RESUMEN
The hepatoprotective effects of sarmentosin-containing extracts of Sedum sarmentosum (SS) in D-galactosamine (D-GalN) / lipopolysaccharide (LPS)-induced fulminant hepatic failure mouse model. Pretreatment with SS markedly protected mice from lethal liver injury, which has known to be associated with an abrupt elevation of serum tumor necrosis factor (TNF)-α level. Indeed, SS significantly blocked the elevation of TNF-α and alanine aminotransferase and aspartate aminotransferase as well. SS also remarkably reduced number of apoptotic hepatocytes and DNA fragmentation in the liver, which correlated with blockade of caspase-3 activation. In addition, SS suppressed the increased expression of toll-like receptor 4 (TLR4). The activation of c-Jun NH(2)-terminal kinase, extracellular signal-regulated kinase, and p38 induced by D-GalN/LPS was also significantly suppressed by SS treatment. Furthermore, SS significantly inhibited the activation of nuclear factor-κB. In RAW 264.7 cells stimulated with LPS, TNF-α release and TLR4 expression was suppressed by SS pretreatment, which was in line with in vivo results. These findings suggested that SS prevents D-GalN/LPS-induced fulminant hepatic failure, and this protection is likely associated with its anti-apoptotic activity and the down-regulation of mitogen activated protein kinase activity associated at least in part with suppressing the transcription of LPS receptors.
Asunto(s)
Glucosa/análogos & derivados , Fallo Hepático Agudo/prevención & control , Nitrilos/farmacología , Extractos Vegetales/farmacología , Sedum/metabolismo , Alanina Transaminasa/sangre , Animales , Aspartato Aminotransferasas/sangre , Caspasa 3/metabolismo , Fragmentación del ADN , Modelos Animales de Enfermedad , Regulación hacia Abajo , Galactosamina , Glucosa/farmacología , Hepatocitos/metabolismo , Hepatocitos/patología , Lipopolisacáridos , Hígado/metabolismo , Hígado/patología , Fallo Hepático Agudo/inducido químicamente , Fallo Hepático Agudo/metabolismo , Fallo Hepático Agudo/patología , Masculino , Ratones , Ratones Endogámicos C57BL , Receptor Toll-Like 4/metabolismo , Factor de Necrosis Tumoral alfa/sangreRESUMEN
Six new triterpenoids (1-6) with a carboxylic acid functionality at C-27 were isolated from the rhizomes of a Korean native perennial herb, Astilbe chinensis, along with nine known triterpenoids. The structures of 1-6 were elucidated on the basis of spectroscopic data interpretation. All compounds isolated were evaluated for cytotoxic effects against a small panel of human cancer lines.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Plantas Medicinales/química , Saxifragaceae/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antineoplásicos Fitogénicos/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Corea (Geográfico) , Estructura Molecular , Rizoma/química , Triterpenos/químicaRESUMEN
The hexane-soluble fraction of the roots of Aceriphyllum rossii was used to isolate seven new oleanane-type triterpenoids, aceriphyllic acids C-I (1-7), together with seven known triterpenoids. The structures of aceriphyllic acids C-I were determined as 3alpha-hydroxyolean-12-en-23,29-dioic acid (1), 3beta-hydroxyolean-12-en-23,29-dioic acid (2), 3beta,23-dihydroxyolean-12-en-29-oic acid (3), 3alpha-O-acetylolean-12-en-23,27-dioic acid (4), 3alpha-O-caffeoylolean-12-en-27-oic acid (5), 3alpha-O-acetylolean-12-en-23,29-dioic acid (6), and 3alpha-hydroxyolean-12-en-23-al-27-oic acid (7) by spectroscopic analyses. In the evaluation of the in vitro cytotoxicity of these compounds against the MCF-7 and LLC cancer cell lines, compounds 10 and 13 exhibited cytotoxic activity against the LLC cancer cell line with IC(50) values of 7.63 and 6.56 microM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Plantas Medicinales/química , Saxifragaceae/química , Antineoplásicos Fitogénicos/química , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Corea (Geográfico) , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Ácido Oleanólico/química , Raíces de Plantas/químicaRESUMEN
