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Influenza is an important zoonotic disease that persistently threatens global public health. While it is widely acknowledged that probiotics can modulate the host response to protect the host against infectious disease, the prophylactic efficacy on respiratory viral infection and the detailed mechanism remains elusive. Lactobacillus, the most commonly used probiotic widely applied in food production, has garnered significant attention. In our study utilizing both C57BL/6 and BALB/c mouse models, we explored the protective effect against two strains of influenza virus, A/Mink/China/01/2014(H9N2) and A/California/04/2009(H1N1), through the administration of Lactiplantibacillus plantarum strain 16 (L. plantarum 16) and Lacticaseibacillus rhamnosus strain P118 (L. rhamnosus P118), aiming to identify robust probiotic strains with antiviral properties. Our findings indicate that administering L. plantarum 16 or L. rhamnosus P118 alone does not provide sufficient protection against influenza. However, the co-administration of L. plantarum 16 and L. rhamnosus P118 dramatically reduces viral titers in the respiratory tract and lung, thereby markedly alleviating the clinical symptoms, improving prognosis, and reducing mortality. The mechanisms underlying this effect involve the modulation of host gut microbiota and metabolism through the co-administration of L. plantarum 16 and L. rhamnosus P118, resulting in enrichment of Firmicutes and enhancement of phenylalanine-related metabolism, ultimately leading to an augmentation of the antiviral immune response. Notably, we identified that the circulating metabolic molecule 2-Hydroxycinnamic acid plays a significant role in combating influenza. Our data suggest the potential utility of L. plantarum 16 and L. rhamnosus P118 two-bacterium or 2-Hydroxycinnamic acid in preventing influenza.IMPORTANCEVaccination represents the most optimal strategy to control influenza. Nevertheless, influenza viruses constantly evolve due to antigenic drift and shift, leading to the need for regular updates on influenza vaccines. Additionally, vaccination failure poses significant challenges to influenza prevention. Therefore, it is essential and beneficial to identify novel or universal antiviral measures to protect against influenza. While cumulative data suggest that probiotics offer protection against infectious diseases, the specific mechanisms, such as the effective metabolites or components, remain largely unknown. Our research discovered the capacity of combinational two-bacterium Lactiplantibacillus plantarum 16 and Lacticaseibacillus rhamnosus P118 to fight against influenza infection in a mouse model. The protection may occur through modulating the host's gut microbiota and metabolism, further influencing the host's antiviral immune response. Notably, we have identified a novel metabolic molecule, 2-Hydroxycinnamic acid, capable of enhancing antiviral response and restricting viral replication in vivo.

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OBJECTIVE: To evaluate whether p-hydroxycinnamic acid (pHCA) alone and in combination with niacinamide (Nam) can mitigate UV-induced erythema, barrier disruption, and inflammation. METHODS: Three independent placebo-controlled double-blinded studies were conducted on female panellists who were pretreated on sites on their backs for 2 weeks with skin care formulations which contained 0.3% or 1% pHCA with 5% Nam, 1% pHCA alone, 1.8% octinoxate, or control formula. Treated sites were then exposed to 1.5 minimal erythemal dose (MED) solar simulated radiation (SSR) and had chromameter and expert grading measures for erythema, barrier integrity via TEWL, and the skin surface IL-1RA/IL-1α inflammatory biomarkers isolated from D-Squame tapes. RESULTS: Across the three independent studies, pHCA alone or in combination with Nam showed a significant mitigation of UV-induced erythema, barrier disruption, and levels of the surface inflammatory biomarkers IL-1RA/IL-1α. The cinnamate analogue Octinoxate did not replicate the effects of pHCA. CONCLUSION: The study results show that pHCA alone or in combination with Nam can mitigate UV-induced damage to skin. These include mitigation of UV-induced erythema as measured by instrument and expert grade visualization. Additionally, pHCA with Nam protected damage to the barrier and reduced the induction of the SASP-related surface inflammatory biomarker IL-1RA/IL-1α. The inability of Octinoxate to have any protective effect and the detection of low levels of pHCA on skin surface after 24 h of application supports that these effects are based on a biological response to pHCA. These findings add to the body of evidence that pHCA alone or in combination with Nam can enhance the skin's biological response to UV-induced damage. This supports pHCA can potentially impact aging and senescence, thereby maintain skin's functionality and appearance.

