RESUMO
This study aims to identify the chemical constituents from Callicarpa kwangtungensis and determine their activities. MCI, ODS, and Sephadex LH-20 chromatography and semi-preparative HPLC were employed to separate the chemical constituents. A total of 15 compounds were separated, and their structures were identified on the basis of spectroscopic analysis and comparison with the data in relevant literature. Specifically, the 15 compounds were 3-O-α-L-rhamnopyranosyl-6-O-β-D-apiofuranosyl-4-O-E-caffeoyl-D-glucopyranoside(1), 3,6-O-α-L-dirhamnopyranosyl-4-O-E-caffeoyl-D-glucopyranoside(2), β-OH-forsythoside B(3), β-OH-poliumoside(4),(+)-lyoniresinol-3α-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside(5),(+)-lyoniresinol-3α-O-β-D-glucopyranoside(6),(-)-lyoniresinol-3α-O-β-D-glucopyranoside(7), kelampayoside A(8), descaffeoylpoliumoside(9), acteoside(10), alyssonoside(11), poliumoside(12), isacteoside(13), acetyl forsythoside B(14), and forsythoside B(15). Compounds 1 and 2 were novel, and the NMR data of compounds 3 and 4 were reported here for the first time. Furthermore, the hemostatic activities of the extract and abundant ingredients(compounds 12 and 15) of C. kwangtungensis were determined with Yunnan Baiyao as the positive control and normal saline as the negative control. The extract and compounds 12 and 15 significantly shortened the tail tip bleeding time in mice.
Assuntos
Animais , Camundongos , Callicarpa , Hemostáticos , China , Glicosídeos/químicaRESUMO
Three new cucurbitane-type triterpenoid glycosides were separated from the ethyl acetate extract of Citrullus colocynthis by a variety of chromatographic techniques. According to the data of NMR, HR-ESI-MS, and/or comparison with the reported data, the three novel cucurbitane-type triterpenoid glycosides were identified as colocynthenin E(1), colocynthenin G(2), and colocynthenin H(3). The cell inflammation model was established with RAW264.7 macrophages exposed to lipopolysaccharide and then used to determine the anti-inflammatory activities of the three compounds. Compounds 2 and 3 showed mild anti-inflammatory activities with the IC_(50) of 48.21 and 40.11 μmol·L~(-1), respectively, compared with that(IC_(50)=7.57 μmol·L~(-1)) of the positive control dexamethasone.
Assuntos
Citrullus colocynthis/química , Triterpenos/química , Glicosídeos/química , Extratos Vegetais/química , Anti-Inflamatórios/farmacologiaRESUMO
Alkaloids are important active ingredients occurring in many traditional Chinese medicines, and alkaloid glycosides are one of their existence forms. The introduction of saccharide units improves the water solubility of alkaloid glycosides thus presenting better biological activity.Because of the low content in plants, alkaloid glycosides have been not comprehensively studied. In this study, ultrahigh performance liquid chromatography-quadrupole time of flight-tandem mass spectrometry(UPLC-QTOF-MS/MS) was employed to identify and analyze the alkaloid glycosides in Coptis chinensis, Phellodendron chinense, Menispermum dauricum, Sinomenium acutum, Tinospora sagittata and Stephania tetrandra. The results showed that except Tinospora sagittata, the other five herbal medicines contained alkaloid glycosides. Furthermore, the alkaloid glycosides in each herbal medicine were identified based on UV absorption spectra, quasimolecular ion peaks in MS, fragment ions information in the MS/MS, and previous literature reports. A total of 42 alkaloid glycosides were identified. More alkaloid glycosides were identified in C. chinensis and Menispermum dauricum, and eleven in C. chinensis were potential new compounds. Furthermore, the alkaloid glycosides in the water extract of C. chinensis were coarsely se-parated by macroporous adsorption resin, purified by column chromatography with D151 cation exchange resin, ODS and MCI, combined with semi-preparative high performance liquid chromatography. Two new alkaloid glycosides were obtained, and their structures were identified by mass spectrometry and NMR data as(S)-7-hydroxy-1-(p-hydroxybenzyl)-2,2-N,N-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-O-β-D-glucopyranoside and(S)-N-methyltetrahydropalmatubine-9-O-β-D-glucopyranoside, respectively. This study is of great significance for enriching the information about the chemical composition and the in-depth development of C. chinensis. Meanwhile, it can provide a reference for rapid identification and isolation of alkaloid glycosides from other Chinese herbal medicines.
