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p-Coumaric acid (p-CA) is a phenolic compound that plays a crucial role in mediating multiple signaling pathways. It serves as a defense strategy against plant wounding and is also presumed to play a role in plant development and lignin biosynthesis. This study aimed to investigate the physiological and ionomic effect of p-CA on chia seedlings under salt stress. To this end, chia seedlings were supplemented with Nitrosol® containing 100 μM of p-CA, 100 of mM NaCI, and their combined (100 mM NaCI + 100 μM p-CA) solutions in 2-day intervals for a period of 14 days along with a control containing Nitrosol® only. The treatment of chia seedlings with 100 mM of NaCI decreased their growth parameters and the content of the majority of the essential macro-elements (K, P, Ca, and Mg), except for that of sodium (Na). The simultaneous application of p-CA and a salt stress treatment (p-CA + NaCI) alleviated the effect of salt stress on chia seedlings’ shoots, and this was indicated by the increase in chia biomass. Furthermore, this combined treatment significantly enhanced the levels of the essential microelements Mg and Ca. In summary, this brief report is built on the foundational work of our previous study, which demonstrated that p-CA promotes growth in chia seedlings via activation of O2−. In this brief report, we further show that p-CA not only promotes growth but also mitigates the effects of salt stress on chia seedlings. This mitigation effect may result from the presence of Mg and Ca, which are vital nutrients involved in regulating metabolic pathways, enzyme activity, and amino acid synthesis.

Growing concern over antimicrobial resistance in chronic wound patients necessitates the exploration of alternative treatments from natural sources. This study suggests that honey’s phenolic compounds may offer antimicrobial benefits, warranting further investigation for therapeutic development. The main aim of this study was to investigate the antimicrobial activity of phenolic compounds and to determine the effects of their sub-inhibitory concentrations against Escherichia coli (E. coli). 3-phenyllactic acid (PLA), p-coumaric acid (PCA), and phloretin were tested against the bacterial strain of E. coli ATCC 25922. Comparison of the antimicrobial activity of honey constituents in vitro was performed using a broth culture assay. Measurement of the inhibitory properties of constituents in vitro was conducted using disc and well diffusion assays. The effects of sub-inhibitory concentrations of PCA on the susceptibility of E. coli ATCC 25922 to penicillin–streptomycin were tested. The results demonstrated that PLA was the most efficient antimicrobial agent, followed by PCA, whereas phloretin, at lower (2 mg/mL) concentrations, led to an increase in the growth of E. coli. Various modifications of the agar diffusion assay did not reveal the antibacterial properties of the studied phytochemicals. The enhancing effect of a sub-inhibitory concentration of PCA in cooperation with penicillin–streptomycin was shown. These findings might be helpful for the further investigation and development of new antimicrobial agents for the treatment of skin infections and wounds.

This paper presents the results of a study of the effects of the lanthanide ions Ce3+, Pr3+, Nd3+ and Sm3+ on the electronic structure and antioxidant and biological (antimicrobial and cytotoxic) properties of p-coumaric acid (p-CAH2). Structural studies were conducted via spectroscopic methods (FTIR, ATR, UV). Thermal degradation studies of the complexes were performed. The results are presented in the form of TG, DTG and DSC curves. Antioxidant properties were determined via activity tests against DPPH, ABTS and OH radicals. The reducing ability was tested via CUPRAC assays. Minimum inhibitory concentrations (MICs) of the ligand and lanthanide complexes were determined on E. coli, B. subtilis and C. albicans microorganisms. The antimicrobial activity was also determined using the MTT assay. The results were presented as the relative cell viability of C. albicans, P. aeruginosa, E. coli and S. aureus compared to controls and expressed as percentages. In the obtained complexes in the solid phase, lanthanide ions coordinate three ligands in a bidentate chelating coordination mode through the carboxyl group of the acid. Spectroscopic analysis showed that lanthanide ions increase the aromaticity of the pi electron system of the ligand. Thermal analysis showed that the complexes are hydrated and have a higher thermal stability than the ligand. The products of thermal decomposition of the complexes are lanthanide oxides. In the aqueous phase, the metal combines with the ligand in a 1:1 molar ratio. Antioxidant activity tests showed that the complexes have a similar ability to remove free radicals. ABTS and DPPH tests showed that the complexes have twice the ability to neutralise radicals than the ligand, and a much higher ability to remove the hydroxyl radical. The abilities of the complexes and the free ligand to reduce Cu2+ ions in the CUPRAC test are at a similar level. Lanthanide complexes of p-coumaric acid are characterised by a higher antimicrobial capacity than the free ligand against Escherichia coli bacteria, Bacillus subtilis and Candida albicans fungi.

In situ poloxamer-based gels are increasingly being explored as ocular drug delivery carriers to extend the release of active substances, thereby enhancing bioavailability. The objective of this study was to develop thermally stable in situ gels incorporating balsam poplar bud extract, propolis extract, and p-coumaric acid solution and to evaluate the physicochemical parameters of these gelified eye drops. This research assessed the compatibility of poloxamer-based eye drops with active components, their physicochemical properties, stability post-sterilization and during storage, and the release profiles of the active compounds. Fifteen eye drop formulations were prepared and categorized into three groups based on active components. One of the active components was propolis extract. As an alternative to propolis, eye drops containing the plant precursor, balsam poplar bud extract, were developed. The third group’s active component was p-coumaric acid, a dominant phenolic acid in propolis and balsam poplar bud extracts. The study reported phenolic contents of 76.63 CAE mg/g for propolis and 83.25 CAE mg/g for balsam poplar bud aqueous extracts, with balsam poplar bud extracts showing higher SPF values (14.0) compared to propolis (12.7), while p-coumaric acid solution exhibited the highest SPF values (25.5). All eye drops were transparent, with pH values meeting the requirements for ocular drops. Formulations containing 8–10% poloxamer 407 met the criteria for in situ gels. All formulations remained stable for 90 days. Conclusion: The study results indicate that the formulated gels possess suitable physicochemical properties, are resistant to applied autoclaving conditions, and exhibit an extended release of active compounds with an increase in poloxamer content.

