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1.
Food Chem ; 303: 125363, 2020 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-31472383

RESUMO

Present in many plant foods, biogenic phenolic compounds are important bioactive phytonutrients with high anti-oxidant activity and thereby are praised for their health-promoting properties. However, current food nutrient improvement by high phenolic content in staples is limited by the shortage of genetic resources rich in phenolic compounds. To resolve this obstacle, we developed a non-destructive massive analytical approach to screen wheat phenolic mutants. In grains, multiple mutant lines showed significantly higher contents of flavonoids or cell wall-bound phenolic esters. Moreover, five mutants showed higher anti-oxidant potentials in wall-bound phenolic compounds ranging from 15% to 20%, with the maximal close to natural black wheat. In contrast to black wheat, two mutants accumulated higher phenolic compounds in the endosperm. lrf4 was mapped by BSR to a concentrated genomic region in the short arm of chromosome 1A. The present work represents an efficient high-throughput strategy to increase wheat anti-oxidant potential through traditional mutagenesis.


Assuntos
Antioxidantes/metabolismo , Mutação , Fenóis/metabolismo , Triticum/genética , Triticum/metabolismo , Flavonoides/metabolismo
2.
World J Microbiol Biotechnol ; 35(9): 136, 2019 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-31432249

RESUMO

Volatile phenols such as 4-ethylphenol are produced from hydroxycinnamic acids by Dekkera bruxellensis, an important yeast contaminating alcoholic fermentations. 4-ethylphenol results from the decarboxylation and reduction of p-coumaric acid, a compound found in sugarcane musts. In wine, volatile phenols are responsible by sensorial alterations whereas in the context of bioethanol fermentation, little is known about their effects on the main yeast, Saccharomyces cerevisiae. Here we evaluated the interaction of 4-ethylphenol and pH, sucrose and ethanol on the growth and fermentation capacity of the industrial strain of S. cerevisiae PE-2. A central compound rotational design was utilized to evaluate the effect of 4-ethylphenol, pH, ethanol and sucrose concentration on the yeast maximum specific growth rate (µmax) in microplate experiments in YPS medium (Yeast extract-Peptone-Sucrose), at 30 °C. Following, single-cycle fermentations in YPS medium, pH 4.5, 17% sucrose, at 30 °C, with 4-ethylphenol in concentrations of 10 and 20 mg L-1 being added at the start or after 4 h of fermentation, were carried out. 4-ethylphenol affected µmax of S. cerevisiae in situations that resemble the conditions of industrial bioethanol production, especially the low pH of the fermentation medium and the high ethanol concentration because of the anaerobic sucrose uptake. The addition of 4-ethylphenol on fermentation resulted in significant effect on the cell yeast concentration, pH and alcohol production, with significant decrease from 86% to the range of 65-74% in the fermentative efficiency. The industrial yeast S. cerevisiae PE-2 growth and fermentative capacity were affected by the presence of 4-ethylphenol, a metabolite produced by D. bruxellensis, which may contribute to explain the impact of this yeast on bioethanol industrial production.


Assuntos
Etanol/metabolismo , Fermentação , Microbiologia Industrial , Fenóis/metabolismo , Saccharomyces cerevisiae/crescimento & desenvolvimento , Saccharomyces cerevisiae/metabolismo , Sacarose/metabolismo , Meios de Cultura/química , Inibidores do Crescimento/metabolismo , Concentração de Íons de Hidrogênio , Saccharomyces cerevisiae/efeitos dos fármacos , Temperatura Ambiente
3.
World J Microbiol Biotechnol ; 35(9): 137, 2019 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-31432268

RESUMO

The presence of very high concentrations of organic pollutants, phenols, tannins and heavy metals mainly chromium in wastewater discharged from leather industries, tags it as one of the most polluting industries. The phenolic syntans discharged from tanning units have an adverse effect on living organisms and cause serious environmental pollution, thereby making it very imperative to remove it. Among various treatment methods available for removal of phenols, biodegradation is environment friendly. The present study aims at the remediation of phenolic syntan used in the leather industry employing individual as well as co-culture of Bacillus cereus and Pseudomonas aeruginosa at varying syntan concentration in the medium. Parameters such as chemical oxygen demand (COD), total organic carbon (TOC), total phenol content (TPC) and Fourier Transform Infrared Spectroscopy (FTIR) indicating biodegradation were analyzed. Promising results were observed with P. aeruginosa, which exhibited a reduction in TPC by 62-72% in all the concentrations of syntan tested just within 12 h of inoculation, whereas about 67 and 83% reduction in COD and TOC respectively was observed for 2000 ppm concentration at the end of 5 days. B. cereus also demonstrated very good reduction in the above parameters however; percentage was less as compared to P. aeruginosa. In the case of co-culture, the TPC reduction was higher than B. cereus but lesser than P. aeruginosa. The percentage reduction in TOC and COD was highest for 500 ppm which eventually decreased for subsequent concentrations.