Assuntos
Glicosídeos/química , Medicina Tradicional Chinesa , Espectrometria de Massas em Tandem/métodos , Coptis chinensis , Medicamentos de Ervas Chinesas/química , Alcaloides/análise , Extratos Vegetais/química , Antineoplásicos , Plantas Medicinais/química , Água , Cromatografia Líquida de Alta Pressão/métodos , Coptis/químicaRESUMO
The tandem mass spectrum of apigenin-6,8-C-di-glucoside( 1) and apigenin-6-C-glucose-8-C-rhamnoside( 2) were obtained by high resolution electrospray ionization mass spectrometry( HR-ESI-MS/MS) in both positive and negative ion modes. The elemental composition of each ion was determined according to its accurate mass-to-charge,hence,the fragmentation pathways of each compound were proposed in both negative and positive ion modes. Comprehensive analysis of each ion and its proposed fragmentation pathways of the two compounds was initially conducted in both negative and positive ion mode HR-ESI-MS/MS to explore the diagnostic ions for flavone-6,8-C-di-glycosides and the characteristic ions for each compound and their cleavage rules. The results showed that a family of fragmentation ions with m/z 353,325,311,297 in ESI(-)-MS and m/z 355,325,307,295 in ESI( +)-MS could be the diagnostic ions of flavone-6,8-C-di-glycoside,and characteristic neutral loss could be assigned to glycosyl substitution,for example,neutral losses of C_4H_8O_4( 120),C_3H_6O_3( 90),C_2H_4O_2( 60) for glucoside substitution while neutral losses of C_4H_8O_3(104),C_3H_6O_2( 74),C_2H_4O( 44) for rhamnoside substitution. Furthermore,only one H_2O loss from mother ion( [M-H]-) was observed for 1 & 2 in ESI(-)-MS while five to six H2 O loss from mother ion( [M+H]+) was observed for 1 & 2 in ESI( +)-MS to produce a family of ions by subsequent loss of H_2O,which could be applied for glucosyl difference. The flavone-6,8-C-di-glycosides in both ESI( +)-MS and ESI(-)-MS showed the cleavage similarity at sugar substitutions. However,there were much more differences by the fragmentation pathways and neutral losses between ESI( +)-MS and ESI(-)-MS as following,hyperconjugation ions by subsequent loss of H_2O from precursor ions of flavone-6,8-C-di-glycosides in ESI( +)-MS were not observed in ESI(-)-MS; the subsequent neutral loss of CH_2O in ESI( +)-MS were rarely observed in ESI(-)-MS; the loss of CO only happen at C-ring of flavone ESI( +)-MS other than glycosyl position in ESI(-)-MS; the C4-chain neutral loss of flavone-6,8-C-di-glycosides happened at 8-C-glycosyl position other than at 6-C-glycosyl position. The above cleavage rules and diagnostic ions of ESI( +)-MS were successfully applied for the structure identification of 4 flavone-6 C,8 C-diglycosides from the stem extract of Dendrobium officinale as vicenin Ⅱ,vicenin Ⅰ,isoschaftoside,schaftoside as well as one flavone-O-glysoside named rutin,which were supported by ESI(-)-MS data as well.
