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1.
Phytother Res ; 38(5): 2388-2405, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38430052

RESUMO

The prevalence of overweight and obesity has progressively increased in the last few years, becoming a real threat to healthcare systems. To date, the clinical management of body weight gain is an unmet medical need, as there are few approved anti-obesity drugs and most require an extensive monitoring and vigilance due to risk of adverse effects and poor patient adherence/persistence. Growing evidence has shown that the gasotransmitter hydrogen sulfide (H2S) and, therefore, H2S-donors could have a central role in the prevention and treatment of overweight/obesity. The main natural sources of H2S-donors are plants from the Alliaceae (garlic and onion), Brassicaceae (e.g., broccoli, cabbage, and wasabi), and Moringaceae botanical families. In particular, polysulfides and isothiocyanates, which slowly release H2S, derive from the hydrolysis of alliin from Alliaceae and glucosinolates from Brassicaceae/Moringaceae, respectively. In this review, we describe the emerging role of endogenous H2S in regulating adipose tissue function and the potential efficacy of natural H2S-donors in animal models of overweight/obesity, with a final focus on the preliminary results from clinical trials. We conclude that organosulfur-containing plants and their extracts could be used before or in combination with conventional anti-obesity agents to improve treatment efficacy and reduce inflammation in obesogenic conditions. However, further high-quality studies are needed to firmly establish their clinical efficacy.


Assuntos
Sulfeto de Hidrogênio , Obesidade , Sobrepeso , Humanos , Obesidade/tratamento farmacológico , Animais , Sobrepeso/tratamento farmacológico , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Fármacos Antiobesidade/farmacologia , Glucosinolatos/farmacologia , Glucosinolatos/química , Isotiocianatos/farmacologia , Brassicaceae/química
2.
J Am Soc Mass Spectrom ; 33(11): 2108-2119, 2022 Nov 02.
Artigo em Inglês | MEDLINE | ID: mdl-36264209

RESUMO

An analytical approach based on reversed-phase liquid chromatography coupled to electrospray ionization Fourier-transform mass spectrometry in negative ion mode (RPLC-ESI-(-)-FTMS) was developed for the untargeted characterization of glucosinolates (GSL) in the polar extracts of four Brassica microgreen crops, namely, garden cress, rapeseed, kale, and broccoli raab. Specifically, the all ion fragmentation (AIF) operation mode enabled by a quadrupole-Orbitrap mass spectrometer, i.e., the systematic fragmentation of all ions generated in the electrospray source, followed by the acquisition of an FTMS spectrum, was exploited. First, the best qualifying product ions for GSL were recognized from higher-energy collisional dissociation (HCD)-FTMS2 spectra of representative standard GSL. Extracted ion chromatograms (EIC) were subsequently obtained for those ions from RPLC-ESI(-)-AIF-FTMS data referred to microgreen extracts, by plotting the intensity of their signals as a function of retention time. The alignment of peaks detected in the EIC traces was finally exploited for the recognition of peaks potentially related to GSL, with the EIC obtained for the sulfate radical anion [SO4]•- (exact m/z 95.9523) providing the highest selectivity. Each putative GSL was subsequently characterized by HCD-FTMS2 analyses and by collisionally induced dissociation (CID) multistage MSn (n = 2, 3) acquisitions based on a linear ion trap mass spectrometer. As a result, up to 27 different GSLs were identified in the four Brassica microgreens. The general method described in this work appears as a promising approach for the study of GSL, known and novel, in plant extracts.


Assuntos
Brassica , Glucosinolatos , Glucosinolatos/análise , Glucosinolatos/química , Cromatografia Líquida/métodos , Espectrometria de Massas por Ionização por Electrospray/métodos , Íons/química , Extratos Vegetais
3.
Fitoterapia ; 162: 105282, 2022 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-35988845

