RESUMO
The anti-inflammatory activity of handelin (1), a guaianolide dimer from Chrysanthemum boreale flowers, was evaluated in vivo, and the effects on mediators nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor-α (TNF-α), and interleukin-1ß (IL-1ß) and the nuclear factor-κB (NF-κB) and ERK/JNK signaling pathways were investigated in vitro. Compound 1 inhibited lipopolysaccharide (LPS)-induced production of NO and PGE2 in cultured mouse macrophage RAW 264.7 cells. The suppression of NO and PGE2 production by 1 was correlated with the downregulation of mRNA and protein expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2). Compound 1 also suppressed the induction of pro-inflammatory cytokines TNF-α and IL-1ß in LPS-stimulated RAW 264.7 cells. To further clarify the transcriptional regulatory pathway in the expression of iNOS and COX-2 by 1, the role of NF-κB was determined in RAW 264.7 cells. Compound 1 inhibits the binding activity of NF-κB into the nuclear proteins. The transcriptional activity of NF-κB stimulated with LPS was also suppressed by 1, which coincided with the inhibition of IκB degradation. Compound 1 also suppressed the activation of mitogen-activated protein kinases, including ERK and JNK signaling. In addition, the LPS-stimulated upregulation of miRNA-155 expression was suppressed by 1. The oral administration of 1 inhibited acute inflammation in carrageenan-induced paw and 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ear edema models. The serum level of IL-1ß was also inhibited by 1 in a carrageenan-induced paw edema model. These findings suggest that the suppression of NF-κB activation and pro-inflammatory cytokine production may be a plausible mechanism of action for the anti-inflammatory activity of handelin.
Assuntos
Anti-Inflamatórios/farmacologia , Chrysanthemum/química , Citocinas/metabolismo , Proteínas I-kappa B/metabolismo , NF-kappa B/efeitos dos fármacos , Terpenos/farmacologia , Animais , Anti-Inflamatórios/química , Ciclo-Oxigenase 2 , Dinoprostona/metabolismo , Regulação para Baixo , Edema/induzido quimicamente , Edema/tratamento farmacológico , Proteínas I-kappa B/efeitos dos fármacos , Interleucina-1beta/efeitos dos fármacos , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Proteínas Quinases Ativadas por Mitógeno/metabolismo , Modelos Animais , Estrutura Molecular , Inibidor de NF-kappaB alfa , Óxido Nítrico/metabolismo , Óxido Nítrico Sintase Tipo II/efeitos dos fármacos , Óxido Nítrico Sintase Tipo II/metabolismo , Fitoterapia , Transdução de Sinais/efeitos dos fármacos , Terpenos/química , Fator de Necrose Tumoral alfa/efeitos dos fármacosRESUMO
An investigation of the Korean medicinal plant Patrinia villosa (THUNB.) JUSS. (Valerianaceae) led to the isolation of two new flavonoid glycosides, patrivilosides 1 (1) and 2 (2), a new iridoid glycoside, patrinovalerosidate (3), and two new saponins, patrinovilosides A (4) and B (5), along with six known compounds including three flavonoid glycosides and three iridoid glycosides. The structures of the new compounds were elucidated based on analysis of their one dimensional (1D)- and 2D-NMR spectra along with their mass spectrometric data and the results of acid hydrolysis.
Assuntos
Flavonoides/química , Glicosídeos/química , Patrinia/química , Componentes Aéreos da Planta/química , Flavonoides/isolamento & purificação , Glicosídeos/isolamento & purificação , Hidrólise , Plantas Medicinais/químicaRESUMO
Rehmanniae Radix Preparata, the steamed root of Rehmannia glutinosa Libosch, has been widely used for the treatment of inflammatory conditions in Oriental medicines. In this study we evaluated the effects of 2,5-dihydroxyacetophenone (DHAP) isolated from Rehmanniae Radix Preparata on inflammatory responses in lipopolysaccharide (LPS)-stimulated RAW264.7 mouse macrophages. LPS-stimulated RAW264.7 cells were used to investigate the anti-inflammatory activity of DHAP on the production of inflammatory mediators such as nitric oxide (NO), inducible NO synthase (iNOS), tumor necrosis factor-α (TNF-α), and interleukin (IL)-6. DHAP significantly inhibited NO production via the suppression of iNOS expression and significantly decreased levels of the pro-inflammatory cytokines TNF-α and IL-6 via the down-regulation of their mRNA expression in LPS-stimulated RAW264.7 cells. DHAP potently inhibited the phosphorylation of extracellular signal-related kinase (ERK) 1/2 and the nuclear translocation of nuclear factor-κB (NF-κB) p65 in LPS-stimulated cells. These results indicate that DHAP inhibits the production of inflammatory mediators in activated macrophages by blocking the ERK1/2 and NF-κB signaling pathways. Our results suggest that DHAP from Rehmanniae Radix Preparata has anti-inflammatory activity in activated macrophages, raising the possibility that this compound has a therapeutic potential for inflammatory conditions.