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OBJECTIF: Évaluer si l'acide p­hydroxycinnamique (p­hydroxycinnamic acid, pHCA) seul et en association avec le niacinamide (Nam) peut atténuer l'érythème induit par les UV, la rupture de la barrière et l'inflammation. MÉTHODES: Trois études en double aveugle, contrôlées par placebo et indépendantes, ont été menées auprès de femmes panélistes ayant reçu un traitement préalable sur le dos pendant deux semaines avec des formulations de soins cutanés contenant 0.3% ou 1% de pHCA avec 5% de Nam, 1% de pHCA seul, 1.8% d'octinoxate ou une formule témoin. Les sites traités ont ensuite été exposés à une dose érythémateuse minimale (MED) de 1.5 de radiation solaire simulée (SSR) et ont été évalués à l'aide de mesures par chromamètre et de cotations par des experts concernant l'érythème, l'intégrité de la barrière via la perte insensible en eau (TEWL), et les biomarqueurs inflammatoires de la surface cutanée IL­1RA/IL­1 α isolés à partir de bandes D­Squame. RÉSULTATS: Dans les 3 études indépendantes, le pHCA seul ou en association avec le Nam a montré une atténuation significative de l'érythème induit par les UV, de la perturbation de la barrière et des taux des biomarqueurs inflammatoires de surface IL­1RA/IL­1α. L'analogue du cinnamate, l'octinoxate, n'a pas reproduit les effets du pHCA. CONCLUSION: Les résultats des études montrent que le pHCA seul ou en association avec le Nam peut atténuer les dommages cutanés induits par les UV. Ceux­ci comprennent l'atténuation de l'érythème induit par les UV, mesuré par instrument et une visualisation de qualité experte. En outre, le pHCA en association avec le Nam a protégé contre les dommages de la barrière et a réduit l'induction du biomarqueur inflammatoire de surface lié à la SASP IL­1RA/IL­1α. L'incapacité de l'octinoxate à avoir un effet protecteur, ainsi que la détection de faibles niveaux de pHCA à la surface de la peau après 24 heures d'application, confirme que ces effets sont basés sur une réponse biologique au pHCA. Ces résultats viennent s'ajouter à l'ensemble des preuves montrant que le pHCA seul ou en association avec le Nam peut améliorer la réponse biologique de la peau aux dommages induits par les UV. Cela soutient l'hypothèse que le pHCA peut avoir une incidence potentielle sur le vieillissement et la sénescence, maintenant ainsi la fonctionnalité et l'aspect de la peau.

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Para-hydroxycinnamic acid (pHCA) is one of the most abundant naturally occurring hydroxycinnamic acids, a class of chemistries known for their antioxidant properties. In this study, we evaluated the impact of pHCA on different parameters of skin aging in in vitro skin models after H2O2 and UV exposure. These parameters include keratinocyte senescence and differentiation, inflammation, and energy metabolism, as well as the underlying molecular mechanisms. Here we demonstrate that pHCA prevents oxidative stress-induced premature senescence of human primary keratinocytes in both 2D and 3D skin models, while improving clonogenicity in 2D. As aging is linked to inflammation, referred to as inflammaging, we analyzed the release of IL-6, IL-8, and PGE2, known to be associated with senescence. All of them were downregulated by pHCA in both normal and oxidative stress conditions. Mechanistically, DNA damage induced by oxidative stress is prevented by pHCA, while pHCA also exerts a positive effect on the mitochondrial and glycolytic functions under stress. Altogether, these results highlight the protective effects of pHCA against inflammaging, and importantly, help to elucidate its potential mechanisms of action.

