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1.
Food Chem ; 367: 130682, 2022 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34364147

RESUMO

Basil is an edible, aromatic plant, which makes the study of the ecotoxicity of metals in plant metabolism relevant. Given the above, the objective of this study was to evaluate the effects of metals, aluminum, lead, and cadmium, in the synthesis of phenolic compounds and in the dry mass of basil plants (O. basilicum L.) grown in a hydroponic system. The plants were subjected to four different concentrations of cadmium (0.2, 0.6, 1.2, and 1.8 mmol L-1), lead and aluminum (0.04, 0.08, 0.12, and 0.16 mmol L-1), and compared with the control. After desiccation of the plant material, the total dry mass was obtained and then, hydroethanolic extracts (43% distilled water and 57% ethanol) were made for biochemical analyzes, which consisted of the determination of caffeic acid (CA) and rosmarinic acid (RA) by high performance liquid chromatography analysis with a diode detector (HPLC-DAD); total phenolics (TP) and total flavonoids (TF) by spectrophotometry. The data were submitted to analysis of variance and multivariate analysis (principal component analysis-PCA and hierarchical cluster analysis-HCA) was applied for data association. The phenolic compounds showed a high positive correlation with each other, and the total dry mass showed low and negative correlations with the analyzed variables. The results showed that the metals aluminum, lead, and cadmium promoted a stress condition in basil plants, which resulted in the reduction of the dry matter mass and an increase in the synthesis of phenolic compounds, according to the type and concentration of the metal.


Assuntos
Ocimum basilicum , Antioxidantes , Cádmio , Ácidos Cafeicos , Cinamatos , Depsídeos , Flavonoides , Chumbo , Análise Multivariada
2.
J Agric Food Chem ; 69(40): 11804-11815, 2021 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-34597041

RESUMO

There is a lack of effective antibacterial agents against rice bacterial leaf streak and leaf blight. Cinnamic acid derivatives containing the 1,3,4-oxadiazole moiety were synthesized, and their antibacterial activities against Xanthomonas oryzae pv. oryzicola (Xoc) and X. oryzae pv. oryzae (Xoo) were evaluated. Based on the three-dimensional quantitative structure-activity relationship (3D-QSAR) model, compound 31 with better antibacterial activity against Xoc was designed and synthesized, and the 50% effective concentration (EC50) value was 0.2 mg/L. The curative and protective activities of compound 31 against rice bacterial leaf streak at 100 mg/L were 39.5 and 35.4%, respectively, which were higher than those of thiodiazole copper (28.4 and 20.7%, respectively). The antibacterial activity of compound 31 against rice bacterial leaf streak is closely associated with the activity of related defensive enzymes and the increase in glutathione metabolism.


Assuntos
Oryza , Xanthomonas , Antibacterianos/farmacologia , Cinamatos , Testes de Sensibilidade Microbiana , Oxidiazóis , Doenças das Plantas
3.
Ecotoxicol Environ Saf ; 227: 112879, 2021 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-34649142

RESUMO

Cinnamic acid (CA), one of the main autotoxins secreted by cucumber roots during continuous cropping, inhibits plant growth and reduces yield. Silicon (Si) is an environmentally friendly element that alleviates abiotic stresses in plants, but the mechanism underlying its resistance to autotoxicity remain unclear. Here, we used 0.8 mmol L-1 CA to study the effects of Si application on the growth, chlorophyll fluorescence, and ascorbate-glutathione (AsA-GSH) cycle of cucumber seedlings under CA inducing conditions. Our results indicated that CA significantly induced photoinhibition and overaccumulation of reactive oxygen species (ROS), thereby inhibiting cucumber growth. Treatment with 1.0 mmol L-1 Si improved plant height, stem diameter and biomass accumulation, and protected the photosynthetic electron transport function of photosystem II in the presence of CA. Similarly, Si application maintained the ROS status by increasing ascorbate (AsA) and glutathione (GSH) production, as well as the ratios of AsA/DHA and GSH/GSSG in both leaves and roots during CA stress. In addition, Si application in CA-treated seedlings enhanced the activity of key enzymes such as ascorbate peroxidase (APX), monodehydroascorbate reductase (MDHAR), dehydroascorbate reductase (DHAR), glutathione reductase (GR), glutathione S-transferase (GST), and the transcription of several enzyme genes (CsAPX, CsMDHAR and CsGR) from the AsA-GSH cycle. These results suggest that exogenous Si enhances CA tolerance in cucumber seedlings by protecting photosystem II activity, upregulating AsA-GSH pathway, and reducing ROS levels.


