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1.
Planta ; 260(1): 8, 2024 May 24.
Artículo en Inglés | MEDLINE | ID: mdl-38789631

RESUMEN

MAIN CONCLUSION: A gene-to-metabolite approach afforded new insights regarding defence mechanisms in oat plants that can be incorporated into plant breeding programmes for the selection of markers and genes related to disease resistance. Monitoring metabolite levels and changes therein can complement and corroborate transcriptome (mRNA) data on plant-pathogen interactions, thus revealing mechanisms involved in pathogen attack and host defence. A multi-omics approach thus adds new layers of information such as identifying metabolites with antimicrobial properties, elucidating metabolomic profiles of infected and non-infected plants, and reveals pathogenic requirements for infection and colonisation. In this study, two oat cultivars (Dunnart and SWK001) were inoculated with Pseudomonas syringae pathovars, pathogenic and non-pathogenic on oat. Following inoculation, metabolites were extracted with methanol from leaf tissues at 2, 4 and 6 days post-infection and analysed by multiple reaction monitoring (MRM) on a triple quadrupole mass spectrometer system. Relatedly, mRNA was isolated at the same time points, and the cDNA analysed by quantitative PCR (RT-qPCR) for expression levels of selected gene transcripts associated with avenanthramide (Avn) biosynthesis. The targeted amino acids, hydroxycinnamic acids and Avns were successfully quantified. Distinct cultivar-specific differences in the metabolite responses were observed in response to pathogenic and non-pathogenic strains. Trends in aromatic amino acids and hydroxycinnamic acids seem to indicate stronger activation and flux through these pathways in Dunnart as compared to SWK001. A positive correlation between hydroxycinnamoyl-CoA:hydroxyanthranilate N-hydroxycinnamoyl transferase (HHT) gene expression and the abundance of Avn A in both cultivars was documented. However, transcript profiling of selected genes involved in Avn synthesis did not reveal a clear pattern to distinguish between the tolerant and susceptible cultivars.


Asunto(s)
Avena , Perfilación de la Expresión Génica , Metaboloma , Enfermedades de las Plantas , Pseudomonas syringae , Pseudomonas syringae/patogenicidad , Pseudomonas syringae/fisiología , Avena/microbiología , Avena/genética , Avena/metabolismo , Metaboloma/genética , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/genética , Fitoquímicos/metabolismo , Hojas de la Planta/microbiología , Hojas de la Planta/metabolismo , Hojas de la Planta/genética , Regulación de la Expresión Génica de las Plantas , Resistencia a la Enfermedad/genética , Interacciones Huésped-Patógeno , Transcriptoma , ortoaminobenzoatos/metabolismo
2.
Front Nutr ; 11: 1345371, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-38379545

RESUMEN

Introduction: Oat-based milk alternatives (OMAs) have become increasingly popular, perhaps due to their low allergenicity and preferred sensory attributes when compared to other milk alternatives. They may also provide health benefits from unique compounds; avenanthramides, avenacosides, and the dietary fibre beta-glucan. This has led to a variety of commercial options becoming available. Being a fairly new product, in comparison to other plant-based milk alternatives (PBMAs), means little research has been undertaken on the sensory profile, and how it is influenced by the physical and chemical properties. Methods: This study investigated the sensory, physical and chemical profiles of current commercially available OMAs, that varied in fortification, use of stabilisers, and oat content. The volatile compounds and their respective aromas were analysed using solid phase microextraction followed by gas chromatography mass spectrometry (GC-MS) and gas chromatography-olfactometry (GC-O). Liquid chromatography mass spectrometry (LC-MS) was used for identification of avenanthramides and avenacosides. Particle size and polydispersity index (PDI) were analysed using a Mastersizer and Zetasizer, respectively, with colour analysis carried out using a colourimeter, and viscosity measurements using a rheometer. Descriptive sensory profiling was used to assess the impact on the sensory characteristics of the different samples and the sensory data acquired were correlated with the instrumental data. Results: Samples with smaller particle size appeared whiter-both instrumentally and perceptually. The only clear plastic packaged product differed substantially in volatile profile from all other products, with a higher abundance of many volatile compounds, and high overall perceived aroma. Avenanthramides and avenacosides were present in all samples, but differed significantly in abundance between them. Discussion: The results suggested smaller particle size leads to whiter colour, whilst differences in processing and packaging may contribute to significant differences in aroma. Astringency did not differ significantly between samples, suggesting that the variation in the concentrations of avenacosides and avenanthramides were below noticeable differences.