PHBV films incorporating 3, 6 and 9% ferulic acid (FA) or p-coumaric acid (PCA) were obtained by melt blending and compression moulding. The films’ microstructures and thermal behaviours were analysed as well as their mechanical, optical and barrier properties. The overall and specific migration of the materials in different food simulants was also characterised. FA was homogeneously mixed with the polymer, whereas PCA was mainly dispersed as fine particles in the PHBV matrices due to its higher melting point. These structural features promoted differences in the physical properties of the films depending on the compound concentration. As the concentration of both compounds rose, the barrier capacity of the films to oxygen, and to a lesser extent water vapour, was enhanced. While FA promoted the extensibility of the films, 9% PCA enhanced their brittleness. Both compounds affected the crystallisation pattern of the polymer, promoting smaller crystalline formations and a slight decrease in crystallinity. Although the overall migration of every film formulation was lower than the overall migration limit (OML), the release of active compounds was dependent on the food simulant; almost total release was noted in ethanol containing simulants but was more limited in aqueous systems. Therefore, these films could be used as food contact materials, contributing to extending the food’s shelf life.

Basella alba has been used in Thai remedies to treat skin disorders, but scientific evidence supporting its efficacy is currently limited. In this study, we investigated the inhibitory effects of B. alba extracts on melanin production using melanoma cells, as well as their impact on oxidative stress and inflammation in keratinocytes. The results demonstrate that B. alba extracts inhibited melanin content and cellular tyrosinase activity in 3-isobutyl-1-methylxanthine (IBMX)-induced melanoma cells by downregulating MITF and the pigmentary genes TYR , TRP-1 , and DCT. Interestingly, the MITF regulator gene was inhibited by both the 50% and 95% ethanolic extracts of B. alba with levels of 0.97 ± 0.19 and 0.92 ± 0.09 of the control, respectively, which are comparable to those observed in the arbutin treatment group at 0.84 ± 0.05 of the control. Moreover, after hydrogen peroxide (H 2 O 2 ) exposure, pretreatment with B. alba reduced lipid peroxidation byproducts and increased the levels of antioxidant-related genes, including SOD-1 , GPX-1 , and NRF2 . Notably, the suppression of the POMC promoter gene in keratinocytes was observed, which may disrupt melanogenesis in melanocytes involving the MC1R signaling pathway. MC1R mRNA expression decreased in the treatments with 50% and 95% ethanolic extracts of B. alba , with relative levels of 0.97 ± 0.18 and 0.90 ± 0.10 of the control, respectively, similar to the arbutin-treated group (0.88 ± 0.25 of control). A significant reduction in nitric oxide was also observed in the B. alba -treated groups, along with a decrease in genes associated with pro-inflammatory cytokines, including IL-1β , IL-6 , and COX-2 . These findings suggest that B. alba has potential in the prevention of skin-related problems.

Sulfite is a common preservative in wine, but the spoilage yeast Brettanomyces bruxellensis can produce volatile phenols even with the recommended sulfite dose. The purpose of this study was to examine how wine components, p-coumaric acid (a precursor of volatile phenols), and micronutrients influence culturability, viability, and volatile phenols production by B. bruxellensis under sulfite stress. In red wine, a high sulfite dose (potassium metabisulfite, 100 mg L−1) led to an immediate death phase followed by growth recovery after two weeks. However, 4-ethylphenol (4-EP) was continuously produced by dead or nonculturable cells. Nonetheless, an event of growth recovery could not be observed in the case of the model wine. However, when the model wine was supplemented with minerals and vitamins, both growth recovery and 4-EP production were noticed, suggesting that the minerals and vitamins played an important role in maintaining the viability of cells under the sulfite stress. The yeast could also utilize the p-coumaric acid (p-CA) as an energy source, showing a specific growth rate of 0.0142 h−1 with 1 mM of p-CA in model wine. Furthermore, the sulfite-stressed cells exhibited ATP production by means of proton efflux while utilizing the p-CA. This work highlights the novel finding that the conversion of p-CA into 4-EP provides sufficient energy for the cell to remain metabolically active under the sulfite stress.

The infection of soil-borne diseases has the potential to modify root exudation and the rhizosphere microbiome. However, the extent to which these modifications occur in various monocropping histories remains inadequately explored. This study sampled healthy and diseased American ginseng (Panax quinquefolius L.) plants under 1–4 years of monocropping and analyzed the phenolic acids composition by HPLC, microbiome structure by high-throughput sequencing technique, and the abundance of pathogens by quantitative PCR. First, the fungal pathogens of Fusarium solani and Ilyonectria destructans in the rhizosphere soil were more abundant in the diseased plants than the healthy plants. The healthy American ginseng plants exudated more phenolic acid, especially p-coumaric acid, compared to the diseased plants after 1–2 years of monocropping, while this difference gradually diminished with the increase in monocropping years. The pathogen abundance was influenced by the exudation of phenolic acids, e.g., total phenolic acids (r = −0.455), p-coumaric acid (r = −0.465), and salicylic acid (r = −0.417), and the further in vitro test confirmed that increased concentration of p-coumaric acid inhibited the mycelial growth of the isolated pathogens for root rot. The healthy plants had a higher diversity of rhizosphere bacterial and fungal microbiome than the diseased plants only after a long period of monocropping. Our study has revealed that the cropping history of American ginseng has altered the effect of pathogens infection on rhizosphere microbiota and root exudation.