Assuntos
Bacillus cereus/metabolismo , Resíduos Industriais , Fenóis/metabolismo , Pseudomonas aeruginosa/metabolismo , Poluentes Químicos da Água/metabolismo , Bacillus cereus/crescimento & desenvolvimento , Análise da Demanda Biológica de Oxigênio , Biotransformação , Carbono/análise , Técnicas de Cocultura , Fenóis/análise , Pseudomonas aeruginosa/crescimento & desenvolvimento , Espectroscopia de Infravermelho com Transformada de Fourier , Água/química
4.
Bioresour Technol ; 291: 121858, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31377515

RESUMO

The improved performances during anaerobic degradation of phenol to methane with Fe(OH)3 were usually inapparent, due to its lower solubility (unaccessible to dissimilatory iron reduction) and more positive reduction potential of Fe(III)/Fe(II) (unfavorable for enriching Fe(III)-reducing bacteria [IRBs]). In this study, citrate, the organic chelates, were used to solubilize Fe(III) with the aim of improving the phenol degradation and declining the reduction potential of Fe(III)/Fe(II). Results showed that, in the co-occurrence of citrate and Fe(OH)3, the degradation rates of phenol were about 1.3-fold rapider than that with sole Fe(OH)3. Analysis of cyclic voltammetry demonstrated that the reduction potential of Fe(III)/Fe(II) in the form of Fe(OH)3 (-0.41 to -0.28 V vs Ag/AgCl) declined to -0.61 to -0.41 V. As a result, the Fe(III)-reducing genera, such as Petrimonas and Shewanella, which held a great potential of proceeding syntrophic metabolism via direct interspecies electron transfer (DIET), were significantly enriched.


Assuntos
Quelantes/farmacologia , Compostos Férricos/metabolismo , Ferro/metabolismo , Metano/metabolismo , Fenol/metabolismo , Anaerobiose , Bacteroides/efeitos dos fármacos , Bacteroides/metabolismo , Transporte de Elétrons , Oxirredução , Fenóis/metabolismo , Shewanella/efeitos dos fármacos , Shewanella/metabolismo
5.
Bioresour Technol ; 291: 121862, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31357047

RESUMO

This study evaluated the feasibility of microbial fuel cells (MFCs) for simultaneous electricity generation and degradation of phenolic compounds. The voltage generation was inhibited by 36.18-63.90%, but the degradation rate increased by 146.15-392.31% when the initial concentration of syringic acid (SA), vanillic acid (VA), and 4-hydroxybenzoic acid (HBA) increased from 0.3 to 3.0 g/L. The collaboration among the functional microbes significantly enhanced the degradation rate of parent compounds and their intermediates in MFCs systems, while the accumulated intermediates severely inhibited their complete mineralization in fermentative systems. High-throughput sequencing showed that the growth of fermentative bacteria prevailed, but electrogenic bacteria were inhibited in the anode microbial community (AMC) under high concentrations of phenolic compounds (3.0 g/L). These findings provide a better understanding of the dynamic shift and synergy effects of the AMC to evaluate its potential for the treatment of phenolic-containing wastewater.