3.
Pharmaceuticals (Basel) ; 16(5)2023 May 09.
Artículo en Inglés | MEDLINE | ID: mdl-37242500

RESUMEN

POM analysis and related approaches are significant tools based on calculating various physico-chemical properties and predicting biological activity, ADME parameters, and toxicity of a molecule. These methods are used to evaluate a molecule's potential to become a drug candidate. Avenanthramides (AVNs) are promising secondary metabolites specific to Avena spp. (oat). They comprise the amides of anthranilic acid linked to various polyphenolic acids with or without post-condensation molecule transformation. These natural compounds have been reported to exert numerous biological effects, including antioxidant, anti-inflammatory, hepatoprotective, antiatherogenic, and antiproliferative properties. To date, almost 50 various AVNs have been identified. We performed a modified POM analysis of 42 AVNs using MOLINSPIRATION, SWISSADME, and OSIRIS software. The evaluation of primary in silico parameters revealed significant differences among individual AVNs, highlighting the most promising candidates. These preliminary results may help coordinate and initiate other research projects focused on particular AVNs, especially those with predicted bioactivity, low toxicity, optimal ADME parameters, and promising perspectives.

4.
Polymers (Basel) ; 15(3)2023 Jan 20.
Artículo en Inglés | MEDLINE | ID: mdl-36771840

RESUMEN

Encapsulating bioactive avenanthramides (AVAs) in carriers to respond to the environmental changes of food thermal processing allows the controlled release of AVAs for the effective inhibition of biohazards. In this study, fluorescent molecular imprinted polymers (FMIPs) loaded with AVAs were prepared by reverse microemulsion. The fluorescent signal was generated by carbon dots (CDs), which were derived from oat bran to determine the load of AVAs. The FMIPs were uniformly spherical in appearance and demonstrated favorable properties, such as thermal stability, protection of AVAs against photodegradation, high encapsulation efficiency, and effective scavenging of free radicals. After consideration of the different kinetics models, the release of AVAs from the FMIPs matched the Weibull model and followed a Fickian diffusion mechanism. The FMIPs exhibited good inhibition of pyrraline in a simulated casein-ribose system and in milk samples, indicating the release of AVAs could inhibit the generation of pyrraline.

5.
Molecules ; 27(19)2022 Sep 20.
Artículo en Inglés | MEDLINE | ID: mdl-36234703

RESUMEN

In this study, a method, based on an ultraperformance liquid chromatography coupled with high-field quadrupole orbitrap high-resolution mass spectrometry (UHPLC-QE-HF-HRMS) platform, was established for the trace determination of three major avenanthramides (AVNs). The MS conditions for determining the AVNs were optimized, and the cracking methods of avenanthramides were analyzed. The linear range of the results and the correlation coefficient were 1−2000 µg/L and >0.996, respectively. Further, the established method was employed for the determination of the AVN contents of oats at different germination times, and the results indicated that the AVN contents of Zaohua and Bayou oats increased 19.26 and 6.09 times, respectively, after germination. The total AVN content of both oat varieties reached a maximum on the fifth day of germination (153.51 ± 4.08 and 126.30 ± 3.33 µg/g for the Zaohua and Bayou oats, respectively). Furthermore, this study investigated the antiallergic and antioxidant activities of the germinated oats via hyaluronidase inhibition and 2,2-diphenyl-1-picrylhydrazyl (DPPH)-scavenging assays. The antiallergic and DPPH-scavenging abilities of the ungerminated forms of both oat varieties were weaker. However, on the fifth day of germination, the inhibition rate of anthranilamide hyaluronidase reached 72.7% and 67.3% for the Zaohua and Bayou oat varieties, respectively. The antiallergic abilities of the oats increased significantly on the fifth day of germination in terms of their antiallergic capacities and DPPH clearance (82.67% and 77.64% for the Zaohua and Bayou oats, respectively), and the two indicators exhibited similar trends. These findings demonstrated that AVNs exhibit good antisensitivity and antioxidation properties, and the antisensitivity effect correlated positively with the AVN content.