One trend in agriculture is the replacement of classical pesticides with more ecofriendly solutions, such as elicitation, which is a promising approach consisting of stimulating the natural immune system of a plant to improve its resistance to pathogens. In this fashion, a library of p-coumaric-based compounds were synthesized in accordance with as many principles of green chemistry as possible. Then, these molecules were tested for (1) the direct inhibition of mycelium growth of two pathogens, Botrytis cinerea and Sclerotinia sclerotiorum, and (2) plasma membrane destabilization in Arabidopsis and rapeseed. Finally, the protective effect was evaluated on an Arabidopsis/B. cinerea pathosystem. Total inhibition of the growth of both fungi could be achieved, and significant ion leakage was observed using dihydroxylated fatty p-coumarate esters. A direct effect on plants was also recorded as a ca. three-fold reduction in the necrosis area.

The aim of the research was to evaluate the influence of the ripening stage on the accumulation of polyphenols and antioxidant activity in fruits of Solanum species. The experiment included two factors: I—four different Solanum species (S. melanocerasum, S. nigrum, S. villosum, and S. retroflexum) and II—three ripening stages. High-performance liquid chromatography (HPLC) was used to analyze the individual phenolic compounds (flavonoids and phenolic acids), and the spectrophotometric method was applied to determine antioxidant activity. The results revealed that the accumulation of polyphenols and antioxidant activity in fruits of Solanum species depends on the stage of ripening and species. All studied Solanum species fruits had the highest content of total phenolic acid at ripening stage III and the greatest antioxidant activity at ripening stage I. Fully ripe fruits of S. melanocerasum contained significantly more total flavonoids, whereas S. nigrum contained significantly more total phenolic acids than other investigated Solanum species fruits. The significantly highest antioxidant activity was found in S. melanocerasum fruits at ripening stage I.

It is well established that p-Hydroxycinnamic acids (HCAs), including ferulic, caffeic, sinapic, and p-coumaric acids, possess a characteristic phenylpropanoid C6-C3 backbone and account for about one-third of the phenolic compounds in our diet. HCAs are typically associated with various plant cell wall components, including mono-, di-, and polysaccharides, sterols, polyamines, glycoproteins, and lignins. Interestingly, enzymes produced by intestinal microbes liberate HCAs from these associations. HCAs are completely absorbed in their free form upon ingestion and undergo specific reactions upon absorption in the small intestine or liver. The gut epithelium, composed of intestinal epithelial cells (IECs), acts as a physical barrier against harmful bacteria and a site for regulated interactions between bacteria and the gut lumen. Thus, maintaining the integrity of the epithelial barrier is essential for establishing a physiochemical environment conducive to homeostasis. This review summarizes the protective effects of HCAs on the intestinal barrier, achieved through four mechanisms: preserving tight junction proteins (TJPs), modulating pro-inflammatory cytokines, exerting antioxidant activity, and regulating the intestinal microbiota.

An electrochemical biosensor based on the immobilization of glucose oxidase into an electropolymerized p-coumaric acid membrane on a Pt electrode has been developed and evaluated for glucose detection in the range of 1 to 30 mM. The glucose biosensor exhibits a sensitivity of 36.96 mA/mMcm2, a LOD of 0.66 mM, and a LOQ of 2.18 mM. The biosensing membrane was electropolymerized by cyclic voltammetry in 100 mM phosphates pH 7.00 and 3% ethanol containing glucose oxidase and p-coumaric acid. The glucose biosensors’ stability, repeatability, reproducibility, and selectivity were estimated. The biosensing membrane shows permselective properties and antifouling effects. The applicability of the developed glucose biosensor was evaluated in the presence of 20 mg/mL proteins, and any signal associated with biofouling was observed. The glucose biosensors were employed for the determination of the glucose concentration in three commercial beverages.

p-coumaric acid (p-CA), a common plant phenolic acid with multiple bioactivities, has a lipid-lowering effect. As a dietary polyphenol, its low toxicity, with the advantages of prophylactic and long-term administration, makes it a potential drug for prophylaxis and the treatment of nonalcoholic fatty liver disease (NAFLD). However, the mechanism by which it regulates lipid metabolism is still unclear. In this study, we studied the effect of p-CA on the down-regulation of accumulated lipids in vivo and in vitro. p-CA increased a number of lipase expressions, including hormone-sensitive lipase (HSL), monoacylglycerol lipase (MGL) and hepatic triglyceride lipase (HTGL), as well as the expression of genes related to fatty acid oxidation, including long-chain fatty acyl-CoA synthetase 1 (ACSL1), carnitine palmitoyltransferase-1 (CPT1), by activating peroxisome proliferator-activated receptor α, and γ (PPARα and γ). Furthermore, p-CA promoted adenosine 5′-monophosphate (AMP)-activated protein kinase (AMPK) phosphorylation and enhanced the expression of the mammalian suppressor of Sec4 (MSS4), a critical protein that can inhibit lipid droplet growth. Thus, p-CA can decrease lipid accumulation and inhibit lipid droplet fusion, which are correlated with the enhancement of liver lipases and genes related to fatty acid oxidation as an activator of PPARs. Therefore, p-CA is capable of regulating lipid metabolism and is a potential therapeutic drug or health care product for hyperlipidemia and fatty liver.