Assuntos
Acetofenonas/uso terapêutico , Anti-Inflamatórios/uso terapêutico , Mediadores da Inflamação/metabolismo , Inflamação/tratamento farmacológico , Macrófagos/efeitos dos fármacos , Fitoterapia , Rehmannia/química , Acetofenonas/isolamento & purificação , Acetofenonas/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Citocinas/biossíntese , Citocinas/genética , Citocinas/metabolismo , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Inflamação/induzido quimicamente , Inflamação/metabolismo , Lipopolissacarídeos , Macrófagos/metabolismo , Camundongos , NF-kappa B/metabolismo , Fosforilação , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Raízes de Plantas , RNA Mensageiro/metabolismo , Transdução de SinaisRESUMO
Six new germacranolides, zawadskinolides A-F (1-6), and a new eudesmane glucoside, chrysantiloboside (7) were isolated from the aerial parts of Dendranthema zawadskii var. latilobum, along with thirteen known constituents. Their structures were elucidated by means of spectroscopic evidence. Bioassay showed that flavonoids such as apigenin (9), (-)-eriodictyol (10) and nepetin (12), as well as the sesquiterpene lactone, zawadskinolide F (6), inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage cells with IC50 values of 66.15, 132.55, 35.44, and 91.32 µM, respectively.
Assuntos
Chrysanthemum/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Animais , Células Cultivadas , Flavonoides/química , Flavonoides/farmacologia , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Óxido Nítrico/antagonistas & inibidores , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/farmacologia , Análise Espectral/métodosRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: The roots of Sophora flavescens have long been used in Chinese medicine for the treatment of fever, inflammatory disorders, ulcers and skin burns. Sophora flavescens contains flavonoids and alkaloids. AIM OF THE STUDY: This study was conducted to develop a plant-based anti-inflammatory agent focused on chronic inflammatory disorders. To accomplish this, the alkaloid-free prenylated flavonoid-enriched fraction (PFS) of rhizomes of Sophora flavescens was prepared and its in vitro and in vivo anti-inflammatory activities were then evaluated for the first time. MATERIALS AND METHODS: The inhibitory activity of PFS on PGE(2), NO, IL-6 and TNF-alpha production of lipopolysaccharide (LPS)-treated RAW 264.7 cells was measured. Additionally, adjuvant-induced arthritis in rats was used as an animal model of chronic inflammation to establish the in vivo anti-inflammatory effects of PFS. RESULT: PFS inhibited cyclooxygenase-2 (COX-2)-catalyzed PGE(2) and inducible nitric oxide synthase (iNOS)-catalyzed NO production by lipopolysaccharide (LPS)-treated RAW 264.7 cells at 10-50 microg/ml, and these effects primarily occurred via COX-2 inhibition and iNOS down-regulation, respectively. PFS also inhibited IL-6 and TNF-alpha production. When tested against adjuvant-induced arthritis in rats (chronic inflammation), PFS strongly inhibited arthritic inflammation when administered orally at doses of 10-100mg/kg/day. In addition, PFS administered orally potently inhibited acetic acid-induced writhing in mice. CONCLUSIONS: Our results suggest that PFS inhibits chronic inflammatory response and the inhibition of proinflammatory molecules such as COX-2, iNOS and IL-6 may contribute, at least in part, to the anti-inflammatory activity in vivo. Overall, these results indicate that PFS from Sophora flavescens may have the potential for treatment of chronic inflammatory disorders such as rheumatoid arthritis.