Asunto(s)
Antialérgicos , Avena , Antialérgicos/análisis , Antioxidantes/química , Avena/química , Grano Comestible/química , Germinación , Hialuronoglucosaminidasa , ortoaminobenzoatos/química
6.
Int J Mol Sci ; 23(15)2022 Aug 01.
Artículo en Inglés | MEDLINE | ID: mdl-35955669

RESUMEN

Avena sativa L. is a wholegrain cereal and an important edible crop. Oats possesses high nutritional and health promoting values and contains high levels of bioactive compounds, including a group of phenolic amides, named avenanthramides (Avns), exerting antioxidant, anti-inflammatory, and anticancer activities. Epidermal growth factor receptor (EGFR) represents one of the most known oncogenes and it is frequently up-regulated or mutated in human cancers. The oncogenic effects of EGFR include enhanced cell growth, angiogenesis, and metastasis, and down-regulation or inhibition of EGFR signaling has therapeutic benefit. Front-line EGFR tyrosine kinase inhibitor therapy is the standard therapy for patients with EGFR-mutated lung cancer. However, the clinical effects of EGFR inhibition may be lost after a few months of treatment due to the onset of resistance. Here, we showed the anticancer activity of Avns, focusing on EGFR activation and signaling pathway. Lung cancer cellular models have been used to evaluate the activity of Avns on tumor growth, migration, EMT, and anoikis induced by EGF. In addition, docking and molecular dynamics simulations showed that the Avns bind with high affinity to a region in the vicinity of αC-helix and the DGF motif of EGFR, jeopardizing the target biological function. Altogether, our results reveal a new pharmacological activity of Avns as EGFR tyrosine kinase inhibitors.


Asunto(s)
Avena , Neoplasias Pulmonares , Avena/química , Línea Celular Tumoral , Grano Comestible/química , Factor de Crecimiento Epidérmico , Receptores ErbB/análisis , Receptores ErbB/genética , Humanos , Neoplasias Pulmonares/tratamiento farmacológico , Inhibidores de Proteínas Quinasas/farmacología , ortoaminobenzoatos
7.
Foods ; 11(12)2022 Jun 20.
Artículo en Inglés | MEDLINE | ID: mdl-35742012

RESUMEN

As a special polyphenolic compound in oats, the physiological function of oat avenanthramides (AVAs) drives a variety of biological activities, and plays an important role in the prevention and treatment of common chronic diseases. In this study, the optimum extraction conditions and structural identification of AVAs from oats was studied. The inhibitory effect of AVAs from oats on advanced glycation end-products (AGEs) in a glucose-casein simulation system was evaluated, and this revealed dose-dependent inhibitory effects. The trapping capacity of AVAs to the α-dicarbonyl compounds of AGE intermediate products was determined by HPLC-MS/MS, and the results indicate that AVA 2c, AVA 2p, and AVA 2f exhibited the ability to capture α-dicarbonyl compounds. More importantly, AVA 2f was found to be more efficient than AVA 2p at inhibiting superoxide anion radical (O2-), hydroxyl radical (OH), and singlet oxygen (1O2) radical generation, which may be the main reason that AVA 2f was more efficient than AVA 2p in AGE inhibition. Thus, this research presents a promising application of AVAs from oats in inhibiting the food-borne AGEs formed in food processing.