Any defects in bile formation, secretion, or flow may give rise to cholestasis, liver fibrosis, cirrhosis, and hepatocellular carcinoma. As the pathogenesis of hepatic disorders is multifactorial, targeting parallel pathways potentially increases the outcome of therapy. Hypericum perforatum has been famed for its anti-depressive effects. However, according to traditional Persian medicine, it helps with jaundice and acts as a choleretic medication. Here, we will discuss the underlying molecular mechanisms of Hypericum for its use in hepatobiliary disorders. Differentially expressed genes retrieved from microarray data analysis upon treatment with safe doses of Hypericum extract and intersection with the genes involved in cholestasis are identified. Target genes are located mainly at the endomembrane system with integrin-binding ability. Activation of α5β1 integrins, as osmo-sensors in the liver, activates a non-receptor tyrosine kinase, c-SRC, which leads to the insertion of bile acid transporters into the canalicular membrane to trigger choleresis. Hypericum upregulates CDK6 that controls cell proliferation, compensating for the bile acid damage to hepatocytes. It induces ICAM1 to stimulate liver regeneration and regulates nischarin, a hepatoprotective receptor. The extract targets the expression of conserved oligomeric Golgi (COG) and facilitates the movement of bile acids toward the canalicular membrane via Golgi-derived vesicles. In addition, Hypericum induces SCP2, an intracellular cholesterol transporter, to maintain cholesterol homeostasis. We have also provided a comprehensive view of the target genes affected by Hypericum’s main metabolites, such as hypericin, hyperforin, quercitrin, isoquercitrin, quercetin, kaempferol, rutin, and p-coumaric acid to enlighten a new scope in the management of chronic liver disorders. Altogether, standard trials using Hypericum as a neo-adjuvant or second-line therapy in ursodeoxycholic-acid-non-responder patients define the future trajectories of cholestasis treatment with this product.

Propolis is known for its immunomodulatory properties. We investigated the effects of three recently developed propolis extract formulations: polar propolis fraction (PPF), soluble propolis dry extract (PSDE), and microencapsulated propolis extract (MPE), and some of their components, on pro- and anti-inflammatory cytokine production in a macrophage model. Bone marrow cell-derived macrophages (BMDM) in cell culture were E. coli lipopolysaccharide (500 ng/mL) stimulated for two hours and subsequently incubated for 20 hours with one of the three propolis extract formulations (1, 10, 25, 50, 100 and 300 µg/mL) or with isolated propolis components (caffeic acid, p-coumaric acid, artepillin C, or baccharin) (10, 25, 50 and 100 µg/mL) to determine how they affected secretion of the pro-inflammatory cytokines IL-6 and TNF-α, and the anti-inflammatory cytokine, IL-10. PPF increased IL-6 and IL-10 levels. PSDE increased IL-6 and IL-10 at lower concentrations, while at higher concentrations it increased TNF-α and decreased IL-10. MPE increased IL-10. Caffeic acid and PPF increased both IL-6 and IL-10. Artepillin C and PSDE decreased IL-10. Baccharin and MPE increased IL-10. Baccharin also decreased IL-6. p-coumaric acid did not affect secretion of these cytokines. Pro- and anti-inflammatory cytokine production by the different propolis extracts differed; however, all three propolis extract formulations have potential as immunomodulatory agents in food supplement and pharmaceutical products.

Lignins are the most abundant biopolymers that consist of aromatic units. Lignins are obtained by fractionation of lignocellulose in the form of “technical lignins”. The depolymerization (conversion) of lignin and the treatment of depolymerized lignin are challenging processes due to the complexity and resistance of lignins. Progress toward mild work-up of lignins has been discussed in numerous reviews. The next step in the valorization of lignin is the conversion of lignin-based monomers, which are limited in number, into a wider range of bulk and fine chemicals. These reactions may need chemicals, catalysts, solvents, or energy from fossil resources. This is counterintuitive to green, sustainable chemistry. Therefore, in this review, we focus on biocatalyzed reactions of lignin monomers, e.g., vanillin, vanillic acid, syringaldehyde, guaiacols, (iso)eugenol, ferulic acid, p-coumaric acid, and alkylphenols. For each monomer, its production from lignin or lignocellulose is summarized, and, mainly, its biotransformations that provide useful chemicals are discussed. The technological maturity of these processes is characterized based on, e.g., scale, volumetric productivities, or isolated yields. The biocatalyzed reactions are compared with their chemically catalyzed counterparts if the latter are available.

