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1.
Food Chem ; 335: 127650, 2021 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-32745842

RESUMO

Flavonol glucosides was extracted from red onion solid waste (ROSW) and multi-functional properties were determined to develop alternative strategy for therapeutic beneficiation and utilisation as functional food. The major flavonol glucosides extracted from ROSW were confirmed as quercetin-3, 4'-O-diglucoside (QDG), quercetin-3-O-glucoside (isoquercetin), quercetin-4'-O-glucoside (spiraeoside), isorhamnetin- 4'-glucoside (IMG), quercetin glycoside (QG), and quercetin (Q) using a combination of chromatographic, spectroscopic and scientific literature data. The ROSW solvent fractions and extracted flavonol glucosides showed significant antioxidant effect with DPPH, ABTS, FRAP, and ORAC radical scavenging assays. The in vitro and in silico study revealed that the QG, QDG, isoquercetin, and spiraeoside from ROSW exhibited potent α-glucosidase, tyrosinase and xanthine oxidase enzyme inhibitory activity. In addition, QG, QDG, isoquercetin, and spiraeoside showed potent anticancer effect on HeLa cancer lines. Considering these results, the utilization of ROSW and their flavonol glucosides might be helpful for developing potential antioxidant, anticancer and enzyme inhibitory agents.


Assuntos
Flavonóis/análise , Glucosídeos/análise , Cebolas/química , Extratos Vegetais/análise , Resíduos/análise , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Linhagem Celular , Simulação por Computador , Flavonóis/isolamento & purificação , Flavonóis/farmacologia , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Humanos , Oxirredução , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Rutina/análise , Rutina/isolamento & purificação
2.
PLoS One ; 15(12): e0242486, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-33326432

RESUMO

Paper wasps (Polistes dominula), parasitized by the strepsipteran Xenos vesparum, are castrated and desert the colony to gather on plants where the parasite mates and releases primary larvae, thus completing its lifecycle. One of these plants is the trumpet creeper Campsis radicans: in a previous study the majority of all wasps collected from this plant were parasitized and focused their foraging activity on C. radicans buds. The unexpected prevalence and unusual feeding strategy prompted us to investigate the influence of this plant on wasp behavior and physiology through a multidisciplinary approach. First, in a series of laboratory bioassays, we observed that parasitized wasps spent more time than non-parasitized ones on fresh C. radicans buds, rich of extra-floral nectaries (EFNs), while the same wasps ignored treated buds that lacked nectar drops. Then, we described the structure and ultra-structure of EFNs secreting cells, compatible with the synthesis of phenolic compounds. Subsequently, we analysed extracts from different bud tissues by HPLC-DAD-MS and found that verbascoside was the most abundant bioactive molecule in those tissues rich in EFNs. Finally, we tested the immune-stimulant properties of verbascoside, as the biochemical nature of this compound indicates it might function as an antibacterial and antioxidant. We measured bacterial clearance in wasps, as a proxy for overall immune competence, and observed that it was enhanced after administration of verbascoside-even more so if the wasp was parasitized. We hypothesize that the parasite manipulates wasp behavior to preferentially feed on C. radicans EFNs, since the bioactive properties of verbascoside likely increase host survival and thus the parasite own fitness.


Assuntos
Antibacterianos/farmacologia , Glucosídeos/farmacologia , Holometábolos/fisiologia , Interações Hospedeiro-Parasita , Fenóis/farmacologia , Vespas/parasitologia , Animais , Antibacterianos/química , Antibacterianos/isolamento & purificação , Bignoniaceae/parasitologia , Cromatografia Líquida de Alta Pressão , Comportamento Alimentar/efeitos dos fármacos , Glucosídeos/química , Glucosídeos/isolamento & purificação , Imunidade Inata/efeitos dos fármacos , Imunocompetência , Larva/fisiologia , Masculino , Espectrometria de Massas/métodos , Fenóis/química , Fenóis/isolamento & purificação , Néctar de Plantas/química , Vespas/efeitos dos fármacos , Vespas/imunologia
3.
PLoS One ; 15(6): e0234435, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32574221

