RESUMO
Carrageenans are sulfated galactans found in certain red seaweeds with proven biological activities. In this work, we have prepared purified native and degraded κ-, ι-; and λ-carrageenans, including the disaccharides (carrabioses) and disaccharide-alditols (carrabiitols) from seaweed extracts as potential antitumor compounds and identified the active principle of the cytotoxic and potential antitumor properties of these compounds. Both κ and ι-carrageenan, as well as carrageenan oligosaccharides showed cytotoxic effect over LM2 tumor cells. Characterized disaccharides (carrabioses) and the reduced product carrabiitols, were also tested. Only carrabioses were cytotoxic, and among them, κ-carrabiose was the most effective, showing high cytotoxic properties, killing the cells through an apoptotic pathway. In addition, the cells surviving treatment with κ-carrabiose, showed a decreased metastatic ability in vitro, together with a decreased cell-cell and cell-matrix interactions, thus suggesting possible antitumor potential. Overall, our results indicate that most cytotoxic compounds derived from carrageenans have lower molecular weights and sulfate content. Potential applications of the results emerging from the present work include the use of disaccharide units such as carrabioses coupled to antineoplasics in order to improve its cytotoxicity and antimetastatic properties, and the use of ι-carrageenan as adjuvant or carrier in anticancer treatments.
Assuntos
Antineoplásicos/farmacologia , Produtos Biológicos/farmacologia , Carragenina/química , Dissacarídeos/farmacologia , Animais , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Camundongos , Estrutura MolecularRESUMO
Alternanthera maritima are used in Brazilian popular medicine for the treatment of inflammatory and infectious diseases. Species of Alternanthera have demonstrated biological activities in previous scientific studies. The aim of this study was to determine whether the ethanol extract of the aerial parts of A. maritima (EEAM) and the isolated compound 2â³-O-α-L-rhamnopyranosyl-vitexin inhibit mechanical hyperalgesia and parameters of inflammation in mice. The oral administration of EEAM significantly inhibited carrageenan (Cg)-induced paw edema and reduced leukocyte migration into the pleural cavity. 2â³-O-α-L-rhamnopyranosylvitexin significantly inhibited paw edema and reduced both leukocyte migration and the leakage of protein into the pleural cavity. Both EEAM and 2â³-O-α-L-rhamnopyranosylvitexin significantly prevented the Cg-induced hyperalgesia. Local administration of 2â³-O-α-L-rhamnopyranosylvitexin significantly prevented the Cg- and tumor necrosis factor (TNF)-induced hyperalgesia. In conclusion, this study demonstrated that EEAM is an anti-inflammatory and anti-hyperalgesic agent, and the results suggested that 2â³-O-α-L-rhamnopyranosylvitexin is responsible for the effects of EEAM and the mechanism involves the TNF pathway.
Assuntos
Amaranthaceae/química , Analgésicos/farmacologia , Anti-Inflamatórios/farmacologia , Apigenina/farmacologia , Dissacarídeos/farmacologia , Edema/prevenção & controle , Flavonas/farmacologia , Hiperalgesia/prevenção & controle , Extratos Vegetais/farmacologia , Analgésicos/isolamento & purificação , Animais , Anti-Inflamatórios/isolamento & purificação , Apigenina/isolamento & purificação , Carragenina , Quimiotaxia de Leucócito/efeitos dos fármacos , Dissacarídeos/isolamento & purificação , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Edema/induzido quimicamente , Edema/imunologia , Edema/metabolismo , Feminino , Flavonas/isolamento & purificação , Hiperalgesia/induzido quimicamente , Hiperalgesia/fisiopatologia , Levodopa , Masculino , Camundongos , Limiar da Dor/efeitos dos fármacos , Fitoterapia , Componentes Aéreos da Planta , Extratos Vegetais/isolamento & purificação , Plantas Medicinais , Pleurisia/induzido quimicamente , Pleurisia/imunologia , Pleurisia/metabolismo , Pleurisia/prevenção & controle , Fatores de Tempo , Fator de Necrose Tumoral alfaRESUMO
Saccharides and chitooligosaccharides can be separated in electrophoretic conditions by raising the pH of the medium, which renders the corresponding alcoholate forms. These anionic species can be separated and detected with capacitively coupled contactless conductivity detection as negative peaks because of their low mobilities when compared to the hydroxyl mobility, which is the main co-ion in the background electrolyte. Three methods for different matrixes are presented in this chapter.