Phenolic acid is a well-known allelochemical, but also a pollutant in soil and water impeding crop production. Biochar is a multifunctional material widely used to mitigate the phenolic acids allelopathic effect. However, phenolic acid absorbed by biochar can still be released. In order to improve the removal efficiency of phenolic acids by biochar, the biochar-dual oxidant (BDO) composite particles were synthesized in this study, and the underlying mechanism of the BDO particles in ameliorating p-coumaric acid (p-CA) oxidative damage to tomato seed germination was revealed. Upon p-CA treatment, the BDO composite particles application increased the radical length, radical surface area, and germination index by 95.0%, 52.8%, and 114.6%, respectively. Compared to using biochar or oxidants alone, the BDO particles addition resulted in a higher removal rate of p-CA and produced more O2•−, HO•, SO4•− and 1O2 radicals via autocatalytic action, suggesting that BDO particles removed phenolic acid by both adsorption and free radical oxidation. The addition of BDO particles maintained the levels of the antioxidant enzyme activity close to the control, and reduced the malondialdehyde and H2O2 by 49.7% and 49.5%, compared to the p-CA treatment. Integrative metabolomic and transcriptomic analyses revealed that 14 key metabolites and 62 genes were involved in phenylalanine and linoleic acid metabolism, which increased dramatically under p-CA stress but down-regulated with the addition of BDO particles. This study proved that the use of BDO composite particles could alleviate the oxidative stress of phenolic acid on tomato seeds. The findings will provide unprecedented insights into the application and mechanism of such composite particles as continuous cropping soil conditioners.

The technologies used to produce the different dosage forms of propolis can selectively affect the original propolis compounds and their biological activities. The most common type of propolis extract is hydroethanolic. However, there is considerable demand for ethanol-free propolis presentations, including stable powder forms. Three propolis extract formulations were developed and investigated for chemical composition and antioxidant and antimicrobial activity: polar propolis fraction (PPF), soluble propolis dry extract (PSDE), and microencapsulated propolis extract (MPE). The different technologies used to produce the extracts affected their physical appearance, chemical profile, and biological activity. PPF was found to contain mainly caffeic and p-Coumaric acid, while PSDE and MPE showed a chemical fingerprint closer to the original green propolis hydroalcoholic extract used. MPE, a fine powder (40% propolis in gum Arabic), was readily dispersible in water, and had less intense flavor, taste, and color than PSDE. PSDE, a fine powder (80% propolis) in maltodextrin as a carrier, was perfectly water-soluble and could be used in liquid formulations; it is transparent and has a strong bitter taste. PPF, a purified solid with large amounts of caffeic and p-Coumaric acids, had the highest antioxidant and antimicrobial activity, and therefore merits further study. PSDE and MPE had antioxidant and antimicrobial properties and could be used in products tailored to specific needs.

The demand for bee products has been growing, especially regarding their application in complementary medicine. Apis mellifera bees using Baccharis dracunculifolia D.C. (Asteraceae) as substrate produce green propolis. Among the examples of bioactivity of this matrix are antioxidant, antimicrobial, and antiviral actions. This work aimed to verify the impact of the experimental conditions applied in low- and high-pressure extractions of green propolis, using sonication (60 kHz) as pretreatment to determine the antioxidant profile in the extracts. Total flavonoid content (18.82 ± 1.15–50.47 ± 0.77 mgQE·g−1), total phenolic compounds (194.12 ± 3.40–439.05 ± 0.90 mgGAE·g−1) and antioxidant capacity by DPPH (33.86 ± 1.99–201.29 ± 0.31 µg·mL−1) of the twelve green propolis extracts were determined. By means of HPLC-DAD, it was possible to quantify nine of the fifteen compounds analyzed. The results highlighted formononetin (4.76 ± 0.16–14.80 ± 0.02 mg·g−1) and p-coumaric acid (−1) as majority compounds in the extracts. Based on the principal component analysis, it was possible to conclude that higher temperatures favored the release of antioxidant compounds; in contrast, they decreased the flavonoid content. Thus, the obtained results showed that samples pretreated with 50 °C associated with ultrasound displayed a better performance, which may support the elucidation of the use of these conditions.

Previous studies reported that p-coumaric acid modulates melanoma growth. Because the esterification of p-coumaric acid (p-CA) enhanced its activity as an antimelanogenic agent, we aimed to determine the antitumor potential of two derivatives, the ethyl and butyl esters, against the murine B16-F10 and the human SK-MEL-25 melanoma cells. Cell viability was determined in vitro by the lactate dehydrogenase release and violet crystal absorption assays. The cell proliferation rate and cell cycle behavior were determined by the colony formation assay and flow cytometry analysis. Although p-CA, at the concentration of 1 mM, failed to exert a significant antitumor activity, the ethyl and butyl ester derivatives caused substantial tumor cell death at doses < 1 mM. Despite a reduction in their direct cytotoxicity at minor doses, both products controlled the melanoma growth by arresting the cell cycle at the G0/G1 (B16-F10) or S/G2 (SK-MEL-25). Furthermore, the in vivo experiments showed that the butyl ester derivative suppressed the lung B16-F10 burden, compared to the p-CA-treated mice. Thus, the esterification of p-coumaric acid improved the control over the proliferation of murine and human melanoma cells and can be considered an approach for designing novel anticancer agents.