Assuntos
Flavonas/química , Glicosídeos/química , Íons , Espectrometria de Massas por Ionização por Electrospray , Espectrometria de Massas em TandemRESUMO
ABSTRACT The aim of this study was to determine the composition and antioxidant potential of leaves of a new variety of Stevia rebaudiana (Stevia UEM-13). Stevia leaves of UEM-13 contain rebaudioside A as the main glycoside, while most wild Stevia plants contain stevioside. Furthermore can be multiplied by seed, which reduces the cost of plant culture techniques as other clonal varieties are multiplied by buds, requiring sophisticated and expensive seedling production systems. Ethanol and methanol were used in the extraction to determine the bioactive compounds. The methanolic extract was fractionated sequentially with hexane, chloroform, ethyl acetate and isobutanol, and the highest concentration of phenolic compounds and flavonoids was obtained in the ethyl acetate fraction (524.20 mg galic acid equivalent/g; 380.62 µg quercetin equivalent/g). The glycoside content varied greatly among the fractions (0.5% - 65.3%). Higher antioxidant potential was found in the methanol extract and the ethyl acetate fraction with 93.5% and 97.32%, respectively. In addition to being an excellent source for obtaining of extracts rich in glycoside, this new variety can also be used as raw material for the production of extracts or fractions with a significant amount of antioxidant activity and potential to be used as additives in food.
Assuntos
Fenóis/química , Extratos Vegetais/química , Folhas de Planta/química , Stevia/química , Glicosídeos/química , Antioxidantes/química , Fenóis/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Stevia/classificação , Glicosídeos/isolamento & purificação , Antioxidantes/isolamento & purificaçãoRESUMO
ABSTRACT This study aims to identify special metabolites in polar extracts from Urochloa humidicola (synonym Brachiaria humidicola) that have allelopathic effects and induce secondary photosensitization in ruminants. The compounds were isolated and identified via chromatographic and spectroscopic techniques. The compounds 4-hydroxy-3-methoxy-benzoic acid, trans-4-hydroxycinnamic acid, and p-hydroxy-benzoic acid; the flavonols isorhamnetin-3-O-β-d-glucopyranoside and methyl quercetin-3-O-β-d-glucuronate; and kaempferitrin, quercetin-3-O-α-l-rhamnopyranoside, and tricin were identified in the extract from the leaves of Urochloa humidicola. Two furostanic saponins, namely, dioscin and 3-O-α-l-rhamnopyranosyl-(1-4)-[α-l-rhamnopyranosyl-(1-2)]-β-d-glucopyranosyl-penogenin, as well as catechin-7-O-β-d-glucopyranoside were identified in the methanolic extract obtained from the roots of this plant. This species features a range of metabolites that may be toxic for animals if used in food and may interfere with the growth medium, thereby inhibiting the development of other species.
Assuntos
Flavonoides/isolamento & purificação , Extratos Vegetais/química , Brachiaria/química , Parabenos/isolamento & purificação , Parabenos/química , Saponinas/química , Ácido Vanílico/química , Flavonoides/química , Crotonatos/isolamento & purificação , Crotonatos/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Cromatografia em Camada Fina , Glicosídeos/isolamento & purificação , Glicosídeos/químicaRESUMO
The polar hydroethanolic extract from Selaginella sellowii(SSPHE) has been previously proven active on intracellular amastigotes (in vitro test) and now was tested on hamsters infected with Leishmania (Leishmania) amazonensis (in vivo test). SSPHE suppressed a 100% of the parasite load in the infection site and draining lymph nodes at an intralesional dose of 50 mg/kg/day × 5, which was similar to the results observed in hamsters treated with N-methylglucamine antimonate (Sb) (28 mg/Kg/day × 5). When orally administered, SSPHE (50 mg/kg/day × 20) suppressed 99.2% of the parasite load in infected footpads, while Sb suppressed 98.5%. SSPHE also enhanced the release of nitric oxide through the intralesional route in comparison to Sb. The chemical fingerprint of SSPHE by high-performance liquid chromatography with diode-array detection and tandem mass spectrometry showed the presence of biflavonoids and high molecular weight phenylpropanoid glycosides. These compounds may have a synergistic action in vivo. Histopathological study revealed that the intralesional treatment with SSPHE induced an intense inflammatory infiltrate, composed mainly of mononuclear cells. The present findings reinforce the potential of this natural product as a source of future drug candidates for American cutaneous leishmaniasis.