Assuntos
Dissacarídeos/isolamento & purificação , Monossacarídeos/isolamento & purificação , Cromatografia por Troca Iônica , Café/química , Dissacarídeos/química , Condutividade Elétrica , Eletrólitos/química , Eletroforese Capilar/métodos , Eletroforese Capilar/normas , Hidrólise , Monossacarídeos/química , Oligossacarídeos/química , Oligossacarídeos/isolamento & purificação , Padrões de ReferênciaRESUMO
Eleven known triterpenes (alpha-amyrin, beta-amyrin, lupeol, and their respective acetates, 3-O-acetyl derivatives of betulinic, oleanolic, and ursolic acids, cycloartenol, and tirucall-7,24-dienol), two new flavonols presenting an uncommon interglycosidic O-(1-->3) linkage (kaempferol 3-O-alpha-L-arabinofuranosyl(1-->3)-alpha-L-rhamnoside and quercetin 3-O-alpha-L-arabinofuranosyl-(1-->3)-alpha-L-rhamnoside), beta-sitosterol, stigmasterol, quercetin, and gallic acid were isolated from the Amazonian medicinal mistletoe, Cladocolea micrantha Kuijt (Loranthaceae). Their structures were established by spectral methods and eventual chromatographic comparisons. The quercetin derivative was not cytotoxic to MV3 human melanoma cells, but was able, when administered at 1 microg/mL, to promote a twofold inhibition of the migration of the cells through the transwell system when compared with paclitaxel at 5 microM.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Dissacarídeos/farmacologia , Flavonoides/química , Loranthaceae/química , Melanoma/tratamento farmacológico , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Movimento Celular/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Espectroscopia de Ressonância Magnética , Folhas de Planta/química , Caules de Planta/química , Quercetina/química , Quercetina/isolamento & purificação , Solventes , Espectrofotometria Infravermelho , Espectrofotometria UltravioletaRESUMO
Chemical investigation of the n-hexane and EtOAc fractions of the ethanolic extract from Styrax pohlii (Styracaceae) aerial parts resulted in the isolation of the benzofuran nor-neolignan derivatives egonol (1), homoegonol (2), homoegonol gentiobioside (3), homoegonol glucoside (4) and egonol gentiobioside (5). This is the first report of compounds 1-5 in S. pohlii. Compounds 1-5, the acetyl derivatives 1 a and 2 a, the ethanolic extract (EE), the n-hexane fraction (HF) and EtOAc fraction (EF) were tested for their inhibitory activities against COX-1 and COX-2. The results showed that EE, HF, EF and compounds 1-5 and 1 a-2 a shown weak to moderate inhibition of COX-1 and COX-2. Among the assayed nor-neolignans, 4 gave a COX-1 inhibition of 35.7% at 30 µM. Compound 5 displayed a COX-2 inhibition of 19.7% at 30 µM.
Assuntos
Inibidores de Ciclo-Oxigenase/farmacologia , Lignanas/farmacologia , Extratos Vegetais/farmacologia , Styrax/química , Benzofuranos/isolamento & purificação , Benzofuranos/farmacologia , Brasil , Inibidores de Ciclo-Oxigenase/química , Inibidores de Ciclo-Oxigenase/isolamento & purificação , Dissacarídeos/isolamento & purificação , Dissacarídeos/farmacologia , Etanol , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Hexanos , Lignanas/química , Lignanas/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/isolamento & purificaçãoRESUMO
The use of CO(2) as a massive and polarizable drift gas is shown to greatly improve peak-to-peak resolution (R(p-p) ), as compared with N(2) , for the separation of disaccharides in a Synapt G2 traveling wave ion mobility cell. Near or baseline R(p-p) was achieved for three pairs of sodiated molecules of disaccharide isomers, that is, cellobiose and sucrose (R(p-p) = 0.76), maltose and sucrose (R(p-p) = 1.04), and maltose and lactose (R(p-p) = 0.74). Ion mobility mass spectrometry using CO(2) as the drift gas offers therefore an attractive alternative for fast and efficient separation of isomeric disaccharides.