Assuntos
Cucumis sativus , Silício , Cinamatos , Glutationa , Complexo de Proteína do Fotossistema II , Folhas de Planta
4.
Molecules ; 26(19)2021 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-34641602

RESUMO

Surfactants have been used for decades in the food industry for the preparation of lipid-based emulsified food stuffs. They play two main roles in the emulsification processes: first they decrease the interfacial tension between the oil and water, facilitating droplet deformation and rupture; second, they reduce droplet coalescence by forming steric barriers. However, addition of surfactants to binary oil-water mixtures also brings up the formation of three-dimensional interfacial layers, surrounding each emulsion droplet, that significantly alter chemical reactivity. This is the case, for instance, in the inhibition reaction between antioxidants and the lipid radicals formed in the course of the spontaneous oxidation reaction of unsaturated lipids, which are commonly employed in the preparation of food-grade emulsions. The rate of the inhibition reaction depends on the effective concentrations of antioxidants, which are mostly controlled by the amount of surfactant employed in the preparation of the emulsion. In this work, we analyze the effects of the surfactant Tween 20 on the oxidative stability and on the effective concentrations of two model antioxidants derived from cinnamic acid, determining their interfacial concentrations in the intact emulsions to avoid disrupting the existing equilibria and biasing results. For this purpose, a recently developed methodology was employed, and experimental results were interpreted on the grounds of a pseudophase kinetic model.


Assuntos
Cinamatos/química , Óleo de Milho/química , Ácidos Cumáricos/química , Emulsificantes/química , Emulsões/química , Polissorbatos/química , Tensoativos/química , Antioxidantes/química , Fenômenos Químicos , Interações Hidrofóbicas e Hidrofílicas , Oxirredução , Tensão Superficial , Água
5.
Molecules ; 26(19)2021 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-34641608

RESUMO

The effect of spontaneous fermentation by lactic acid bacteria on the extraction yield of bioactive compounds and antioxidant activity from rosemary leaf extracts was investigated using high-performance thin-layer chromatography (HPTLC). Brining and spontaneous fermentation with lactic acid bacteria more than doubled extraction of polyphenolics and antioxidants from the rosemary leaves. The results show that lactic acid fermentation enhances antioxidant activity in extracts by increasing the total phenolic content but does not increase extraction of phytosterols. Increased extraction of phenolic oxidants during fermentation assisted extraction, results from the in situ generated natural eutectic solvent from the plant sample. ATR-FTIR spectra from the bioactive bands suggests that this increased antioxidant activity is associated with increased extraction of rosmarinic acid, depolymerised lignin, abietane diterpenoids and 15-hydroxy-7-oxodehydroabietic acid.


Assuntos
Antioxidantes/química , Antioxidantes/metabolismo , Lactobacillales/metabolismo , Extratos Vegetais/química , Extratos Vegetais/metabolismo , Rosmarinus/química , Rosmarinus/metabolismo , Abietanos/química , Abietanos/metabolismo , Cromatografia em Camada Delgada , Cinamatos/química , Cinamatos/metabolismo , Depsídeos/química , Depsídeos/metabolismo , Fermentação , Humanos , Lignina/química , Lignina/metabolismo , Fenóis/química , Fenóis/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Espectroscopia de Infravermelho com Transformada de Fourier
6.
Int J Mol Sci ; 22(19)2021 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-34638940

RESUMO

Several phytochemical-containing herbal extracts are increasingly marketed as health-promoting products. In particular, chamomile (Matricaria recutita L.) is well known for its anti-inflammatory, analgesic, and antitumor properties. Here, we evaluated differences in chemical composition among six commercially available products and their potential impact on biological activity in human immortalized colonocytes. Our investigation encompassed: (i) preparation of dry extracts and yield evaluation; (ii) qualitative and quantitative analysis of phenol content; (iii) modulation of redox state; and (iv) bioavailability of main bioactive compounds. We demonstrated that apparently identical products showed huge heterogeneity, in terms of yield extraction, chemical composition, and antioxidant effects. All samples contained high amounts of flavonoids and cinnamic acid derivatives, but differentially concentrated in the six extracts. Depending on polyphenol content, chamomile samples possessed variable antioxidant potential, in terms of decreased radical generation and increased reduced glutathione levels. The observed effects might be ascribed to flavones (apigenin, luteolin, and their glycones) highly represented in the six extracts. Nonetheless, chamomile extracts exerted cytotoxic effects at high concentrations, suggesting that a herbal medicine is not always safe. In conclusion, due to the complexity and variability of plant matrices, studies evaluating effectiveness of chamomile should always be accompanied by preliminary characterization of phytochemical composition.


