivados , Ácido Ascórbico/farmacologia , Compostos de Bifenilo/química , Diarileptanoides/farmacologia , Avaliação Pré-Clínica de Medicamentos/métodos , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Ácido Gálico/química , Ácido Gálico/farmacologia , Glucosídeos/farmacologia , Taninos Hidrolisáveis/farmacologia , Espectroscopia de Ressonância Magnética , Fenóis/química , Picratos/química , Extratos Vegetais/química , Ácido Chiquímico/química , Ácido Chiquímico/farmacologia , Superóxidos/químicaRESUMO
The Stewartia koreana Nakai (SK) had been used in oriental traditional medicine as a remedy for acute gastroenteritis, liver diseases, quadriplegia and pain. The antioxidant activity guided isolation 80% methyl extract from stems of SK yielded eight phenolic compounds. We evaluated the anti-oxidative and anti-inflammatory effects of these compounds via assays of 1,1-diphenyl-2-picrylhydazyl (DPPH) radicals and inhibition of nitric oxide (NO) production in lipopolysaccharide-stimulated RAW 264.7 macrophage cells. The results demonstrated that syringaresinol (6) exhibited significant DPPH radical-scavenging activity and inhibitory effects on NO production compared with its positive controls, ascorbic acid and L-NMMA, respectively.
Assuntos
Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Compostos de Bifenilo/farmacologia , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Fenóis/isolamento & purificação , Fenóis/farmacologia , Picratos/farmacologia , Theaceae/química , Animais , Anti-Inflamatórios/química , Antioxidantes/química , Ácido Ascórbico/farmacologia , Sequestradores de Radicais Livres/química , Furanos/química , Furanos/isolamento & purificação , Furanos/farmacologia , Lignanas/química , Lignanas/isolamento & purificação , Lignanas/farmacologia , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Oxirredução , Fenóis/química , Caules de Planta/química , ômega-N-Metilarginina/farmacologiaRESUMO
Microbial components have been shown to be involved in the pathogenesis of inflammatory skin diseases. The extract of from the barks of Ilex rotunda Thunb has demonstrated anti-inflammatory and anti-oxidant effects. However, the effect of hemiterpene rotundarpene (4-caffeoyl-3-methyl-but-2-ene-1,4-diol) on the Toll-like receptor (TLR)-2 activation-induced production of inflammatory mediators in keratinocytes has not been studied. Using human keratinocytes, we investigated the effect of rotundarpene on the inflammatory mediator production in relation to the TLR-2-mediated-Akt and NF-κB pathways, which regulates the transcription genes involved in immune and inflammatory responses. Rotundarpene, Akt inhibitor, Bay 11-7085 and N-acetylcysteine each attenuated the lipoteichoic acid- or peptidoglycan-induced production of cytokines and chemokines, expression of TLR-2, activation of NF-κB and Akt, and formation of reactive oxygen species in keratinocytes. Cyclosporine A attenuated the bacterial component-induced production of inflammatory mediators but did not reduce the formation of reactive oxygen species. The results show that rotundarpene may attenuate the bacterial component-stimulated production of inflammatory mediators in keratinocytes by suppressing the TLR-2-mediated activation of the Akt and NF-κB pathways. The effect of rotundarpene may be attributed to its inhibitory effect on the formation of reactive oxygen species. Rotundarpene may exert a preventive effect against the bacterial component-mediated inflammatory skin diseases.
Assuntos
Anti-Inflamatórios/farmacologia , Ácidos Cafeicos/farmacologia , Hemiterpenos/farmacologia , NF-kappa B/antagonistas & inibidores , Proteínas Proto-Oncogênicas c-akt/antagonistas & inibidores , Receptor 2 Toll-Like/antagonistas & inibidores , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Citocinas/metabolismo , Dinoprostona/metabolismo , Humanos , Ilex , Queratinócitos , Lipopolissacarídeos/farmacologia , Casca de Planta , Espécies Reativas de Oxigênio/metabolismo , Ácidos Teicoicos/farmacologiaRESUMO
The leaves of Myrica rubra sieb. et zucc. have been used in oriental traditional medicine for the treatment of burns, skin diseases, and as an antidiarrheal in China, Japan, and Korea. Activity guided isolation of the leaves of M. rubra has led to the isolation of five flavonoid: myricetin (1), myricitrin (2), myricetin 3-O-(2â³-O-galloyl)-α-L-rhamnopyranoside (3), myricetin 3-O-(2â³-O-galloyl)-ß-D-galactopyranoside (4), and quercetin 3-O-(2â³-O-galloyl)-ß-D-galactopyranoside (5). All isolates were evaluated for their antioxidant potency against the superoxide anion (O2 (-)), and compounds 3-5 showed potent scavenging activities with 50 % inhibition concentration (IC50) values compared to the positive control, allopurinol. Compounds 1-5 were evaluated as inhibitors of various macrophage functions involved in the inflammatory process. These five compounds significantly and dose dependently inhibited lipopolysaccharide (LPS)-stimulated nitric oxide (NO), pro-inflammatory cytokines, and the protein levels of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in LPS-stimulated RAW 264.7 macrophages. Our results suggest that galloyl flavonol glycosides (3-5) isolated from M. rubra might be beneficial for the treatment of inflammation-related diseases.
Assuntos
Anti-Inflamatórios/farmacologia , Flavonoides/farmacologia , Myrica , Extratos Vegetais/farmacologia , Folhas de Planta , Animais , Anti-Inflamatórios/isolamento & purificação , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Flavonoides/isolamento & purificação , Camundongos , Extratos Vegetais/isolamento & purificaçãoRESUMO
Chromatographic separation of the 80% MeOH extract of the leaves of Ilex rotunda (IR) led to isolation of two new hemiterpene glycosides, tentatively named as rotundarpenoside A (1) and rotundarpenoside B (2), along with five known caffeoyl derivatives (3-7). The chemical structures of these compounds were elucidated using 1D/2D NMR, HR-MS, and the absolute configuration was confirmed by Mosher's method. In order to evaluate their anti-oxidative activities, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity and xanthine oxidase superoxide scavenging activities (NBT) were determined.