Assuntos
Analgésicos/uso terapêutico , Anti-Inflamatórios/uso terapêutico , Artrite/tratamento farmacológico , Flavonoides/uso terapêutico , Mediadores da Inflamação/metabolismo , Extratos Vegetais/uso terapêutico , Sophora/química , Ácido Acético , Analgésicos/administração & dosagem , Analgésicos/farmacologia , Animais , Anti-Inflamatórios/administração & dosagem , Anti-Inflamatórios/farmacologia , Artrite/induzido quimicamente , Comportamento Animal/efeitos dos fármacos , Linhagem Celular , Modelos Animais de Doenças , Regulação para Baixo , Flavonoides/administração & dosagem , Flavonoides/farmacologia , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Lipopolissacarídeos , Masculino , Camundongos , Camundongos Endogâmicos ICR , Fitoterapia , Extratos Vegetais/administração & dosagem , Extratos Vegetais/farmacologia , Raízes de Plantas , Prenilação , Ratos , Ratos Wistar , RizomaRESUMO
Bioassay-guided fractionation of MeOH extract from fenugreek (Trigonella foenum-graecum L.) seeds resulted in the isolation of two rat growth-hormone release stimulators in vitro, fenugreek saponin I (1) and dioscin (9), along with two new, i.e., 2 and 3, and five known analogues, i.e., 4-8. The structures of the new steroidal saponins, fenugreek saponins I, II, and III (1-3, resp.), were determined as gitogenin 3-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, sarsasapogenin 3-O-beta-D-xylopyranosyl-(1-->6)-beta-D-glucopyranoside, and gitogenin 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranoside, respectively. Fenugreek saponin I (1) and dioscin (9) caused ca. 12.5- and 17.7-fold stimulation of release, respectively, of rat growth hormone from rat pituitary cells, whereas gitogenin (5) showed moderate activity. To our knowledge, this is the first study to demonstrate that steroidal saponins stimulate rat growth-hormone release in rat pituitary cells.
Assuntos
Hormônio do Crescimento/metabolismo , Trigonella/química , Animais , Células Cultivadas , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Hipófise/efeitos dos fármacos , Hipófise/metabolismo , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Ratos , Ratos Sprague-Dawley , Sementes/químicaRESUMO
Two new cycloartane-type triterpenoid saponins were isolated from the roots of Astragalus membranaceus (FISCH.) BGE. (Leguminosae) cultivated in Kangwon province, Korea. These saponins were named astramembranosides A and B and were established to be cycloastragenol 6,25-di-O-beta-D-glucopyranoside (astramembranoside A) and cyclocanthogenin 3-O-beta-D-glucopyranosyl(1-->2)-beta-D-xylopyranoside (astramembranoside B) on the basis of chemical and spectral evidence. In addition, 12 known saponins were also isolated from the same materials. Although cycloastragenol 3-O-xyloside and agroastragalosides I and II have already been isolated from A. membranaceus adventitious roots, these three saponins together with brachyoside B and azukisaponin V methyl ester were isolated for the first time from this plant.
Assuntos
Astragalus propinquus/química , Plantas Medicinais/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Coreia (Geográfico) , Estrutura Molecular , Raízes de Plantas/química , Saponinas/química , Triterpenos/químicaRESUMO
The aim of this study was to investigate the effects of paeoniflorin (PF) and paeonol (PN), the main active compounds of the Paeonia albiflora Pallas, on myocardial ischemia and reperfusion (I/R)-induced injury in Sprague-Dawley rats IN VIVO. Under anesthesia, the rats were subjected to 25 min of ischemia by ligation of the left anterior descending coronary artery (LAD) followed by 6 h (Western blot analysis) or 24 h (hemodynamics and infarct size) of reperfusion. When the infarct size was measured as the percentage of the area at risk, both PF (25.0 % +/- 7.0 %) and PN (24.1 % +/- 5.5 %) significantly (P < 0.05) reduced it compared to I/R control (54.8 % +/- 2.6 %). Administration of 10 mg/kg PF or PN 1 h prior to I/R injury also resulted in a significant improvement of the hemodynamic parameters. Furthermore, both PF and PN decreased the caspase-3 and Bax expressions but up-regulated Bcl-2 in the left ventricles. The results show that both PF and PN reduced myocardial damage in rat through protection from apoptosis, suggesting that Paeonia albiflora Pallas might be useful in treating myocardial infarction.