Assuntos
Antioxidantes/química , Camomila/química , Matricaria/química , Compostos Fitoquímicos/química , Extratos Vegetais/química , Plantas Medicinais/química , Polifenóis/análise , Antioxidantes/farmacologia , Células CACO-2 , Sobrevivência Celular/efeitos dos fármacos , Cinamatos/análise , Flavonas/análise , Flavonoides/análise , Humanos , Oxirredução/efeitos dos fármacos , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Transdução de Sinais/efeitos dos fármacos
7.
Nutrients ; 13(10)2021 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-34684619

RESUMO

BACKGROUND: Insulin resistance (IR) is a condition in which the physiological amount of insulin is insufficient to evoke a proper response of the cell, that is, glucose utilization. Metformin is the first choice for therapy, thanks to its glycemic efficacy and general tolerability. In addition, various natural compounds from plant extracts, spices, and essential oils have been shown to provide health benefits regarding insulin sensitivity. In the present study, we analyzed the effect of phospholipid derivatives of selected natural aromatic acids on insulin action and their potential use to overcome insulin resistance. METHODS: The 3T3-L1 fibroblasts were differentiated into mature adipocytes; next, insulin resistance was induced by palmitic acid (16:0). Cells were further cultured with phenophospholipids at appropriate concentrations. To assess insulin sensitivity, we measured the insulin-stimulated glucose uptake, using a glucose uptake test. RESULTS: We showed that cinnamic acid (CA) and 3-methoxycinnamic acid (3-OMe-CA) restored the proper insulin response. However, 1,2-dicinnamoyl-sn-glycero-3-phosphocholine (1,2-diCA-PC) and 1-cinnamoyl-2-palmitoyl-sn-glycero-3-phosphocholine (1-CA-2-PA-PC) improved insulin sensitivity in insulin-resistant adipocytes even stronger, exhibiting more beneficial effects. CONCLUSIONS: The binding of aromatic acids to phosphatidylcholine increases their beneficial effect on insulin sensitivity in adipocytes and expands their potential practical application as nutraceutical health-promoting agents.


Assuntos
Adipócitos/patologia , Cinamatos/farmacologia , Fosfolipídeos/farmacologia , Células 3T3-L1 , Adipócitos/efeitos dos fármacos , Adipócitos/metabolismo , Animais , Sobrevivência Celular/efeitos dos fármacos , Cinamatos/química , Glucose/metabolismo , Insulina/farmacologia , Resistência à Insulina , Camundongos , Fosfolipídeos/química
8.
Rev Bras Parasitol Vet ; 30(3): e009221, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34495124

RESUMO

This study aimed to chemically characterize the essential oils (EOs) of Cinnamomum zeylanicum (cinnamon) and Eremanthus erythropappus (candeia) and evaluate their acaricidal activity, together with that of their major compounds and cinnamyl acetate derivative, against Rhipicephalus microplus. Essential oil compounds were identified through gas chromatography. The larval packet test (LPT) at concentrations ranging from 0.31 to 10.0 mg/mL and the adult immersion test (AIT) at concentrations between 2.5 and 60.0 mg/mL were performed. (E)-cinnamaldehyde and α-bisabolol were the major compounds in cinnamon (86.93%) and candeia (78.41%) EOs, respectively. In the LPT, the EOs of cinnamon and candeia and the compounds (E)-cinnamaldehyde, α-bisabolol and cinnamyl acetate resulted in 100% mortality at concentrations of 2.5, 2.5, 5.0, 10.0 and 10.0 mg/mL respectively. In the AIT, percentage control values > 95% were observed for cinnamon and candeia EOs, (E)-cinnamaldehyde and α-bisabolol at the concentrations of 5.0, 60.0, 20.0, and 20.0 mg/mL, respectively, whereas cinnamyl acetate showed low activity. We conclude that EOs and their compounds showed high acaricidal activity, whereas the acetylated derivative of (E)-cinnamaldehyde presented less acaricidal activity on R. microplus engorged females.