Assuntos
Dióxido de Carbono/química , Dissacarídeos/isolamento & purificação , Espectrometria de Massas/métodos , Dissacarídeos/análise , Dissacarídeos/químicaRESUMO
In this work, high performance thin layer liquid chromatography (HTPLC) is applied to the determination of sugars in fast pyrolysis liquids (bio-oil) and fractions thereof. The proposed procedure allows the separation of anhydrosugar levoglucosan and cellobiosan, as well as glucose, arabinose, xylose and cellobiose. Pre-treatment and derivatization of samples are not necessary and volatile compounds present in bio-oil do not interfere with sugar analysis. The detrimental effect of the complex bio-oil matrix on columns and detector lifetime is avoided by using disposable HTPLC plates. Prior screening of glucose, present especially in aged and aqueous bio-oil fractions, is required to quantify cellobiosan without interference. Concentrations of levoglucosan and cellobiosan in bio-oil samples obtained from Pinus radiata sawdust were ranged between 1.27-2.26% and 0.98-1.96% respectively, while a bio-oil sample obtained from native wood contained a higher levoglucosan concentration.
Assuntos
Biocombustíveis/análise , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia em Camada Fina/métodos , Dissacarídeos/análise , Glucose/análogos & derivados , Dissacarídeos/isolamento & purificação , Glucose/análise , Glucose/isolamento & purificação , Temperatura Alta , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Madeira/químicaRESUMO
ETHNOPHARMACOLOGICAL RELEVANCE: The beverages of Hibiscus sabdariffa calyces are widely used in Mexico as diuretic, for treating gastrointestinal disorders, liver diseases, fever, hypercholesterolemia and hypertension. Different works have demonstrated that Hibiscus sabdariffa extracts reduce blood pressure in humans, and recently, we demonstrated that this effect is due to angiotensin converting enzyme (ACE) inhibitor activity. AIM OF THE STUDY: The aim of the current study was to isolate and characterizer the constituents responsible of the ACE activity of the aqueous extract of Hibiscus sabdariffa. MATERIALS AND METHODS: Bioassay-guided fractionation of the aqueous extract of dried calyces of Hibiscus sabdariffa using preparative reversed-phase HPLC, and the in vitro ACE Inhibition assay, as biological monitor model, were used for the isolation. The isolated compounds were characterized by spectroscopic methods. RESULTS: The anthocyanins delphinidin-3-O-sambubioside (1) and cyanidin-3-O-sambubioside (2) were isolated by bioassay-guided purification. These compounds showed IC(50) values (84.5 and 68.4 microg/mL, respectively), which are similar to those obtained by related flavonoid glycosides. Kinetic determinations suggested that these compounds inhibit the enzyme activity by competing with the substrate for the active site. CONCLUSIONS: The competitive ACE inhibitor activity of the anthocyanins 1 and 2 is reported for the first time. This activity is in good agreement with the folk medicinal use of Hibiscus sabdariffa calyces as antihypertensive.