Non-alcoholic fatty liver disease (NAFLD) is the most common liver disease and has become a growing public health concern worldwide. Polyphenols may improve high-fat diet (HFD)-related NAFLD. Our previous study found that ferulic acid (FA) and p-coumaric acid (p-CA) were the polyphenols with the highest content in foxtail millet. In this study, we investigated the mechanism underlying the impact of ferulic acid and p-coumaric acid (FA/p-CA) on non-alcoholic fatty liver (NAFLD). The association of FA and p-CA with fatty liver was first analyzed by network pharmacology. Synergistic ameliorating of NAFLD by FA and p-CA was verified in oleic acid (OA) and palmitic acid (PA) (FFA)-treated hepatocytes. Meanwhile, FA/p-CA suppressed final body weight and TG content and improved liver dysfunction in HFD-induced NAFLD mice. Mechanistically, our data indicated that FA and p-CA bind to histone deacetylase 1 (HDAC1) to inhibit its expression. The results showed that peroxisome proliferator activated receptor gamma (PPARG), which is positively related to HDAC1, was inhibited by FA/p-CA, and further suppressed fatty acid binding protein (FABP) and fatty acid translocase (CD36). It suggests that FA/p-CA ameliorate NAFLD by inhibiting free fatty acid uptake via the HDAC1/PPARG axis, which may provide potential dietary supplements and drugs for prevention of NAFLD.

p -Coumaric acid ( p -CA) is a phenolic compound that plays a crucial role in mediating multiple signaling pathways. It serves as a defense strategy against plant wounding and is also presumed to play a role in plant development and lignin biosynthesis. This study aimed to investigate the physiological and ionomic effect of p -CA on chia seedlings under salt stress. To this end, chia seedlings were supplemented with Nitrosol ® containing 100 μM of p -CA, 100 of mM NaCI, and their combined (100 mM NaCI + 100 μM p -CA) solutions in 2-day intervals for a period of 14 days along with a control containing Nitrosol ® only. The treatment of chia seedlings with 100 mM of NaCI decreased their growth parameters and the content of the majority of the essential macro-elements (K, P, Ca, and Mg), except for that of sodium (Na). The simultaneous application of p -CA and a salt stress treatment ( p -CA + NaCI) alleviated the effect of salt stress on chia seedlings' shoots, and this was indicated by the increase in chia biomass. Furthermore, this combined treatment significantly enhanced the levels of the essential microelements Mg and Ca. In summary, this brief report is built on the foundational work of our previous study, which demonstrated that p -CA promotes growth in chia seedlings via activation of O 2 - . In this brief report, we further show that p -CA not only promotes growth but also mitigates the effects of salt stress on chia seedlings. This mitigation effect may result from the presence of Mg and Ca, which are vital nutrients involved in regulating metabolic pathways, enzyme activity, and amino acid synthesis.

In this study, two types of mesoporous silica with different pore structures and volumes were synthesized by the soft-templating method. The two types of mesoporous silica, type MCM-41 and MCM-48, were loaded with three polyphenols—caffeic acid, p-coumaric acid and trans-ferulic acid—in the same ratio of mesoporous silica:polyphenol (1:0.4 w/w). The materials obtained were characterized from a morphological and structural point of view through different analysis techniques. Through X-ray diffraction (XRD), the crystallization plane and the ordered structure of the mesoporous silica were observed. The difference between the two types of materials containing MCM-41 and MCM-48 was observed through the different morphologies of the silica particles through scanning electron microscopy (SEM) and also through the Brunauer–Emmet–Teller (BET) analysis, that the surface areas and volumes of pores was different between the two types of mesoporous silica, and, after loading with polyphenols, the values were reduced. The characteristic bands of silica and of polyphenols were easily observed by Fourier-transform infrared spectroscopy (FTIR), and, through thermogravimetric analysis (TGA), the residual mass was determined and the estimated amount of polyphenol in the materials and the efficient loading of mesoporous silica with polyphenols could be determined. The in vitro study was performed in two types of simulated biological fluids with different pH—simulated gastric fluid (SGF) and simulated intestinal fluid (SIF). The obtained materials could be used in various biomedical applications as systems with controlled release of natural polyphenols and the most suitable application could be as food supplements especially when a mixture of such materials is used or when the polyphenols are co-loaded within the mesoporous silica.

Trans-cinnamic acid and p-coumaric acid are valuable intermediates in the synthesis of flavonoids and are widely employed in food, flavor and pharmaceutical industries. These products can be produced by the deamination of L-phenylalanine and L-tyrosine catalyzed by phenylalanine ammonia lyase or tyrosine ammonia lyase. Phenylalanine ammonia-lyase (PAL, EC 4.3.1.5) from Rhodotorula glutinis do not exhibit strong substrate specificity and can convert both L-phenylalanine and L-tyrosine. In this study, the PAL was utilized as the whole-cell biocatalyst, and the reaction conditions were optimized, and the production of trans-cinnamic acid and p-coumaric acid of 597 mg/L and 525 mg/L were achieved with high purity (>98%).

This study highlights the dynamics of phenolic acids, antioxidation, and 4-vinylguaiacol in beer produced with dark purple rice malt, also known as Riceberry rice malt, as an adjunct and base malt. Riceberry rice malt substituted barley malt at 40% (w/w), 60% (w/w), 80% (w/w), and 100% (w/w) with 100% (w/w) barley malt as the control. Two types of ale beer were produced with two yeasts, designated as POF− and POF+. The wort produced with the Riceberry rice malt had higher anthocyanin and vanillic acids relative to all barley malt wort. Fermentation and beer maturation reduced phenolic acids and antioxidant activity in all treatment. Nevertheless, beer produced from 40% (w/w)–80% (w/w) Riceberry rice malt maintained higher p-coumaric acid, vanillic acid, anthocyanin, and antioxidant activity in beers with lower 4-vinylguaiacol relative to all barley malt beer, which also had higher ferulic acid and sinapic acid contents. The beers made from POF+ yeast contained more 4-vinylguaiacol contents than those found in beers made from POF− yeasts. This study suggests that Riceberry rice malt or POF− yeast are suitable raw materials for phenolic acid off-flavour reduction and the stabilisation of antioxidant activity in beer.