Bisacurone, one of the active compounds of the traditionally used indigenous herb Curcuma longa Linne (Zingiberaceae), has anti-oxidant, anti-inflammatory, and anti-metastatic activities. We studied how the level of vascular cell adhesion molecule-1 (VCAM-1), one of the key molecules in the development of atherosclerosis as well as carcinogenesis and metastasis, might be affected by bisacurone in tumor necrosis factor-alpha (TNF-alpha)-activated human umbilical vein endothelial cells (HUVECs). Bisacurone dose-dependently inhibited TNF-alpha-mediated expression of VCAM-1. It showed significant suppressive effect on ROS generation in response to TNF-alpha stimulation and it blocked nuclear factor-kappa B (NF-kappaB) p65 translocation into the nucleus and phosphorylation of inhibitory factor kappaBalpha (IkappaBalpha). It also inhibited phosphorylation of Akt and PKC, which are upstream in the regulation of VCAM-1 by TNF-alpha. Furthermore, bisacurone decreased U937 monocyte and human oral cancer cell (Hep-2, QLL-I, SCC-15) adhesion to HUVECs stimulated by TNF-alpha, suggesting that it may inhibit the binding of these cells by regulating the expression of critical adhesion molecules by TNF-alpha. Thus, bisacurone may be beneficial in the treatment of inflammatory diseases, such as atherosclerosis, where inflammatory monocytes are involved in their pathology, and, moreover, in the development of tumors.
Asunto(s)
Antiinflamatorios no Esteroideos/farmacología , Ciclohexanoles/farmacología , Células Endoteliales/metabolismo , Células Endoteliales/patología , Inflamación/metabolismo , Inflamación/patología , Monocitos/efectos de los fármacos , Sesquiterpenos/farmacología , Molécula 1 de Adhesión Celular Vascular/biosíntesis , Western Blotting , Adhesión Celular/efectos de los fármacos , Células Cultivadas , Regulación hacia Abajo/efectos de los fármacos , Quinasas MAP Reguladas por Señal Extracelular/biosíntesis , Quinasas MAP Reguladas por Señal Extracelular/genética , Genes Reporteros , Humanos , Luciferasas/genética , Proteína Oncogénica v-akt/biosíntesis , Proteína Oncogénica v-akt/genética , Oxidantes/metabolismo , Extractos Vegetales/química , Extractos Vegetales/farmacología , Plásmidos/genética , Proteína Quinasa C/biosíntesis , Proteína Quinasa C/genética , Transfección , Factor de Necrosis Tumoral alfa/biosíntesis , Factor de Necrosis Tumoral alfa/farmacologíaRESUMEN
Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12'S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-kappaB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-kappaB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.
Asunto(s)
Factor 1 Inducible por Hipoxia/antagonistas & inhibidores , FN-kappa B/antagonistas & inhibidores , Fenoles/química , Fenoles/farmacología , Psoralea/química , Terpenos/química , Línea Celular Tumoral , Humanos , Factor 1 Inducible por Hipoxia/metabolismo , Espectroscopía de Resonancia Magnética , Estructura Molecular , FN-kappa B/metabolismo , Semillas/química , Relación Estructura-ActividadRESUMEN
Demethoxycurcumin and bisdemethoxycurcumin are the main active ingredients isolated from Curcumae Longae Radix. Recent studies demonstrated that both compounds exhibit antioxidative and anti-inflammatory effects as well as effects on cancer cell lines. In this study, we compared the activities of demethoxycurcumin and bisdemethoxycurcumin, and both compounds were evaluated on lipopolysaccharide (LPS)-induced nitric oxide (NO) production, inducible nitric oxide synthase (iNOS), cycloxygenase-2 (COX-2) and nuclear factor-kappaB (NF-kappaB) activity in a RAW 264.7 macrophage cell line. The evaluation:results suggested that the anti-inflammatory properties of demethoxycurcumin and bisdemethoxycurcumin were attributed to the inhibition of iNOS and COX-2 expression, as initiated by the inhibition of NF-kappaB activity. Additionally, both of them significantly inhibited carrageenan-induced paw edema in mice. Taken together, all of the results showed that the suppressive effect of demethoxycurcumin was stronger than that of bisdemethoxycurcumin, indicating that the methoxy group had enhanced demethoxycurcumin's anti-inflammation effects.