Asunto(s)

Senescencia Celular , Ácidos Cumáricos , Queratinocitos , Estrés Oxidativo , Envejecimiento de la Piel , Piel , Humanos , Ácidos Cumáricos/farmacología , Senescencia Celular/efectos de los fármacos , Queratinocitos/efectos de los fármacos , Queratinocitos/metabolismo , Estrés Oxidativo/efectos de los fármacos , Piel/metabolismo , Piel/efectos de los fármacos , Envejecimiento de la Piel/efectos de los fármacos , Inflamación/metabolismo , Daño del ADN/efectos de los fármacos , Peróxido de Hidrógeno/metabolismo , Rayos Ultravioleta/efectos adversos , Antioxidantes/farmacología , Células Cultivadas , Interleucina-8/metabolismo , Interleucina-6/metabolismo

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Our research group previously identified graviquinone (1) as a promising antitumor metabolite that is formed in situ when the antioxidant methyl caffeate scavenges free radicals. Furthermore, it exerted a DNA damaging effect on cancer cells and a DNA protective effect on normal keratinocytes. To expand and explore chemical space around qraviquinone, in the current work we synthesized 9 new alkyl-substituted derivatives and tested their in vitro antitumor potential. All new compounds bypassed ABCB1-mediated multidrug resistance and showed highly different cell line specificity compared with 1. All compounds were more potent in MDA-MB-231 than on MCF-7 cells. The n-butyl-substituted derivatives 2 and 8 modulated the cell cycle and inhibited the ATR-mediated phosphorylation of checkpoint kinase-1 in MCF-7 cells. As a significant expansion of our previous findings, our results highlight the potential antitumor value of alkyl-substituted graviquinone derivatives.

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This study investigated the therapeutic benefits of para-hydroxycinnamic acid in mice with bleomycin-induced lung fibrosis. Forty male BALB/c mice were randomly assigned to four groups: normal, which received 0.9% normal saline; induced, which received a single dose of bleomycin (5 mg/kg) by oropharyngeal challenge; pirfenidone-treated; and para-hydroxycinnamic acid-treated, which challenged with bleomycin and received a daily oral dose of 300 and 50 mg/kg, respectively, from day 7 to day 21. Tissue pro-fibrotic and inflammatory cytokines, oxidative indicators, pulmonary histopathology, immunohistochemistry of fibrotic proteins and the assessment of gene expression by RT-qPCR were evaluated on day 22 after euthanizing animals. Pirfenidone and para-hydroxycinnamic acid managed to alleviate the fibrotic endpoints by statistically improving the weight index, histopathological score and reduced expression of fibrotic-related proteins in immune-stained lung sections, as well as fibrotic markers measured in serum samples. They also managed to alleviate tissue levels of oxidative stress and inflammatory and pro-fibrotic mediators. para-Hydroxycinnamic acid enhanced the expression of crucial genes associated with oxidative stress, inflammation and fibrosis in vivo. para-Hydroxycinnamic acid has demonstrated similar effectiveness to pirfenidone, suggesting it could be a promising treatment for fibrotic lung conditions by inhibiting the TGF-ß1/Smad3 pathway or through its anti-inflammatory and antioxidant properties.

Asunto(s)

Bleomicina , Ácidos Cumáricos , Pulmón , Ratones Endogámicos BALB C , Estrés Oxidativo , Fibrosis Pulmonar , Animales , Bleomicina/toxicidad , Fibrosis Pulmonar/inducido químicamente , Fibrosis Pulmonar/tratamiento farmacológico , Fibrosis Pulmonar/metabolismo , Fibrosis Pulmonar/prevención & control , Masculino , Estrés Oxidativo/efectos de los fármacos , Ratones , Ácidos Cumáricos/farmacología , Pulmón/efectos de los fármacos , Pulmón/patología , Pulmón/metabolismo , Piridonas/farmacología , Inflamación/tratamiento farmacológico , Inflamación/inducido químicamente , Inflamación/metabolismo , Citocinas/metabolismo , Modelos Animales de Enfermedad , Antioxidantes/farmacología , Factor de Crecimiento Transformador beta1/metabolismo , Factor de Crecimiento Transformador beta1/genética