The use of innate products for the fast and efficient promotion of healing process has been one of the biomedical sector’s main bets for lesion treatment modernization process. The aim of this study was to develop and characterize bacterial cellulose-based (BC) wound dressings incorporated with green and red propolis extract (2 to 4%) and the active compounds p-coumaric acid and biochanin A (8 to 16 mg). The characterization of the nine developed samples (one control and eight active wound dressings) evidenced that the mechanics, physics, morphological, and barrier properties depended not only on the type of active principle incorporated onto the cellulosic matrix, but also on its concentration. Of note were the results found for transparency (28.59–110.62T600 mm−1), thickness (0.023–0.046 mm), swelling index (48.93–405.55%), water vapor permeability rate (7.86–38.11 g m2 day−1), elongation (99.13–262.39%), and antioxidant capacity (21.23–86.76 μg mL−1). The wound dressing based on BC and red propolis was the only one that presented antimicrobial activity. The permeation and retention test revealed that the wound dressing containing propolis extract presented the most corneal stratum when compared with viable skin. Overall, the developed wound dressing showed potential to be used for treatment against different types of dermal lesions, according to its determined proprieties.

Depression, a mood disorder, affects one in fifteen adults, has multiple risk factors and is associated with complicated underlying pathological mechanisms. P-coumaric acid (p-CA), a phenolic acid, is widely distributed in vegetables, fruits and mushrooms. P-CA has demonstrated a protective role against oxidative stress and inflammation in various diseases, including cardiovascular disease, diabetes and cancer. In the current study, we investigated the protection of p-CA against depression and memory impairment in a corticosterone (CORT)-induced chronic depressive mouse model. CORT administration resulted in depression-like behaviors and memory impairment. P-CA treatment alleviated CORT-induced depression-related behaviors and memory impairment. Network pharmacology predicted that p-CA had multiple targets and mediated various signaling pathways, of which inflammation-associated targets and signaling pathways are predominant. Western blotting showed CORT-induced activation of the advanced glycation end product (AGE)-receptor of AGE (RAGE) (AGE-RAGE) signaling and increased expression of the proinflammatory cytokines interleukin-1 beta (IL-1β) and tumor necrosis factor-alpha (TNFα) in the hippocampus, while p-CA treatment inactivated AGE-RAGE signaling and decreased the levels of IL-1β and TNFα, suggesting that protection against depression and memory impairment by p-CA is mediated by the inhibition of inflammation, mainly via the AGE-RAGE signaling pathway. Our data suggest that p-CA treatment will benefit patients with depression.

Hemp (Cannabis sativa L.) contains a variety of secondary metabolites, including cannabinoids, such as psychoactive (−)-trans-Δ⁹-tetrahydrocannabinol. The present study was conducted to identify the major phenolic components contained in hemp root, which has been relatively under-researched compared to other parts of hemp. The aqueous ethanol extract of hemp roots was fractionated into methylene chloride (MC), ethyl acetate (EA), and water (WT) fractions, and high-performance liquid chromatography with photodiode array detection (HPLC-DAD) analysis was performed. The main ultraviolet (UV)-absorbing phenolic compound contained in the EA fraction was identified as p-coumaric acid by comparing the retention time and UV absorption spectrum with a standard. Silica gel column chromatography was performed to isolate a hydrophobic derivative of p-coumaric acid contained in the MC fraction. Nuclear magnetic resonance (NMR) analysis identified the isolated compound as ethyl p-coumarate. For comparative purposes, ethyl p-coumarate was also chemically synthesized by the esterification reaction of p-coumaric acid. The content of p-coumaric acid and ethyl p-coumarate in the total extract of hemp root was estimated to be 2.61 mg g−1 and 6.47 mg g−1, respectively, by HPLC-DAD analysis. These values correspond to 84 mg Kg−1 dry root and 216 mg Kg−1 dry root, respectively. In conclusion, this study identified p-coumaric acid and ethyl p-coumarate as the main phenolic compounds contained in the hemp roots.

In this work, we obtain mesoporous silica systems loaded with polyphenolic compounds (p-coumaric acid, trans-ferulic acid, epicatechin, and catechin). Polyphenolic compounds are used as biologically active agents for the treatment of various diseases. These compounds have high antioxidant activity. As a carrier, two types of mesoporous silica have been proposed and obtained according to the classical templating method with cetyltrimethylammonium bromide, CTAB, under alkaline conditions. Polyphenols (p-coumaric acid, trans-ferulic acid, epicatechin, and catechin) were loaded under vacuum into the mesoporous silica. The materials obtained were characterized by Scanning Electron Microscopy, X-ray Diffraction, the Brunauer–Emmett–Teller Method, Complex Thermal Analysis–DTA-TG and Fourier Transform Infrared Spectroscopy. In this study, mesoporous silica systems were obtained and further loaded with p-coumaric acid, trans-ferulic acid, epicatechin and catechin. The results highlight that the materials can be used as drug delivery systems, with the results being promising (simulated gastric fluid, SGF, and simulated intestinal fluid, SIF) for various environments. The proposed loading methodology is suitable for loading these natural agents, mostly, inside the pores.