Asunto(s)
Antiinflamatorios/farmacología , Curcumina/análogos & derivados , Edema/prevención & control , Mediadores de Inflamación/metabolismo , Macrófagos/efectos de los fármacos , Animales , Antiinflamatorios/uso terapéutico , Carragenina , Línea Celular , Curcumina/farmacología , Curcumina/uso terapéutico , Ciclooxigenasa 2/genética , Ciclooxigenasa 2/metabolismo , Diarilheptanoides , Modelos Animales de Enfermedad , Relación Dosis-Respuesta a Droga , Edema/inducido químicamente , Edema/metabolismo , Regulación Enzimológica de la Expresión Génica/efectos de los fármacos , Proteínas I-kappa B/metabolismo , Lipopolisacáridos/farmacología , Macrófagos/enzimología , Macrófagos/metabolismo , Ratones , Inhibidor NF-kappaB alfa , FN-kappa B/genética , FN-kappa B/metabolismo , Óxido Nítrico/metabolismo , Óxido Nítrico Sintasa de Tipo II/genética , Óxido Nítrico Sintasa de Tipo II/metabolismo , Fosforilación , TransfecciónRESUMEN
Bioassay-guided fractionation and purification of the EtOAc soluble fraction from the MeOH extract of the stem bark of Alnus hirsuta (Betulaceae), using an in vitro HIF-1 assay, led to the isolation of four triterpenoids (1-4) and six diarylheptanoids (5-10). Their structures were determined by comparison with the physicochemical and spectroscopic data in the literature. These compounds were investigated for their effects on the hypoxia-induced HIF-1 activation using an HIF-1a mediated reporter gene assay in AGS cells. Among them, two diarylheptanoids, 2-oxatrycyclo[13.2.2.13,7]eicosa-3,5,7(20),15,17,18-hexaen-10-16-diol (6) and 2-oxatrycyclo [13.2.2.13,7]eicosa-3,5,7-(20),15,17,18-hexaen-10-one (7), inhibited HIF-1 activation dose-dependently with IC50 values of 11.2 microM and 12.3 microM, respectively. These two compounds had no significant cytotoxicity to the AGS cells at the effective concentration for the inhibition of HIF-1 activation.
Asunto(s)
Alnus/química , Diarilheptanoides/farmacología , Factor 1 Inducible por Hipoxia/antagonistas & inhibidores , Triterpenos/farmacología , Línea Celular Tumoral , Diarilheptanoides/química , Diarilheptanoides/aislamiento & purificación , Humanos , Neoplasias Gástricas/patología , Triterpenos/química , Triterpenos/aislamiento & purificaciónRESUMEN
Acanthoic acid (AA) is a pimaradiene diterpene isolated from the Korean medicinal plant, Acanthopanax koreanum (Araliaceae). In the present study, we examined whether AA has the inhibitory effect on the production of inflammatory mediators and activating signals induced in trypsin-treated human leukemic mast cell-1 (HMC-1). HMC-1 cells were stimulated with trypsin (100 nM) in the presence or absence of AA (1, 10, and 100 microg/ml). We assessed the production of TNF-alpha and tryptase by enzyme-linked immunosorbent assay (ELISA) or reverse transcription-PCR, ERK activation by Western blot, and NF-kappaB activation by gel shift assay. AA (10 and 100 microg/ml) significantly inhibited production of both TNF-alpha and tryptase in a dose-dependent manner in trypsin-stimulated HMC-1. Furthermore, AA inhibited ERK phosphorylation and NF-kappaB activation induced by trypsin treatment without blocking of trypsin activity even with 100 microg/ml. These results suggest that AA may inhibit the production of inflammatory mediators through inhibition of ERK phosphorylation and NF-kappaB activation pathway in human mast cells. It supports the evidence that AA may be used to blocks the development of inflammation caused from mast cells.