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To aid valorisation of beer brewing by-products, more insight into their composition is essential. We have analysed the phenolic compound composition of four brewing by-products, namely barley rootlets, spent grain, hot trub, and cold trub. The main phenolics detected were hydroxycinnamoylagmatines and dimers thereof. Barley rootlets contained the highest hydroxycinnamoylagmatine content and cold trub the highest dimer content. Additionally, variations in (dimeric) hydroxycinnamoylagmatine composition and content were observed in fourteen barley rootlet samples. The most abundant compound in all rootlets was the glycosylated 4-O-7'/3-8'-linked heterodimer of coumaroylagmatine and feruloylagmatine, i.e. CouAgm-4-O-7'/3-8'-(4'Hex)-DFerAgm. Structures of glycosylated and hydroxylated derivatives of coumaroylagmatine were elucidated by NMR spectroscopy after their purification from a rootlet extract. An MS-based decision tree was developed, which aids in identifying hydroxycinnamoylagmatine dimers in complex mixtures. In conclusion, this study shows that the diversity of phenolamides and (neo)lignanamides in barley-derived by-products is larger than previously reported.

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Cerveza , Hordeum , Hordeum/química , Cerveza/análisis , Dimerización , Residuos/análisis , Fenoles/química , Fenoles/análisis , Ácidos Cumáricos/química , Ácidos Cumáricos/análisis , Estructura Molecular

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Yerba Mate (Ilex paraguariensis) is historically used as a beverage and its extracts are considered traditional medicine in South America. Extract use has been expanding to North American and European markets and the currently available genetic toxicology literature indicate discrepancies in genotoxicity findings for yerba mate. As botanical extract use expands, assumption in safety should be made with caution assuring a good understanding of the test material characterization. Authoritative agencies suggest a two-step paradigm to investigate genotoxicity, and this was implemented to evaluate the safety of yerba mate hydroxycinnamic acid extract. Four OECD compliant assays were employed: bacterial reverse mutation, in vitro micronucleus and a parallel in vivo micronucleus, and comet assay. No evidence of mutagenicity was observed in the in vitro Ames assay, but the results of an in vitro micronucleus study were inconclusive. However, oral gavage treatment of rats for the in vivo micronucleus and comet assays demonstrated negative findings. The results from this battery of tests, supports that this yerba mate hydroxycinnamic acid extract is not anticipated to pose genotoxicity concerns. A high-level comparison of results to other available genotoxicity literature on yerba mate is presented with emphasis on the importance of identity when drawing conclusions on botanicals.

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Aim This study aimed to evaluate the cytotoxicity of a novel compound, 4-hydroxycinnamic acid (4-HCA), with the help of a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and zebrafish embryotoxicity. Materials and methods In this in vitro study, MTT fibroblast assays using dental pulp stem cells, which were cultured in Modified Eagle's Medium or Dulbecco's Modified Eagle Medium, and zebrafish cytotoxicity and embryotoxicity were done to evaluate the cytotoxicity of the novel compound 4-HCA. The data was analyzed by plotting cell number versus absorbance, allowing quantitation of changes in cell proliferation. Results 4-HCA (40 µl) showed acceptable levels of cell viability according to the American Society for Testing and Materials standards. Cell viability is reduced with increased exposure time and concentrations of 4-HCA. Similarly, the cytotoxicity assessment in zebrafish (Danio rerio) showed an acceptable range of toxicity levels in embryonic stages used to evaluate the mortality rate of zebrafish embryos. Conclusion Considering the constraints of this research, it can be deduced that hydroxycinnamic acid at a concentration of 40 µl was non-toxic. The findings from the MTT assay indicated a correlation between the concentration and the toxicity of the compound. Likewise, the zebrafish test demonstrated minimal toxicological effects.