Assuntos
Fontes de Energia Bioelétrica/microbiologia , Microbiota , Fenóis/metabolismo , Eletricidade , Eletrodos , Fermentação
6.
J Sci Food Agric ; 99(13): 6049-6059, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31342530

RESUMO

BACKGROUND: The scarcity of irrigation water is severely affecting global crop production. In this context, biostimulants are increasingly used as alternatives means against abiotic stress conditions. In this study, phenolic compounds composition and bioactive properties of common bean (Phaseolus vulgaris L.) plants grown under water stress conditions and biostimulants application were investigated. RESULTS: Sixteen individual phenolic compounds were detected in both pods and seeds with a notable difference in their compositional profile. A significant effect on phenolic compounds content and composition was also observed for the biostimulants tested. Regarding the antibacterial activity, pods of the second harvest and seed extracts showed significant efficacy against Bacillus cereus, especially in water-stressed plants, where all biostimulant treatments were more effective than positive controls. Moreover, all biostimulant treatments for seed extracts of water-stressed plants were more effective against Staphylococcus aureus compared with ampicillin, whereas streptomycin showed the best results. Extracts from pods of the second harvest from normally irrigated plants showed the best results against the fungi tested, except for Penicillium verrucosum var. cyclopium. Finally, no significant cytotoxic effects were detected. CONCLUSION: In conclusion, the biostimulants tested increased total phenolic compounds content compared with control treatment, especially in pods of the first harvest and seeds of water-stressed plants. Moreover, bioactive properties showed a varied response in regard to irrigation and biostimulant treatment. Therefore, biostimulants can be considered as a useful means towards increasing phenolic compounds content, and they may also affect the antimicrobial properties of pods and seeds extracts. © 2019 Society of Chemical Industry.


Assuntos
Desidratação , Phaseolus/química , Phaseolus/fisiologia , Fenóis/farmacologia , Extratos Vegetais/farmacologia , Água/metabolismo , Bacillus cereus/efeitos dos fármacos , Bacillus cereus/crescimento & desenvolvimento , Phaseolus/crescimento & desenvolvimento , Phaseolus/microbiologia , Fenóis/química , Fenóis/metabolismo , Extratos Vegetais/química , Extratos Vegetais/metabolismo , Sementes/química , Sementes/crescimento & desenvolvimento , Sementes/metabolismo , Sementes/microbiologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/crescimento & desenvolvimento , Estresse Fisiológico , Água/análise
7.
J Agric Food Chem ; 67(32): 8819-8838, 2019 Aug 14.
Artigo em Inglês | MEDLINE | ID: mdl-31322880

RESUMO

Recent studies about hot-water extracts from sugar maple (Acer saccharum Marsh.) bark and buds demonstrated that they contain high amounts of phenolic structures that may be used as antioxidant food additives. However, the detailed chemical composition of these maple-derived extracts has yet to be determined. By performing high-performance liquid chromatography-diode array detector-high-resolution mass spectrometry (HPLC-DAD-HRMS)-based dereplication, we were able to spike and classify almost 100 metabolites in each hot-water extract. The sugar maple bark hot-water extract is rich in simple phenolic compounds and phenylpropanoid derivatives, while bud extract contains predominantly flavonoids, benzoic acids, and their complex derivatives (condensed and hydrolyzable tannins). Among those chemical structures, we tentatively identified 69 phenolic compounds potentially reported for the first time in the genus Acer. Considering the growing commercial demand in natural products, the phenolic fingerprints of sugar maple bark and bud hot-water extracts will help in promoting these two maple-derived products as new sources of bioactive compounds in the food, nutraceutical, and cosmetic industries.


Assuntos
Acer/química , Casca de Planta/química , Extratos Vegetais/química , Acer/metabolismo , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/metabolismo , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/metabolismo , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/metabolismo , Espectrometria de Massas por Ionização por Electrospray
8.
J Sci Food Agric ; 99(14): 6350-6363, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31273796

RESUMO

BACKGROUND: Recent studies report that Ascophyllum nodosum extracts, once applied on the canopy of different crops, deliver positive effects, increasing yield, inducing tolerance to biotic stress, and improving the quality of products. However, the mechanisms of action are still unclear. In this research, vines subjected to multiple foliar applications of an A. nodosum extract (ANE) at label doses were compared with untreated vines (NTV) in accordance with a comparative approach. The investigation coupled a field experiment with a second trial conducted under semi-controlled conditions, to clarify the mechanisms of action involved. RESULTS: The biostimulant did not affect soluble solids or the acidity of grapes; instead, it improved their anthocyanin and phenolic concentrations and the respective profiles. At the time of harvest, anthocyanin, and phenolic concentration were increased by 10.4% and 14.5%, respectively, when compared to the NTV. These effects correlated with a specific modulation of genes involved in the flavonoid metabolic pathways. Moreover, grapes from ANE vines witnessed a significant reduction in the spreading of gray mold when they were either assessed in field conditions or in vitro, compared to the grapes of NTV vines. This was related to a significant upregulation of the defense-related genes of the plant. CONCLUSIONS: Overall, the results showed that A. nodosum extracts can be valuable tools in viticulture considering the emergence of challenging environmental conditions; hence, the regulation of specific metabolic pathways is the mechanism of action that leads to an increased tolerance of biotic stress and of changes in the content of grape metabolites. © 2019 Society of Chemical Industry.