Asunto(s)
Diterpenos/farmacología , Mastocitos/efectos de los fármacos , Inhibidores de Tripsina/farmacología , Células Cultivadas , Quinasas MAP Reguladas por Señal Extracelular/metabolismo , Humanos , FN-kappa B/metabolismo , Fosforilación , ARN Mensajero/análisis , Triptasas/genética , Factor de Necrosis Tumoral alfa/biosíntesis , Factor de Necrosis Tumoral alfa/genéticaRESUMEN
The fruits of Evodia rutaecarpa Benth (Rutaceae) has long been used for inflammatory disorders and some anti-inflammatory actions of its constituents such as dehydroevodiamine, evodiamine and rutaecarpine were previously reported. Since the pharmacological data is not sufficient to clearly establish the scientific rationale of anti-inflammatory medicinal use of this plant material and the search for its active principles is limited so far, three major constituents (evodiamine, rutaecarpine, goshuyuamide II) were evaluated for their anti-inflammatory cellular action mechanisms in the present study. From the results, evodiamine and rutaecarpine were found to strongly inhibit prostaglandin E2 synthesis from lipopolysaccharide-treated RAW 264.7 cells at 1-10 microM. Evodiamine inhibited cyclooxygenase-2 induction and NF-kappaB activation, while rutaecarpine did not. On the other hand, goshuyuamide II inhibited 5-lipoxygenase from RBL-1 cells (IC50 = 6.6 microM), resulting in the reduced synthesis of leukotrienes. However, these three compounds were not inhibitory against inducible nitric oxide synthase-mediated nitric oxide production from RAW cells up to 50 micorM. These pharmacological properties may provide the additional scientific rationale for anti-inflammatory use of the fruits of E. rutaecarpa.
Asunto(s)
Alcaloides/farmacología , Antiinflamatorios/farmacología , Evodia , Macrófagos/efectos de los fármacos , Alcaloides/aislamiento & purificación , Animales , Antiinflamatorios/aislamiento & purificación , Araquidonato 5-Lipooxigenasa/metabolismo , Calcimicina , Línea Celular , Ciclooxigenasa 2/metabolismo , Inhibidores de la Ciclooxigenasa 2/aislamiento & purificación , Inhibidores de la Ciclooxigenasa 2/farmacología , Dinoprostona/metabolismo , Relación Dosis-Respuesta a Droga , Evodia/química , Frutas/química , Alcaloides Indólicos , Leucotrieno C4/metabolismo , Lipopolisacáridos , Inhibidores de la Lipooxigenasa/aislamiento & purificación , Inhibidores de la Lipooxigenasa/farmacología , Macrófagos/metabolismo , Ratones , FN-kappa B/metabolismo , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Quinazolinas/aislamiento & purificación , Quinazolinas/farmacologíaRESUMEN
A new 7,20-epoxy kaurane diterpenoid, 15-acetyldemethylkamebacetal A (1) and six known kaurane diterpenoids (2-7) were isolated from the aerial parts of Isodon inflexus in nuclear transcription factor-κB (NF-κB)-dependent reporter gene assay-guided fractionation. Their chemical structures were determined on the basis of extensive spectroscopic analysis (UV, IR, MS, 1D- and 2D-NMR) and comparison with literature data. The isolated compounds were evaluated for their inhibitory effects on TNF-α-induced NF-κB activation, and all compounds exhibited NF-κB inhibitory activities with IC50 values ranging from 1.91 to 20.15 µM.