RESUMO

This study was designed to investigate the antioxidant properties of the extracts and subfractions of various polarities from Clerodendrum cyrtophyllum Turcz leaves and the related phenolic compound profiles. The ethyl acetate fraction (EAF) showed the most potent radical-scavenging activity for DPPH radicals, ABTS radicals, and superoxide anion (O2·-) radicals as well as the highest reducing power of the fractions tested; the n-butyl alcohol fraction (BAF) was the most effective in scavenging hydroxyl radical (OH·), and the dichloromethane fraction (DMF) exhibited the highest ferrous ion chelating activity. Twelve phenolic components were identified from the EAF of C. cyrtophyllum. Additionally, acteoside (1) was found to be a major component (0.803 g, 0.54%) and show DPPH and ABTS radical scavenging activities with IC50 values of 79.65±3.4 and 23.00±1.5 µg/ml, indicating it is principally responsible for the significant total antioxidant effect of C. cyrtophyllum. Our work offers a theoretical basis for further utilization of C. cyrtophyllum as a potential source of natural, green antioxidants derived from plants.


Assuntos
Antioxidantes/farmacologia , Clerodendrum/química , Glucosídeos/farmacologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Antioxidantes/análise , Antioxidantes/isolamento & purificação , Glucosídeos/análise , Glucosídeos/isolamento & purificação , Radical Hidroxila/metabolismo , Fenóis/análise , Fenóis/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Superóxidos/metabolismo
4.
Food Chem ; 331: 127305, 2020 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-32593038

RESUMO

An ultra-high-performance liquid chromatography-triple quadrupole tandem mass spectrometry (UHPLC-QqQ-MS/MS) method was established and validated for the simultaneous quantification of eight cyanogenic glucosides (CNGs) in agri-food. The eight CNGs were linamarin, lotaustralin, linustatin, neolinustatin, taxiphyllin, amygdalin, dhurrin and prunasin. CNGs were extracted with aqueous methanol and cleaned via solid-phase extraction. Analytes were separated with a C18 column via gradient elution. MS/MS analysis was performed with electrospray ionisation in positive mode. Quantification was performed in multiple reaction monitoring mode. Satisfactory validation results were obtained in terms of linearity, sensitivity, precision and accuracy, matrix effect and stability. The method was applied in typical cyanogenic agri-food. CNGs in cassava, linseed, bamboo, sorghum, apricot, almond and lima bean were analyzed.


Assuntos
Cromatografia Líquida de Alta Pressão/métodos , Análise de Alimentos/métodos , Glucosídeos/análise , Glucosídeos/química , Nitrilos/química , Espectrometria de Massas em Tandem/métodos , Agricultura , Glucosídeos/isolamento & purificação , Extração em Fase Sólida , Fatores de Tempo
5.
J Chromatogr A ; 1622: 461129, 2020 Jul 05.
Artigo em Inglês | MEDLINE | ID: mdl-32376025

RESUMO

This work describes the development of capacity orthogonal chromatography (COC), a new technique for simultaneously determining the loading capacity and orthogonality during the construction of two-dimensional (2D) separations. Three steps were required for the construction of a COC based on the correlation between the selectivity factor (α) and both orthogonality and loading capacity. (1) α values of the impurities-target compound were used to normalize the retention of the impurities around the target compound. (2) α values were input into four quadrants of a coordinate system to identify correlations between orthogonality and loading capacity. α values of the impurities must be greater in the first dimension than the second dimension, with iterated analyses performed until an αmax is obtained for the two purification methods. (3) Touch-peak separation using the first-dimensional αmax was performed and the target compound was collected. The co-eluted impurities are further separated in the second dimension. To test the efficiency of this technique, a COC using two methods on a standard C18 column was developed to purify corilagin from pomegranate flower extract. Despite its low abundance, 288 mg of corilagin was obtained by COC and further purified by LH-20 gel chromatography to obtain the compound with an 80.0% recovery and 98.4% purity. Compared to COC, the purity of corilagin independently obtained using the same purification methods and identical loading capacity was poor (60.1% and 61.6%). These results indicate that COC is a useful tool for extending loading capacity in the development of preparative 2D separations.