Assuntos
Acetofenonas/farmacologia , Benzoatos/farmacologia , Hidrocarbonetos Aromáticos com Pontes/farmacologia , Cardiotônicos/farmacologia , Glucosídeos/farmacologia , Traumatismo por Reperfusão Miocárdica/prevenção & controle , Paeonia , Fitoterapia , Função Ventricular Esquerda/efeitos dos fármacos , Acetofenonas/administração & dosagem , Acetofenonas/uso terapêutico , Animais , Benzoatos/administração & dosagem , Benzoatos/uso terapêutico , Hidrocarbonetos Aromáticos com Pontes/administração & dosagem , Hidrocarbonetos Aromáticos com Pontes/uso terapêutico , Cardiotônicos/administração & dosagem , Cardiotônicos/uso terapêutico , Glucosídeos/administração & dosagem , Glucosídeos/uso terapêutico , Masculino , Monoterpenos , Extratos Vegetais/administração & dosagem , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Ratos , Ratos Sprague-Dawley , Função Ventricular Esquerda/fisiologiaRESUMO
Induction of growth hormone (GH) by Glycyrrhizae Radix (GR), one of the most popular herbal medicine, and its major ingredients were studied in rat pituitary cells in vitro and in vivo assay. The MeOH extract and the n-hexane (HX) fraction of GR induced rat GH (rGH) release up to 1.89 times (0.34 +/- 0.04 nM) and 4.59 times (0.83 +/- 0.03 nM), compared to the basal level (p < 0.05). Among many ingredients isolated and purified from GR both glycyrrhetinic acid and glycyrrhizin induced significantly rGH release compared to the control (p < 0.05). After an intravenous injection of rat growth hormone releasing hormone (rGHRH) (10 microg/kg) as positive control, in SD rats, Tmax of plasma rGH level was 10 min, C(max) was 3.84 +/- 0.01 nM (n = 3), and enhanced plasma rGH level returned to the baseline in 90 min. Both AUC(0-90) (area under the curve) of plasma rGH level after HX fraction and that after rGHRH administration were increased significantly from the basal level, respectively (p < 0.01). In conclusions, HX fraction is the most active fraction of MeOH extract of GR in rGH induction.
Assuntos
Glycyrrhiza , Hormônio do Crescimento/metabolismo , Hormônio Adrenocorticotrópico/metabolismo , Animais , Células Cultivadas , Ácido Glicirretínico/isolamento & purificação , Ácido Glicirretínico/farmacologia , Ácido Glicirrízico/isolamento & purificação , Ácido Glicirrízico/farmacologia , Hormônio do Crescimento/sangue , Hormônio Liberador de Hormônio do Crescimento/farmacologia , Hormônio Luteinizante/metabolismo , Masculino , Hipófise/efeitos dos fármacos , Hipófise/metabolismo , Extratos Vegetais/farmacologia , Plantas Medicinais , Ratos , Ratos Sprague-DawleyRESUMO
In the present study, we investigated immunomodulatory effect of daucosterol, a beta-sitosterol glycoside, against disseminated candidiasis caused by Candida albicans. Results showed that direct interaction of daucosterol with C. albicans yeast cells resulted in no growth-inhibition by in vitro susceptibility analysis. In contrast, mice given daucosterol (DS) intraperitoneally before intravenous challenge with live C. albicans yeast cells survived longer than DS-untreated control mice against disseminated candidiasis (P<0.05). By assessment of the fungal CFU in kidneys, DS-treated mice before the challenge developed about 81% fewer kidney CFU than untreated controls. This protection was removable by pretreatment of mice with anti-CD4+ antibody before the DS-treatment and challenge with the yeast. However, the protection was transferable by the CD4+ T cells from DS-treated mice not infected with the yeast. ELISA analysis revealed there were predominant production of IFNgamma and IL-2 cytokines as compared to IL-4, and IL-10 productions in DS-treated mice. By treatment of DS-given mice with anti-mouse IFNgamma, the protection was also abolished. Our studies show that DS protects mice against disseminated candidiasis by the CD4+ Th1 immune response.