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Dimers of hydroxycinnamoylagmatines are phenolic compounds found in barley and beer. Although they are bioactive and sensory-active compounds, systematic reports on their structure-property relationships are missing. This is partly due to lack of protocols to obtain a diverse set of hydroxycinnamoylagmatine homo- and heterodimers. To better understand dimer formation in complex systems, combinations of the monomers coumaroylagmatine (CouAgm), feruloylagmatine (FerAgm), and sinapoylagmatine (SinAgm) were incubated with horseradish peroxidase. For all combinations, the main oxidative coupling products were homodimers. Additionally, minor amounts of heterodimers were formed, except for the combination of FerAgm and CouAgm. Oxidative coupling was also performed with laccases from Agaricus bisporus and Trametes versicolor, resulting in formation of the same coupling products and no formation of CouAgm-FerAgm heterodimers. Our protocol for oxidative coupling combinations of hydroxycinnamoylagmatines yielded a structurally diverse set of coupling products, facilitating production of dimers for future research on their structure-property relationships.

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Hordeum , Hordeum/metabolismo , Trametes/metabolismo , Oxidación-Reducción , Fenoles , Estrés Oxidativo , Lacasa/metabolismo

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Aegle marmelos (L.) Correa is an economically and therapeutically valuable tree. It is cultivated as a fruit plant in southeast Asian countries. In this research, we investigated the allelopathy and possible allelochemicals in the leaves of A. marmelos. Aqueous methanol extracts of A. marmelos exhibited significant inhibitory effects against the growth of Lepidium sativum, Lactuca sativa, Medicago sativa, Echinochloa crusgalli, Lolium multiflorum, and Phleum pratense. Bioassay-directed chromatographic purification of the A. marmelos extracts resulted in identifying five active compounds: umbelliferone (1), trans-ferulic acid (2), (E)-4-hydroxycinnamic acid methyl ester (3), trans-cinnamic acid (4), and methyl (E)-3'-hydroxyl-4'-methoxycinnamate (5). The hypocotyl and root growth of L. sativum were considerably suppressed by these compounds. Methyl (E)-3'-hydroxyl-4'-methoxycinnamate also suppressed the coleoptile and root growth of E. crusgalli. The concentrations of these compounds, causing 50% growth reduction (I50) of L. sativum, were in the range of 74.19-785.4 µM. The findings suggest that these isolated compounds might function in the allelopathy of A. marmelos.

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Variations between fruit cultivars can significantly impact their biochemical composition. The present research examined the variability in the qualitative and quantitative content of phenolic compounds in berry extracts of Actinidia kolomikta and Actinidia arguta cultivars. Additionally, antioxidant activities of berry extracts were evaluated. The total phenolic, flavonoid, proanthocyanidin contents and hydroxycinnamic acid derivatives were determined using the appropriate methodologies. The average amount of phenolic compounds in A. kolomikta berries (177.80 mg/g) was three times higher than that of A. arguta (54.45 mg/g). Our findings revealed that berries of A. kolomikta and A. arguta accumulated, on average, 1.58 RE/g DW (rutin equivalent/g dry weight) and 0.615 mg RE/g DW of total flavonoids, 1439.31 mg EE/g DW (epicatechin equivalent/g dry weight) and 439.97 mg EE/g DW of proanthocyanidins, and 23.51 mg CAE/g DW (chlorogenic acid equivalent/g dry weight) and 5.65 mg CAE/g DW of hydroxycinnamic acid derivatives, respectively. The cultivars of both species were characterized by higher antioxidant activity of total phenolic compounds determined using CUPRAC and FRAP methods compared to the ABTS•+ method. The variability in phenolic compounds' qualitative and quantitative content in tested berry extracts was evaluated by applying ultra-high performance liquid chromatography (UHPLC) coupled to mass spectrometry in tandem with electrospray ionization. Significant intraspecific differences in the amounts of total phenolic compounds, total flavonoid compounds, proanthocyanidins, and hydroxycinnamic acid derivatives were determined among cultivars. Four phenolic acids, eight flavonols, two flavones, and five flavon-3-ols were identified in the berry extracts.

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Maize production is pivotal in ensuring food security, particularly in developing countries. However, the crop encounters multiple challenges stemming from climatic changes that adversely affect its yield, including biotic and abiotic stresses during production and storage. A promising strategy for enhancing maize resilience to these challenges involves modulating its hydroxycinnamic acid amides (HCAAs) content. HCAAs are secondary metabolites present in plants that are essential in developmental processes, substantially contributing to defense mechanisms against environmental stressors, pests, and pathogens, and exhibiting beneficial effects on human health. This mini-review aims to provide a comprehensive overview of HCAAs in maize, including their biosynthesis, functions, distribution, and health potential applications.