Assuntos
Flores/química , Glucosídeos/isolamento & purificação , Taninos Hidrolisáveis/isolamento & purificação , Extratos Vegetais/química , Romã (Fruta)/química , Glucosídeos/química , Taninos Hidrolisáveis/química
6.
Biomed Pharmacother ; 124: 109911, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-32004939

RESUMO

Total glucosides of paeony (TGP), an active mixture extracted from paeony root, has anti-inflammatory and immunoregulatory effects and is widely used for the treatment of autoimmune diseases such as rheumatoid arthritis. However, the role of TGP in autoimmune hepatitis (AIH) is still unknown. In this study, we aimed to investigate the effect of TGP in autoimmune liver disease (AILD) patients and in concanavalin A (Con A)-induced experimental autoimmune hepatitis (EAH). Changes in biochemical parameters of AILD patients showed that treatment with TGP exerts significant protective effects on liver function, as reflected by decreased levels of serum alanine transaminase, aspartate transaminase, γ-glutamyl transpeptidase and total bilirubin. In EAH mice, we found that pretreatment with TGP reduced the levels of serum liver enzyme levels, histopathological damage and hepatocyte apoptosis. Importantly, flow cytometry analysis showed that pretreatment with TGP reduced the infiltration of mature dendritic cells in the liver. In vitro, TGP pretreatment ameliorated the Con A-induced mitochondrial membrane potential decline, reactive oxygen species increase, and apoptosis increase in hepatocytes. In addition, the levels of Bax, Cleaved Caspase-3 and cytoplasmic Cytochrome C decreased during this process, whereas those of Bcl-2 and mitochondrial Cytochrome C increased. Therefore, TGP might decrease hepatocyte apoptosis through the mitochondrial apoptotic pathway. Moreover, the maturation of bone marrow dendritic cells was also inhibited by TGP treatment. In conclusion, TGP treatment ameliorates AIH by regulating hepatocyte apoptosis and DC maturation. TGP is a potential compound for AIH treatment.


Assuntos
Glucosídeos/farmacologia , Hepatite Autoimune/tratamento farmacológico , Hepatócitos/efeitos dos fármacos , Paeonia/química , Adulto , Idoso , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Apoptose/efeitos dos fármacos , Células Dendríticas/efeitos dos fármacos , Feminino , Glucosídeos/isolamento & purificação , Hepatite Autoimune/fisiopatologia , Humanos , Masculino , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Camundongos , Camundongos Endogâmicos C57BL , Pessoa de Meia-Idade , Extratos Vegetais/farmacologia , Espécies Reativas de Oxigênio/metabolismo
7.
Phytochemistry ; 171: 112234, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31901735

RESUMO

A total of fifteen grayanane diterpenoid glucosides including eight undescribed ones, pierisjaponosides A-H, were isolated from the leaves of Pieris japonica (Thunb.) D. Don ex G. Don (Ericaceae). Their structures were established by extensive spectros copic techniques including HRESIMS and NMR, as well as chemical methods. The absolute configurations of pierisjaponosides A, B, and D were finally established by single-crystal X-ray diffraction with Cu Kα radiation. This is the first time to report the crystal structure of a 5,9-epoxygrayanane diterpenoid glucoside. Pierisjaponoside E represents the first example of a 9ß-hydroxygrayan-1(10)-ene diterpenoid. All the isolated grayanane diterpenoid glucosides were evaluated for their analgesic activities in the acetic acid-induced writhing models in mice, and showed significant analgesic effects. Pierisjaponosides A and C-H, micranthanoside A, pieroside A, and craiobiosides A and B displayed significant analgesic effects with the writhe inhibition rates over 50% at a dose of 5.0 mg/kg. Pierisjaponoside E exhibited significant analgesic activities with the percentage inhibitions of 81.7%, 70.4%, and 52.1% at the doses of 5.0, 1.0, and 0.2 mg/kg, respectively. The preliminary structure-activity relationships of grayanane diterpenoid glucosides as potent analgesics were discussed, giving some clues to design novel analgesics.