Assuntos
Inibidores da Enzima Conversora de Angiotensina/farmacologia , Antocianinas/farmacologia , Dissacarídeos/farmacologia , Inibidores Enzimáticos/farmacologia , Hibiscus/química , Animais , Antocianinas/química , Antocianinas/isolamento & purificação , Ligação Competitiva , Cromatografia Líquida de Alta Pressão , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Flores/química , Cinética , Pulmão/enzimologia , Medicina Tradicional , México , Peptidil Dipeptidase A/metabolismo , Fitoterapia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Coelhos , Análise EspectralRESUMO
Asthma is a chronic respiratory disease characterized by airway inflammation and airway hyperresponsiveness (AHR). One strategy to treat allergic diseases is the development of new drugs. Flavonoids are compounds derived from plants and are known to have antiallergic, anti-inflammatory, and antioxidant properties. To investigate whether the flavonoid kaempferol glycoside 3-O-[beta-d-glycopiranosil-(1-->6)-alpha-l-ramnopiranosil]-7-O-alpha-l-ramnopiranosil-kaempferol (GRRK) would be capable of modulating allergic airway disease (AAD) either as a preventive (GRRK P) or curative (GRRK C) treatment in an experimental model of asthma. At weekly intervals, BALB/c mice were subcutaneously (sc) sensitized twice with ovalbumin (OVA)/alum and challenged twice with OVA administered intranasally. To evaluate any preventive effect, GRRK was administered 1h (hour) before each OVA-sensitization and challenge, while to analyze the curative effect, mice were first sensitized with OVA, followed by GRRK given at day 18 through 21. The onset of AAD was evaluated 24h after the last OVA challenge. Both treatments resulted in a dose-dependent reduction in total leukocyte and eosinophil counts in the bronchoalveolar lavage fluid (BAL). GRRK also decreased CD4(+), B220(+), MHC class II and CD40 molecule expressions in BAL cells. Histology and lung mechanic showed that GRRK suppressed mucus production and ameliorated the AHR induced by OVA challenge. Furthermore, GRRK impaired Th2 cytokine production (IL-5 and IL-13) and did not induce a Th1 pattern of inflammation. These findings demonstrate that GRRK treatment before or after established allergic lung disease down-regulates key asthmatic features. Therefore, GRRK has a potential clinical use for the treatment of allergic asthma.
Assuntos
Asma/tratamento farmacológico , Dissacarídeos/administração & dosagem , Eosinófilos/efeitos dos fármacos , Glicosídeos/administração & dosagem , Quempferóis/administração & dosagem , Leucócitos/efeitos dos fármacos , Pulmão/efeitos dos fármacos , Animais , Antígenos CD/biossíntese , Antígenos CD/genética , Líquido da Lavagem Broncoalveolar/citologia , Contagem de Células , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Eosinófilos/patologia , Feminino , Glicosídeos/química , Glicosídeos/isolamento & purificação , Antígenos de Histocompatibilidade Classe II/biossíntese , Antígenos de Histocompatibilidade Classe II/genética , Interleucina-13/metabolismo , Interleucina-5/metabolismo , Quempferóis/química , Quempferóis/isolamento & purificação , Leucócitos/patologia , Pulmão/imunologia , Pulmão/metabolismo , Pulmão/patologia , Camundongos , Camundongos Endogâmicos BALB C , Muco/metabolismo , Ovalbumina/imunologia , Células Th2/imunologiaRESUMO
There has been a growing interest in hypoglycemic agents from natural products, particularly those derived from plants. Flavonoids are naturally occurring phenolic compounds with a broad range of biological activities and the beneficial effects of flavonoids have been studied in relation to diabetes mellitus, either through their capacity to avoid glucose absorption or to improve glucose tolerance. The purpose of this study was to investigate the mechanism of action of the stimulatory effect of apigenin-6-C-(2''-O-alpha-L-rhamnopyranosyl)-beta-L-fucopyranoside (1), isolated from Averrhoa carambola L. (Oxalidaceae) leaves, on (14)C-glucose uptake. This compound (1) was found to have an acute effect on blood glucose lowering in diabetic rats and stimulated glucose-induced insulin secretion after oral treatment in hyperglycemic rats. A significant stimulatory effect of compound 1 on (14)C-glucose uptake was observed at 50 and 100 microM. The effect of compound 1 on glucose uptake was completely nullified by wortmannin, an inhibitor of phosphatidylinositol 3-kinase (PI3K), RO318220, an inhibitor of protein kinase C (PKC), PD98059, a specific inhibitor of mitogen-activated protein kinase (MEK), cycloheximide, an inhibitor of protein synthesis, and colchicine, a microtubule-depolymerizing agent. Compound 1 (100 microM) and insulin (10 nM) did not show any synergistic effect on glucose uptake. These results suggest that the flavonoid may have a dual target of action, as an insulin-secretagogue and also as an insulin-mimetic agent.
