RESUMO
The aim of the study was to determine the relationship between anti-inflammatory effects of the natural polyphenolic compound tannic acid (CAS number: 1401-55-4) and myeloperoxidase (MPO) enzyme activity in paw edema model. Thirty-five female rats were divided into five groups. The paws of rats were injected subcutaneously in the plantar surface with formalin except for the control group. Indomethacin and tannic acid were intraperitoneally administered 1 h after formalin injection. The paws volume was measured by using vernier caliper. MPO enzyme activity was determined using 4-aminoantipyrine-phenol solution as the substrate for MPO-mediated oxidation by H2O2. About 17% and 13% edema inhibition has detected in the indomethacin-applied group, at the measurements run every other hour right after the treatment. An inhibition of 16% was found at the group treated with 25 mg/kg tannic acid. However, in the group treated with 50 mg/kg tannic acid, 15% and 7% of the edema inhibition was observed. Serum and paw tissue MPO activities were decreased in treated groups with indomethacin and tannic acid according to formalin control group. Our study results suggest that tannic acid may contribute to the treatment of inflammation by decreasing MPO enzyme activity, but the molecular mechanism is still not clear.
Assuntos
Anti-Inflamatórios/uso terapêutico , Edema/tratamento farmacológico , Taninos/uso terapêutico , Animais , Anti-Inflamatórios/farmacologia , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/metabolismo , Feminino , Pé , Formaldeído , Peroxidase/metabolismo , Ratos Sprague-Dawley , Taninos/farmacologiaRESUMO
Two new aromatic monoterpenoid glycosides, cruciaside A (2,5-O-beta-D-diglucopyranosyl-3-hydroxy-p-cymene) (1) and cruciaside B (5-O-beta-D-glucopyranosyl-2,3-dihydroxy-p-cymene) (2), were isolated from aerial parts of Cruciata taurica. The structures of the new compounds were determined by spectral and chemical methods. The new compounds seem to be promising as taxonomic markers for C. taurica.
Assuntos
Glicosídeos/química , Monoterpenos/química , Fitoterapia , Extratos Vegetais/química , Rubiaceae , Humanos , Espectroscopia de Ressonância MagnéticaRESUMO
Chemical investigation of the aerial parts of Digitalis cariensis Boiss. ex Jaub. & Spach resulted in the isolation of a new pregnane glycoside, cariensisoside (1) and a furostanol glycoside, uttroside A (2), along with the two known phenylethanoid glycosides, lugrandoside (3) and maxoside (4). On the basis of spectral (UV, IR, NMR, MS) and chemical methods, compounds 1 and 2 were identified as digifologenin-3-O-beta-glucopyranosyl-(1-->4)-beta-oleandropyranoside and 3-O-(beta-lycotetraosyl)-26-O-(beta-glucopyranosyl)-(25R)-22 alpha-methoxy-5-furostane-3 beta,26-diol, respectively.
Assuntos
Digitalis/química , Glicosídeos/química , Pregnanos/química , Esteróis/química , Acetilação , Compostos de Bifenilo , Sequência de Carboidratos , Cromatografia em Camada Fina , Glicosídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Dados de Sequência Molecular , Oxirredução , Picratos , Pregnanos/isolamento & purificação , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Esteróis/isolamento & purificaçãoRESUMO
Three new cycloartane-type triterpene glycosides have been isolated from the aerial parts of Astragalus trojanus. The structures were established mainly by a combination of one- and two-dimensional NMR techniques [1H-1H-correlation spectroscopy (COSY), 1H-13C-heteronuclear multiple quantum correlation spectroscopy (HMQC), and 1H-13C-heteronuclear multiple-bond correlation spectroscopy (HMBC)] and high resolution electrospray ionization mass spectrometry (HR-ESI-MS) as 3-O-beta-(2',3'-di-O-acetyl)-D-xylopyranosyl-6-O-beta-D-glucopyranosyl-16-O- acetoxy-20(R),24(S)-epoxycycloartane-3beta,6alpha,16beta,25-tetrol, 3-0-[alpha-L-rhamnopyranosyl-(1-->2)-beta-(3',4'-di-O-acetyl)-D-xylopyranosyll-6-O-beta-D-xylopyranosyl-20(R),24(S)-epoxycycloartane-3p,6alpha,16beta,25-tetrol, 3-O-beta-D-xylopyranosyl-6,16-di-O-beta-D-glucopyranosyl-20(R)24(S)-epoxycycloartane-3beta,6alpha,16beta,25-tetrol.