Assuntos
Analgésicos/uso terapêutico , Diterpenos/uso terapêutico , Ericaceae/química , Glucosídeos/uso terapêutico , Dor/tratamento farmacológico , Compostos Fitoquímicos/uso terapêutico , Ácido Acético , Analgésicos/química , Analgésicos/isolamento & purificação , Animais , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Feminino , Glucosídeos/química , Glucosídeos/isolamento & purificação , Masculino , Camundongos , Camundongos Endogâmicos , Modelos Moleculares , Estrutura Molecular , Dor/induzido quimicamente , Medição da Dor , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Folhas de Planta/química , Relação Estrutura-Atividade
8.
Chem Pharm Bull (Tokyo) ; 68(1): 91-95, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31902904

RESUMO

Magnolia Flower is a crude drug used for the treatment of headaches, toothaches, and nasal congestion. Here, we focused on Magnolia kobus, one of the botanical origins of Magnolia Flower, and collected the flower parts at different growth stages to compare chemical compositions and investigate potential inhibitory activities against interleukin-2 (IL-2) production in murine splenic T cells. After determining the structures, we examined the inhibitory effects of the constituents of the bud, the medicinal part of the crude drug, against IL-2 production. We first extracted the flower parts of M. kobus from the bud to fallen bloom stages and analysed the chemical compositions to identify the constituents characteristic to the buds. We found that the inhibitory activity of the buds against IL-2 production was more potent than that of the blooms. We isolated two known compounds, tiliroside (1) and syringin (2), characteristic to the buds from the methanol (MeOH) extract of Magnolia Flower. Moreover, we examined the inhibitory activities of both compounds against IL-2 production and found that tiliroside (1) but not syringin (2), showed strong inhibitory activity against IL-2 production and inhibited its mRNA expression. Thus, our strategy to examine the relationship between chemical compositions and biological activities during plant maturation could not only contribute to the scientific evaluation of medicinal parts of crude drugs but also assist in identifying biologically active constituents that have not yet been reported.


Assuntos
Interleucina-2/metabolismo , Magnolia/química , Extratos Vegetais/química , Animais , Linhagem Celular , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Flores/química , Flores/metabolismo , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glucosídeos/farmacologia , Interleucina-2/genética , Magnolia/metabolismo , Camundongos , Fenilpropionatos/química , Fenilpropionatos/isolamento & purificação , Fenilpropionatos/farmacologia , Linfócitos T/citologia , Linfócitos T/efeitos dos fármacos , Linfócitos T/metabolismo
9.
Phytochemistry ; 171: 112247, 2020 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-31927201

RESUMO

Four previously undescribed acylated iridoid glucosides, linaburiosides A‒D, one undescribed iridoid, 7-deoxyiridolactonic acid, and one known acylated iridoid glucoside, iridolinarin C, were isolated from the aerial parts of a Mongolian traditional herbal medicine, Linaria buriatica. Linaburiosides A‒D had an acyl moiety corresponding to 7-deoxyiridolactonic acid. Detailed spectroscopic analyses of linaburiosides A‒D and 7-deoxyiridolactonic acid led to the assignment of their structures. The absolute configuration of 7-deoxyiridolactonic acid was elucidated by application of the PGME method; those of linaburiosides A‒D were assigned on the basis of chemical conversions, as well as application of the modified Mosher's method. The absolute configuration of iridolinarin C was also elucidated in this study. Anti-inflammatory and antiproliferative activities of isolated compounds and their derivatives were evaluated.


Assuntos
Anti-Inflamatórios/farmacologia , Glucosídeos/farmacologia , Iridoides/farmacologia , Linaria/química , Compostos Fitoquímicos/farmacologia , Células A549 , Acilação , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Humanos , Interleucina-1beta/antagonistas & inibidores , Interleucina-1beta/biossíntese , Iridoides/química , Iridoides/isolamento & purificação , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Células MCF-7 , Microglia/efeitos dos fármacos , Microglia/metabolismo , Conformação Molecular , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Células Tumorais Cultivadas
10.
PLoS One ; 15(1): e0225514, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-31929529