Assuntos
Glicemia/efeitos dos fármacos , Dissacarídeos/farmacologia , Flavonas/farmacologia , Glucose/metabolismo , Aloxano/administração & dosagem , Androstadienos/farmacologia , Animais , Transporte Biológico/efeitos dos fármacos , Glicemia/metabolismo , Radioisótopos de Carbono , Colchicina/farmacologia , Cicloeximida/farmacologia , Diabetes Mellitus Experimental/tratamento farmacológico , Diabetes Mellitus Experimental/metabolismo , Dissacarídeos/química , Dissacarídeos/isolamento & purificação , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Flavonas/química , Flavonas/isolamento & purificação , Flavonoides/farmacologia , Hiperglicemia/tratamento farmacológico , Hiperglicemia/metabolismo , Indóis/farmacologia , Insulina/sangue , Insulina/metabolismo , Secreção de Insulina , Magnoliopsida/química , Masculino , Músculo Esquelético/química , Folhas de Planta/química , Ratos , Ratos Wistar , Distribuição Tecidual , WortmaninaRESUMO
The paper deals with the separation and identification of a flavonoid glycoside from the petals of Lilium candidum L. and the antioxidative properties of the ethanolic extract of the flowers and selected compounds isolated from this species. The isolated flavonoid glycoside was identified as isorhamnetin-3-O-rutinoside by acid hydrolysis, TLC comparison with authentic samples, and UV and mass spectra. Isorhamnetin rutinoside was isolated from Lilium candidum L. for the first time. The antioxidative activity of the ethanolic extract of the flowers and some isolated compounds were determined using DPPH assays.
Assuntos
Antioxidantes/isolamento & purificação , Flavonoides/isolamento & purificação , Lilium/química , Extratos Vegetais/química , Dissacarídeos/isolamento & purificação , Flores/químicaRESUMO
Benzhydrylamine-resin (BHAR), a copolymer of styrene-divinylbenzene containing phenylmethylamine groups, used as solid support for peptide synthesis, was examined regarding physicochemical and anion exchanger chromatographic properties. The greater the ionic strength of the medium the poorer the solvation of beads. This effect is less pronounced the higher the amino group content of BHAR. The BHAR chromatographic behavior was compared with commercial cationic resins in columns of constant cation binding capacity. Three negatively charged heparan sulfate disaccharides were successfully purified in a 2.4 mmol/g BHAR that showed as good or better anion exchange performance than classical tertiary or quaternary amino group-containing resins. The BHAR chromatographic resin exclusion limit was estimated to be 30 kDa based on purification experiments of heparins of different molecular weight.
Assuntos
Resinas de Troca Aniônica/química , Compostos Benzidrílicos/química , DEAE-Dextrano/análogos & derivados , Aminas/química , Cromatografia por Troca Iônica/métodos , DEAE-Dextrano/química , Dissacarídeos/isolamento & purificação , Heparina/análogos & derivados , Peso Molecular , Concentração Osmolar , Solventes/químicaRESUMO
The water-soluble acid agaran isolated from Acanthophora spicifera (Rhodophyta) was submitted to alkaline treatment for the complete cyclization of alpha-L-Galp 6-sulfate to 3,6-An-alpha-L-Galp units. The modified agaran was then partially depolymerized using partial reductive hydrolysis. The resulting oligosaccharide mixture was fractionated by adsorption and ion-exchange chromatography. Fractions were purified by gel-filtration chromatography and studied by ESIMS and NMR spectroscopy, including 1D 1H, 13C, DEPT and 2D 1H, 1H COSY, TOCSY and 1H, 13C HMQC procedures. The following neutral, pyruvylated, sulfated and sulfated/pyruvylated disaccharide alditols were obtained: beta-D-Galp-(1-->4)-3,6-An-L-GalOH; 4,6-O-(1-carboxyethylidene)-beta-D-Galp-(1-->4)-3,6-An-L-GalOH; beta-D-Galp 2-sulfate-(1-->4)-3,6-An-L-GalOH and 4,6-O-(1-carboxyethylidene)-beta-D-Galp 2-sulfate-(1-->4)-3,6-An-L-GalOH.