Assuntos
Astrágalo/química , Glicosídeos/química , Saponinas/química , Triterpenos , Glicosídeos/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Brotos de Planta/química , Saponinas/isolamento & purificaçãoRESUMO
A new iridoid glucoside, 8-O-acetylshanzhiside (1), was isolated from the aerial parts of Phlomis tuberosa, together with two known iridoid glucosides, shanzhiside methyl ester and lamalbide. The known phenylethanoid glycosides acteoside and forsythoside B were also obtained and characterized. The structure of 1 was determined by means of 1D- and 2D-NMR spectroscopic evidence.
Assuntos
Glucosídeos/química , Glicosídeos/química , Lamiaceae/química , Álcool Feniletílico/química , Piranos/química , Bulgária , Glucosídeos/isolamento & purificação , Glicosídeos/isolamento & purificação , Iridoides , Espectroscopia de Ressonância Magnética , Álcool Feniletílico/isolamento & purificação , Piranos/isolamento & purificação , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Four new phenolic glycosides, beta-apiofuranosyl-(1-->2)-beta-glucopyranosides (1-4), along with the cycloartane triterpenes 20(R),25-epoxy-3beta,6alpha,16beta,24alpha-tetrahydroxycycloartane (5) and 20(R),24(S)-epoxy-3beta,6alpha,25-trihydroxycycloartan-16-one (6) were isolated from roots of Astragalus zahlbruckneri. The structure elucidation of all compounds was based on their (1)H and (13)C NMR spectral data including 1D-TOCSY, DQF-COSY, HSQC, and HMBC experiments.
Assuntos
Astrágalo/química , Glicosídeos/isolamento & purificação , Triterpenos/isolamento & purificação , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Fenóis/química , Raízes de Plantas/química , Plantas Medicinais/química , Sapogeninas/química , Triterpenos/química , TurquiaRESUMO
From the aerial parts of Putoria calabrica, two new flavonol triglycosides were isolated and their structures were elucidated as quercetin-3-O-[alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (1, calabricoside A) and quercetin-3-O-[4' "-O-caffeoyl-alpha-L-rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside]-7-O-beta-D-glucopyranoside (2, calabricoside B). Additionally, seven iridoid and three lignan glycosides were isolated and characterized. Radical scavenging activities of all compounds were determined by quantifying their effects on luminol-enhanced chemiluminescence in formyl-methionyl-leucyl-phenylalanine (FMLP) stimulated human polymorphonuclear neutrophils (PMNs). Calabricoside A and B showed strong radical scavenging activity with IC(50) values of 0.25 and 0.3 microM, respectively.
Assuntos
Flavonoides/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Glucosídeos/isolamento & purificação , Lignanas/isolamento & purificação , Plantas Medicinais/química , Quercetina , Rubiaceae/química , Cromatografia , Ésteres/química , Flavonoides/química , Flavonoides/farmacologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Glucosídeos/química , Glucosídeos/farmacologia , Humanos , Lignanas/química , Lignanas/farmacologia , Medições Luminescentes , Estrutura Molecular , N-Formilmetionina Leucil-Fenilalanina/farmacologia , Neutrófilos/efeitos dos fármacos , Espectrofotometria Infravermelho , Relação Estrutura-Atividade , TurquiaRESUMO
A new iridoid glycoside, deacetylalpinoside (2), was isolated from the aerial parts of Globularia trichosantha together with nine known iridoid glycosides: catalpol, 10-O-benzoyl-catalpol, aucubin, asperuloside, deacetylasperuloside, asperulosidic acid, scandoside, geniposidic acid, and alpinoside (1). From the underground parts of the same plant, two new bisiridoid glycosides, globulosides A (3) and B (4); a known iridoid glycoside, globularidin; a lignan glycoside, liriodendrin; and seven phenylethanoid glycosides, arenarioside, verbascoside (= acteoside), isoacteoside, crenatoside, isocrenatoside, and trichosanthosides A and B, were isolated. Compounds 2-4 are new iridoids containing an 8,9 double bond representing a rare carbon skeleton. Their structures were established by spectroscopic methods.