Assuntos
Ascophyllum/química , Extratos Vegetais/farmacologia , Vitis/efeitos dos fármacos , Vitis/metabolismo , Antocianinas/análise , Antocianinas/metabolismo , Flavonoides/análise , Flavonoides/metabolismo , Frutas/química , Frutas/efeitos dos fármacos , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Fenóis/análise , Fenóis/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Vitis/química , Vitis/crescimento & desenvolvimento
9.
Food Chem ; 299: 125110, 2019 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-31284244

RESUMO

This study was undertaken in order to estimate the effect of in vitro propagation on antioxidant activity in strawberry. Results of this research exhibited differences between conventionally and in vitro propagated plants in respect of all traits analyzed. In spite of the decrease in range and mean content of vitamin C and polyphenols as well as antioxidant activity, the genetic gain expressed as percent of mean was higher in microplants regarding phenolics, flavonoids and antioxidant activity in contrast to conventional plants (22.39-20.83, 21.79-15.61, 9.52-3.39; resp.). Correlation and path coefficients showed changes of antioxidants inter-relations between micropropagated and conventional plants. Phenolics and vitamin C correlated positively with antioxidant activity in all genotypes. The highest positive direct effect on antioxidant activity was observed via vitamin C in microplants (0.705), while in conventional plants via phenolics (0.834). Flavonoids affected directly and positively antioxidant activity in microplants (0.103) and negatively in conventional plants (-0.143).


Assuntos
Antioxidantes/metabolismo , Flavonoides/metabolismo , Fragaria/crescimento & desenvolvimento , Fragaria/genética , Ácido Ascórbico/genética , Ácido Ascórbico/metabolismo , Flavonoides/genética , Fragaria/metabolismo , Genótipo , Fenóis/metabolismo , Polifenóis/genética , Polifenóis/metabolismo
10.
Food Chem ; 298: 125030, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31260978

RESUMO

Plant extracts from rosemary (RE), green tea (GTE), and maté (ME) were compared for the protection against iron-induced oxidation in porcine homogenates at total phenolic concentrations from 25 to 250 ppm. Lipid oxidation as indicated by TBARS was in all cases sufficiently suppressed, especially for RE. Hydrophobic RE retarded overall oxidation in the homogenates with an inverted dose-dependent response. Optimum delay of oxygen consumption was found at the lowest concentration applied, similar to protection against thiols and formation of protein radicals as measured by ESR, whereas the high concentration increased oxygen consumption and caused additionally thiol loss possibly due to thiol-quinone interactions, generating protein-phenol complexes. Hydrophilic ME or GTE increased the initial oxygen consumption rate as an indication of prooxidant activities at elevated concentrations. However, they were found to protect myoglobin and protein at those high concentrations with GTE being more efficient, possibly due to better chelation effect.


Assuntos
Antioxidantes/farmacologia , Músculo Esquelético/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Animais , Antioxidantes/química , Relação Dose-Resposta a Droga , Ilex paraguariensis/química , Ferro/química , Ferro/toxicidade , Metabolismo dos Lipídeos/efeitos dos fármacos , Músculo Esquelético/metabolismo , Mioglobina/metabolismo , Oxirredução , Fenóis/metabolismo , Extratos Vegetais/química , Rosmarinus/química , Suínos , Chá/química
11.
Food Chem ; 298: 125004, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31260986

RESUMO

There is general interest in strategies to control polyphenol oxidase (PPO)-initiated enzymatic browning because it is often associated with declining food quality. Cyclodextrins are cyclic glucan oligosaccharides that form inclusion complexes with a number of PPO substrates. This study focuses on the effect of ß-cyclodextrins (ßCyD) on PPO-catalyzed reactions. Potato enzyme extracts and semi-purified potato PPO served as enzyme sources. Substrates included phenolics endogenous to potatoes. Reaction time-courses were followed spectrophotometrically; rates were compared by analysis of variance. Extents of ßCyD inhibition of PPO-catalyzed reactions are shown to be substrate specific and can be quantitatively accounted for based on degrees of ßCyD substrate sequestration. There was no evidence for direct irreversible ßCyD inactivation of potato PPO. An apparent "direct PPO inactivation" by ßCyD is shown to result from a sequence of sequestration-dependent reactions that occur in commonly employed assay systems for the quantification of PPO in fruits and vegetables.