Assuntos
Acaricidas , Óleos Voláteis , Rhipicephalus , Acaricidas/farmacologia , Animais , Cinamatos , Cinnamomum zeylanicum , Larva , Óleos Voláteis/farmacologia
9.
Int J Mol Sci ; 22(18)2021 Sep 10.
Artigo em Inglês | MEDLINE | ID: mdl-34575950

RESUMO

Cinnamic acid and its derivatives have been studied for a variety of biological properties, including anti-inflammatory, antioxidant, anticancer, antihypertensive, and antibacterial. Many hybrids of cinnamic derivatives with other bioactive molecules have been synthesized and evaluated as nitric oxide (NO) donors. Since NO plays a significant role in various biological processes, including vasodilation, inflammation, and neurotransmission, NO donor groups are incorporated into the structures of already-known bioactive molecules to enhance their biological properties. In this review, we present cinnamic hybrids with NO-donating ability useful in the treatment of several diseases.


Assuntos
Cinamatos/química , Inflamação/terapia , Óxido Nítrico/química , Cinamatos/uso terapêutico , Humanos , Inflamação/metabolismo , Inflamação/patologia , Óxido Nítrico/genética , Óxido Nítrico/uso terapêutico , Vasodilatação/genética
10.
Molecules ; 26(18)2021 Sep 12.
Artigo em Inglês | MEDLINE | ID: mdl-34577004

RESUMO

The present work was aimed at studying the potential of elicitation on the accumulation of phenolic compounds in in vitro shoot cultures of Eryngium alpinum L., a protected plant from the Apiaceae family. The study examined the influence of (+)-usnic acid on the biomass growth as well as on the biosynthesis of the desired flavonoids and phenolic acids in the cultured microshoots. The phenolic compound content was determined by HPLC-DAD. The flavonoid of the highest concentration was isoquercetin, and the phenolic acids of the highest amount were rosmarinic acid, caffeic acid and 3,4-dihydroxyphenylacetic acid, both in the non-elicited and elicited biomass. Isoquercetin accumulation was efficiently increased by a longer elicitation with a lower concentration of lichenic compound (107.17 ± 4.67 mg/100 g DW) or a shorter elicitation with a higher concentration of acid (127.54 ± 11.34 and 108.37 ± 12.1 mg/100 g DW). Rosmarinic acid production generally remained high in all elicited and non-elicited microshoots. The highest content of this acid was recorded at 24 h of elicitation with 3.125 µM usnic acid (512.69 ± 4.89 mg/100 g DW). The process of elicitation with (+)-usnic acid, a well-known lichenic compound with allelopathic nature, may therefore be an effective technique of enhancing phenolic compound accumulation in alpine eryngo microshoot biomass.


Assuntos
Benzofuranos/farmacologia , Eryngium/química , Flavonoides/metabolismo , Hidroxibenzoatos/metabolismo , Brotos de Planta/química , Ácido 3,4-Di-Hidroxifenilacético/análise , Ácido 3,4-Di-Hidroxifenilacético/metabolismo , Biomassa , Ácidos Cafeicos/análise , Ácidos Cafeicos/metabolismo , Cromatografia Líquida de Alta Pressão , Cinamatos/análise , Cinamatos/metabolismo , Depsídeos/análise , Depsídeos/metabolismo , Eryngium/efeitos dos fármacos , Eryngium/crescimento & desenvolvimento , Eryngium/metabolismo , Flavonoides/análise , Hidroxibenzoatos/análise , Reguladores de Crescimento de Plantas/farmacologia , Brotos de Planta/efeitos dos fármacos , Brotos de Planta/crescimento & desenvolvimento , Quercetina/análogos & derivados , Quercetina/análise , Quercetina/metabolismo
11.
Plant Physiol Biochem ; 167: 934-945, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34555667

