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1.
Planta Med ; 87(12-13): 1018-1024, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-33906246

RESUMO

Euphorbia myrsinites is one of the oldest spurges described and used in folk medicine. It is characterized by blue-grey stems similar to myrtle, and it is spread in the Mediterranean region, Asia, and the USA. Chemical analysis of E. myrsinites collected in Turkey afforded the isolation of 4 diterpenes based on the so-called myrsinane skeleton being tetraesters of the tetracyclic diterpene alcohol myrsinol. In this study, the phytochemical analysis of this species collected in Italy has been undertaken to afford the isolation of a new atisane diterpene, named myrsatisane, 3 ingenol derivatives, along with the 4 tetraester derivatives previously found. A triterpene compound based on the euphane skeleton has also been isolated. Structural elucidation of the new myrsatisane was based on spectroscopic techniques, including HR-MS and 1- and 2-dimensional NMR experiments. Its relative configuration was determined by NOE correlations, while absolute stereochemistry was obtained by quantum-mechanical DFT studies. While diterpenes with the atisane skeleton are relatively common in Euphorbia species, this is the first report of an atisane diterpene from E. myrsinites. All the isolated terpenes were tested for anti-inflammatory activity on J774A.1 macrophages stimulated with lipopolysaccharide by evaluation of nitrite and pro-inflammatory cytokine Il-1ß levels. Among tested compounds, the 3 ingenol diterpenes exhibited a dose-dependent (0.001 - 3 µM) significant activity, thus showing their potential as anti-inflammatory drug candidates.


Assuntos
Diterpenos , Euphorbia , Triterpenos , Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Estrutura Molecular , Terpenos
2.
J Sci Food Agric ; 101(14): 6010-6019, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-33855720

RESUMO

BACKGROUND: Chia (Salvia hispanica L.) is a functional food from Central America. Interest in it is growing rapidly due to the many health benefits from the seed. However, when chia is grown at high latitudes, seed yield may be low whereas a high stem biomass and immature inflorescences are produced. Little is known about the chemical composition and the properties of stems and flowers. In this work, the metabolite profile, the antioxidant activity, and the total polyphenol content of stems and inflorescences were evaluated in a factorial experiment with different chia populations (commercial black chia and long-day flowering mutants G3, G8, and G17) and irrigation (100% and 50% of evapotranspiration). RESULTS: The results show the influence of irrigation and seed source on the antioxidant activity and total polyphenol content of chia flower and stem. Inflorescences exhibit higher antioxidant activity, suggesting their potential use as natural antioxidant. The mutants G3 and G8, at 50% irrigation, contained the highest amounts of compounds with nutraceutical value, especially within the flower. The mutant G17 showed lower antioxidant activity and polyphenol content compared to other seed sources but exhibited high omega 3 content in flowers but low in stems. This indicates that chia varieties should be chosen according to the objective of cultivation. CONCLUSION: These findings, indicating a close relation of metabolite content with irrigation and seed source, may provide the basis for the use of chia flower and stem for their nutraceutical value in the food, feed, and supplement industries. © 2021 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.


Assuntos
Antioxidantes/química , Extratos Vegetais/química , Salvia/crescimento & desenvolvimento , Salvia/metabolismo , Irrigação Agrícola , Antioxidantes/metabolismo , América Central , Suplementos Nutricionais/análise , Flores/química , Flores/genética , Flores/crescimento & desenvolvimento , Flores/metabolismo , Metabolômica , Mutação , Extratos Vegetais/metabolismo , Caules de Planta/química , Caules de Planta/genética , Caules de Planta/crescimento & desenvolvimento , Caules de Planta/metabolismo , Salvia/química , Salvia/genética , Água/análise , Água/metabolismo
3.
Food Res Int ; 130: 108923, 2020 04.
Artigo em Inglês | MEDLINE | ID: mdl-32156371