8.
Molecules ; 27(7)2022 Mar 28.
Artículo en Inglés | MEDLINE | ID: mdl-35408599

RESUMEN

Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure-bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N'-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%.


Asunto(s)
Amidas , Ácidos Cumáricos , Amidas/química , Ácidos Cumáricos/química , Fenol , Fenoles , Tiramina
9.
Foods ; 11(4)2022 Feb 16.
Artículo en Inglés | MEDLINE | ID: mdl-35206037

RESUMEN

Uniquely, oats contain avenanthramides (AVAs), a group of phenolic alkaloids, exhibiting many health benefits. AVA analysis involves extraction with alcohol-based solvents and HPLC separation with UV and/or mass spectrometer detectors. There are many reported methods to extract AVAs. Almost all entail multiple extractions. The whole procedure is time- and labor-intensive. Furthermore, most quantifications are limited to three common AVAs (2f, 2p, 2c). The present study compared three extraction methods (all at 50 °C) for their effects on AVA concentrations and composition (% relative to total AVA) of oat grains. These included triplicate extractions with 80% ethanol containing 10 mM phosphate buffer (pH 2.0) (A), triplicate extractions with 80% ethanol (B), and a single extraction with 80% ethanol (C), while keeping solid/total solvent ratio at 1/60 (g/mL) and total extraction time of 60 min. Results showed that 80% buffered ethanol gave significantly lower AVA contents than 80% ethanol, while single and triplicate extractions with 80% ethanol produced the same extractability. However, the extraction method had no effect on AVA composition. Using 0.25 g sample size instead of 0.5 g saved extractants by half, without affecting AVA measurements. Consequently, a simplified method of extraction was developed, featuring Method C. The present study also expanded profiling individual AVAs beyond AVA 2c, 2p and 2f. Other AVAs identified and semi-quantified included 5p, 4p, 3f/4f, and 2pd. The simplified analysis was validated by measuring 16 selected oat grain samples. Some of these grains had relatively high contents of 4p, 3f/4f and 2pd, which have been considered minor AVAs previously.

10.
J Agric Food Chem ; 70(2): 446-457, 2022 Jan 19.
Artículo en Inglés | MEDLINE | ID: mdl-34994561

RESUMEN

Oats are among the most commonly consumed whole grains and are widely grown worldwide, and they contain numerous nutrients, including proteins, lipids, vitamins, minerals, ß-glucan, and unique phytochemical polyphenol avenanthramides (Avns). Recent studies have indicated that Avns play essential roles in mediating the health benefits of oats. This review systemically summarized the nomenclature and structures of Avns, effect of germination on promoting Avns production, and in vivo metabolites produced after Avns consumption. The classical functions and novel potential bioactivities of Avns were further elucidated. The classical functions of Avns in cancer prevention, antioxidative response, anti-inflammatory reaction, and maintaining muscle health were expounded, and the internal mechanisms of these functions were analyzed. The potential novel bioactivities of Avns in modulating gut microbiota, alleviating obesity, and preventing chronic diseases, such as atherosclerosis and osteoporosis, were further revealed. This review may provide new prospects and directions for the development and utilization of oat Avns.


Asunto(s)
Avena , ortoaminobenzoatos , Antioxidantes , Fitoquímicos
11.
Plants (Basel) ; 10(11)2021 Nov 17.
Artículo en Inglés | MEDLINE | ID: mdl-34834847