RESUMO

Methoxylated flavonoids, mainly xanthomicrol and cirsimaritin that can be extracted from Dracocephalum kotschyi Boiss, have anticancer, antispasmodic and antiplatelet effects. The production of these valuable pharmaceutical compounds is one of the major goals of biotechnology studies. In this work, induced transformed roots were influenced by various concentrations of titanium dioxide nanoparticles (TiO2 NPs) at 24 or 48 h exposure time. The effects of TiO2 NPs were assessed on growth rate, activity of antioxidant enzymes, total phenol and flavonoid content (TPC and TFC) and rosmarinic acid (RA) and some flavonoids accumulation. The gene expression level of phenylalanine ammonia-lyase (pal) and rosmarinic acid synthase (ras) genes were assessed by real time PCR analysis. The transformed roots biomass was substantially increased in elicited roots in comparison with the control. The TPC, TFC and antioxidant enzymes activitywere affected by TiO2 NPs concentration and exposure time. Valuable flavonoids with anticancer characteristics along with xanthomicrol, cirsimaritin and isokaempferide exhibited an increase (70, 34.28 and 7.81-fold, respectively) versus the control. The maximum content of RA (530.5 µg g-1 FW), which was 4.30 times as great as that of control was detected in samples treated with TiO2 NPs (50 mg L-1) 24 h after elicitation. Real-time PCR analysis revealed a considerable increase in pal and ras expression rate engaged by TiO2 NPs levels and exposure time. Overall D. kotschyi transformed roots elicitation by TiO2 NPs led to a massive increment in the production of valuable anticancer flavonoids such as xanthomicrol, cirsimaritin and RA as polyphenol.


Assuntos
Lamiaceae , Nanopartículas , Cinamatos , Depsídeos/farmacologia , Titânio
12.
Life Sci ; 284: 119938, 2021 Nov 01.
Artigo em Inglês | MEDLINE | ID: mdl-34506837

RESUMO

AIMS: The relationship between stress to endoplasmic reticulum (ER) and periodontitis has been known, and ER stress induced by Porphyromonas gingivalis results in the loss of alveolar bone. Salubrinal is a small synthetic compound and attenuates ER stress through inhibition of de-phosphorylation of eukaryotic translation initiation factor 2 alpha (eIF2α). In this study, we examined whether salubrinal attenuates periodontitis in a mouse model of experimental periodontal disease. MATERIALS AND METHODS: We evaluated loss of alveolar bone and attachment levels in periodontium using micro-computed tomography (µCT) and hematoxylin-eosin (HE) staining, respectively. Furthermore, we measured osteoclast numbers using tartrate-resistant acid phosphatase (TRAP) staining and osteoblast numbers using HE staining for bone resorption and for bone formation, respectively. To examine the inhibitory effects of salubrinal against pro-inflammatory cytokines, we measured TNF-α and IL1-ß score in periodontium using immunohistostaining. KEY FINDINGS: The results revealed that salubrinal suppressed loss of alveolar bone and attachment levels in periodontium induced by periodontitis. It decreased osteoclast numbers and increased osteoblasts. It also suppressed the expression levels of TNF-α in periodontium. SIGNIFICANCE: These results show that salubrinal alleviates periodontitis through suppression of alveolar bone resorption and the pro-inflammatory cytokine, and promotion of the bone formation. Since salubrinal has been shown to have these beneficial effects for periodontal disease, it may provide a novel therapeutic possibility for the disease.


Assuntos
Perda do Osso Alveolar/tratamento farmacológico , Cinamatos/uso terapêutico , Tioureia/análogos & derivados , Perda do Osso Alveolar/complicações , Perda do Osso Alveolar/diagnóstico por imagem , Perda do Osso Alveolar/patologia , Animais , Contagem de Células , Cinamatos/administração & dosagem , Cinamatos/farmacologia , Modelos Animais de Doenças , Estresse do Retículo Endoplasmático/efeitos dos fármacos , Interleucina-1beta/metabolismo , Masculino , Camundongos Endogâmicos C57BL , Osteoblastos/efeitos dos fármacos , Osteoblastos/patologia , Periodontite/complicações , Periodontite/tratamento farmacológico , Periodontite/patologia , Tioureia/administração & dosagem , Tioureia/farmacologia , Tioureia/uso terapêutico , Fator de Transcrição CHOP/metabolismo , Fator de Necrose Tumoral alfa/metabolismo , Microtomografia por Raio-X
13.
Molecules ; 26(17)2021 Sep 06.
Artigo em Inglês | MEDLINE | ID: mdl-34500838

RESUMO

Phenolic acids comprise a class of phytochemical compounds that can be extracted from various plant sources and are well known for their antioxidant and anti-inflammatory properties. A few of the most common naturally occurring phenolic acids (i.e., caffeic, carnosic, ferulic, gallic, p-coumaric, rosmarinic, vanillic) have been identified as ingredients of edible botanicals (thyme, oregano, rosemary, sage, mint, etc.). Over the last decade, clinical research has focused on a number of in vitro (in human cells) and in vivo (animal) studies aimed at exploring the health protective effects of phenolic acids against the most severe human diseases. In this review paper, the authors first report on the main structural features of phenolic acids, their most important natural sources and their extraction techniques. Subsequently, the main target of this analysis is to provide an overview of the most recent clinical studies on phenolic acids that investigate their health effects against a range of severe pathologic conditions (e.g., cancer, cardiovascular diseases, hepatotoxicity, neurotoxicity, and viral infections-including coronaviruses-based ones).


Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/farmacologia , Cinamatos/farmacologia , Hidroxibenzoatos/farmacologia , Extratos Vegetais/farmacologia , Anti-Inflamatórios/uso terapêutico , Antioxidantes/uso terapêutico , Doenças Cardiovasculares/diagnóstico , Doenças Cardiovasculares/tratamento farmacológico , Cinamatos/uso terapêutico , Ensaios Clínicos como Assunto , Infecções por Coronavirus/diagnóstico , Infecções por Coronavirus/tratamento farmacológico , Humanos , Hidroxibenzoatos/uso terapêutico , Hepatopatias/diagnóstico , Hepatopatias/tratamento farmacológico , Neoplasias/diagnóstico , Neoplasias/tratamento farmacológico , Doenças do Sistema Nervoso/diagnóstico , Doenças do Sistema Nervoso/tratamento farmacológico , Extratos Vegetais/uso terapêutico , Índice de Gravidade de Doença , Resultado do Tratamento
14.
Int J Mol Sci ; 22(17)2021 Aug 28.
Artigo em Inglês | MEDLINE | ID: mdl-34502255

RESUMO

The increasing interest towards greener antioxidants obtained via natural sources and more sustainable processes encourages the development of new theoretical and experimental methods in the field of those compounds. Two advanced separation methods using supercritical CO2 are applied to obtain valuable antioxidants from Salvia officinalis, and a first approximation to a QSAR model relating molecular structure with antioxidant activity is explored in order to be used, in the future, as a guide for the preselection of compounds of interest in these processes. Separation experiments through antisolvent fractionation with supercritical CO2 were designed using a Response Surface Methodology to study the effect of pressure and CO2 flow rate on both mass yields and capability to obtain fractions enriched in three antioxidant compounds: chlorogenic acid, caffeic acid and rosmarinic acid which were tracked using HPLC PDA. Rosmarinic acid was completely retained in the precipitation vessel while chlorogenic and caffeic acids, though distributed between the two separated fractions, had a major presence in the precipitation vessel too. The conditions predicted for an optimal overall yield and enrichment were 148 bar and 10 g/min. Although a training dataset including much more compounds than those now considered can be recommended, descriptors calculated from the σ-profiles provided by COSMO-RS model seem to be adequate for estimating the antioxidant activity of pure compounds through QSAR.


Assuntos
Antioxidantes/química , Antioxidantes/isolamento & purificação , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Salvia officinalis/química , Antioxidantes/análise , Ácidos Cafeicos/química , Fracionamento Químico/métodos , Ácido Clorogênico/química , Cromatografia Líquida de Alta Pressão , Cromatografia com Fluido Supercrítico/métodos , Cinamatos/química , Depsídeos/química , Conformação Molecular , Extratos Vegetais/análise , Relação Quantitativa Estrutura-Atividade
15.
J Food Sci ; 86(10): 4491-4499, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34486122

RESUMO

A new rapid method has been developed for the determination of low levels of rosmarinic acid extracted from rosemary (Rosmarinus officinalis L.) and has been used as an antioxidant in meat and meat products after cold storage at 4°C. The method is a high performance liquid chromatography using a coulometric electrochemical detector. It provides a significant improvement on the limit of detection, which was 0.33 ppb, while the limit of quantification was 1 ppb of rosmarinic acid. The advantage of the method also lies in the simpler and faster sample preparation, which can quantify a very low concentration of rosmarinic acid (60 ppb), and is more than 40 ppb below the limits of previously existing methods. A coulometric method is well suited for determining low analyte concentrations and is one of the most sensitive analytical approaches available today, in addition to being time efficient and cost effective. PRACTICAL APPLICATION: A new method for determining low concentrations (60 ppb) of rosmarinic acid in meat and meat products is presented. The method is user-friendly, as it does not require complex sample preparation. It is a selective, precise, and accurate method that makes it useful for routine applications in the meat and other food industries.