RESUMO

BACKGROUND: The roots of horseradish (Armoracia rusticana) are used for infections of respiratory airway and for urinary tract infections due to isothiocyanates (ITC), enzymatically formed during fermentation of glucosinolates by myrosinase. HYPOTHESIS/PURPOSE: The present study aims to present a comprehensive overview on the phytochemical composition of A. rusticana roots, especially concerning isothiocyanates and respective glucosinolates. The complex flavonoid spectrum of the herbal material is reviewed. Published data on in vitro activity of horseradish extracts and isolated compounds are summarized. These data indicate well-established use of horseradish as an antibacterial remedy against bacterial infections of the airway and urinary tract. STUDY DESIGN: To answer the question if other compounds from A. rusticana beside ITC contribute to the antibacterial activity, non-targeted LC-MS studies were performed with fermented and non-fermented horseradish extracts, and detailed phytochemical profiles were established. RESULTS: Comparative investigations on the antibacterial activity indicated that only ITC-containing extracts and fractions exert antibacterial activity. The huge variety of non-ITC compounds do not significantly contribute to the antibacterial activity, but can be used for analytical characterisation and quality control of the herbal material. Detailed phytochemical analysis additionally revealed a variety of compounds, not described until now for horseradish roots: the flavonol glycosides kaempferol-3-O-ß-d-xylopyranosyl-(1''' â†’ 2'')-ß-d-galactopyranoside, kaempferol-3-O-α-l-rhamnopyranosyl-(1''' â†’ 6'')-ß-d-glucopyranoside, kaempferol-3-O-ß-d-glucopyranoside, Kaempferol-3-O-ß-d-xylopyranosyl-7-O-ß-d-glucopyranoside, Kaempferol-3-O-ß-d-xylopyranosyl-(1'''' â†’ 2''')-ß-d-galactopyranoside-7-O-ß-d-glucopyranoside, the oxo-indole derivative spirobrassinin, the phenylthiazole 2-methylsulfanyl-4-phenyl-4,5-dihydro-1,3-thiazole, a series of lysophophatidylethanolamine and 13 different N-phenylpropenoyl-L-amino acids. CONCLUSION: The antibacterial effects of horseradish are only due to the presence of glucosinolates resp. the corresponding ITC, and the detailed overall composition of horseradish extracts has been reported.


Assuntos
Armoracia , Glucosinolatos , Aminoácidos , Antibacterianos/farmacologia , Armoracia/química , Galactose/análise , Glucosinolatos/análise , Glucosinolatos/química , Glucosinolatos/farmacologia , Glicosídeos/análise , Indóis , Isotiocianatos/farmacologia , Quempferóis , Estrutura Molecular , Compostos Fitoquímicos/análise , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/análise , Extratos Vegetais/farmacologia , Raízes de Plantas/química , Tiazóis/análise
4.
Food Funct ; 13(2): 664-674, 2022 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-34933325

RESUMO

We prepared a detoxified rapeseed protein isolate (RPI) by phytase/ethanol treatment based on alkaline extraction and acidic precipitation. Contents of protein, fat, ash, moisture, crude fiber, glucosinolates, phytic acid, and phenolics and color were determined. To evaluate the safety of detoxified RPI, five groups of C57 mice (detoxified RPI [10 and 20 g kg-1]; commercial soybean protein isolate (SPI) [10 g kg-1]; non-detoxified RPI [10 g kg-1]; control) were used in the acute-toxicity test. Bodyweight and pathology parameters were recorded at different time points, followed by macroscopic examination, organ-weight measurement and microstructure examination. After pretreatment of rapeseed meals with phytase (enzyme : substrate ratio, 1 : 5 mg g-1) for 1.5 h and two-time ethanol extraction for precipitated protein, the chemical characteristics in RPI were protein (88.26%), fat (0.57%), ash (2.72%), moisture (1.90%), crude fiber (0.77%), glucosinolates (0 µmol g-1), phytic acid (0.17%), phenolics (0.36%) and whiteness (73.38). Treatment resulted in significant removal of anti-nutritional factors (ANFs) and increased whiteness in detoxified RPI compared with non-detoxified RPI, and lower than in cruciferin-rich canola protein isolate (Puratein®). Experimental-related effects on bodyweight, clinical observations, or clinicopathology, in mice treated with detoxified RPI were not observed except for a decreased thyroid gland/parathyroid gland index in mice treated with non-detoxified RPI. Furthermore, the no-observed-effect level (NOEL) was 10 g kg-1 of detoxified RPI, whereas the no-observed-adverse-effect-level (NOAEL) was the highest fed level of 20 g kg-1 of detoxified RPI. Overall, detoxified RPI prepared by the combined treatment of phytase and ethanol was considered safe under the conditions tested, in which the contents of the main ANFs were reduced significantly.


Assuntos
Brassica napus/química , Glucosinolatos , Extratos Vegetais , Proteínas de Plantas , Animais , Peso Corporal/efeitos dos fármacos , Feminino , Glucosinolatos/análise , Glucosinolatos/química , Glucosinolatos/isolamento & purificação , Glucosinolatos/toxicidade , Masculino , Camundongos , Tamanho do Órgão/efeitos dos fármacos , Extratos Vegetais/análise , Extratos Vegetais/química , Extratos Vegetais/toxicidade , Proteínas de Plantas/análise , Proteínas de Plantas/química , Proteínas de Plantas/toxicidade
5.
Molecules ; 26(13)2021 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-34279379