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Tissue engineering is an interdisciplinary field that develops new methods to enhance the regeneration of damaged tissues, including those of wounds. Polymer systems containing bioactive molecules can play an important role in accelerating tissue regeneration, mitigating inflammation process, and fighting bacterial infection. Chitosan (CS) has attracted much attention regarding its use in wound healing system fabrication thanks to its biocompatibility, biodegradability, and the presence of functional groups in its structure. In this work, bioactive chitosan-based membranes were obtained by both chemical and physical modifications of the polymer with glycidyl methacrylate and glycerol (GLY), respectively. The most suitable GLY concentration to obtain wound healing systems with good elongation at break, a good water vapor transmission rate (WVTR), and good wettability values was 20% (w/w). Afterwards, the membranes were crosslinked with different concentrations of ethylene glycol dimethacrylate (EGDMA). By using a concentration of 0.05 mM EGDMA, membranes with a contact angle and WVTR values suitable for the application were obtained. To make the system bioactive, 3,4-dihydrocinnamic acid (HCAF) was introduced into the membranes, either by imbibition or chemical reaction, using laccase as a catalyst. Thermal and mechanical analyses confirmed the formation of a cohesive network, which limited the plasticizing effect of GLY, particularly when HCAF was chemically bound. The HCAF-imbibed membrane showed a good antioxidant and antimicrobial activity, highlighting the potential of this system for the treatment of wound healing.

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Antiinfecciosos , Quitosano , Quitosano/farmacología , Quitosano/química , Antioxidantes/farmacología , Antiinfecciosos/farmacología , Cicatrización de Heridas , Polímeros/farmacología , Antibacterianos/farmacología

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The fabacean Enterolobium cyclocarpum is a tree with multiple uses in production systems and its fruits serve as food for livestock, in addition, they contain phenolic compounds. The ovicidal effect of the secondary compounds of the Enterolobium cyclocarpum fruits extracted with hydroalcoholic solvent (HA-E) and the aqueous (Aq-F) and organic (AcOEt-F) fractions was evaluated. Additionally, a phytochemical analysis of the extract and fractions was performed by high performance liquid chromatography (HPLC). The HA-E showed an ovicidal effect close to 100% with the concentration evaluated of the 100 mg/mL. The fractionation of the extract allowed to potentiate the activity in the Aq (94.05% at 12 mg/mL) and AcOEt (99.45% at 3 mg/mL) fractions. The secondary compounds extracted from the fruits of E. cyclocarpum in the HA-E and fractions were flavonols, coumaric and ferulic acids and other derivatives of hydroxycinnamic acid and were responsible for the ovicidal activity observed against H. contortus.

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The pharmacological treatments that are now recommended for the therapy of chronic illnesses are examined in a great number of studies to determine whether or not they are both safe and effective. Therefore, it is important to investigate various alternative therapeutic assistance, such as natural remedies derived from medicinal plants. In this context, chicoric acid, classified as a hydroxycinnamic acid, has been documented to exhibit a range of health advantages. These include antiviral, antioxidant, anti-inflammatory, obesity-preventing, and neuroprotective effects. Due to its considerable pharmacological properties, chicoric acid has found extensive applications in food, pharmaceuticals, animal husbandry, and various other commercial sectors. This article provides a comprehensive overview of in vitro and in vivo investigations on chicoric acid, highlighting its beneficial effects and therapeutic activity when used as a preventative and management aid for public health conditions, including diabetes, cardiovascular disease, and hepatic illnesses like non-alcoholic steatohepatitis. Moreover, further investigation of this compound can lead to its development as a potential phytopharmaceutical candidate.