Assuntos
Cromatografia Líquida de Alta Pressão , Cinamatos , Depsídeos , Análise de Alimentos , Produtos da Carne , Cinamatos/análise , Depsídeos/análise , Análise de Alimentos/métodos , Produtos da Carne/análise
16.
J Med Microbiol ; 70(9)2021 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-34491156

RESUMO

Introduction. The increase of invasive fungal infections (IFIs) and associated treatment failure in populations at risk is driving us to look for new treatments.Hypothesis. The CIN-102 compound, derived from cinnamon essential oil, could be a new antifungal class with an activity, in particular, on strains resistant to current antifungals but also on biofilms, a factor of virulence and resistance of fungi.Aim. The aim of this study is to show the activity of CIN-102 on various strains resistant to current antifungals, on the biofilm and to determine the possibility of resistance induced with this compound.Methodology. We studied the MIC of CIN-102 and of current antifungals (voriconazole and amphotericin B) using CLSI techniques against eight different strains of three genera of filamentous fungi involved in IFIs and having resistance phenotypes to current antifungals. We also determined their effects on biofilm formation, and the induced resistance by voriconazole (VRC) and CIN-102.Results. MIC values determined for CIN-102 were between 62.5 and 250 µg ml-1. We demonstrated the antifungal effect of CIN-102 on biofilm, and more particularly on its formation, with 100 % inhibition achieved for most of the strains. CIN-102 at a sub-inhibitory concentration in the medium did not induce resistance in our strains, even after 30 generations.Conclusions. In this study we show that CIN-102 is effective against resistant filamentous fungi and against biofilm formation. In addition, our strains did not acquire a resistance phenotype against CIN-102 over time, unlike with VRC. CIN-102 is therefore an interesting candidate for the treatment of IFIs, including in cases of therapeutic failure linked to resistance, although further studies on its efficacy, safety and mechanism of action are needed.


Assuntos
Antifúngicos/farmacologia , Benzoatos/farmacologia , Biofilmes/efeitos dos fármacos , Cinamatos/farmacologia , Fungos/efeitos dos fármacos , Micoses , Terpenos/farmacologia , Anfotericina B/farmacologia , Combinação de Medicamentos , Humanos , Testes de Sensibilidade Microbiana , Micoses/tratamento farmacológico , Micoses/microbiologia , Voriconazol/farmacologia
17.
J Org Chem ; 86(18): 13118-13128, 2021 09 17.
Artigo em Inglês | MEDLINE | ID: mdl-34469153

RESUMO

We developed a general method for the selective photochemical homo- and heterodimerization of cinnamic acid derivatives with the use of commercially available 1,8-dihydroxynaphthalene as a covalent template. A variety of symmetrical and unsymmetrical ß-truxinic acids were obtained in high yields and as single diastereomers. The use of a template not only provides the alignment of the two olefins with suitable proximity (<4.2 Å) but also allows the heterodimerization of two different cinnamic acids, leading to unsymmetrical ß-truxinic acid products.


Assuntos
Cinamatos , Dimerização
18.
Mar Environ Res ; 171: 105469, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34500299

RESUMO

Products designed to filter ultraviolet (UV) light are responsible for growing levels of anthropogenic environmental contamination. Octinoxate (ONT) is among the most common UV filtering active ingredients in cosmetics and sunscreens. The present study was designed to evaluate the toxicological effects of ONT on the photosynthetic activity of the Chlorella species of marine microalgae. These analyses identified ONT as a potent photo-toxicant, the effects of which were more pronounced upon light exposure relative to in the dark. Short-term ONT exposure had no effect on photosynthetic electron transport capacity in the dark but did significantly reduce the ribulose-1,5-bisphosphate carboxylase/oxygenase activity in Chlorella cells, suggesting that this compound can directly suppress the photosynthetic Calvin cycle. When cells were subsequently exposed to light, the disruption of this cycle resulted in an excess of excitation energy, in turn driving the excessive generation of reactive oxygen species (ROS). ROS-mediated disruption of cellular metabolism further aggravated this ONT-induced microalgal damage. As such, under natural light conditions, these microalgae cells are exposed to increased oxidative stress that impairs their growth and causes pigment bleaching. Restricting the utilization of ONT-containing sunscreens thus has the potential to better preserve the integrity of aquatic and terrestrial ecosystems.