RESUMO

Sulforaphane (SFN) is a powerful health-promoting compound found in broccoli in the form of its inactive precursor, glucoraphanin (GFN). SFN formation occurs through the enzymatic hydrolysis of glucoraphanin by myrosinase under specific chemical conditions. Its incorporation in food formulations has been hindered by the thermal instability of SFN and low concentration in Brassicaceae. Then, extracting SFN from broccoli at a temperature below 40 °C appears as an option to recover and stabilize SFN, aiming at delivering it as a nutraceutical. We studied an eco-friendly extraction process to obtain an SFN-rich extract from broccoli. The effect of the broccoli mass/solvent ratio, ethanol concentration in the extractant solution, and extraction time on the recovery of SFN, GFN, phenolic compounds, and antioxidant activity were studied through a Box-Behnken design. The regression models explained more than 70% of the variability in the responses, adequately representing the system. The experimental factors differently affected the bioactive compound recovery and antioxidant activity of the extracts. The extraction conditions that allowed the highest recovery of bioactive compounds and antioxidant activity were identified and experimentally validated. The results may provide the basis for the design of a process to produce a sulforaphane-rich food supplement or nutraceutical by using a GRAS extractant.


Assuntos
Brassica/química , Fracionamento Químico/métodos , Isotiocianatos/química , Sulfóxidos/química , Etanol/química , Glucosinolatos/análise , Glucosinolatos/química , Isotiocianatos/análise , Oximas/análise , Oximas/química , Extratos Vegetais/química , Sulfóxidos/análise
6.
J Sci Food Agric ; 101(14): 5872-5879, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-33788976

RESUMO

BACKGROUND: This study investigated the chemical profile and biological activity of Diplotaxis erucoides subsp. erucoides (L.) DC. (Brassicaceae) collected in Sicily (Italy). RESULTS: Liquid chromatography coupled with electrospray ionization and high-resolution mass spectrometry (LC-ESI/HRMS) analysis of the ethanol extract revealed the presence of 42 compounds - glucosinolates, hydroxycinnamic acids, flavonoids, and oxylipins. The extract was tested for its antioxidant activity using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic) acid (ABTS), ferric reducing ability power (FRAP), and ß-carotene bleaching tests. Promising protection from lipid peroxidation was observed after 30 min of incubation in a ß-carotene bleaching test (IC50 of 3.32 µg mL-1 ). The inhibition of carbohydrates-hydrolyzing enzymes resulted in IC50 values of 85.18 and 92.36 µg mL-1 for α-amylase and α-glucosidase, respectively. Significant inhibition against lipase enzyme was observed (IC50 of 61.27 µg mL-1 ). CONCLUSION: Diplotaxis erucoides can be considered a potential source of antioxidant, hypoglycemic, and hypolipidemic bioactives. © 2021 Society of Chemical Industry.


Assuntos
Brassicaceae/química , Glucosinolatos/química , Oxilipinas/química , Extratos Vegetais/química , Antioxidantes/química , Cromatografia Líquida , Inibidores Enzimáticos/química , Flavonoides/química , Inibidores de Glicosídeo Hidrolases , Humanos , Espectrometria de Massas , Saladas/análise , Sicília , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/química , alfa-Glucosidases/química
7.
Biosci Biotechnol Biochem ; 85(5): 1194-1204, 2021 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-33704369

RESUMO

Papaya (Carica papaya L.) is widely cultivated in tropical and subtropical countries. While ripe fruit is a popular food item globally, the unripe fruit is only consumed in some Asian countries. To promote the utilization of unripe papaya based on the compositional changes of biological active metabolites, we performed liquid chromatography-Orbitrap-mass spectrometry-based analysis to reveal the comprehensive metabolite profile of the peel and pulp of unripe and ripe papaya fruits. The number of peaks annotated as phenolics and aminocarboxylic acids increased in the pulp and peel of ripe fruit, respectively. Putative carpaine derivatives, known alkaloids with cardiovascular effects, decreased, while carpamic acid derivatives increased in the peel of ripe fruit. Furthermore, the functionality of unripe fruit, the benzyl glucosinolate content, total polyphenol content, and proteolytic activity were detectable after heating and powder processing treatments, suggesting a potential utilization in powdered form as functional material.