Assuntos
Candida albicans/efeitos dos fármacos , Candidíase/tratamento farmacológico , Candidíase/imunologia , Sitosteroides/uso terapêutico , Células Th1/imunologia , Animais , Astragalus propinquus/química , Linfócitos T CD4-Positivos/imunologia , Candidíase/microbiologia , Citocinas/imunologia , Citocinas/metabolismo , Feminino , Ativação Linfocitária , Camundongos , Camundongos Endogâmicos BALB C , Testes de Sensibilidade Microbiana , Sitosteroides/química , Sitosteroides/imunologia , Sitosteroides/farmacologiaRESUMO
The structure and antioxidant properties of a new natural glycoside, trichotomoside (1), isolated from Clerodendron trichotomum, were investigated. Trichotomoside was identified as 2-(3-hydroxy-4-methoxyphenyl)ethyl 3-O-(2,3-di-O-acetyl-alpha-L-rhamnopyranosyl)-4-O-[(2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]-beta-D-glucopyranoside. The compound was active towards intracellular reactive oxygen species (ROS) and exhibited DPPH-radical-scavenging effects. The radical-scavenging activity of 1 was found to protect the viability of Chinese hamster lung fibroblasts (V79-4 cells) exposed to H2O2 and gamma-irradiation.
Assuntos
Antioxidantes/isolamento & purificação , Clerodendrum , Glicosídeos/isolamento & purificação , Propanóis/isolamento & purificação , Animais , Antioxidantes/química , Antioxidantes/farmacologia , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Cricetinae , Cricetulus , Relação Dose-Resposta a Droga , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Caules de Planta , Propanóis/química , Propanóis/farmacologiaRESUMO
In our ongoing search for bioactive compounds originating from the endemic species in Korea, we found that the hexane and EtOAc fractions of the MeOH extract from the root of Dystaenia takeshimana (Nakai) Kitagawa (Umbelliferae) showed cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX) dual inhibitory activity by assessing their effects on the production of prostaglandin D2 (PGD2) and leukotriene C4 (LTC4) in mouse bone marrow-derived mast cells. By activity-guided fractionation, five coumarins, viz. psoralen (2), xanthotoxin (3), scopoletin (4), umbelliferone (5), and (+)-marmesin (6), together with beta-sitosterol (1), were isolated from the hexane fraction, and two phenethyl alcohol derivatives, viz. 2-methoxy-2-(4'-hydroxyphenyl)ethanol (7) and 2-hydroxy-2-(4'-hydroxyphenyl)ethanol (8), three flavonoids, viz. apigenin (9), luteolin (10), and cynaroside (11), as well as daucosterol (12) were isolated from the EtOAc fraction using silica gel column chromatography. In addition, D-mannitol (13) was isolated from the BuOH fraction by recrystallization. Two of the coumarins, scopoletin (4) and (+)-marmesin (6), the two phenethyl alcohol derivatives (7, 8) and the three flavonoids (9-11) were isolated for the first time from this plant. Among the compounds isolated from this plant, the five coumarins as well as the three flavonoids showed COX-2/5-LOX dual inhibitory activity. These results suggest that the anti-inflammatory activity of D. takeshimana might in part occur via the inhibition of the generation of eicosanoids.
Assuntos
Anti-Inflamatórios/farmacologia , Apiaceae/química , Animais , Anti-Inflamatórios/isolamento & purificação , Células da Medula Óssea/efeitos dos fármacos , Inibidores de Ciclo-Oxigenase 2/farmacologia , Técnicas In Vitro , Coreia (Geográfico) , Inibidores de Lipoxigenase , Masculino , Mastócitos/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos BALB C , Extratos Vegetais/farmacologia , Raízes de Plantas/químicaRESUMO
One new quinazoline (1) and two new norditerpenoid (2 and 3) alkaloids along with 10 known compounds were isolated from the roots of Aconitum pseudo-laeve var. erectum. The new alkaloids were assigned as 2-(2-methyl-4-oxo-4H-quinazoline-3-yl)benzoic acid methyl ester (1), 18-O-2-(2-methyl-4-oxo-4H-quinazoline-3-yl)benzoyllycoctonine (2), and 14-O-acetyl-8-O-methyl-18-O-2-(2-methyl-4-oxo-4H-quinazoline-3-yl)benzoylcammaconine (3). The structures of the new alkaloids were established by spectroscopic methods. This is the first report of the 2-(2-methyl-4-oxo-4H-quinazoline-3-yl)benzoyl ester group being found as an acyl substituent in norditerpenoid alkaloids (compounds 2 and 3).