Assuntos
Catecol Oxidase/química , Catecol Oxidase/metabolismo , Solanum tuberosum/enzimologia , beta-Ciclodextrinas/química , Catálise , Catecol Oxidase/antagonistas & inibidores , Fenóis/química , Fenóis/metabolismo , Proteínas de Plantas/antagonistas & inibidores , Proteínas de Plantas/química , Proteínas de Plantas/metabolismo , Especificidade por Substrato , beta-Ciclodextrinas/metabolismo
12.
J Food Sci ; 84(8): 2347-2356, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31313311

RESUMO

This study determined the effects of blueberry fermentation by Lactobacillus plantarum on antioxidant and anticancer activities. The fermented blueberries extracted with 80% ethanol (FBE) showed increased superoxide dismutase-like activity, increased scavenging of DPPH and alkyl radicals, and increased antiproliferative activity against human cervical carcinoma HeLa cells by inducing apoptosis. Seven representative phenolic compounds (malvidin 3-O-glucopyranoside, gallic acid, protocatechuic acid, catechol, chlorogenic acid, syringic acid, and epigallocatechin) in FBE were measured by high-performance liquid chromatography at different fermentation times. The content of each phenolic compound in the FBE was dependent on the fermentation period. Protocatechuic acid and catechol levels increased significantly with fermentation time. Of these three major compounds (protocatechuic acid, catechol, and chlorogenic acid), catechol showed the most significant anticancer activity when HeLa cells were treated with each of these three compounds alone or mixed in various ratios. Pearson's product-moment correlation analysis revealed that the increases in antioxidant and anticancer activities following blueberry fermentation were positively correlated with the phenolic acids present in FBE. PRACTICAL APPLICATION: Blueberries fermented with a tannase-producing lactic acid bacteria (LAB), Lactobacillus plantarum showed higher antioxidant activities and antiproliferative activities against human cervical carcinoma HeLa cells than did raw blueberries. L. plantarum fermentation biotransformed blueberry polyphenols into active phenol metabolites with strong antioxidant and antiproliferative activities. Our results suggest that fermented blueberries are rich in phenolic acids, which are a promising source of natural antioxidants and anticancer drugs and can be used as additives in food, pharmaceuticals, and cosmetic preparations.


Assuntos
Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/metabolismo , Antioxidantes/química , Antioxidantes/metabolismo , Mirtilos Azuis (Planta)/química , Lactobacillus plantarum/metabolismo , Fenóis/química , Fenóis/metabolismo , Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Apoptose/efeitos dos fármacos , Mirtilos Azuis (Planta)/microbiologia , Cromatografia Líquida de Alta Pressão , Fermentação , Células HeLa , Humanos , Fenóis/farmacologia
13.
Sheng Wu Gong Cheng Xue Bao ; 35(7): 1184-1192, 2019 Jul 25.
Artigo em Chinês | MEDLINE | ID: mdl-31328475

RESUMO

Salidroside, as one of the main active ingredients of Rhodiala plant, has the effects of anti-hypoxia, anti-radiation, anti-fatigue, anti-tumor, hypoglycemia and improving immunity. With the increasing demand for salidroside and the decreasing of plant resources, microbial production of salidroside has attracted much attention due to its advantages of short period and easy controlling. At present, microbial production of salidroside is still at the basic research stage. In order to make it easier for researchers to understand the advances of microbial synthesis of salidroside, the biosynthesis pathways, uridine diphosphate glucosyltransferases, wild strain/natural enzymes and engineered strain/recombinant enzymes were reviewed.