Assuntos
Alcaloides/metabolismo , Ácidos Carboxílicos/metabolismo , Carica/metabolismo , Glucosinolatos/metabolismo , Redes e Vias Metabólicas/fisiologia , Polifenóis/metabolismo , Alcaloides/química , Alcaloides/classificação , Alcaloides/isolamento & purificação , Ácidos Carboxílicos/química , Ácidos Carboxílicos/classificação , Ácidos Carboxílicos/isolamento & purificação , Carica/química , Cromatografia Líquida , Culinária/métodos , Frutas/química , Frutas/metabolismo , Alimento Funcional/análise , Glucosinolatos/química , Glucosinolatos/classificação , Glucosinolatos/isolamento & purificação , Humanos , Extratos Vegetais/química , Polifenóis/química , Polifenóis/classificação , Polifenóis/isolamento & purificação , Análise de Componente Principal , Espectrometria de Massas em Tandem
8.
Biomolecules ; 11(2)2021 02 20.
Artigo em Inglês | MEDLINE | ID: mdl-33672547

RESUMO

A large proportion of broccoli biomass is lost during primary production, distribution, processing, and consumption. This biomass is rich in polyphenols and glucosinolates and can be used for the production of bioactive rich ingredients for food and nutraceutical applications. This study evaluated thermosonication (TS) (18 kHz, 0.6 W/g, 40-60 °C, 3-7 min) for the pre-treatment of broccoli florets to enhance enzymatic conversion of glucoraphanin into the bioactive sulforaphane. TS significantly increased sulforaphane yield, despite a decrease in myrosinase activity with increasing treatment intensity. The highest sulforaphane yield of ~2.9 times that of untreated broccoli was observed for broccoli thermosonicated for 7 min at 60 °C, which was 15.8% higher than the corresponding yield for thermal processing without sonication (TP) at the same condition. This was accompanied by increase in the residual level of glucoraphanin (~1.8 and 2.3 time respectively after TP and TS at 60 °C for 7 min compared to control samples) indicating that treatment-induced release of bound glucoraphanin from the cell wall matrix and improved accessibility could be at least partially responsible for the enhanced sulforaphane yield. The result indicates the potential of TS for the conversion of broccoli biomass into high sulforaphane broccoli-based ingredients.


Assuntos
Biomassa , Brassica/metabolismo , Manipulação de Alimentos , Tecnologia de Alimentos , Isotiocianatos/química , Sonicação , Sulfóxidos/química , Parede Celular/metabolismo , Suplementos Nutricionais , Glucosinolatos/química , Glicosídeo Hidrolases/química , Glicosídeo Hidrolases/metabolismo , Temperatura Alta , Oximas/química , Polifenóis/química , Temperatura
9.
J Mass Spectrom ; 56(2): e4690, 2021 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-33410238

RESUMO

Maca is a Peruvian tuberous root of the Brassicaceae family grown in the central Andes between altitudes of 4000 and 4500 m. The medicinal plant is a nutraceutical with important biological activities and health effects. In this study, we report a rapid high-performance thin layer chromatography (HPTLC)-(-)desorption electrospray ionization (DESI)-mass spectrometry (MS) method to profile and separate intact glucosinolates without prior biochemical modifications from the hydromethanolic extracts of two phenotypes, red and black Maca (Lepidium peruvianum) seeds. In the first stage of the plant's life cycle, aromatic glucosinolates were the main chemical constituents whereby six aromatic, three indole, and one aliphatic glucosinolate were tentatively identified. At the seedling stage, glucolepigramin/Glucosinalbin was the most predominant precursor, rather than Glucotropaeolin, which is mainly found in hypocotyls and roots. These findings lead us to suggest that glucolepigramin/glucosinalbin play a major role as active precursors in the biosynthetic pathways of other secondary metabolites in the early stages of plant development. Between red and black Maca seeds, only minor differences in the relative abundances of glucosinolates were observed rather than different plant metabolites. For the first time, we report six potential plant antibiotics, phytoanticipins: glycosylated ascorbigens and dihydroascorbigens from Maca seeds. We also investigated a targeted reverse phase C18 functionalized TLC-DESI-MS method with high sensitivity and specificity for Brassicaceae fatty acids in Maca seeds and health supplements such as black Maca root lyophilized powder and tinctures. The investigation of secondary metabolites by normal and reverse phase TLC-DESI-MS methods, described in this study, can aid in their identification as they begin to emerge in later stages of development in plant tissues such as leaves, hypocotyls, and roots.


Assuntos
Cromatografia em Camada Fina/métodos , Glucosinolatos/análise , Lepidium/química , Compostos Fitoquímicos/análise , Espectrometria de Massas por Ionização por Electrospray/métodos , Cromatografia de Fase Reversa/métodos , Suplementos Nutricionais , Glucosinolatos/química , Glucosinolatos/isolamento & purificação , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/química , Sementes/química
10.
Molecules ; 25(22)2020 Nov 11.
Artigo em Inglês | MEDLINE | ID: mdl-33187324