Assuntos
Aconitina , Aconitum/química , Alcaloides/química , Alcaloides/isolamento & purificação , Plantas Medicinais/química , Quinazolinas/química , Quinazolinas/isolamento & purificação , Aconitina/análogos & derivados , Aconitina/química , Aconitina/isolamento & purificação , Coreia (Geográfico) , Estrutura Molecular , Raízes de Plantas/química , Relação Estrutura-AtividadeRESUMO
Aldose reductase, the key enzyme of the polyol pathway, is known to play important roles in diabetic complications. Therefore, inhibitors of aldose reductase would be potential agents for the prevention of diabetic complications. To evaluate the inhibitory potential of aldose reductase from Ganoderma applanatum (Polyporaceae), methanol (MeOH) and water extracts were tested for their effects on rat lens aldose reductase (RLAR). The effects of both extracts on streptozotocin (STZ)-induced diabetes in rats were also investigated. The MeOH extract exhibited a potent rat lens aldose reductase (RLAR) inhibition in vitro, and showed a significant inhibition, of not only serum glucose concentrations, but also of sorbitol accumulations in the lens, red blood cells (RBC) and sciatic nerves in STZ-induced diabetic rats. Associated with a reduction in serum glucose concentration in STZ-induced diabetic rats, this extract was found to cause a significant glucose tolerance effect. These results suggested that G. applanatum might possess constituents with antidiabetic and inhibitory effects on diabetic complications.
Assuntos
Ganoderma , Hipoglicemiantes/farmacologia , Cristalino/efeitos dos fármacos , Fitoterapia , Extratos Vegetais/farmacologia , Aldeído Redutase/antagonistas & inibidores , Aldeído Redutase/biossíntese , Aldeído Redutase/efeitos dos fármacos , Animais , Glicemia/efeitos dos fármacos , Diabetes Mellitus Experimental/induzido quimicamente , Diabetes Mellitus Experimental/prevenção & controle , Retinopatia Diabética/induzido quimicamente , Retinopatia Diabética/prevenção & controle , Inibidores Enzimáticos/administração & dosagem , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/uso terapêutico , Hipoglicemiantes/administração & dosagem , Hipoglicemiantes/uso terapêutico , Cristalino/enzimologia , Extratos Vegetais/administração & dosagem , Extratos Vegetais/uso terapêutico , Ratos , Sorbitol/metabolismo , Organismos Livres de Patógenos Específicos , EstreptozocinaRESUMO
A new triterpenoid saponin, together with five known saponins, were isolated from the nonpolar n-hexane fraction of the leaves of Aralia elata. The structure of the new saponin, durupcoside C, was elucidated as hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside on the basis of spectroscopic analysis. The known saponins were characterized as 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranosyl ester, hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, oleanolic acid 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside, hederagenin 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranoside (alpha-hederin), and hederagenin 3-O-beta-D-glucopyranosyl(1-->3)-alpha-L-arabinopyranoside (collinsonidin). In addition, two known lipids, Arisaema glyceride 3 and ceramide mixtures were also isolated and characterized. Collinsonidin and two known lipids were isolated for the first time from this plant.
Assuntos
Aralia , Saponinas/química , Saponinas/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de PlantaRESUMO
The antioxidant properties of isoacteoside, isolated from Clerodendron trichotomum (Verbenaceae), were investigated. This compound scavenged intracellular reactive oxygen species (ROS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, and prevented lipid peroxidation. This radical scavenging activity of isoacteoside protected cell viability of Chinese hamster lung fibroblast (V79-4) cells exposed to hydrogen peroxide (H2O2). Furthermore, isoacteoside reduced the apoptotic cells formation induced by H2O2, as demonstrated by the decreased number of sub-G1 hypo-diploid cells and apoptotic cell body formation. However, isoacteoside increased the activities of cellular antioxidant enzymes, superoxide dismutase (SOD) and catalase (CAT). Taken together, these findings suggest that isoacteoside, isolated from C. trichotomum, possesses antioxidant properties.
Assuntos
Antioxidantes/farmacologia , Clerodendrum/química , Glucosídeos/farmacologia , Fenóis/farmacologia , Animais , Apoptose , Catalase/biossíntese , Catalase/farmacologia , Técnicas de Cultura de Células , Cricetinae , Cricetulus , Citotoxinas , Fibroblastos , Glucosídeos/isolamento & purificação , Peróxido de Hidrogênio/análise , Peroxidação de Lipídeos , Pulmão/citologia , Fenóis/isolamento & purificação , Extratos Vegetais/farmacologia , Espécies Reativas de Oxigênio , Superóxido Dismutase/biossíntese , Superóxido Dismutase/farmacologia , VerbenaceaeRESUMO
Anti-estrogenic activity of (-)-sesamin (1), helioxanthin (2), savinin (3), taiwanin C (4), and 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone (5) isolated from the root of Acanthopanax chiisanensis was tested using Ishikawa cells. Among them, compound 3 exhibited anti-estrogenic activity (IC50 = 4.86 microM).