RESUMO

Both the Maillard reaction (MR) and thermal treatment influence the nutritional value of milk. In this paper, the capability of polyphenolic berry extract (PBE) to inhibit MR in an ultra-high temperature (UHT) treated milk was investigated. Total polyphenol content and antioxidant capacity of blueberry (BE) and raspberry extracts (RE) were also tested. A gas chromatography-mass spectrometry (GC-MS) method was developed to monitor the MR product N ε-(carboxymethyl)-L-lysine (CML) and L-lysine (LYS). PBE was added to milk at 0.05 and 0.1% w/v prior to UHT processing. Data revealed that formation of CML was significantly reduced (23.4 ± 5.1%) by addition of 0.1% w/v BE. The final concentrations of LYS measured following the addition of PBE prior to thermal treatment were statistically similar to the control milk which was not subjected to thermal processing. Additionally, the metabolic profile of milk samples was investigated by GC-MS and visualised using 'FancyTiles'.


Assuntos
Manipulação de Alimentos/métodos , Frutas/metabolismo , Lisina/análogos & derivados , Lisina/metabolismo , Leite/metabolismo , Extratos Vegetais/metabolismo , Animais , Temperatura Alta , Lisina/análise , Leite/química
4.
Chem Res Toxicol ; 32(10): 2053-2062, 2019 10 21.
Artigo em Inglês | MEDLINE | ID: mdl-31515993

RESUMO

Analyzing harmful constituents in e-cigarette aerosols typically involves adopting a methodology used for analyzing tobacco smoke. Cambridge filter pads (CFP) are the basis of numerous protocols for analyzing the various classes of compounds representing 93 harmful and potentially harmful constituents identified in tobacco smoke by the FDA. This paper describes a simplified method for trapping the low volatility components of e-cigarette aerosols using a single trapping procedure followed by physical extraction. The trap is a plug of amorphous silica fibers (0.75 g of 4 µm diameter) within a 10 mL syringe inserted between the e-cigarette mouthpiece and the pump of the vaping machine. The method is evaluated for emissions from three generations of e-cigarette device (Kangertech CE4, EVOD, and Subox Mini-C). On average, the silica wool traps about 94% of the vaporized liquid mass in the three devices and higher levels of condensate is retained before reaching saturation compared with CFP. The condensate is then physically extracted from the silica wool plug using a centrifuge. Condensate is then available for use directly in multiple analytical procedures or toxicological experiments. The method is tested by comparison with published analyses of carbonyls, among the most potent toxicants and carcinogens in e-cigarette emissions. Ranges for HPLC-DAD analyses of carbonyl-DNPH derivatives in a laboratory formulation of e-liquid are formaldehyde (0.182 ± 0.023 to 9.896 ± 0.709 µg puff-1), acetaldehyde (0.059 ± 0.005 to 0.791 ± 0.073 µg puff-1), and propionaldehyde (0.008 ± 0.0001 to 0.033 ± 0.023 µg puff-1); other carbonyls are identified and quantified. Carbonyl concentrations are also consistent with published experiments showing marked increases with variable power settings (10W to 50W). Compared with CFPs, e-cigarette aerosol collection by silica wool requires only one vaping session for multiple analyte groups, traps more condensate per puff, and collects more condensate before saturation.


Assuntos
Acetona/análise , Aerossóis/química , Aldeídos/análise , Sistemas Eletrônicos de Liberação de Nicotina , Dióxido de Silício/química
5.
Phytochem Anal ; 30(5): 556-563, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31286582

RESUMO

INTRODUCTION: Tuta absoluta (Meyrick) (Lepidoptera: Gelechiidae) is one of the most devastating and harmful pests of tomato (Solanum lycopersicum) crops causing up to 80-100% yield losses. A large arsenal of plant metabolites is induced by the leafminer feeding including defence compounds that could differ among varieties. OBJECTIVE: To compare the metabolomic changes of different genotypes of tomato (tolerant "T", susceptible "S" and "F1" hybrid obtained between T and S) after exposition to T. absoluta. METHODOLOGY: Nuclear magnetic resonance (NMR) spectroscopy followed by multivariate data analysis were performed to analyse the metabolic profiles of control and infested samples on three different tomato genotypes. RESULTS: Signals related to GABA (γ-aminobutyric acid) were relatively much higher in all infested samples compared to the non-infested plants used as control. Infested T genotype samples were the most abundant in organic acids, including fatty acids and acyl sugars, chlorogenic acid, neo-chlorogenic acid and feruloyl quinic acid, indicating a clear link between the exposure to leafminer. Results also showed an increase of trigonelline in all tomato varieties after exposition to T. absoluta. CONCLUSION: Metabolomics approach based on NMR spectroscopy followed by multivariate data analysis allowed for a detailed metabolite profile of plant defences, providing fundamental information for breeding programmes in plant crops.