Assuntos
Glucosídeos/metabolismo , Fenóis/metabolismo , Vias Biossintéticas
14.
Food Chem Toxicol ; 131: 110529, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31150784

RESUMO

The health promoting effects of extra virgin olive oil (EVOO) relate to its unique repertoire of phenolic compounds. Here, we used a chemoinformatics approach to computationally identify endogenous ligands and assign putative biomolecular targets to oleacein, one of the most abundant secoiridoids in EVOO. Using a structure-based virtual profiling software tool and reference databases containing more than 9000 binding sites protein cavities, we identified 996 putative oleacein targets involving more than 700 proteins. We subsequently identified the high-level functions of oleacein in terms of biomolecular interactions, signaling pathways, and protein-protein interaction (PPI) networks. Delineation of the oleacein target landscape revealed that the most significant modules affected by oleacein were associated with metabolic processes (e.g., glucose and lipid metabolism) and chromatin-modifying enzymatic activities (i.e., histone post-translational modifications). We experimentally confirmed that, in a low-micromolar physiological range (<20 µmol/l), oleacein was capable of inhibiting the catalytic activities of predicted metabolic and epigenetic targets including nicotinamide N-methyltransferase, ATP-citrate lyase, lysine-specific demethylase 6A, and N-methyltransferase 4. Our computational de-orphanization of oleacein provides new mechanisms through which EVOO biophenols might operate as chemical prototypes capable of modulating the biologic machinery of healthy aging.


Assuntos
Aldeídos/metabolismo , Fenóis/metabolismo , Proteômica/métodos , ATP Citrato (pro-S)-Liase/química , ATP Citrato (pro-S)-Liase/metabolismo , Aldeídos/química , Domínio Catalítico , Ensaios Enzimáticos , Epigenômica/métodos , Ontologia Genética/estatística & dados numéricos , Histona Desmetilases/química , Histona Desmetilases/metabolismo , Humanos , Informática/métodos , Metiltransferases/química , Metiltransferases/metabolismo , Simulação de Acoplamento Molecular , Nicotinamida N-Metiltransferase/química , Nicotinamida N-Metiltransferase/metabolismo , Olea/química , Azeite de Oliva/química , Fenóis/química , Ligação Proteica , Mapeamento de Interação de Proteínas , Software
15.
Eur J Med Chem ; 178: 93-107, 2019 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-31176098

RESUMO

Estrogens are the major female sex steroid hormones, estradiol (E2) being the most potent form in humans. Disturbing the balance between E2 and its weakly active oxidized form estrone (E1) leads to diverse types of estrogen-dependent diseases such as endometriosis or osteoporosis. 17ß-Hydroxysteroid dehydrogenase type 1 (17ß-HSD1) catalyzes the biosynthesis of E2 by reduction of E1 while the type 2 enzyme catalyzes the reverse reaction. Thus, 17ß-HSD1 and 17ß-HSD2 are attractive targets for treatment of estrogen-dependent diseases. Recently, we reported the first proof-of-principle study of a 17ß-HSD2 inhibitor in a bone fracture mouse model, using subcutaneous administration. In the present study, our aim was to improve the in vitro ADME profile of the most potent 17ß-HSD1 and 17ß-HSD2 inhibitors described so far. The optimized compounds show strong and selective inhibition of both the human enzymes and their murine orthologs. In addition, they display good metabolic stability in human liver microsomes (S9 fraction), low in vitro cytotoxicity as well as better aqueous solubility and physicochemical properties compared to the lead compounds. These achievements make the compounds eligible for testing in preclinical in vivo animal model studies on the effects of inhibition of 17ß-HSD1 and 17ß-HSD2.


Assuntos
17-Hidroxiesteroide Desidrogenases/antagonistas & inibidores , Inibidores Enzimáticos/farmacocinética , Estradiol Desidrogenases/antagonistas & inibidores , Fenóis/farmacocinética , Tiofenos/farmacocinética , Animais , Sítios de Ligação , Desenho de Drogas , Estabilidade de Medicamentos , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/metabolismo , Estradiol Desidrogenases/química , Estradiol Desidrogenases/metabolismo , Células HEK293 , Humanos , Camundongos , Microssomos Hepáticos/metabolismo , Simulação de Acoplamento Molecular , Estrutura Molecular , Fenóis/síntese química , Fenóis/química , Fenóis/metabolismo , Ligação Proteica , Solubilidade , Relação Estrutura-Atividade , Tiofenos/síntese química , Tiofenos/química , Tiofenos/metabolismo
16.
J Plant Physiol ; 239: 1-9, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31177025