Assuntos
Glucosídeos/isolamento & purificação , Plantas Medicinais/química , Piranos/isolamento & purificação , Glucosídeos/química , Iridoides , Folhas de Planta/química , Raízes de Plantas/química , Piranos/química , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Two new polyphenolic compounds, myricetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside and (-)-6-chloroepicatechin, were isolated from the aerial parts of Geranium pratense subsp. finitimum (Woronow) Knuth, along with three known polyphenolic compounds [quercetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside, quercetin 3-O-(2"-O-galloyl)-beta-D-galactopyranoside, methyl gallate] and tryptophan. Quercetin 3-O-beta-D-glucopyranoside, quercetin 3-O-beta-D-galactopyranoside, quercetin 3-O-(2"-O-galloyl)-beta-D-glucopyranoside and quercetin 3-O-(2"-O-galloyl)-beta-D-galactopyranoside were found to be effective against free radical induced impairment of endothelium-dependent relaxation in isolated rat aorta.
Assuntos
Catequina/isolamento & purificação , Sequestradores de Radicais Livres/isolamento & purificação , Glicosídeos/isolamento & purificação , Rosales/química , Animais , Catequina/análogos & derivados , Catequina/química , Catequina/farmacologia , Endotélio Vascular/efeitos dos fármacos , Endotélio Vascular/fisiologia , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Glicosídeos/química , Glicosídeos/farmacologia , Técnicas In Vitro , Masculino , Estrutura Molecular , Relaxamento Muscular/efeitos dos fármacos , Ratos , Análise EspectralRESUMO
2,6-Dimethylocta-2,7-diene-1,6-diol 6-O-[6'-O-beta-D-apiofuranosyl]-beta-D-glucopyranoside (1) was isolated from Viscum album ssp. album.
Assuntos
Glucosídeos/química , Erva-de-Passarinho , Monoterpenos , Plantas Medicinais , Terpenos/química , Glucosídeos/isolamento & purificação , Humanos , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Plantas Medicinais/química , Terpenos/isolamento & purificaçãoRESUMO
From the aerial parts of Phlomis longifolia var. longifolia four iridoid glucosides, shanzhiside methyl ester (1), 5-deoxypulchelloside I (2), lamalbide (3), phlomiol (4) and three phenylethanoid glycosides, verbascoside (5), forsythoside B (6), leucosceptoside A (7) along with the caffeic acid ester, chlorogenic acid (8) were isolated. The structures of the isolated compounds were established by spectroscopic (UV, IR, 1D- and 2D-NMR, FABMS) and chemical evidence. The structure elucidation of the iridoid compounds 2 and 3 are discussed in detail.
Assuntos
Glucosídeos/isolamento & purificação , Lamiaceae/química , Plantas Medicinais/química , Piranos/isolamento & purificação , Cromatografia Líquida , Glucosídeos/química , Iridoides , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Piranos/química , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , TurquiaRESUMO
A new iridoid glucoside, 5beta,6beta-dihydroxyboschnaloside (1), was isolated from the aerial parts of Euphrasia pectinata. Five known iridoid glucosides, 6beta-hydroxyboschnaloside (2), aucubin, euphroside, plantarenaloside, and geniposidic acid, and two known phenylethanoid glycosides, verbascoside (= acteoside) and leucosceptoside A, were also obtained and characterized. The structure of compound 1 was established by spectroscopic evidence.