RESUMO

The main compounds in both extracts were gluconasturtiin, 4-methoxyglucobrassicin and rutoside, the amounts of which were, respectively, determined as 182.93, 58.86 and 23.24 mg/100 g dry weight (DW) in biomass extracts and 640.94, 23.47 and 7.20 mg/100 g DW in plant herb extracts. The antioxidant potential of all the studied extracts evaluated using CUPRAC (CUPric Reducing Antioxidant Activity), FRAP (Ferric Reducing Ability of Plasma), and DPPH (1,1-diphenyl-2-picrylhydrazyl) assays was comparable. The anti-inflammatory activity of the extracts was tested based on the inhibition of 15-lipoxygenase, cyclooxygenase-1, cyclooxygenase-2 (COX-2), and phospholipase A2. The results demonstrate significantly higher inhibition of COX-2 for in vitro cultured biomass compared with the herb extracts (75.4 and 41.1%, respectively). Moreover, all the studied extracts showed almost similar antibacterial and antifungal potential. Based on these findings, and due to the fact that the growth of in vitro microshoots is independent of environmental conditions and unaffected by environmental pollution, we propose that biomass that can be rapidly grown in RITA® bioreactors can serve as an alternative source of bioactive compounds with valuable biological properties.


Assuntos
Antioxidantes/farmacologia , Glucosinolatos/química , Nasturtium/química , Extratos Vegetais/química , Antibacterianos/farmacologia , Anti-Inflamatórios/farmacologia , Antifúngicos/farmacologia , Biomassa , Reatores Biológicos , Compostos de Bifenilo/química , Cromatografia Líquida de Alta Pressão , Ciclo-Oxigenase 1/química , Ciclo-Oxigenase 2/química , Flavonoides/química , Imersão , Nasturtium/crescimento & desenvolvimento , Compostos Fitoquímicos/química , Picratos/química , Brotos de Planta/química , Brotos de Planta/crescimento & desenvolvimento
11.
Molecules ; 25(14)2020 Jul 20.
Artigo em Inglês | MEDLINE | ID: mdl-32698371

RESUMO

Glucosinolates (GLs) are of great interest for their potential as antioxidant and anticancer compounds. In this study, macroporous crosslinked copolymer adsorbents of poly (glycidyl methacrylate) (PGMA) and its amine (ethylenediamine, diethylamine, triethylamine)-modified derivatives were prepared and used to purify the GLS glucoerucin in a crude extract obtained from a cruciferous plant. These four adsorbents were evaluated by comparing their adsorption/desorption and decolorization performance for the purification of glucoerucin from crude plant extracts. According to the results, the strongly basic triethylamine modified PGMA (PGMA-III) adsorbent showed the best adsorption and desorption capacity of glucoerucin, and its adsorption data was a good fit to the Freundlich isotherm model and pseudo-second-order kinetics; the PGMA adsorbent gave the optimum decolorization performance. Furthermore, dynamic adsorption/desorption experiments were carried out to optimize the purification process. Two glass columns were serially connected and respectively wet-packed with PGMA and PGMA-III adsorbents so that glucoerucin could be decolorized and isolated from crude extracts in one process. Compared with KCl solution, aqueous ammonia was a preferable desorption solvent for the purification of glucoerucin and overcame the challenges of desalination efficiency, residual methanol and high operation costs. The results showed that after desorption with 10% aqueous ammonia, the purity of isolated glucoerucin was 74.39% with a recovery of 80.63%; after decolorization with PGMA adsorbent, the appearance of glucoerucin was improved and the purity increased by 11.30%. The process of using serially connected glass columns, wet-packed with PGMA and PGMA-III, may provide a simple, low-cost, and efficient method for the purification of GLs from cruciferous plants.


Assuntos
Aminas/química , Brassicaceae/química , Glucosinolatos/isolamento & purificação , Ácidos Polimetacrílicos/química , Adsorção , Glucose/análogos & derivados , Glucose/química , Glucose/isolamento & purificação , Glucosinolatos/química , Concentração de Íons de Hidrogênio , Imidoésteres/química , Imidoésteres/isolamento & purificação , Cinética , Ácidos Polimetacrílicos/síntese química , Soluções , Solventes/química , Espectroscopia de Infravermelho com Transformada de Fourier
12.
Nutrients ; 12(3)2020 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-32213900