RESUMO

Elicitation is an economic and sustainable technique for increasing the content of secondary metabolites, mainly bioactive compounds, in plants grown for better human nutrition. The aim of this study was to compare the physiological responses (water relations and mineral nutrition) and the enrichment in glucosinolates (GLSs) and phenolic compounds of broccoli plants (Brassica oleracea L. var. italica) receiving different elicitation treatments. The treatments involved the priming of seeds with KCl and the exposure of plants to elicitors, including K2SO4 and NaCl solutions and foliar sprays of methyl jasmonate (MeJA), salicylic acid (SA), and methionine (Met). The physiological response of the plants in terms of root hydraulic conductance was improved by priming with KCl and elicitation with MeJA or Met. Foliar application of Met significantly increased the plant biomass and enhanced mineral nutrition. In general, all treatments increased the accumulation of indole GLSs, but K2SO4 and MeJA gave the best response and MeJA also favored the formation of a newly described compound, cinnamic-GLS, in the plants. Also, the use of Met and SA as elicitors and the supply of K2SO4 increased the abundance of phenolic compounds; K2SO4 also enhanced growth but did not alter the water relations or the accumulation of mineral nutrients. Therefore, although the response to elicitation was positive, with an increased content of bioactive compounds, regulation of the water relations and of the mineral status of the broccoli plants was critical to maintain the yield.


Assuntos
Brassica/efeitos dos fármacos , Brassica/fisiologia , Cloreto de Potássio/administração & dosagem , Cloreto de Sódio/administração & dosagem , Sulfatos/administração & dosagem , Acetatos/administração & dosagem , Ciclopentanos/administração & dosagem , Glucosinolatos/metabolismo , Metionina/administração & dosagem , Minerais/metabolismo , Nutrientes/metabolismo , Oxilipinas/administração & dosagem , Fenóis/metabolismo , Reguladores de Crescimento de Planta , Ácido Salicílico/administração & dosagem , Água/metabolismo
17.
Chemosphere ; 232: 76-86, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31152906

RESUMO

The goal of this work was to investigate the genetics of an acidophilic phenol-degrading yeast strain using whole-genome sequencing (WGS), characterize the growth of the strain and phenol degradation capability as well as degradation pathway under extremely acidic conditions. The result showed that the strain ZM1 isolated from an acid mine drainage (AMD) belongs to basidiomycetous yeast Rhodotorula sp., which possesses some unique genes compared to other four closely related Rhodotorula species. Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis suggested that ZM1 possessed the degradation potentials for aromatic compounds. ZM1 was acidophilic with the optimum growth at the initial pH of 3.0. It could adjust pH to desired levels probably by acid production during the cultivation. Notably, at pH 3.0, the strain ZM1 showed a high phenol-degrading capability that almost completely degraded 1100 mg/L of phenol in 120 h with the highest degradation rate of 0.074 g/(g cell dry weight h). Under the same pH, the strain could completely degrade 500 mg/L phenol within 48 h at NaCl concentration up to 10 g/L. The identification of the gene catA by the KEGG analysis, together with the presence of metabolic intermediate of cis, cis-muconic acid detected by gas chromatography-mass spectrometry, confirmed that the strain ZM1 degraded phenol via ortho-cleavage pathway. These findings suggest that the indigenous yeasts strain ZM1 could be exploited as an important member for in-situ biodegradation of aromatic compounds in the extremely acidic environments.


Assuntos
Biodegradação Ambiental , Fenol/metabolismo , Rhodotorula/metabolismo , Redes e Vias Metabólicas , Fenóis/metabolismo , Leveduras
18.
J Agric Food Chem ; 67(25): 7016-7024, 2019 Jun 26.
Artigo em Inglês | MEDLINE | ID: mdl-31194907

RESUMO

Most of the previous in vitro digestion treatments were conducted directly to whole grains without extraction of free phenolics, thus the bioaccessible phenolics contained both free phenolics that survived the digestion and digested phenolics released by digestion. However, the profiles of digested phenolics released by digestion remain unknown. This study was designed to investigate the phytochemical contents, peroxyl radical scavenging capacities (PSCs), and cellular antioxidant activities (CAAs) of free, digested, and bound fractions of whole grains. Total phenolic contents of whole grains were highest in digested fraction, followed by free and bound fractions. The predominant phenolics were 12 phenolic acids and one flavonoid, which mostly existed in bound forms, then in digested and free forms. The digested phenolics bound to proteins were in conjugated form. The bound fractions had the highest PSCs, followed by free and digested fractions. CAAs were highest in bound fractions, followed by digested and free fractions.