RESUMO

Based on ethnopharmacological studies, a lot of plants, as well as its compounds, have been investigated for the potential use as wound healing agents. In Brazil, Curatella americana is traditionally used by local people to treat wounds, ulcers and inflammations. However, to the best of our knowledge, its traditional use in the treatment of wounds has not been validated by a scientific study. Here, some compounds, many of them flavonoids, were identified in the hydroethanolic extract from the leaves of C. americana (HECA) by LC-HRMS and LC-MS/MS. Besides that, solutions containing different concentrations of HECA and a gel produced with this extract were evaluated for its antimicrobial, coagulant and wound healing activities on an excision mouse wound model as well as its acute dermal safety. A total of thirteen compounds were identified in HECA, mainly quercetin, kaempferol and glucoside derivatives of both, besides catechin and epicatechin known as wound healing agents. The group treated with 1% of HECA exhibited highest wound healing activity and best rate of wound contraction confirmed by histopathology results. The present study provides scientific evidence of, this extract (HECA) possess remarkable wound healing activity, thereby, supporting the traditional use.


Assuntos
Dilleniaceae/química , Extratos Vegetais/farmacologia , Cicatrização/efeitos dos fármacos , Animais , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Brasil , Catequina/isolamento & purificação , Cromatografia Líquida , Flavonoides/química , Flavonoides/farmacologia , Glucosídeos/química , Glucosídeos/isolamento & purificação , Humanos , Quempferóis/química , Quempferóis/isolamento & purificação , Camundongos , Extratos Vegetais/química , Folhas de Planta/química , Quercetina/química , Quercetina/isolamento & purificação , Espectrometria de Massas em Tandem
11.
Biomed Pharmacother ; 124: 109923, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31986418

RESUMO

2,3,5,4,-Tetrahydroxystilbene-2-O-ß-d-glucoside (TSG) is the main active constituent of the traditional Chinese medicine, Polygonum multiflorum; it was discovered that the compound has various biological activities and medicinal value including anti-aging, antioxidative (via scavenging free radicals), antihypercholesterolemic, anti-atherosclerotic, anti-inflammatory, hepatoprotective, and anti-tumor effects. TSG aids in prevention and treatment of Alzheimer's disease. With its wide clinical application, its separation and purification has become a research hotspot. In this paper, the pharmacological action, extraction process, and application prospects of TSG were reviewed in order to provide references for further development of TSG.


Assuntos
Fallopia multiflora/química , Glucosídeos/isolamento & purificação , Estilbenos/isolamento & purificação , Animais , Glucosídeos/farmacologia , Humanos , Medicina Tradicional Chinesa , Estilbenos/farmacologia
12.
Pharm Biol ; 58(1): 80-88, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31887257

RESUMO

Context: Traditionally, Clematis tangutica Korsh. (Ranunculaceae) is used as a Tibetan herb for treating indigestion and blood stasis in China. Recently, a flavonoid glycoside, apigenin-7-O-ß-d-(6″-p-coumaroyl)-glucopyranoside (APG), was isolated from the whole plant of C. tangutica.Objective: To investigate the cardioprotective effects of APG against myocardial ischaemia/reperfusion injury (MI/RI) and the possible mechanism.Materials and methods: Animals were subjected to 30 min/3 h MI/RI model. At the end of reperfusion, infarct size (IS), histopathology, serum levels CK-MB, LDH, TNF-α, IL-6 and MPO activities were detected. Phospho-IκB-α, ICAM-1 and NF-κB were assessed in vivo. Neonatal rat cardiomyocytes were pre-treated with or without APG, followed by stimulation with 8 h/2 h oxygen and glucose deprived/reoxygenation (OGD/R) model. Cell viability, LDH and cardiomyocyte apoptosis were assessed. The expression levels of phospho-IκB-α and NF-κB were measured in vitro.Results: Treatment with APG significantly reduced the following indicators in vivo (p < 0.05): (1) the IS (16.2%); (2) morphology score (1.67); (3) myocardial injury enzymes: CK-MB (26.2 ng/mL) and LDH (688 U/L); (4) pro-inflammatory cytokines: TNF-α (31.5 pg/mL) and IL-6 (163.8 pg/mL); (5) MPO activity (2.75 U/mg); (6) expression levels of phospho-IκB-α (0.47), NF-κB (2.87) and ICAM-1 (10.2). Moreover, treatment with APG also remarkably (p < 0.05) attenuated the following indicators in vitro: (1) LDH level (206 U/L); (2) cardiomyocyte apoptosis; (3) phospho-IκB-α (1.37) and NF-κB (2.50).Conclusions: APG possesses protective effects against MI/RI injury in rats and OGD/R-induced injury in cardiomyocytes by suppressing translocation of NF-κB and reducing inflammatory response; consequently, APG is helpful for treatment of ischaemic heart disease.