RESUMO

Cancer is the main cause of mortality and morbidity worldwide. Although a large variety of therapeutic approaches have been developed and translated into clinical protocols, the toxic side effects of cancer treatments negatively impact patients, allowing cancer to grow. Brassica metabolites are emerging as new weapons for anti-cancer therapeutics. The beneficial role of the consumption of brassica vegetables, the most-used vegetables in the Mediterranean diet, particularly broccoli, in the prevention of chronic diseases, including cardiovascular diseases, diabetes, and obesity, has been well-documented. In this review, we discuss the anti-tumor effects of the bioactive compounds from Brassica vegetables with regard to the compounds and types of cancer against which they show activity, providing current knowledge on the anti-cancer effects of Brassica metabolites against major types of tumors. In addition, we discuss the impacts of industrial and domestic processing on the compounds' functional properties before their consumption as well as the main strategies used to increase the content of health-promoting metabolites in Brassica plants through biofortification. Finally, the impacts of microbiota on the compounds' bioactivity are considered. This information will be helpful for the further development of efficacious anti-cancer drugs.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Brassica/química , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/uso terapêutico , Disponibilidade Biológica , Brassica/classificação , Estudos Clínicos como Assunto , Avaliação Pré-Clínica de Medicamentos , Glucosinolatos/química , Glucosinolatos/metabolismo , Glucosinolatos/farmacologia , Humanos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico , Relação Estrutura-Atividade
13.
J Agric Food Chem ; 68(10): 3121-3131, 2020 Mar 11.
Artigo em Inglês | MEDLINE | ID: mdl-32053364

RESUMO

A new method to simultaneously analyze various glucosinolates (GSLs) and isothiocyanates (ITCs) by reversed-phase ultra-high-performance liquid chromatography-electron spray ionization-tandem mass spectrometry has been developed and validated for 14 GSLs and 15 ITCs. It involved derivatization of ITCs with N-acetyl-l-cysteine (NAC). The limits of detection were 0.4-1.6 µM for GSLs and 0.9-2.6 µM for NAC-ITCs. The analysis of Sinapis alba, Brassica napus, and Brassica juncea extracts spiked with 14 GSLs and 15 ITCs indicated that the method generally had good intraday (≤10% RSD) and interday precisions (≤16% RSD). Recovery of the method was unaffected by the extracts and within 71-110% for GSLs and 66-122% for NAC-ITCs. The method was able to monitor the enzymatic hydrolysis of standard GSLs to ITCs in mixtures. Furthermore, GSLs and ITCs were simultaneously determined in Brassicaceae plant extracts before and after myrosinase treatment. This method can be applied to further investigate the enzymatic conversion of GSLs to ITCs in complex mixtures.


Assuntos
Brassicaceae/química , Cromatografia Líquida de Alta Pressão/métodos , Glucosinolatos/química , Isotiocianatos/química , Extratos Vegetais/química , Sinapis/química , Espectrometria de Massas em Tandem/métodos , Cromatografia de Fase Reversa/métodos , Espectrometria de Massas por Ionização por Electrospray/métodos
14.
Carbohydr Res ; 488: 107898, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31918339

RESUMO

The glucosinolate (GSL) profiles of wild-growing plants from the genus Hesperis, i.e. Hesperis laciniata All. (leaf, stem, flower, and root) from Croatia and Hesperis matronalis L. (leaf, stem, flower, seed, and root) from Canada, were established by LC-MS. During this investigation, 5-(methylsulfanyl)pentyl- (3), 6-(methylsulfanyl)hexyl- (4), 6-(methylsulfinyl)hexyl- (6), and 4'-α-l-rhamnopyranosyloxybenzyl- (17) GSLs were identified. In addition, the presence of 7-(methylsulfinyl)heptyl GSL (18), hydroxy-(α-l-rhamnopyranosyloxy)benzyl GSL, and of one d-apiosylated analogue of 17 were suggested. Moreover, one new GSL, 4'-O-ß-d-apiofuranosylglucomatronalin (19) was isolated from H. laciniata (flower, steam and leaf) and characterized by spectroscopic data interpretation. Finally, we report the presence of 3, 4, 6, 19, glucosinalbin (12), and 4-hydroxyglucobrassicin (20) in H. matronalis and hypothesize the presence of glucomatronalin (13) and 3-hydroxy-6-(methylsulfanyl)hexyl GSL (21).


Assuntos
Brassicaceae/química , Glucosinolatos/análise , Extratos Vegetais/análise , Canadá , Cromatografia Líquida , Croácia , Glucosinolatos/química , Espectrometria de Massas , Estrutura Molecular , Extratos Vegetais/química , Folhas de Planta/química , Raízes de Plantas/química , Sementes/química
15.
Molecules ; 24(24)2019 Dec 13.
Artigo em Inglês | MEDLINE | ID: mdl-31847178

RESUMO

Sisymbrium officinale (L.) Scop., commonly known as "hedge mustard" or "the singer's plant" is a wild plant common in Eurasian regions. Its cultivation is mainly dedicated to herboristic applications and it has only recently been introduced into Italy. The active botanicals in S. officinale are glucosinolates, generally estimated by using UV or high-performance liquid chromatography (HPLC). Using both techniques, we measured the total glucosinolates from S. officinale in different parts of the plant as roots, leaves, seeds, and flowers. A comparison was made for cultivated and wild samples, and for samples obtained with different pre-treatment and fresh, frozen, and dried storage conditions. Cultivated and wild plants have a comparable amount of total glucosinolates, while drying procedures can reduce the final glucosinolates content. The content in glucoputranjivin, which is the chemical marker for glucosinolates in S. officinale, has been determined using HPLC and a pure reference standard. Glucoputranjivin and two isothiocyanates from S. officinale have been submitted to in vitro assays with the platform of bitter taste receptors of the T2Rs family. The results show that glucoputranjivin is a selective agonist of receptor T2R16.