Assuntos
Antioxidantes/metabolismo , Compostos Fitoquímicos/metabolismo , Extratos Vegetais/metabolismo , Grãos Integrais/metabolismo , Antioxidantes/química , Linhagem Celular , Digestão , Flavonoides/química , Flavonoides/metabolismo , Células Hep G2 , Humanos , Modelos Biológicos , Fenóis/química , Fenóis/metabolismo , Compostos Fitoquímicos/química , Extratos Vegetais/química , Sementes/química , Sementes/metabolismo
19.
J Plant Res ; 132(4): 509-520, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31250145

RESUMO

The expression of plant secondary metabolism is strongly controlled by plant both in time and space. Although the variation of secondary metabolites, such as soluble and structural phenolics (e.g., lignins), has been largely observed in gall-inducing insects, and compared to their non-galled host organs, only a few datasets recording such variation are available. Accordingly, the relative importance of spatiotemporal variability in phenolic contents, and the influence of gall developmental stages on the original composition of host organs are poorly discussed. To address this knowledge gap, we histochemically determined the sites of polyphenol and lignin accumulation, and the polyphenol contents in three developmental stages of two calophyid galls and their correspondent host organs. Current results indicate that the compartmentalization of phenolics and lignins on Schinus polygama (Cav.) Cabrera follows a similar pattern in the two-calophyid galls, accumulating in the outer (the external tissue layers) and in the inner tissue compartments (the cell layers in contact with the gall chamber). The non-accumulation in the median compartment (median parenchyma layers of gall wall with vascular bundles, where gall inducer feeds) is important for the inducer, because its mouth apparatus enter in contact with the cells of this compartment. Also, the concentration of phenolics has opposite dynamics, decreasing in leaf galls and increasing in stem galls, in temporal scale, i.e., from maturation toward senescence. The concentration of phenolics in non-galled host organs, and in both galls indicated the extended phenotype of Calophya rubra (Blanchard) and C. mammifex Burckhardt & Basset (Hemiptera: Sternorrhyncha: Psylloidea: Calophyidae) over the same host plant metabolic potentiality.


Assuntos
Anacardiaceae/parasitologia , Hemípteros/parasitologia , Fenóis/metabolismo , Tumores de Planta/parasitologia , Anacardiaceae/metabolismo , Animais , Lignina/metabolismo , Polifenóis/metabolismo
20.
J Sci Food Agric ; 99(12): 5601-5605, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31149731

RESUMO

BACKGROUND: Microgreens (i.e. tender immature greens) are a popular alternative to sprouts (i.e. germinating seeds) because of their higher content of vitamins, carotenoids and phenols, as well as their lower content of nitrates. Their nutritional value can be improved by biofortification, which increases micronutrient levels during plant growth. Because selenium (Se) plays a significant role in antioxidant defense, biofortification with Se is a good way of improving the nutritional quality of sprouts and microgreens. The present study investigated the production of Se-fortified microgreens from Se-enriched seeds of sweet basil (Ocimum basilicum L.). These microgreens could be used as new beneficial dietary supplements. RESULTS: Basil plants were grown in a nutrient solution, containing 0 (control), 4 or 8 mg Se L-1 as sodium selenate, to full maturity. Seeds accumulated a high amount of Se and were then used to produce microgreens. The germination index was higher in the seeds from Se-treated plants and the microgreens were enriched in Se. The antioxidant capacity of Se-fortified microgreens was higher compared to the control. CONCLUSION: The production of microgreens from Se-enriched seeds could comprise a good system for obtaining microgreens with a high nutritional value. Basil plants treated with Se could be used to produce both Se-fortified leaves and microgreens. © 2019 Society of Chemical Industry.


Assuntos
Ocimum basilicum/química , Selênio/análise , Antioxidantes/análise , Antioxidantes/metabolismo , Biofortificação , Fertilizantes/análise , Alimentos Fortificados/análise , Germinação , Valor Nutritivo , Ocimum basilicum/crescimento & desenvolvimento , Ocimum basilicum/metabolismo , Fenóis/análise , Fenóis/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Sementes/química , Sementes/crescimento & desenvolvimento , Sementes/metabolismo , Selênio/metabolismo
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