Assuntos
Apigenina/farmacologia , Cardiotônicos/farmacologia , Glucosídeos/farmacologia , Inflamação/tratamento farmacológico , Traumatismo por Reperfusão Miocárdica/tratamento farmacológico , Animais , Animais Recém-Nascidos , Apigenina/isolamento & purificação , Apoptose/efeitos dos fármacos , Cardiotônicos/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Clematis/química , Citocinas/metabolismo , Modelos Animais de Doenças , Glucosídeos/isolamento & purificação , Inflamação/patologia , Masculino , Isquemia Miocárdica/tratamento farmacológico , Isquemia Miocárdica/fisiopatologia , Traumatismo por Reperfusão Miocárdica/fisiopatologia , Miócitos Cardíacos/efeitos dos fármacos , NF-kappa B/metabolismo , Ratos , Ratos Sprague-Dawley
13.
Z Naturforsch C J Biosci ; 75(1-2): 7-12, 2020 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-31639104

RESUMO

6-Tuliposides A (6-PosA) and B (6-PosB) are major defensive secondary metabolites in tulip cultivars (Tulipa gesneriana), having an acyl group at the C-6 position of d-glucose. Although some wild tulip species produce 1,6-diacyl-glucose type of Pos (PosD and PosF), as well as 6-PosA/B, they have not yet been isolated from tulip cultivars. Here, aiming at verifying the presence of PosD and PosF in tulip cultivars, tissue extracts of 25 cultivars were analyzed by high-performance liquid chromatography (HPLC). Although no HPLC peaks for PosD nor PosF were detected in most cultivars, we found two cultivars giving a minute HPLC peak for PosD and the other two cultivars giving that for PosF. PosD and PosF were then purified from petals of cultivar 'Orca' and from pistils of cultivar 'Murasakizuisho', respectively, and their identities were verified by spectroscopic analyses. This is the first report that substantiates the presence of 1,6-diacyl-glucose type of Pos in tulip cultivars.


Assuntos
Glucose/química , Glucosídeos/química , Oxibato de Sódio/análogos & derivados , Tulipa/química , Cromatografia Líquida de Alta Pressão , Flores/química , Glucose/análogos & derivados , Glucosídeos/isolamento & purificação , Glicosídeos/química , Hidroxibutiratos/química , Oxibato de Sódio/química , Oxibato de Sódio/isolamento & purificação
14.
Nat Prod Res ; 34(12): 1772-1776, 2020 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30499349

RESUMO

Seventeen compounds were isolated from the capitula of Coreopsis tinctoria Nutt. with various column chromatographic methods and semi-preparative HPLC. Their structures were identified by the spectroscopic data and comparison with literatures as 2'-hydroxy-4,4'-dimethoxy-chalcone; (1), isoliquiritigenin (2), eriodictyol (3), naringenin (4), maritimetin (5), butin (6), taxifolin (7), luteolin (8), 7,3',4'-trihydroxyflavone (9), 8,3',4'-trihydroxyflavone-7-O-ß-d-glucoside (10), quercetin (11), quercetagitin-7-O-ß-d-glucoside (12), quercetin-7-O-ß-d-glucoside (13), 3,4-dihydroxybenzoic acid (14), caffeic acid (15), coreoside B (16), and myo-inositol (17). Compounds 1, 4, 9, 10 and 17 were isolated from C. tinctoria Nutt. for the first time. Compounds 7 and 12 possessed the highest antioxidant activity (IC50 = 64.37 and 32.86 µg/ml, respectively) among the tested compounds (IC50 value of positive control was 5.34 µg/ml). Compound 7 exhibited potent PTP1B enzymatic inhibition with an IC50 value of 7.73 µg/ml (IC50 value of positive control is 1.46 µg/ml). Furthermore, compound 5 showed strong antibacterial activity against the Gram-positive bacterium, S. aureus.