RESUMEN

Our study was focused on the evaluation of the content of a wider spectrum of eight avenanthramides (AVNs) as unique components of oat grain under the effects of four selected factors (cultivar, locality, cropping system, and year). The weather effects on changes in the AVN content and their relationship to other important parameters of oat grain were further evaluated in more detail. A sensitive UHPLC system coupled with a QExactive Orbitrap mass spectrometer was used for AVN quantification. AVNs confirmed a high variability (RDS = 72.7-113.5%), which was dominantly influenced by the locality and year factors. While most AVN types confirmed mutually high correlations (r = 0.7-0.9), their correlations with the other 10 grain parameters were lower (r ≤ 0.48). Their significant correlations (0.27-0.46) with ß-D-glucan could be used in perspective in breeding programs for the synergetic increase of both parameters. PCA analysis and Spearman correlations based on individual cultivars confirmed a significant effect of June and July precipitation on the increase of Σ AVNs. However, the results also indicated that higher precipitation can generate favorable conditions for related factors, such as preharvest sprouting evoking a direct increase of AVNs synthesis in oat grain.

12.
Nutrients ; 13(6)2021 Jun 12.
Artículo en Inglés | MEDLINE | ID: mdl-34204635

RESUMEN

Wholegrain oats contain a variety of phenolic compounds thought to help maintain healthy vascular function, through the maintenance of local levels of the vasodilator nitric oxide (NO). Thus, the full molecular mechanisms involved are not yet clear. With this work we aim to understand the possible cellular mechanisms by which avenanthramides and ferulic acid derivatives, present in oats, may help maintain a healthy vascular function through the modulation of the NO pathway. Primary Human Umbilical Vein Endothelial Cells (HUVEC) were exposed to ferulic acid, isoferulic acid, hydroferulic acid, ferulic acid 4-O-glucuronide, isoferulic acid 3-O-sulfate, dihydroferulic acid 4-O-glucuronide, avenanthramide A, avenanthramide B and avenanthramide C (1 µM) or vehicle (methanol) for 24 h. Apocynin and Nω-Nitro-L-arginine (L-NNA) were additionally included as controls. NO and cyclic GMP (cGMP) levels, superoxide production and the activation of the Akt1/eNOS pathway were assessed. The statistical analysis was performed using one-way ANOVA followed by a Tukey post-hoc t-test. Apocynin and all phenolic compounds increased NO levels in HUVEC cells (increased DAF2-DA fluorescence and cGMP), and significantly reduced superoxide levels. Protein expression results highlighted an increase in the Akt1 activation state, and increased eNOS expression. Overall, our results indicated that the glucuronide metabolites do not enhance NO production through the Akt1/eNOS pathway, thus all compounds tested are able to reduce NO degradation through reduced superoxide formation.


Asunto(s)
Ácidos Cumáricos/farmacología , Endotelio Vascular/efectos de los fármacos , Células Endoteliales de la Vena Umbilical Humana/efectos de los fármacos , Óxido Nítrico/metabolismo , ortoaminobenzoatos/farmacología , Humanos , Transducción de Señal/efectos de los fármacos , Vasodilatadores/metabolismo
13.
J Agric Food Chem ; 69(25): 7178-7189, 2021 Jun 30.
Artículo en Inglés | MEDLINE | ID: mdl-34156855

RESUMEN

Avenanthramides (AVAs), unique phenolic compounds in oats, have attracted increasing interest due to their health benefits. Eight representative AVAs were studied using the density functional theory (DFT) method to elucidate their antioxidant activity and mechanism. Preference of different mechanisms was evaluated based on thermodynamic descriptors involved in double (2H+/2e-) free radical scavenging reactions. It was found that the hydrogen atom transfer (HAT) mechanism is more favorable in the gas and benzene phases, while sequential proton loss electron transfer (SPLET) is preferred in polar media. The results suggest the feasibility of the double HAT and double SPLET mechanisms for 2s and c-series AVAs. The sequential triple proton loss double electron transfer (StPLdET) mechanism represents the dominant pathway in aqueous solution at physiological pH. In addition, the sequential proton loss hydrogen atom transfer (SPLHAT) mechanism provides an alternative pathway to trap free radicals. Results also revealed the important role of the catechol, guaiacyl, and carboxyl moieties.