Assuntos
Dissacarídeos/isolamento & purificação , Galactanos/química , Galactose/análogos & derivados , Rodófitas/química , Álcoois Açúcares/isolamento & purificação , Cromatografia , Ciclização , Dissacarídeos/análise , Galactanos/análise , Hidrólise , Ressonância Magnética Nuclear Biomolecular , Oligossacarídeos/análise , Oligossacarídeos/isolamento & purificação , Piruvatos , Alga Marinha/química , Espectrometria de Massas por Ionização por Electrospray , Álcoois Açúcares/análise , Ésteres do Ácido SulfúricoRESUMO
The 3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside of ethyl 3-hydroxyoctanoate and the diastereomeric 3-O-alpha-L-arabinopyranosyl-(1-->6)-beta-D-glucopyranosides of (3R) and (3S)-butyl 3-hydroxybutanoate, respectively, were isolated by chromatographic methods from fruits of cape gooseberry (Physalis peruviana) harvested in Colombia. Their structures were identified by ESI-MS/MS and NMR spectroscopy. The three glycoconjugates can be considered as immediate precursors of ethyl 3-hydroxyoctanoate and butyl 3-hydroxybutanoate, which are important aroma volatiles found in the fruit.
Assuntos
Dissacarídeos/química , Frutas/química , Solanaceae/química , Dissacarídeos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura MolecularRESUMO
A new glycosylated furanocoumarin, alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl-bergaptol (1), has been isolated from Dorstenia contrajerva together with three known furanocoumarins, catechin and epicatechin. Their structures were established using high field 2D NMR techniques.
Assuntos
Cumarínicos/isolamento & purificação , Dissacarídeos/isolamento & purificação , Flavonoides/isolamento & purificação , Furanos/isolamento & purificação , Plantas Medicinais , Rosales , Cumarínicos/química , Dissacarídeos/química , Flavonoides/química , Furanos/química , Humanos , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Estruturas VegetaisRESUMO
Two new withanolide glycosides, (20R,22R)-O-(3)-alpha-L-rhamnopyranosyl(1-->4)-beta-D-glucopyranosyl-1 alpha,12 beta-diacetoxy-20-hydroxywitha-5,24-dienolide (3) and (20R,22R)-O-(3)-beta-D-xylopyranosyl(1-->3)-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranosyl-1 alpha-acetoxy-12 beta,20-dihydroxywitha-5,24-dienolide (4), were isolated from the leaves and root of Dunalia brachyacantha. Their aglycones, (20R,22R)-1 alpha,12 beta-diacetoxy-3 beta,20-dihydroxywitha-5,24-dienolide (or 1 alpha,12 beta-diacetyldunawithagenine) and (20R,22R)-1 alpha-acetoxy-3 beta,12 beta,20-trihydroxywitha-5,24-dienolide (or 1 alpha-acetyl-12 beta-hydroxydunawithagenine), are novel. The known 18-acetoxywithanolide D (1) and 18-acetoxy-5,6-deoxy-5-withenolide D (2) were also isolated from the leaves. These last two compounds were shown to be responsible for the trypanocidal, leishmanicidal, and bactericidal activities manifested by the crude ethanolic extract. The structures were deduced from spectroscopic data and on the basis of chemical evidence.