Assuntos
Lepidópteros/fisiologia , Lycopersicon esculentum/parasitologia , Espectroscopia de Ressonância Magnética/métodos , Metabolômica , Animais , Comportamento Alimentar , Genes de Plantas , Lycopersicon esculentum/genética , Análise Multivariada
7.
Food Funct ; 9(11): 5674-5681, 2018 Nov 14.
Artigo em Inglês | MEDLINE | ID: mdl-30306992

RESUMO

The formation of advanced glycation end-products (AGEs) in biological systems is increased during hyperglycaemia due to higher levels of circulating glucose and carbonyl reactive species. AGEs are causative factors of common chronic diseases. Since synthetic AGE-inhibitors exert unwanted side effects and polyphenols act as potent antiglycative agents, vegetables (fruits, seeds and related by-products) are good candidates when searching for natural inhibitors. The aim of this research is to explore the suitability of a polyphenol-rich rapeseed cake extract (RCext) to decrease the formation of AGEs in an in vitro model. Different phenols, amino acids, carbohydrates, organic acids and fatty acids were identified in the RCext by GC-MS. The results confirm a high concentration of polyphenols (73.85 ± 0.64 and 86.85 ± 2.08 mg of gallic acid equivalents per g of RCext spray dried and freeze dried, respectively) which is correlated with the antioxidant capacity and anti-glycative activity in a dose dependent manner. Rapeseed cake extract (3.7 mg mL-1) significantly reduced the formation of free fluorescent AGEs and pentosidine up to 34.85%. The anti-glycative activity of the extract is likely to be due to the high concentration of sinapinic acid (0.108 ± 0.0043 mg g-1) in its metabolic profile, and the mechanism of action is mediated by methylglyoxal trapping. The results show promising potential for using rapeseed cake extract as a food supplement to ameliorate the formation of AGEs. Rapeseed cake extract should therefore be considered a potential candidate for the prevention of glycation-associated complications of age-related pathologies.


Assuntos
Antioxidantes/farmacologia , Brassica rapa/química , Produtos Finais de Glicação Avançada/antagonistas & inibidores , Glicosilação/efeitos dos fármacos , Polifenóis/farmacologia , Arginina/análogos & derivados , Arginina/análise , Frutas/química , Lisina/análogos & derivados , Lisina/análise , Ornitina/análogos & derivados , Ornitina/análise , Extratos Vegetais/farmacologia , Pirimidinas/análise , Sementes/química , Verduras/química
8.
Food Chem ; 254: 137-143, 2018 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-29548434

RESUMO

Chia is a food plant producing seeds which have seen increasing interest owing to their health benefits. This work is the first report on the metabolite profile, total polyphenols and antioxidant activity of chia seeds, determined by ultrasound-assisted extraction, coupled with gas chromatography-mass spectrometry (UAE GC-MS). Different chia sources were compared: two commercial (black and white) and three early flowering (G3, G8 and G17) mutant genotypes. Organic extracts were mainly composed of mono- and polyunsaturated fatty acids with alpha-linolenic being the most abundant. Polar extracts contained sucrose, methylgalactoside and glucose as main sugars. Antioxidant activity and total polyphenolic content were correlated. Chemical composition and yield potential of early flowering genotypes were different from commercial chia, and while white chia showed the highest content of omega-3 fatty acids, the high content of nutraceuticals in G17 and G8 suggests them as a potential source of raw materials for the food/feed industry.