Assuntos
Chlorella , Microalgas , Cinamatos , Ecossistema , Fotossíntese , Protetores Solares/toxicidade
19.
J Agric Food Chem ; 69(32): 9443-9450, 2021 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-34351749

RESUMO

Styrene is a food-borne toxicant in wheat beer and due to its classification as possibly carcinogenic to humans by the International Agency for Research on Cancer in 2002, mitigation strategies had to be developed. Aiming at understanding the impact of the barley to wheat malt ratio (grain bill) during mashing on the contents of soluble and free (i) cinnamic, (ii) p-coumaric, and (iii) ferulic acid, precursors of (i) styrene and the desired vinyl aromatics (ii) 4-vinylphenol and (iii) 2-methoxy-4-vinylphenol in wheat beer, wort was prepared at four different barley to wheat malt ratios of 100:0, 25:75, 50:50, and 0:100 (w/w). Additionally, the malts were produced at different germination temperatures and aeration rates (12/32, 18/35, 18/25, 24/18, and 26/25 (°C; L/min)) to consider these two further parameters as well. Thereby, soluble and free phenolic acid contents in wort showed linear correlations to the percentage of wheat in the grain bill, highlighting the absence of synergistic effects when mixing barley and wheat malts. In contrast, the results described the phenolic acid contents as a function of the concentrations in the respective barley and wheat wort, multiplied by their percentage in the grain bill. However, a clear recommendation for favorable barley to wheat malt ratios leading to a decrease of soluble and free cinnamic acid in wort could not be made, as the contents in the present study proved to be highly dependent on the barley and wheat varieties used during mashing and the parameters applied during malting. This was not the case for p-coumaric acid for which a clear decrease of the soluble and free forms was found with increasing wheat malt contents. Differently, the soluble form of ferulic acid increased with an increasing percentage of wheat malt, while the free form decreased. The malting parameters clearly recommended high germination temperatures and low aeration rates when aiming at a reduction of undesired cinnamic acid in wort. Fortunately, soluble and free p-coumaric and ferulic acid contents were only slightly affected, indicating that the formation of the characteristic wheat beer aroma might not suffer when applying these favorable conditions for styrene reduction.


Assuntos
Hordeum , Cerveja/análise , Cinamatos , Grão Comestível/química , Humanos , Estireno/análise , Triticum
20.
Int J Mol Sci ; 22(16)2021 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-34445501

RESUMO

Lipid dysregulation in diabetes mellitus escalates endothelial dysfunction, the initial event in the development and progression of diabetic atherosclerosis. In addition, lipid-laden macrophage accumulation in the arterial wall plays a significant role in the pathology of diabetes-associated atherosclerosis. Therefore, inhibition of endothelial dysfunction and enhancement of macrophage cholesterol efflux is the important antiatherogenic mechanism. Rosmarinic acid (RA) possesses beneficial properties, including its anti-inflammatory, antioxidant, antidiabetic and cardioprotective effects. We previously reported that RA effectively inhibits diabetic endothelial dysfunction by inhibiting inflammasome activation in endothelial cells. However, its effect on cholesterol efflux remains unknown. Therefore, in this study, we aimed to assess the effect of RA on cholesterol efflux and its underlying mechanisms in macrophages. RA effectively reduced oxLDL-induced cholesterol contents under high glucose (HG) conditions in macrophages. RA enhanced ATP-binding cassette transporter A1 (ABCA1) and G1 (ABCG1) expression, promoting macrophage cholesterol efflux. Mechanistically, RA differentially regulated ABCA1 expression through JAK2/STAT3, JNK and PKC-p38 and ABCG1 expression through JAK2/STAT3, JNK and PKC-ERK1/2/p38 in macrophages. Moreover, RA primarily stabilized ABCA1 rather than ABCG1 protein levels by impairing protein degradation. These findings suggest RA as a candidate therapeutic to prevent atherosclerotic cardiovascular disease complications related to diabetes by regulating cholesterol efflux in macrophages.


Assuntos
Transportador 1 de Cassete de Ligação de ATP/metabolismo , Membro 1 da Subfamília G de Transportadores de Cassetes de Ligação de ATP/metabolismo , Colesterol/metabolismo , Cinamatos/farmacologia , Depsídeos/farmacologia , Glucose/efeitos adversos , Lipoproteínas LDL/efeitos adversos , Macrófagos/citologia , Transportador 1 de Cassete de Ligação de ATP/química , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Modelos Biológicos , Proteólise/efeitos dos fármacos , Transdução de Sinais , Células THP-1
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