Asunto(s)
Antioxidantes , Catecoles , Radicales Libres , Termodinámica , ortoaminobenzoatos
14.
Food Chem ; 355: 129585, 2021 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-33799237

RESUMEN

Oats (Avena sativa L.) are a healthy food, being high in dietary fibre (e.g. ß-glucans), antioxidants, minerals, and vitamins. Understanding the effect of variety and crop management on nutritional quality is important. The response of four oat varieties to increased nitrogen levels was investigated across multiple locations and years with respect to yield, grain quality and metabolites (assessed via GC- and LC- MS). A novel high-resolution UHPLC-PDA-MS/MS method was developed, providing improved metabolite enrichment, resolution, and identification. The combined phenotyping approach revealed that, amino acid levels were increased by nitrogen supplementation, as were total protein and nitrogen containing lipid levels, whereas health-beneficial avenanthramides were decreased. Although nitrogen addition significantly increased grain yield and ß-glucan content, supporting increasing the total nitrogen levels recommended within agricultural guidelines, oat varietal choice as well as negative impacts upon health beneficial secondary metabolites and the environmental burdens associated with nitrogen fertilisation, require further consideration.


Asunto(s)
Avena/metabolismo , Metaboloma , Nitrógeno/administración & dosificación , Espectrometría de Masas en Tándem/métodos , Antioxidantes/química , Avena/crecimiento & desarrollo , Cromatografía Líquida de Alta Presión , Análisis Discriminante , Grano Comestible/química , Grano Comestible/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Valor Nutritivo , Fenotipo , beta-Glucanos/análisis
15.
J Food Biochem ; 45(6): e13738, 2021 06.
Artículo en Inglés | MEDLINE | ID: mdl-33899247

RESUMEN

This study aimed to evaluate the effect of polyphenol (PE) and avenanthramide (AE) extracts from oat grains (OG) and sprouts (OS) on genes related to glucose and lipid metabolisms in 3T3 L1 adipocytes. The AE-OS exerted the greatest effect on genes involved in glucose metabolism, increasing Glut4, Irs1, and Pi3k expression by 3.0- to 3.9-fold. Conversely, the PE-OS exerted the greatest effect on genes involved in lipid metabolism, decreasing Fasn and Acaca expression by 0.2- to 0.3-fold, and increasing Cpt1a and Acadm expression by 2.7- to 3.0-fold. These effects were mainly related to their high content of avenanthramides A (2p), B (2f), and C (2c), quercetin 3-O-rutinoside, kaempferol, sinapoylquinic acid, and apigenin and luteolin derivatives according to the chemometric analysis. In conclusion, this study demonstrated that oat sprouts extract exerts a greater effect than oat grains on the regulation of genes involved in glucose and lipid metabolisms in adipocytes. PRACTICAL APPLICATIONS: This study demonstrates that polyphenols and avenanthramides extracted from oat (Avena sativa L.) grains and sprouts modulate key genes involved in glucose and lipid metabolisms in adipocytes and that oat sprouts exert a greatest health beneficial effect than oat grains due to their higher content of bioactive compounds. In addition, the chemometric analysis identified the bioactive compounds that can be associated with the beneficial effects of oat grains and sprouts, which can be further used for the identification of oat varieties and oat-derived products with high content of these bioactive compounds and, thus, with high nutraceutical potential.