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p-Hydroxycinnamic acids, such as sinapic, ferulic, p-coumaric and caffeic acids, are among the most abundant phenolic compounds found in plant biomass and agro-industrial by-products (e.g. cereal brans, sugar-beet and coffee pulps, oilseed meals). These p-hydroxycinnamic acids, and their resulting decarboxylation products named vinylphenols (canolol, 4-vinylguaiacol, 4-vinylphenol, 4-vinylcatechol), are bioactive molecules with many properties including antioxidant, anti-inflammatory and antimicrobial activities, and potential applications in food, cosmetic or pharmaceutical industries. They were also shown to be suitable precursors of new sustainable polymers and biobased substitutes for fine chemicals such as bisphenol A diglycidyl ethers. Non-oxidative microbial decarboxylation of p-hydroxycinnamic acids into vinylphenols involves cofactor-free and metal-independent phenolic acid decarboxylases (EC 4.1.1 carboxyl lyase family). Historically purified from bacteria (Bacillus, Lactobacillus, Pseudomonas, Enterobacter genera) and some yeasts (e.g. Brettanomyces or Candida), these enzymes were described for the decarboxylation of ferulic and p-coumaric acids into 4-vinylguaiacol and 4-vinylphenol, respectively. The catalytic mechanism comprised a first step involving p-hydroxycinnamic acid conversion into a semi-quinone that then decarboxylated spontaneously into the corresponding vinyl compound, in a second step. Bioconversion processes for synthesizing 4-vinylguaiacol and 4-vinylphenol by microbial decarboxylation of ferulic and p-coumaric acids historically attracted the most research using bacterial recombinant phenolic acid decarboxylases (especially Bacillus enzymes) and the processes developed to date included mono- or biphasic systems, and the use of free- or immobilized cells. More recently, filamentous fungi of the Neolentinus lepideus species were shown to natively produce a more versatile phenolic acid decarboxylase with high activity on sinapic acid in addition to the others p-hydroxycinnamic acids, opening the way to the production of canolol by biotechnological processes applied to rapeseed meal. Few studies have described the further microbial/enzymatic bioconversion of these vinylphenols into valuable compounds: (i) synthesis of flavours such as vanillin, 4-ethylguaiacol and 4-ethylphenol from 4-vinylguaiacol and 4-vinylphenol, (ii) laccase-mediated polymer synthesis from canolol, 4-vinylguaiacol and 4-vinylphenol.

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INTRODUCTION: Twisted-leaf garlic (Allium obliquum L.) is a wild Allium species, which is traditionally used as aroma plant for culinary purposes due to its unique, garlic-like flavor. It represents an interesting candidate for domestication, breeding and cultivation. OBJECTIVES: The objective of this work was to explore and comprehensively characterize polar and semi-polar phytochemicals accumulating in leaves and bulbs of A. obliquum. METHOD: Plant material obtained from a multiyear field trial was analyzed using a metabolite profiling workflow based on ultra-high performance liquid chromatography-coupled electrospray ionization quadrupole time-of-flight mass spectrometry (UHPLC/ESI-QTOFMS) and two chromatographic methods. For annotation of metabolites, tandem mass spectrometry experiments were carried out and the resulting accurate-mass collision-induced dissociation (CID) mass spectra interpreted. Onion and garlic bulb extracts were used as reference samples. RESULTS: Important metabolite classes influencing nutritional, sensory and technological properties were detected and structurally characterized including fructooligosaccharides with a degree of polymerization of 3-5, S-alk(en)ylcysteine sulfoxides and other S-substituted cysteine conjugates, flavonoids including O- and C-glycosylated flavones as well as O-glycosylated flavonols, steroidal saponins, hydroxycinnamic acid conjugates, phenylethanoids and free sphingoid bases. In addition, quantitative data for non-structural carbohydrates, S-alk(en)ylcysteine sulfoxides and flavonoids are provided. CONCLUSION: The compiled analytical data including CID mass spectra of more than 160 annotated metabolites provide for the first time a phytochemical inventory of A. obliquum and lay the foundation for its further use as aroma plant in food industry.