Assuntos
Glucosídeos/isolamento & purificação , Magnoliopsida/química , Piranos/isolamento & purificação , Glucosídeos/química , Iridoides , Espectroscopia de Ressonância Magnética , Piranos/químicaRESUMO
Viscum album L. has been used in the indigenous system of medicine for treatment of various diseases such as atherosclerosis and hypertension. In the literature, phenylpropan and flavonoid derivatives were suggested to play a role in the inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE) and a correlation was proposed between the in vitro inhibition of PDE and in vivo pharmacological activity. The vascular effects of the phenolic compounds and subfractions isolated from n-butanolic fraction of V. album ssp. album were studied on noradrenaline-contracted rat aortic rings. Isolated phenolic compounds (Syringin (VA-1), Coniferin (VA-9), 5, 7-dimethoxy-flavanone-4'-O-[beta-D-apiofuranosyl(1-->2)]-beta-D-gl uco pyranoside (VA-4)) produced concentration-dependent contractions in rat aortic rings. Only one compound (Kalopanaxin D (VA-15)) displayed very slight relaxant response. The weak concentration-dependent relaxing effect of the subfractions gave the idea that vasodilator activity were observed in the less polar subfractions. In addition, there was no clear correlation between the weak relaxant effects of subfractions and an inhibitory effect on cAMP-PDE.
Assuntos
Fármacos Cardiovasculares/farmacologia , Erva-de-Passarinho/química , Fenóis/farmacologia , Plantas Medicinais , 3',5'-AMP Cíclico Fosfodiesterases/antagonistas & inibidores , Agonistas alfa-Adrenérgicos/farmacologia , Animais , Aorta Torácica/efeitos dos fármacos , Fármacos Cardiovasculares/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Técnicas In Vitro , Masculino , Relaxamento Muscular/efeitos dos fármacos , Músculo Liso Vascular/efeitos dos fármacos , Norepinefrina/farmacologia , Fenóis/isolamento & purificação , Extratos Vegetais/química , RatosRESUMO
In the course of our research on the oligoglycosidic constituents of Turkish Astragalus species, we have isolated a number of cycloartane-type triterpene glycosides. The current study examines the immunostimulatory effects of nineteen of these cycloartane-type compounds using a transcription-based bioassay for Nuclear Factor kappa B (NF-kappaB) activation in a human macrophage/monocyte cell line, THP-1. All compounds were inactive at 100 microg/ml except astragaloside I which increased NF-kappaB directed luciferase expression to levels about 65% as compared with maximal stimulation by E. coli lipopolysaccharide (LPS) at 10 microg/ml. None of the compounds were active at low dosage levels (0.1 microg/ml) in combination with 50 ng/ml LPS. Astragaloside I also increased mRNA expression of the inflammatory cytokines interleukin-1beta (IL-1beta) and tumor necrosis factor-alpha (TNF-alpha) as measured using reverse transcriptase-polymerase chain reaction (RT)-PCR. Based on these results it is clear that certain structural features are required for immunostimulation of cycloartane-type triterpene glycosides.
Assuntos
Adjuvantes Imunológicos/farmacologia , Glicosídeos/farmacologia , Macrófagos/efeitos dos fármacos , Magnoliopsida/química , Triterpenos/farmacologia , Células Cultivadas , Glicosídeos/química , Humanos , Ativação de Macrófagos/efeitos dos fármacos , Macrófagos/imunologia , NF-kappa B/metabolismo , Saponinas/química , Saponinas/farmacologia , Triterpenos/químicaRESUMO
Macrophyllosaponin E, a novel cycloartane-type triterpene, has been isolated from the roots of Astragalus oleifolius. The structure elucidation of the compound was achieved by a combination of one- and two-dimensional NMR techniques [1H-1H-correlation spectroscopy (COSY), 1H-13C-heteronuclear multiple guantum correlation spectroscopy (HMQC), and 1H-13C-heteronuclear multiple-bond correlation spectroscopy (HMBC)l and high resolution electrospray ionization Fourier transformation mass spectrometry (HR-ESI-FT-MS).