Asunto(s)
Avena , Polifenoles , Células 3T3-L1 , Adipocitos , Animales , Avena/genética , Cromatografía Líquida de Alta Presión , Glucosa , Metabolismo de los Lípidos/genética , Ratones , Polifenoles/farmacología , ortoaminobenzoatos
16.
Arch Biochem Biophys ; 706: 108857, 2021 07 30.
Artículo en Inglés | MEDLINE | ID: mdl-33781769

RESUMEN

Accumulating evidence has demonstrated that cellular antioxidant systems play essential roles in retarding oxidative stress-related diseases, such as Parkinson's disease. Because nuclear factor erythroid 2-related factor 2 (Nrf2) is a chief regulator of cellular antioxidant systems, small molecules with Nrf2-activating ability may be promising neuroprotective agents. Avenanthramide-2c (Aven-2c), avenanthramide-2f (Aven-2f) and avenanthramide-2p (Aven-2p) are the most abundant avenanthramides in oats, and they have been documented to possess multiple pharmacological benefits. In this work, we synthesized these three compounds and evaluated their cytoprotective effect against oxidative stress-induced PC12 cell injuries. Aven-2c displayed the best protective potency among them. Aven-2c conferred protection on PC12 cells by scavenging free radicals and activating the Nrf2-ARE signaling pathway. Pretreatment of PC12 cells with Aven-2c efficiently enhanced Nrf2 nuclear accumulation and evoked the expression of a set of cytoprotective molecules. The mechanistic study also supports that Nrf2 activation is the molecular basis for the cellular action of Aven-2c. Collectively, this study demonstrates that Aven-2c is a potent Nrf2 agonist, shedding light on the potential usage of Aven-2c in the treatment of neuroprotective diseases.


Asunto(s)
Elementos de Respuesta Antioxidante , Antioxidantes/farmacología , Factor 2 Relacionado con NF-E2/genética , Fármacos Neuroprotectores/farmacología , Transducción de Señal/genética , ortoaminobenzoatos/farmacología , Animales , Avena/química , Supervivencia Celular/efectos de los fármacos , Regulación de la Expresión Génica , Glutamato-Cisteína Ligasa/genética , Glutamato-Cisteína Ligasa/metabolismo , Hemo Oxigenasa (Desciclizante)/genética , Hemo Oxigenasa (Desciclizante)/metabolismo , Peróxido de Hidrógeno/antagonistas & inhibidores , Peróxido de Hidrógeno/farmacología , NAD(P)H Deshidrogenasa (Quinona)/genética , NAD(P)H Deshidrogenasa (Quinona)/metabolismo , Factor 2 Relacionado con NF-E2/metabolismo , Estrés Oxidativo/efectos de los fármacos , Oxidopamina/antagonistas & inhibidores , Oxidopamina/farmacología , Células PC12 , Extractos Vegetales/química , Ratas , Tiorredoxina Reductasa 1/genética , Tiorredoxina Reductasa 1/metabolismo , Tiorredoxinas/genética , Tiorredoxinas/metabolismo
17.
Heliyon ; 7(2): e06125, 2021 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-33553778

RESUMEN

Avenanthramides (AVs) are polyphenolic components found in oats. The present work is devoted to the exploration of structure-based radical scavenging activity of nine AVs; 2p, 2f, 2c, 1p, 1c, 1f, 1s, 2s, and 3f, using M06-2X functional level of density functional theory with basis set 6-31+G(d, p) both in gas and ethanol medium. The act of compounds towards the electron transfer mechanism was analyzed with the help of a Donor-acceptor map (DAM) and classified as antioxidants and anti-reductants. The main mechanism of radical action, HAT, SET-PT, and SPLET were examined and found to be the preference of HAT and SPLET respectively in the gas phase and ethanol medium. The computed quantum mechanical atom in molecule (QTAIM) parameters; the intramolecular H-bonding, Noncovalent interactions, aromaticity also acted as pillars to supports the activity of compounds. The activity was found to be increasing with the stabilizing group ortho to the reactive phenolic OH group.