Asunto(s)

Ajo , Espectrometría de Masa por Ionización de Electrospray , Espectrometría de Masa por Ionización de Electrospray/métodos , Ajo/química , Ajo/metabolismo , Metabolómica , Cromatografía Liquida , Flavonoides/análisis , Sulfóxidos/química , Sulfóxidos/metabolismo , Hojas de la Planta/metabolismo , Antioxidantes/metabolismo , Fitoquímicos , Proteínas Tirosina Quinasas Receptoras/metabolismo

RESUMEN

Antioxidants (AOs) from natural resources are an attractive research area, as petroleum-based products can be replaced in polymer stabilization. Therefore, novel esters based on the p-hydroxycinnamic acids p-coumaric acid, ferulic acid and sinapic acid were synthesized and their structure properties relationships were investigated. The structures of the novel bio-based antioxidants were verified using NMR and Fourier-transform infrared (FTIR) spectrometry. The high thermal stability above 280 °C and, therefore, their suitability as potential plastic stabilizers were shown using thermal gravimetric analysis (TGA). The radical scavenging activity of the synthesized esters was evaluated by using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. Stabilization performance was evaluated in polypropylene (PP) using extended extrusion experiments, oxidation induction time (OIT) measurements and accelerated heat aging. In particular, the sinapic acid derivative provides a processing stability of PP being superior to the commercial state-of-the-art stabilizer octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

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Currently, the interest of consumers towards functional foods as source of bioactive compounds is increasing. The sprouts of Raphanus sativus var longipinnatus (Brassicaceae) are "microgreens" popular, especially in gourmet cuisine, for their appealing aspect and piquant flavour. They represent a functional food due to their high nutritional value and health-promoting effects. Herein, the sprouts of daikon were extracted by different solvent mixtures to highlight how this process can affect the chemical profile and the antioxidant activity. An in-depth investigation based on a preliminary LC-ESI/LTQOrbitrap/MS profiling was carried out, leading to the identification of nineteen compounds, including glucosinolates and hydroxycinnamic acid derivatives. An undescribed compound, 1-O-feruloyl-2-O-sinapoyl-ß-D-glucopyranoside, was isolated, and its structure was elucidated by NMR spectroscopy. The phenolic content and radical scavenging activity (DPPH and TEAC assays), along with the ability to activate Nrf2 (Nrf2-mediated luciferase reporter gene assay) of polar extracts, were evaluated. The results showed the highest antioxidant activity for the 70% EtOH/H2O extract with a TEAC value of 1.95 mM and IC50 = 93.97 µg/mL in the DPPH assay. Some 50% and 70% EtOH/H2O extracts showed a pronounced concentration-dependent induction of Nrf2 activity. The extracts of daikon sprouts were submitted to 1H NMR experiments and then analyzed by untargeted and targeted approaches of multivariate data analysis to highlight differences related to extraction solvents.

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Potato (Solanum tuberosum) chips are the most consumed snacks worldwide today. Colored potato chips prepared from potato cultivars with red and purple flesh are a novel alternative to traditional potato chips because of their higher phenolic compound content, such as anthocyanins and hydroxycinnamic acid derivatives (HCADs), which might make these chips healthier compared with traditional chips. There is little information on the stability of these compounds. In this study, the nutritional value of these chips was evaluated by determining phenolic profiles, antioxidant activity and color parameters with liquid chromatography diode array and mass spectrometry detection (HPLC-DAD-ESI-MS/MS) and spectrophotometric methods during storage for four months. Five anthocyanins and three HCADs were detected, with the latter compounds being the most abundant, with concentrations on average between the first (97.82 mg kg-1) and the last (31.44 mg kg-1) week of storage. Similar trends were observed in antioxidant activity and stability, with the CUPRAC method showing the highest response among all the methods employed. The color indices were stable throughout the storage time. Based on these results, colored-flesh potato chips are an optimal alternative for consumption because of their high retention of phenolic compounds and antioxidant activity during storage, providing potential benefits to human health.

Asunto(s)

Antioxidantes , Solanum tuberosum , Humanos , Antocianinas , Ácidos Cumáricos , Fenoles , Bocadillos , Espectrometría de Masas en Tándem