Asunto(s)
Diterpenos de Tipo Kaurano/análisis , Isodon/química , Genes Reporteros/genética , Células HeLa , Humanos , Espectroscopía de Resonancia Magnética , FN-kappa B/efectos de los fármacos , FN-kappa B/genética , Extractos Vegetales/análisis , Factor de Necrosis Tumoral alfa/antagonistas & inhibidoresRESUMEN
Interleukin (IL)-8 plays a central role in the initiation and maintenance of inflammatory responses in the inflammatory bowel disease. The proinflammatory cytokine-mediated production of IL-8 requires activation of various kinases, which leads to the I kappa B degradation and NF-kappa B activation. We investigated the role of 18 beta-glycyrrhetinic acid (GA), a saponin isolated from licorice roots, on TNF-alpha-induced IL-8 production in human colonic epithelial cells. HT29 cells were stimulated with TNF-alpha in the presence or absence of GA (1, 5 or 10 microM). IL-8 production was measured by enzyme-linked immunosorbent assay (ELISA) and reverse transcriptase-polymerase chain reaction analysis, and the mitogen-activated protein kinases (MAPKs) activation and I kappa B alpha degradation were determined by Western blot analysis. GA suppressed TNF-alpha-induced IL-8 production in a concentration-dependent manner. In addition, GA inhibited TNF-alpha-induced phosphorylation of p38 MAPK and extracellular-regulated kinases (ERK), I kappa B alpha degradation, and NF-kappa B activation. These results suggest that GA has the inhibitory effects on TNF-alpha-induced IL-8 production in the intestinal epithelial cells through blockade in the phosphorylation of MAPKs, following I kappa B alpha degradation and NF-kappa B activation.
Asunto(s)
Ácido Glicirretínico/análogos & derivados , Ácido Glicirretínico/farmacología , Interleucina-8/antagonistas & inhibidores , Western Blotting , Supervivencia Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Activación Enzimática/efectos de los fármacos , Ensayo de Inmunoadsorción Enzimática , Células HT29 , Humanos , Proteínas I-kappa B/metabolismo , Interleucina-8/biosíntesis , Proteína Quinasa 1 Activada por Mitógenos/antagonistas & inhibidores , Proteína Quinasa 3 Activada por Mitógenos/antagonistas & inhibidores , Proteínas Quinasas Activadas por Mitógenos/metabolismo , Inhibidor NF-kappaB alfa , FN-kappa B/antagonistas & inhibidores , Fosforilación/efectos de los fármacos , Reacción en Cadena de la Polimerasa de Transcriptasa Inversa , Factor de Necrosis Tumoral alfa/farmacología , Proteínas Quinasas p38 Activadas por Mitógenos/antagonistas & inhibidoresRESUMEN
A new sorbicillinoid polyketide, dihydrotrichodimerol (2), along with known trichodimerol (1), and rezishanones C (3) and D (4) were isolated by bioassay-guided fractionation from an unidentified fungal strain. Dihydrotrichodimerol (2) specifically activated peroxisome proliferator-activated receptor gamma with an ED50 value of 80 ng/ml as measured by a transactivation assay using a chimeric hPPAR/GAL4 system without affecting peroxisome proliferator-activated receptors alpha and sigma. On the other hand, compounds 1 and 2 suppressed the production of tumor necrosis factor-alpha and nitric oxide in LPS-stimulated RAW264.7 cells to a similar extent.
Asunto(s)
Ciclohexanonas/farmacología , Hongos/química , Óxido Nítrico/antagonistas & inhibidores , PPAR gamma/metabolismo , Hongos/metabolismo , Macrólidos/farmacología , Óxido Nítrico/biosíntesis , PPAR gamma/efectos de los fármacosRESUMEN
A new biflavonol glycoside named as solanoflavone (1) was isolated from aerial part of Solanum melongena. The chemical structure was elucidated as isorhamnetin-3-O-beta-D-glucopyranoside-(4'-->O-->4''')-galangin-3''-O-beta-D-glucopyranoside on the basis of physicochemical and spectroscopic methods, including 2D NMR spectral techniques.