Assuntos
Brassicaceae/crescimento & desenvolvimento , Glucosinolatos/química , Isotiocianatos/farmacologia , Receptores Acoplados a Proteínas G/agonistas , Brassicaceae/química , Cromatografia Líquida de Alta Pressão , Flores/química , Liofilização , Regulação da Expressão Gênica/efeitos dos fármacos , Glucosinolatos/farmacologia , Células HEK293 , Humanos , Isotiocianatos/química , Extratos Vegetais/química , Folhas de Planta/química , Raízes de Plantas/química , Sementes/química , Raios Ultravioleta
16.
J Agric Food Chem ; 67(45): 12528-12537, 2019 Nov 13.
Artigo em Inglês | MEDLINE | ID: mdl-31631662

RESUMO

Seeds of 32 pure lines and 6 commercial broccoli cultivars were used to investigate variation in glucosinolates and their breakdown products. The aliphatic glucosinolate content was 54.5-218.7 µmol/g fresh weight, accounting for >90% of the total glucosinolates. The major glucosinolates found were glucoraphanin and glucoerucin in 27 samples and progoitrin in 7 samples. A gas chromatography-flame ionization detector (GC-FID) method was used to identify glucosinolate breakdown products; nine products were directly determined using standards. Using Arabidopsis thaliana lines myb28myb29 and Landsberg erecta to hydrolyze each reference glucosinolate, seven products were tentatively identified. 4-(Methylsulfinyl)butyl isothiocyanate and 5-(methylsulfinyl)pentanenitrile contents were 2.6-91.1 µmol/g fresh weight and 0-35.4 µmol/g fresh weight, respectively, with epithionitriles being more common than nitriles in accessions rich in alkenyl glucosinolate. Additionally, (S)-5-vinyl-1,3-oxazolidine-2-thione was detected in accessions rich in progoitrin. Specific lines with altered glucosinolate profiles and breakdown products were obtained and discussed according to the putative glucosinolate metabolism pathway.


Assuntos
Brassica/química , Glucosinolatos/química , Extratos Vegetais/química , Arabidopsis/química , Arabidopsis/metabolismo , Brassica/metabolismo , Glucosinolatos/metabolismo , Extratos Vegetais/metabolismo , Sementes/química , Sementes/metabolismo
17.
J Agric Food Chem ; 67(40): 11187-11197, 2019 Oct 09.
Artigo em Inglês | MEDLINE | ID: mdl-31552744

RESUMO

This study aims to investigate the effect of glucosinolate (GSL) degradation on the volatile odor of rapeseed oil (RO) during roasting. Volatile compounds of RO and individual GSL contents in the seeds were identified and measured during roasting, separately. Total GSL content decreased by 30.47-84.44%. Nitriles were the key volatile compounds that were negatively correlated with GSLs for all samples. Results indicate that GSL degradation significantly affects the volatile odor of RO and tends to produce low-carbon nitriles. Furthermore, the thermal degradation pathways of GSLs were explored according to the structure of individual GSLs and nitriles. These results provide information for the thermal degradation pathways of GSLs and the formation mechanism of nitriles during seed roasting.


Assuntos
Glucosinolatos/química , Óleos Voláteis/química , Óleo de Brassica napus/química , Brassica rapa/química , Culinária , Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Odorantes/análise , Compostos Orgânicos Voláteis/química
18.
Nutrients ; 11(7)2019 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-31323988

RESUMO

The tropical tree Moringa oleifera produces high yields of protein-rich leaf biomass, is widely used as a food source, contains an abundance of phytochemicals, and thus has great potential for chronic disease prevention and perhaps, treatment. We have developed and characterized standardized ways of preparing aqueous "teas" from moringa leaves to deliver precisely calibrated levels of phytochemicals for use in clinical trials. These phytochemicals, especially the glucosinolate glucomoringin and the isothiocyanate moringin, produced from it following hydrolysis by the enzyme myrosinase, provide potent anti-inflammatory and cytoprotective indirect antioxidant activity. The taste of both hot and cold teas is palatable without the need for flavor masking. These teas can be easily and reproducibly prepared in underserved tropical regions of the world where moringa is cultivated. Isothiocyanate yield from a cold extraction was rapid and essentially complete after 30 min and its anti-inflammatory potential is comparable to that of equimolar purified moringin. A preparation similar to this may be safe to consume with respect to its bacterial titer even after 48 h without refrigeration. Thus, facile delivery of moringa tea to both adults and children for clinical evaluation of their effects on such conditions as autism, diabetes, and hypertension, is now possible.