Assuntos
Antibacterianos/isolamento & purificação , Antioxidantes/isolamento & purificação , Coreopsis/química , Hipoglicemiantes/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Flavonoides/isolamento & purificação , Glucosídeos/isolamento & purificação , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Estrutura Molecular , Extratos Vegetais/química , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Staphylococcus aureus/efeitos dos fármacos
15.
Nat Prod Res ; 34(9): 1320-1325, 2020 May.
Artigo em Inglês | MEDLINE | ID: mdl-30676780

RESUMO

As part of our continuing efforts to explore bioactive compounds from natural resources, a new iridoid glycoside, adoxosidic acid-6'-oleuroperic ester (1), together with one known phenylethanoid glycoside (2) and two known flavonoid glycosides (3-4) were isolated from the fruit of Forsythia suspensa. The structure of the new compound (1) was elucidated through 1D and 2D NMR spectroscopic data and HR-ESIMS. Interestingly, compound 1 was a monoterpene ester of one iridoid glycoside. Compounds 2-4 were identified as calceolarioside A (2), kaempferol-3-O-rutinoside (3), kampferol-3-O-robinobioside (4) on the basis of NMR spectroscopic data analyses and comparison with the data reported in the literature. The antiviral activity aganisist influenza A (H5N1) virus of compound 1 was studied as well.


Assuntos
Flavonoides/química , Forsythia/química , Glicosídeos/química , Glicosídeos Iridoides/química , Iridoides/química , Antivirais/química , Antivirais/farmacologia , Ácidos Cafeicos/química , Ácidos Cafeicos/isolamento & purificação , Avaliação Pré-Clínica de Medicamentos , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Frutas/química , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Virus da Influenza A Subtipo H5N1/química , Virus da Influenza A Subtipo H5N1/efeitos dos fármacos , Glicosídeos Iridoides/isolamento & purificação , Glicosídeos Iridoides/farmacologia , Espectroscopia de Ressonância Magnética , Espectrometria de Massas por Ionização por Electrospray
16.
Nat Prod Res ; 34(13): 1874-1878, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30689410

RESUMO

A new triterpenoid glucoside, leuctriterpencoside (1), along with two known compounds (2-3) were isolated from Leucas zeylanica. The structure of the new compound was elucidated using comprehensive spectroscopic methods. Compound 1 showed significant inhibitory activity against α-glucosidase (IC50 value of 0.85 ± 0.12 µM).


Assuntos
Glucosídeos/isolamento & purificação , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Lamiaceae/química , Triterpenos/isolamento & purificação , Glucosídeos/química , Inibidores de Glicosídeo Hidrolases/farmacologia , Lamiaceae/metabolismo , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Triterpenos/química , alfa-Glucosidases/efeitos dos fármacos , alfa-Glucosidases/metabolismo
17.
Nat Prod Res ; 34(20): 2894-2899, 2020 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30990071

RESUMO

Astragalus ernestii has been used as a substitute for Radix Astragali (Huang-Qi) in southwest China. To better understand the chemical rationale for the medicinal usage, the phytochemistry of A. ernestii was recently studied. As a result, a novel aurone-phenylpropanoid adduct astrernestin (1), together with five known phenoloids calycosin-7-O-ß-D-glucopyranoside (2), 4,4'-dimethoxy-3'-hydroxy-7,9':7',9-diepoxylignan-3-O-ß-D-glucopyranoside (3), syringaresinol-4-O-ß-D-monoglucoside (4), hedyotol D 4″-O-ß-D-glucopyranoside (5) and trifolirhizin (6), were isolated from the roots of A. ernestii. The structure of compound 1 was elucidated by extensive spectroscopic analysis and optical rotation calculation.