Assuntos
Magnoliopsida/química , Triterpenos/isolamento & purificação , Raízes de Plantas/química , Triterpenos/químicaRESUMO
Six triterpene saponins, including two new compounds, were isolated from the fruits of Hedera helix L. (Araliaceae). The structures of the new compounds, named helixosides A and B, were established as 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, and 3-O-beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl oleanolic acid 28-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester, respectively, on the basis of chemical and spectral data.
Assuntos
Ácido Oleanólico/análogos & derivados , Plantas/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/isolamento & purificação , Anti-Inflamatórios não Esteroides/farmacologia , Bacillus cereus/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Escherichia coli/efeitos dos fármacos , Frutas/química , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Saponinas/química , Saponinas/farmacologia , Espectrofotometria Infravermelho , Staphylococcus epidermidis/efeitos dos fármacos , Triterpenos/química , Triterpenos/farmacologiaRESUMO
The absolute configuration of the title compound has been determined after its enzymatic hydrolysis to 3-hydroxy-5-phenylpentanoic acid, esterification, and identification of the enantiomerically pure methyl (3R)-hydroxy-5-phenylpentanoate by HPLC on Chiralcel(R)OD-H. For reasons of inconsistent literature data, enantioselective reductions of methyl 3-oxo-5-phenylpentanoate have been reinspected and the stereochemical outcome unequivocally confirmed by both chiroptical and HPLC retention data.
Assuntos
Glucosídeos/química , Polygonaceae/química , Cromatografia Líquida de Alta Pressão , EstereoisomerismoRESUMO
Four new bisanthraquinone glycosides, S-(+)-skyrin-6-O-beta-glucopyranoside (1), R-(-)-skyrin-6-O-beta-glucopyranoside (2), S-(+)-skyrin-6-O-beta-xylopyranoside (3) and S-(+)-skyrin-6-O-beta-alpha-arabinofuranoside (4), have been isolated from an ethanol-water (1:1, v/v) dry extract of the aerial parts of Hypericum perforatum L. The structures were elucidated by spectroscopic methods, mainly NMR and mass spectrometry. Circular dichroism was used to determine their axial stereochemistry revealing 1 and 2 to be atropisomers. 1 and 2 inhibited [125I]sauvagine binding to corticotropin releasing hormone (CRH-1) receptors.
Assuntos
Hypericum/química , Plantas Medicinais , Receptores de Hormônio Liberador da Corticotropina/antagonistas & inibidores , Acetilação , Proteínas de Anfíbios , Ligação Competitiva , Interações Medicamentosas , Espectroscopia de Ressonância Magnética , Conformação Molecular , Hormônios Peptídicos , Peptídeos/farmacologia , Receptores de Hormônio Liberador da Corticotropina/metabolismo , Vasodilatadores/farmacologiaRESUMO
Radical scavenger activities of 21 phenylethanoid glycosides, including 15 ester derivatives of caffeic, ferulic, vanillic and syringic acid as well as 6 deacyl derivatives were determined by quantifying their effects on the production of reactive oxygen species (ROS) in a luminol-enhanced chemiluminescence assay with formyl-methionyl-leucyl-phenylalanine (FMLP) stimulated human polymorphonuclear neutrophils (PMNs). All phenylethanoids acylated with phenolic acids showed strong antioxidant activity whereas the deacyl derivatives were more than 30-fold less active. Therefore, the antioxidant activity is mainly related to the number of aromatic methoxy and hydroxy groups and the structure of the acyl moiety (C6-C1 or C6-C3). In contrast, modification of the sugar chain or replacement of hydroxy groups by methoxy groups in the acyl or the phenylethanoid moiety is of minor importance. The position of the acyl moiety is without significance. Free caffeic, ferulic, vanillic and syringic acid are less active compared to the phenylethanoid derivatives. This points to the importance of dissociation and lipophilicity of these acids in a cellular test system.