Assuntos
Dissacarídeos/isolamento & purificação , Ergosterol/análogos & derivados , Lactonas/isolamento & purificação , Plantas Medicinais/química , Solanaceae/química , Trissacarídeos/isolamento & purificação , Tripanossomicidas/isolamento & purificação , Tripanossomicidas/farmacologia , Animais , Bactérias/efeitos dos fármacos , Bolívia , Dissacarídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Lactonas/química , Leishmania/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Testes de Sensibilidade Microbiana , Folhas de Planta/química , Raízes de Plantas/química , Espectrofotometria Infravermelho , Trissacarídeos/química , Trypanosoma cruzi/efeitos dos fármacos , VitanolídeosRESUMO
The kaempferol derivative 3,7-di-O-methyl-4'-O-beta-[alpha rhamnosyl (1 --> 6)]-glucopyranoside (siparunoside) was isolated from the leaves of Sparuna apiosyce. Its structure was established by extensive NMR studies. The alkaloids reticuline and liriodenine were also isolated from the leaves along with the kaempferol derivative tiliroside. Benzylisoquinoline alkaloids were isolated from the wood (liriodenine) and wood bark (liriodenine, laurotetanine, N-methyl-laurotetanine, reticuline), together with a mixture of cis and trans-N-feruloyltyramines. 3,7,4'-tri-O-methylkaempferol was isolated from all organs.
Assuntos
Dissacarídeos/isolamento & purificação , Flavonoides , Glicosídeos/isolamento & purificação , Quempferóis , Lauraceae/química , Quercetina/análogos & derivados , Quercetina/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Dissacarídeos/química , Glicosídeos/química , Espectroscopia de Ressonância Magnética , Folhas de Planta/química , Quercetina/químicaRESUMO
The O-linked N-acetylglucosamine oligosaccharides in the mucins of Trypanosoma cruzi may contain galactofuranose or galactopyranose, depending on the strain, one of the components being the disaccharide. Since galactofuranose is a site for antibody recognition, it is desirable to have a sensitive method for the detection of the galactofuranosyl structures. In this paper, we present procedures for the separation of Galfbeta1-->XGlcNAc and Galpbeta1-->XGlcNAc (X = 3, 4, and 6) as the corresponding alditols by high-pH anion-exchange chromatography with pulse amperometric detection. All the isomeric disaccharides could be resolved on a CarboPac PA-10 column, the galactofuranose-containing disaccharides being more retained in the column. GlcNAcol and Galfbeta1-->4(Galpbeta1-->6)GlcNAcol could be analyzed in the same run. The compounds could also be separated by thin-layer chromatography on silica gel 60, a convenient method for analysis of the radiolabeled alditols obtained by reductive beta-elimination in the presence of NaB(3)H(4). Both methods were applied for the analysis of the O-linked sugars in the mucins of T. cruzi CL 14 and revealed that they contained only N-acetylglucosamine and the disaccharide Galpbeta1-->4GlcNAc.
Assuntos
Cromatografia por Troca Iônica/métodos , Cromatografia em Camada Fina/métodos , Dissacarídeos/isolamento & purificação , Mucinas/química , Trypanosoma cruzi/química , Animais , Sequência de Carboidratos , Dissacarídeos/química , Estudos de Avaliação como Assunto , Concentração de Íons de Hidrogênio , Mucinas/isolamento & purificação , Álcoois Açúcares/química , Álcoois Açúcares/isolamento & purificaçãoRESUMO
Two flavonol diglycosides, tamarixetin 3-O-neohesperidoside, kaempferide 3-O-neohesperidoside and the known quercetin 3-O-neohesperidoside, together with six other known flavonoids were isolated from the leaves of Costus spicatus and their structures were elucidated by a combination of spectroscopic and chemical methods. The flavonol diglycosides were evaluated for inhibitory activity of nitric oxide production by activated macrophages (Fig. 1).