Asunto(s)
Flavonoles/aislamiento & purificación , Glicósidos/aislamiento & purificación , Solanum melongena/química , Antiinflamatorios/aislamiento & purificación , Flavonoles/química , Glicósidos/química , Espectroscopía de Resonancia Magnética/métodos , Estructura Molecular , Análisis EspectralRESUMEN
The EtOAc extract of Youngia koidzumiana significantly inhibited the diacylglycerol acyltransferase (DGAT) from rat liver microsomes. Bioactivity-guided fractionation led to the isolation of nine compounds, the structures of which were established using physicochemical and spectral data. Of the isolated compounds, oleanolic acid (2), methyl ursolate (7) and corosolic aicd (8) inhibited DGAT, with IC50 values of 31.7, 26.4, and 44.3 microM, respectively. However, sesquiterpenoids showed only weak inhibitory effects toward DGAT.
Asunto(s)
Aciltransferasas/antagonistas & inhibidores , Asteraceae/química , Inhibidores Enzimáticos/farmacología , Terpenos/farmacología , Animales , Cromatografía en Capa Delgada , Diacilglicerol O-Acetiltransferasa , Inhibidores Enzimáticos/aislamiento & purificación , Técnicas In Vitro , Hígado/efectos de los fármacos , Hígado/enzimología , Espectroscopía de Resonancia Magnética , Masculino , Microsomas Hepáticos/efectos de los fármacos , Microsomas Hepáticos/enzimología , Extractos Vegetales/farmacología , Ratas , Ratas Sprague-Dawley , Espectrofotometría Infrarroja , Terpenos/aislamiento & purificaciónRESUMEN
The hepatoprotective effects of Acanthopanax koreanum Nakai (Araliaceae) were evaluated in D-galactosamine/lipopolysaccharide-induced fulminant hepatic failure in mouse. Preparations of Acanthopanax koreanum used were an ethanol extract, a water extract, and the ethanol-soluble and ethanol-insoluble components of the water extract of roots or stems of the plant. Mice were pretreated with various extracts by intraperitoneal injection or orally, 12 and 1 h before intraperitoneal injection of D-galactosamine and lipopolysaccharide (LPS). Intraperitoneal pretreatment with the water extract or the ethanol-insoluble component of the water extract markedly reduced the elevated levels of alanine aminotransferase (ALT), aspartate aminotransferase (AST), and tumor necrosis factor-alpha (TNF-alpha), reduced the histological changes in the liver, and attenuated hepatocyte apoptosis confirmed by the terminal deoxynucleotidyl transferase-mediated dUTP nick end-labeling method and DNA fragmentation assay. Oral pretreatment with the ethanol-insoluble component of the water extract also reduced serum AST, ALT, and TNF-alpha levels. The present study shows that the ethanol-insoluble component of a water extract from Acanthopanax koreanum has a protective effect against the induction of fulminant hepatitis in mice by D-galactosamine and lipopolysaccharide.
Asunto(s)
Enfermedad Hepática Inducida por Sustancias y Drogas/prevención & control , Eleutherococcus , Hígado/efectos de los fármacos , Fitoterapia , Extractos Vegetales/farmacología , Sustancias Protectoras/farmacología , Administración Oral , Animales , Apoptosis/efectos de los fármacos , Enfermedad Hepática Inducida por Sustancias y Drogas/etiología , Fragmentación del ADN/efectos de los fármacos , Galactosamina , Hepatocitos/efectos de los fármacos , Inyecciones Intraperitoneales , Lipopolisacáridos , Hígado/enzimología , Hígado/patología , Masculino , Ratones , Ratones Endogámicos C57BL , Extractos Vegetales/administración & dosificación , Extractos Vegetales/uso terapéutico , Raíces de Plantas , Tallos de la Planta , Sustancias Protectoras/administración & dosificación , Sustancias Protectoras/uso terapéutico , Factor de Necrosis Tumoral alfa/efectos de los fármacosRESUMEN
A new 24-nor-lupaneglycoside was isolated from the leaves of Acanthopanax trifoliatus. Based on spectroscopic data its chemical structure was determined as 24-nor-11alpha-hydroxy-3-oxo-lup-20(29)-en-28-oic acid 28-O-alpha-L-rhamnopyranosyl-(1 --> 4)-beta-D-glucopyranosyl-(1 --> 6)-beta-D-glucopyranosyl ester.