18.
Food Chem ; 336: 127668, 2021 Jan 30.
Artículo en Inglés | MEDLINE | ID: mdl-32758805

RESUMEN

Hulled Reins and hulless Lamont oats were dehulled and/or sequentially abraded to produce ten pearling fines and corresponding pearled kernels. Contents of nutrients (protein, oil, starch, beta-glucan, ash and other carbohydrates) and avenanthramides (AVA) 2p, 2c, 2f, and 5p in processing fractions and starting grains were measured. Results show that distribution patterns of nutrients varied with individual nutrients, but those of AVAs varied with variety and individual AVAs. In both varieties, from the surface to inner endosperms, protein and oil increased then decreased; ash and other carbohydrates decreased; starch increased; and beta-glucan unchanged except for the surface area. In Lamont oat, the four AVAs decreased, but in Reins oat, AVA 2p decreased while 2c, 2f and 5p increased, then decreased. Compared to whole grain, pearled oats not only contained lower AVAs, protein, oil, ash, and other carbohydrates and higher beta-glucan and starch but also had a different AVA composition.


Asunto(s)
Avena/química , Semillas/química , ortoaminobenzoatos/análisis , Nutrientes/análisis , Proteínas de Vegetales Comestibles/análisis , Almidón/análisis , beta-Glucanos/análisis
19.
Food Chem ; 342: 128219, 2021 Apr 16.
Artículo en Inglés | MEDLINE | ID: mdl-33077284

RESUMEN

While the development of oat products often requires altered molecular weight (MW) of ß-glucan, the resulting health implications are currently unclear. This 3-leg crossover trial (n = 14) investigated the effects of the consumption of oat bran with High, Medium and Low MW ß-glucan (average > 1000, 524 and 82 kDa respectively) with 3 consequent meals on oat-derived phenolic compounds in urine (UHPLC-MS/MS), bile acids in feces (UHPLC-QTOF), gastrointestinal conditions (ingestible capsule), and perceived gut well-being. Urine excretion of ferulic acid was higher (p < 0.001, p < 0.001), and the fecal excretion of deoxycholic (p < 0.03, p < 0.02) and chenodeoxycholic (p < 0.06, p < 0.02) acids lower after consumption of Low MW ß-glucan compared with both Medium and High MW ß-glucan. Duodenal pressure was higher after consumption of High MW ß-glucan compared to Medium (p < 0.041) and Low (p < 0.022) MW ß-glucan. The MW of ß-glucan did not affect gut well-being, but the perceptions between females and males differed.


Asunto(s)
Ácidos y Sales Biliares/metabolismo , Heces/química , Tracto Gastrointestinal/efectos de los fármacos , Orina/química , beta-Glucanos/química , beta-Glucanos/farmacología , Estudios Cruzados , Fibras de la Dieta , Femenino , Humanos , Masculino , Peso Molecular , Caracteres Sexuales
20.
Food Chem ; 343: 128408, 2021 May 01.
Artículo en Inglés | MEDLINE | ID: mdl-33158678

RESUMEN

From a mutagenized oat population, produced by ethyl methanesulfonate mutagenesis, hulled grains from 17 lines with elevated avenanthramide (AVN) content were selected and their AVN structures, concentrations and antioxidant potentials were determined by HPLC-MS2 and HPLC equipped with an on-line ABTS+ antioxidant detection system. The data obtained showed qualitative and quantitative differences in the synthesis of AVNs in the different lines, with a total AVN concentration up to 227.5 µg/g oat seed flour in the highest line, compared with 78.2 µg/g seed in the commercial line, SW Belinda. In total, 25 different AVNs were identified with avenanthramide B structures being among the most abundant, and AVN C structures having the highest antioxidant activity. The findings indicate the potential of oat mutagenesis in combination with a high precision biochemical selection method for the generation of stable mutagenized lines with a high concentration of total and/or individual AVNs in the oat seed grain.


Asunto(s)
Antioxidantes/química , Avena/química , Avena/genética , ortoaminobenzoatos/análisis , ortoaminobenzoatos/química , Antioxidantes/análisis , Cromatografía Líquida de Alta Presión/métodos , Harina , Espectrometría de Masas , Mutagénesis , Extractos Vegetales/química , Semillas/química , ortoaminobenzoatos/farmacología
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