Assuntos
Eleutherococcus/química , Antagonistas de Estrogênios/farmacologia , Lignanas/farmacologia , Adenosina Trifosfatases/biossíntese , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Indução Enzimática/efeitos dos fármacos , Antagonistas de Estrogênios/isolamento & purificação , Feminino , Humanos , Lignanas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Fitoestrógenos/isolamento & purificação , Fitoestrógenos/farmacologia , Raízes de Plantas/química , Espectrometria de Massas por Ionização por Electrospray , Sais de Tetrazólio , TiazóisRESUMO
The antioxidant property of jionoside D, isolated from Clerodendron trichotomum (Verbenaceae), was investigated. This compound showed scavenging activity of intracellular reactive oxygen species and of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, as well as lipid peroxidation inhibitory activity. This radical scavenging activity of jionoside D protected the cell viability of Chinese hamster lung fibroblast (V79-4) cells exposed H2O2. Furthermore, jionoside D reduced the apoptotic cells induced by H2O2, as demonstrated by the decreased number of sub G1 hypo-diploid cells and apoptotic body formation. However, it increased the activities of cellular antioxidant enzymes, superoxide dismutase and catalase. Taken together, these findings suggest that jionoside D, isolated from C. trichotomum, exhibits antioxidant properties.
Assuntos
Antioxidantes/farmacologia , Clerodendrum , Dissacarídeos/farmacologia , Animais , Antioxidantes/isolamento & purificação , Apoptose/efeitos dos fármacos , Compostos de Bifenilo/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Cricetinae , Cricetulus , Dissacarídeos/isolamento & purificação , Sequestradores de Radicais Livres/farmacologia , Hidrazinas/metabolismo , Peroxidação de Lipídeos/efeitos dos fármacos , Picratos , Extratos Vegetais/farmacologia , Caules de Planta , Espécies Reativas de Oxigênio/metabolismo , Superóxido Dismutase/metabolismoRESUMO
From the roots of Sophora koreensis (Fabaceae), three new oleanene-type triterpene glycosides, echinosophorosides A(1) (1) and B (2), and acetyl-subproside II (5), were isolated as their methyl esters, together with the four known ones sophoraflavoside I, kudzusaponin SA(3), subproside II, and azukisaponin V. The structures of the new saponins were elucidated to be 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->2)-beta-D-glucuronopyranosyl kudzusapogenol A 22-O-alpha-L-arabinopyranoside (1), 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl-(1-->2)-beta-D-glucuronopyranosyl abrisapogenol C 22-O-alpha-L-arabinopyranoside (2), and 3-O-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl(1-->2)-beta-D-glucuronopyranosyl kudzusapogenol A 22-O-acetate (5), respectively. It is noteworthy that two arabinopyranosyl moieties in the same molecule, echinosophoroside B (2), have different conformations. The conformation of the arabinopyranosyl moiety existing in the trisaccharide moiety was determined to be (1)C(4), whereas that of the arabinopyranosyl unit at C-22 was identified as (4)C(1).
Assuntos
Saponinas/química , Saponinas/isolamento & purificação , Sophora , Triterpenos/química , Triterpenos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Raízes de PlantasRESUMO
Five new phenolic glycosides, 2-beta-D-glucopyranosyloxy-5-hydroxyphenylacetic acid methyl ester (4), 4-hydroxy-2-[3-hydroxy-3-methylbutyl]-5-methylphenyl beta-D-glucopyranoside (5), 4-hydroxy-2-[(E)-4-hydroxy-3-methyl-2-butenyl]-5-methylphenyl beta-D-glucopyranoside (7), 4-hydroxy-2-[(2E,6Z)-8-beta-D-glucopyranosyloxy-3,7-dimethylocta-2,6-dien-1-yl]-5-methylphenyl beta-D-glucopyranoside (8), and 2,7-dimethyl-1,4-dihydronaphthalene-5,8-diol 5-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside (10), were isolated from the whole plants of Pyrola japonica (Pyrolaceae), together with androsin, (-)-syringaresinol glucoside, homoarbutin, pirolatin, hyperin, monotropein and chimaphilin.