Assuntos
Animais , Cricetinae , Masculino , Antiprotozoários/farmacologia , Leishmania/efeitos dos fármacos , Extratos Vegetais/química , Selaginellaceae/química , Administração Oral , Antiprotozoários/isolamento & purificação , Biflavonoides/análise , Cromatografia Líquida de Alta Pressão , Drenagem , Pé/parasitologia , Glicosídeos/química , Infusões Intralesionais , Leucócitos Mononucleares/parasitologia , Macrófagos/parasitologia , Meglumina/administração & dosagem , Óxido Nítrico/análise , Compostos Organometálicos/administração & dosagem , Carga Parasitária , Extratos Vegetais/administração & dosagem , Solventes , Espectrometria de Massas em TandemRESUMO
O presente estudo teve por objetivo estimar a presença de cães e gatos em domicílios da zona urbana do município e avaliar a guarda responsável e seus fatores associados. Foi realizado um estudo transversal, de base populacional com processo de amostragem em múltiplos estágios e com os setores censitários do censo demográfico do ano de 2010, realizado pelo IBGE, utilizados como conglomerados. A unidade em estudo foi o domicílio. O desfecho foi a guarda responsável, definida por um escore que levou em consideração as seguintes variáveis: esterilização, vacinação antirrábica, consulta médica veterinária, controle de endoparasitas, acesso dos animais às áreas públicas e o recolhimento das fezes nestes locais e controle de ectoparasitas. Entre os 1.558 domicílios investigados, 58,9% possuíam animais de estimação (cão e/ou gato). O estudo revela que o escore de posse responsável aumenta com a escolaridade do chefe da família e é maior entre os moradores de apartamento. A maioria dos domicílios investigados atendeu apenas a metade dos critérios. Os resultados deste estudo apontam para a necessidade de políticas públicas que orientem a população sobre a guarda responsável e que ofertem serviços de imunizações e esterilização para os animais.
The study sought to estimate the presence of cats and dogs in households in the urban area of the city and assess responsible guardianship and associated factors. A population-based, cross-sectional study was conducted using the multi-stage sampling process and the census sectors of the demographic census of the year 2010 carried out by IBGE were used as conglomerates. The unit under study was the household. The outcome was responsible guardianship, defined by a score that took into account the following variables: sterilization, anti-rabies vaccination, veterinary medical consultation, control of endoparasites, access of animals to public areas, control of ectoparasites and the collection of feces of animals in public areas. Of the 1,558 households investigated, 58.9% had pets (cat or dog). The study reveals that the score of responsible guardianship increases with the education level of the head of the household and is highest among apartment dwellers. The majority of the households investigated met only half of the criteria. The results of this study point to the need for public policies that instruct the population on responsible guardianship, and that offer immunizations and sterilization services for animals.
Assuntos
Glicosídeos/química , Mesilatos/química , Carboidratos/química , Eletroquímica , Galactose/química , Manose/química , Metanol/química , Ressonância Magnética Nuclear Biomolecular , Oxirredução , Compostos de Sulfidrila/químicaRESUMO
The manner by which effects of simultaneous mutations combine to change enzymatic activity is not easily predictable because these effects are not always additive in a linear manner. Hence, the characterization of the effects of simultaneous mutations of amino acid residues that bind the substrate can make a significant contribution to the understanding of the substrate specificity of enzymes. In the â-glycosidase from Spodoptera frugiperda (Sfâgly), both residues Q39 and E451 interact with the substrate and this is essential for defining substrate specificity. Double mutants of Sfâgly (A451E39, S451E39 and S451N39) were prepared by site-directed mutagenesis, expressed in bacteria and purified using affinity chromatography. These enzymes were characterized using p-nitrophenyl â-galactoside and p-nitrophenyl â-fucoside as substrates. The k cat/Km ratio for single and double mutants of Sfâgly containing site-directed mutations at positions Q39 and E451 was used to demonstrate that the effect on the free energy of ES (enzyme-transition state complex) of the double mutations (∆∆Gxy) is not the sum of the effects resulting from the single mutations (∆∆Gx and ∆∆Gy). This difference in ∆∆G indicates that the effects of the single mutations partially overlap. Hence, this common effect counts only once in ∆∆Gxy. Crystallographic data on â-glycosidases reveal the presence of a bidentate hydrogen bond involving residues Q39 and E451 and the same hydroxyl group of the substrate. Therefore, both thermodynamic and crystallographic data suggest that residues Q39 and E451 exert a mutual influence on their respective interactions with the substrate.