Assuntos
Astrágalo (Planta)/química , Benzofuranos/química , Fenóis/química , Raízes de Plantas/química , China , Medicamentos de Ervas Chinesas , Furanos/isolamento & purificação , Glucosídeos/isolamento & purificação , Compostos Heterocíclicos de 4 ou mais Anéis/isolamento & purificação , Isoflavonas/isolamento & purificação , Lignanas/isolamento & purificação , Estrutura Molecular , Fenóis/isolamento & purificação
18.
Nat Prod Res ; 34(2): 300-304, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30375259

RESUMO

A phytochemical study was carried out on Ajuga multiflora, and obtained a novel ursane-type triterpene saponin, i.e., 3-epi-ursolic acid 3-O-palmitoyl 28-O-α-L-arabinofuranosyl ester (1), named ajugoside. Its structure and relative configuration were identified mainly by spectroscopic methods including 1D- and 2D-NMR techniques as well as HR-MS analysis. This paper described the isolation and structural elucidation of ajugoside (1) for the first time.


Assuntos
Ajuga/química , Glucosídeos/química , Piranos/química , Saponinas/isolamento & purificação , Triterpenos/isolamento & purificação , Glucosídeos/isolamento & purificação , Conformação Molecular , Estrutura Molecular , Extratos Vegetais/análise , Extratos Vegetais/química , Piranos/isolamento & purificação , Saponinas/química , Triterpenos/química
19.
Nat Prod Res ; 34(15): 2137-2143, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30810365

RESUMO

The phytochemical examination of the polar constituents of Sambucus ebulus L. leaves led to the identification of patrinoside (1) and of a new diglycoside iridoid, patrinoside-aglycone-11-O-[ß-D-glucopyranosyl-(1→6)-2'-deoxy-ß-D-glucopyranoside] (trivially named as sambuloside) (2). Both of these structures have been assigned by spectroscopic means (NMR and MS).


Assuntos
Glicosídeos/isolamento & purificação , Iridoides/isolamento & purificação , Compostos Fitoquímicos/análise , Sambucus/química , Glucosídeos/química , Glucosídeos/isolamento & purificação , Glicosídeos/química , Iridoides/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Folhas de Planta/química
20.
Sci Rep ; 9(1): 18469, 2019 12 05.
Artigo em Inglês | MEDLINE | ID: mdl-31804561

RESUMO

Paeoniaceae is an abundant germplasm resource with significant medicinal values in China, the principal medicinal components of which include paeoniflorin and paeonol. These compounds are typically obtained from air-dried root samples, which the use of freeze-drying as an alternative method has not been tested. Additionally, the presence of these two compounds in various wild Paeoniaceae species has not been previously explored, nor have the differences between various plant organs been fully evaluated. Here, freeze-drying and air-drying methods were compared to assess the changes in paeoniflorin and paeonol in root samples using ultra-performance liquid chromatography-mass spectrometer. The contents of these compounds in the roots, leaves, stems, and petals were then tested in freeze-dried materials. We also quantitatively detected the paeoniflorin and paeonol contents in the roots of 14 species collected from 20 natural habitats. Results indicated that the paeoniflorin content decreased under air-drying in comparison to freeze-drying, while the opposite trend was observed for paeonol. Our findings also demonstrated that the root xylem of species in Section Moutan, particularly Paeonia ostii, contains considerable paeonol and paeoniflorin and should thus be fully utilized as a medicinal resource. Furthermore, paeonol was mainly detected in the roots, while paeoniflorin was widely distributed in different organs; the highest content was in the leaf at the budding stage, suggesting that the leaves should be developed as a new paeoniflorin resource. Paeoniflorin contents were also found to be higher at earlier development stages. Based on the standards of the Chinese Pharmacopoeia, five species of Section Moutan and six species of Section Paeonia could be used as potential traditional Chinese medicinal resources. These findings of this study enhance our understanding of these two medicinal compounds and provide a foundation for the further development and utilization of Paeoniaceae as medicinal plant resources.


Assuntos
Acetofenonas/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Glucosídeos/isolamento & purificação , Medicina Tradicional Chinesa/métodos , Monoterpenos/isolamento & purificação , Paeonia/química , China , Cromatografia Líquida de Alta Pressão , Medicamentos de Ervas Chinesas/normas , Liofilização , Espectrometria de Massas , Raízes de Plantas/química , Controle de Qualidade
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