Asunto(s)
Eleutherococcus/química , Glicósidos/química , Glicósidos/aislamiento & purificación , Triterpenos/química , Corea (Geográfico) , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Plantas Medicinales , VietnamRESUMEN
A new benzofuran derivative, named gymnastone [5-hydroxy-6-acetyl-2-(2-propane-1,2,3-triol)-benzofuran (1)], was isolated from the aerial part of Gymnaster koraiensis, together with viscidone (2) by repeated column chromatography. The structures of both compounds were identified by physico-chemical and spectral analysis including COSY, HMQC, and HMBC experiments.
Asunto(s)
Asteraceae/química , Benzofuranos/aislamiento & purificación , Acetileno/química , Benzofuranos/química , Cromatografía/métodos , Glicósidos/química , Glicósidos/aislamiento & purificación , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Tallos de la Planta/químicaRESUMEN
Three lignans isolated from the roots of A. koreanum (Araliaceae), namely eleutheroside E (1), tortoside A (2), and hemiariensin (4), were evaluated for their ability to inhibit NFAT transcription factor. Of these compounds, compound 4, possessing a diarylbutane skeleton, exhibited potent inhibitory activity against NFAT transcription factor (IC50: 36.3 +/- 2.5 microM). However, the activities of 1 (IC50: > 500 microM) and 2 (IC50: 136.1 +/- 9.4 microM), which possess bisaryldioxabicyclooctane skeletons, were lower. As the lignan derivatives of the same skeletons, hinokinin (5) and (-)-yatein (6) with diarylbutane skeletons and (+)-syringaresinol (3) with a bisaryldioxabicyclooctane skeleton were also studied for their inhibitory effects on NFAT transcription factor.
Asunto(s)
Proteínas de Unión al ADN/genética , Eleutherococcus/química , Proteínas Nucleares/genética , Factores de Transcripción/genética , Tampones (Química) , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Humanos , Indicadores y Reactivos , Células Jurkat , Lignanos , Espectroscopía de Resonancia Magnética , Factores de Transcripción NFATC , Espectrofotometría Ultravioleta , Transcripción Genética/efectos de los fármacosRESUMEN
Two triterpenoids (1,4) and two triterpenoid glycosides (2,3) were isolated from the root of Acanthopanax koreanum (Araliaceae). Their structures were identified as impressic acid (1), acankoreoside A (2), 3-epi-betulinic acid 28-O-[alpha-L-rhamnopyranosyl(1 --> 4)-beta-D-glucopyranosyl(1 --> 6)]-beta-D-glucopyranosyl] ester (3), and ursolic acid (4) by physicochemical and spectroscopic methods. Of these compounds, impressic acid (1) exhibited a potent inhibitory activity against NFAT transcription factor (IC50: 12.65 microM).
Asunto(s)
Proteínas de Unión al ADN/antagonistas & inhibidores , Eleutherococcus , Proteínas Nucleares/antagonistas & inhibidores , Factores de Transcripción/antagonistas & inhibidores , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Proteínas de Unión al ADN/metabolismo , Factores de Transcripción NFATC , Proteínas Nucleares/metabolismo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Raíces de Plantas , Factores de Transcripción/metabolismo , Triterpenos/químicaRESUMEN
Five known kaurane type diterpenoids, 16alphaH,17-isovaleryloxy-ent-kauran-19-oic acid (1), 16alpha-hydroxy-17-isovaleryloxy-ent-kauran-19-oic acid (2), paniculoside-IV (3), 16alpha-hydroxy-ent-kauran-19-oic acid (4), and ent-kaur-16-en-19-oic acid (5) were isolated from the root of Acanthopanax koreanum by repeated column chromatography and reversed phase preparative HPLC. The structures of these compounds were established from physicochemical and spectral data. Among the isolated compounds 16alphaH,17-isovaleryloxy-ent-kauran-19-oic acid (1) showed potent inhibitory activity (IC50 value, 16.2 uM) on TNF-alpha secretion from HMC-1, a trypsin-stimulated human leukemic mast cell line.