Assuntos
Animais , Spodoptera/enzimologia , beta-Glucosidase/química , beta-Glucosidase/metabolismo , Sequência de Aminoácidos , Substituição de Aminoácidos , Cromatografia Líquida , Glicosídeo Hidrolases/química , Glicosídeo Hidrolases/metabolismo , Glicosídeos/química , Glicosídeos/metabolismo , Dados de Sequência Molecular , Especificidade por Substrato , beta-Glucosidase/genéticaRESUMO
Convicine glycoside is hydrolyzed by intestinal microflora to highly reactive free- radical generation compound isouramil. Isouramil has been strongly implicated as the causative agent of favism. Biological studies were conducted to determine some physiological and biochemical properties of convicine isolated from faba beans. The results obtained revealed that the tested oral dose of convicine [2 mg/100g b.wt.] showed significant increase in W.B.Cs, while it caused significant decrease in serum glucose. The analysis of serum alkaline phosphatase, calcium and phosphate showed that convicine causes significant increases. The results also showed that there were a significant decrease in the level of serum cholesterol, triglycerides and LDL. There were, also significant decreases in serum and tissue malondialdhyde [MDA]. While a significant increase in blood and tissue glutathione peroxidase [GPx] activity was found. On the other hand, there was, significant increase in plasma nitric oxide level. From the results we can conclude that convicine had certain beneficial effects as a good antioxidant agent
Assuntos
Animais de Laboratório , Glicosídeos/fisiologia , Glicosídeos/química , Sementes , Ratos Sprague-Dawley , Contagem de Leucócitos , Fosfatase Alcalina , Cálcio , Glutationa Peroxidase , Malondialdeído , Óxido Nítrico , AntioxidantesRESUMO
Picrorhiza kurroa (Pk), a known hepatoprotective plant, was studied in experimental and clinical situtations. The standardization of active principles--Picroside 1 and 2 was done with High Performance Liquid Chromatography. Picroside 1 ranged from 2.72 to 2.88 mg/capsule and picroside 2 from 5.50 to 6.00 mg/capsule. In the galactosamine-induced liver injury in rats, Pk at a dose of 200 mg/kg p.o. showed a significant reduction (p < 0.05) in liver lipid content, GOT and GPT. In a randomised, double-blind placebo controlled trial in patients diagnosed to have acute viral hepatitis (HBsAg negative), Pk root powder 375 mg three times a day was given for 2 weeks (n = 15) or a matching placebo (n = 18) was given. Difference in values of bilirubin, SGOT and SGPT was significant between placebo and Pk groups. The time in days required for total serum bilirubin to drop to average value of 2.5 mg% was 75.9 days in placebo as against 27.44 days in Pk group. The present study has shown a biological plausability of efficacy of Pk as supported by clinical trial in viral hepatitis, hepatoprotection in animal model and an approach for standardizing extracts based on picroside content.
Assuntos
Doença Aguda , Alanina Transaminase/sangue , Animais , Aspartato Aminotransferases/sangue , Bilirrubina/sangue , Cinamatos/química , Modelos Animais de Doenças , Método Duplo-Cego , Avaliação Pré-Clínica de Medicamentos , Glicosídeos/química , Hepatite Viral Humana/tratamento farmacológico , Humanos , Hepatopatias/tratamento farmacológico , Masculino , Ayurveda , Distribuição Aleatória , Ratos , Ácido Vanílico/químicaRESUMO
After intraperitoneal administration of gradual aqueous doses obtained from Stachytarpheta jamaicensis leaves, the following effects were observed in rats: a reduction of motor activity and the alarm reaction, ataxia, sedation, analgesia, anesthesia, ptosis, piloerection, head tremors and a significant reduction of body temperature of about 8.4 degrees C. Robichaud's sign was present, probably due to some muscular relaxation. There were appreciable changes on respiration, with increment on amplitudes and reduction on the frequency, followed by apnea and the death of the animals, probably due to asphysia. Iridoid polamiide and the phenylpropanoid glycoside, verbascoside, were identified from the same extracts. Both metabolites have been indicated with potential pharmaceuticals properties in accord with ethnobotanical value Tributed to this plant