Assuntos
Glucosinolatos/administração & dosagem , Isotiocianatos/administração & dosagem , Moringa oleifera/química , Folhas de Planta/química , Administração Oral , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Bebidas , Glucosinolatos/química , Isotiocianatos/química , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/antagonistas & inibidores , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Células RAW 264.7
19.
J Sci Food Agric ; 99(12): 5499-5507, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31099412

RESUMO

BACKGROUND: Brassica plants contain a wide spectrum of bioactive components that are responsible for their health-promoting potential such as vitamins, polyphenols and glucosinolates. This study attempted to relate the composition of bioactive phytochemicals and chosen biological activities (antioxidant, cytotoxic, anti-genotoxic, and influence on enzymatic activities) for extracts from differently pigmented cabbage (white and red) and cauliflower (white and purple) varieties. The assumption was that tested varieties of the same plant would exhibit similar chemical composition differing mostly in anthocyanin content and that the latter will be reflected in biological activity. RESULTS: Profiles of antioxidants obtained using post-column derivatization with ABTS radical confirmed, that the content and composition of anthocyanins is strongly correlated with the antioxidant capacity of tested plant extracts measured by spectrophotometric methods (ABTS, FC, DPPH, FRAP), and Cellular Antioxidant Activity (CAA) test. The results of determinations of other biological activities showed that opposite to purified bioactive phytochemicals, in the case of actual plant foods, there was no simple relationship between anthocyanin content and chemopreventive potential. CONCLUSION: Obtained results suggest that there must be some kind of interaction between different phytochemicals, which decides on the final health promoting activity of edible plants as suggested by for example the food synergy concept. © 2019 Society of Chemical Industry.


Assuntos
Brassica/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Antocianinas/química , Antioxidantes/química , Brassica/classificação , Cor , Glucosinolatos/química , Polifenóis/química
20.
Heredity (Edinb) ; 123(3): 318-336, 2019 09.
Artigo em Inglês | MEDLINE | ID: mdl-30911141

RESUMO

Heterosis refers to the superior performance of F1 hybrids over their respective parental inbred lines. Although the genetic and expression basis of heterosis have been previously investigated, the metabolic basis for this phenomenon is poorly understood. In a preliminary morphological study in Brassica juncea, we observed significant heterosis at the 50% flowering stage, wherein both the growth and reproduction of F1 reciprocal hybrids were greater than that of their parents. To identify the possible metabolic causes or consequences of this heterosis, we carried out targeted LC-MS analysis of 48 primary (amino acids and sugars) and secondary metabolites (phytohormones, glucosinolates, flavonoids, and phenolic esters) in five developmental tissues at 50% flowering in hybrids and inbred parents. Principal component analysis (PCA) of metabolites clearly separated inbred lines from their hybrids, particularly in the bud tissues. In general, secondary metabolites displayed more negative heterosis values in comparison to primary metabolites. The tested primary and secondary metabolites displayed both additive and non-additive modes of inheritance in F1 hybrids, wherein the number of metabolites showing an additive mode of inheritance were higher in buds and siliques (52.77-97.14%) compared to leaf tissues (47.37-80%). Partial least regression (PLS) analysis further showed that primary metabolites, in general, displayed higher association with morphological parameters in F1 hybrids. Overall, our results are consistent with a resource-cost model for heterosis in B. juncea, where metabolite allocation in hybrids appears to favor growth, at the expense of secondary metabolism.


Assuntos
Quimera/metabolismo , Vigor Híbrido , Padrões de Herança , Metaboloma , Mostardeira/metabolismo , Metabolismo Secundário/genética , Quimera/genética , Quimera/crescimento & desenvolvimento , Produtos Agrícolas , Flavonoides/biossíntese , Flavonoides/química , Flores/genética , Flores/crescimento & desenvolvimento , Flores/metabolismo , Regulação da Expressão Gênica no Desenvolvimento , Regulação da Expressão Gênica de Plantas , Glucosinolatos/biossíntese , Glucosinolatos/química , Mostardeira/genética , Mostardeira/crescimento & desenvolvimento , Fenóis/química , Fenóis/metabolismo , Melhoramento Vegetal , Reguladores de Crescimento de Plantas/biossíntese , Reguladores de Crescimento de Plantas/química , Folhas de Planta/genética , Folhas de Planta/crescimento & desenvolvimento , Folhas de Planta/metabolismo , Óleos de Plantas/metabolismo , Análise de Componente Principal
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