Assuntos
Antioxidantes/análise , Metabolômica , Mutação , Salvia/química , Sementes/química , Sementes/genética , Suplementos Nutricionais/análise , Ácidos Graxos/análise , Ácidos Graxos Ômega-3/química , Ácidos Graxos Insaturados/análise , Cromatografia Gasosa-Espectrometria de Massas , Genótipo , Açúcares/análise , Ultrassom
9.
Nat Prod Res ; 31(18): 2119-2125, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28105862

RESUMO

Mushrooms produce a wide range of bioactive polysaccharides, different from each other in chemical structure and biological effects. In the last years, the idea to develop functional foods or drugs containing fungal polysaccharides is attracting great attention. Fruiting bodies of Basidiomycetes Ganoderma lucidum are commonly used in Oriental medicine to treat several disorders. G. lucidum polysaccharides - mainly ß-glucans and heteroglycans - have numerous biological properties such as antitumour and immunomodulatory activities. This report shows, by gene expression analyses and bioenergetic assays, immunomodulatory properties and capacity to improve glucose metabolism of a water-soluble heteroglycan extracted from mycelium of an Italian isolate of G. lucidum. The findings suggest the use of the heteroglycan as probiotic or ingredient in functional foods, being easy to produce and disperse in a food matrix thanks to its water-solubility. Heteroglycan could exert protective effects in pro-inflammatory conditions and benefits for people characterised by suppressed immune response.


Assuntos
Polissacarídeos Fúngicos/química , Polissacarídeos Fúngicos/farmacologia , Glucanos/farmacologia , Fatores Imunológicos/farmacologia , Reishi/química , Linhagem Celular , Citocinas/genética , Avaliação Pré-Clínica de Medicamentos/métodos , Regulação da Expressão Gênica/efeitos dos fármacos , Glucanos/química , Glucose/metabolismo , Humanos , Fatores Imunológicos/química , Itália , Espectroscopia de Ressonância Magnética , Medicina Tradicional do Leste Asiático , Micélio/química , Solubilidade , Água
10.
Phytochem Anal ; 27(5): 304-14, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27437863

RESUMO

INTRODUCTION: Globe artichoke (Cynara cardunculus L. var. scolymus L. Fiori) and cardoon (Cynara cardunculus L. var. altilis DC) are sources of nutraceuticals and bioactive compounds. OBJECTIVES: To apply a NMR metabolomic fingerprinting approach to Cynara cardunculus heads to obtain simultaneous identification and quantitation of the major classes of organic compounds. METHODOLOGY: The edible part of 14 Globe artichoke populations, belonging to the Romaneschi varietal group, were extracted to obtain apolar and polar organic extracts. The analysis was also extended to one species of cultivated cardoon for comparison. The (1) H-NMR of the extracts allowed simultaneous identification of the bioactive metabolites whose quantitation have been obtained by spectral integration followed by principal component analysis (PCA). RESULTS: Apolar organic extracts were mainly based on highly unsaturated long chain lipids. Polar organic extracts contained organic acids, amino acids, sugars (mainly inulin), caffeoyl derivatives (mainly cynarin), flavonoids, and terpenes. The level of nutraceuticals was found to be highest in the Italian landraces Bianco di Pertosa zia E and Natalina while cardoon showed the lowest content of all metabolites thus confirming the genetic distance between artichokes and cardoon. CONCLUSION: Metabolomic approach coupling NMR spectroscopy with multivariate data analysis allowed for a detailed metabolite profile of artichoke and cardoon varieties to be obtained. Relevant differences in the relative content of the metabolites were observed for the species analysed. This work is the first application of (1) H-NMR with multivariate statistics to provide a metabolomic fingerprinting of Cynara scolymus. Copyright © 2016 John Wiley & Sons, Ltd.


Assuntos
Metabolômica , Espectroscopia de Prótons por Ressonância Magnética/métodos , Aminoácidos/análise , Carboidratos/análise , Flavonoides/análise , Análise Multivariada , Polifenóis/análise , Análise de Componente Principal
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