This study aimed to investigate whether different doses of specific phenolic acids (chlorogenic acid, caffeic acid, ferulic acid, gallic acid, protocatechuic acid, p-hydroxybenzoic acid, syringic acid, vanillic acid, and p-coumaric acid), alone or in combination, can inhibit the early growth of the common ragweed (Ambrosia artemisiifolia L., Asterales: Asteraceae). A seed bioassay was performed in Petri dishes and placed in a climate chamber to assess the effects of five dose levels of phenolic acids to radicle and shoot length, as well seedling biomass of A. artemisiifolia. The lowest dose of phenolic acid corresponded to the natural phenolic acid concentration previously reported in dry plant tissue samples from Brassicaceae cover crop plants. Results show that the inhibition of the early growth of A. artemisiifolia depends strongly on phenolic acid. Across different treatments, high doses of phenolic acids significantly shortened shoots and radicles, as well as reduced seedling biomass. Treating seeds with ferulic acid alone, vanillic acid alone, p-hydroxybenzoic acid alone, or a mixture of all phenolic acids significantly reduced all early growth parameters. The estimated effective dose for the 50% inhibition (ED50) of radicle growth in A. artemisiifolia seedlings was 368.39 ± 59.85 × 10−8 mol with ferulic acid, 135.41 ± 17.65 × 10−8 mol with p-coumaric acid, 810.36 ± 134.15 × 10−8 mol with p-hydroxybenzoic acid, and 160.11 ± 12.30 × 10−8 mol with the combination of all phenolic acids.

There has been considerable interest in using natural polyphenol oxidase (PPO) inhibitors to control browning in fruit and vegetable products. p-Coumaric acid (pCA), a common secondary metabolite of plants, has been studied as an inhibitor of PPOs/tyrosinases from several foods (e.g., mushroom, apple, and potato). However, studies on the use of pCA for the inhibition of PPO-initiated browning in actual food systems are limited. Therefore, a study was carried out to ascertain the efficacy of using pCA to limit PPO-initiated browning in fresh potato juice. The extent of browning inhibition by pCA was shown to be reaction system-dependent. Browning in potato juice was unexpectedly enhanced by the addition of pCA. This was interpreted as pCA acting as an alternative substrate with significantly higher browning efficiency; extent of browning under this condition was higher than that observed in the native potato juice. The addition of pCA to any of the model reaction mixtures (i.e., those containing semi-purified enzymes and substrates) significantly inhibited browning. The discrepancy in pCA effects on browning inhibition in different reaction systems is postulated to be mainly due to non-enzyme and non-substrate components in potato juice that participate in the post-PPO reaction sequences, which ultimately lead to brown color formation.

The purpose of this study is to evaluate the effect of the bioconversion products of Oenanthe javanica extract fermented by Lactiplantibacillus plantarum (OEFL) on relieving hangovers and improving liver function. In addition, the bioactive substance of the OEFL, which alleviates hangover and ethanol-induced liver damage, was identified and its bioactive property was verified through in vivo experiments. In major substances analysis using high-performance liquid chromatography, OEFL produced 9.5-fold higher p-coumaric acid than the O. Javanica extract (OE). In addition, considering that quinic acid, which is not present in the OE, was produced in the OEFL it was confirmed that chlorogenic acid was decomposed into quinic acid by bioconversion. In the in vivo experiment using Sprague-Dawley rats, the OEFL and p-coumaric acid diets reduced blood ethanol, acetaldehyde, GPT, and ALP concentrations, increasing blood albumin concentrations compared to ethanol-administered groups, demonstrating that OEFL and p-coumaric acid, the main substance in the OEFL, improved ethanol-induced liver damage. Furthermore, the OEFL and its main bioactive substance, p-coumaric acid, alleviated liver fibrosis by downregulating TGF-β, SMAD-2, SMAD-4, α-SMA, and upregulating MMP-1. Therefore, OEFL is expected to be used as a functional food or pharmaceutical material as it has been confirmed to effectively relieve hangovers, prevent liver damage, and delay liver fibrosis in ethanol-induced liver damages.

The contribution of cold-adapted yeasts to the emerging field of lignin biovalorization has not yet been studied. The red-pigmented basidiomycetous yeast strain Rhodosporidiobolus colostri DBVPG 10655 was examined for its potential to degrade five selected lignin-derived aromatic monomers (syringic acid, p-coumaric acid, 4-hydroxybenzoic acid, ferulic acid, and vanillic acid). The strain utilized p-coumaric acid, 4-hydroxybenzoic acid, and ferulic acid not only as the sole carbon source; full biodegradation occurred also in mixtures of multiple monomers. Vanillic acid was not utilized as the sole carbon source, but was degraded in the presence of p-coumaric acid, 4-hydroxybenzoic acid, and ferulic acid. Syringic acid was utilized neither as the sole carbon source nor in mixtures of compounds. Biodegradation of lignin-derived aromatic monomers was detected over a broad temperature range (1–25 °C), which is of ecological significance and of biotechnological relevance.

One of the characteristics of hyperhydric plants is the reduction of cell wall lignification (hypolignification), but how this is related to the observed abnormalities of hyperhydricity (HH), is still unclear. Lignin is hydrophobic, and we speculate that a reduction in lignin levels leads to more capillary action of the cell wall and consequently to more water in the apoplast. p-coumaric acid is the hydroxyl derivative of cinnamic acid and a precursor for lignin and flavonoids in higher plant. In the present study, we examined the role of lignin in the development of HH in Arabidopsis thaliana by checking the wild-types (Ler and Col-0) and mutants affected in phenylpropanoid biosynthesis, in the gene coding for cinnamate 4-hydroxylase, C4H (ref3-1 and ref3-3). Exogenously applied p-coumaric acid decreased the symptoms of HH in both wild-type and less-lignin mutants. Moreover, the results revealed that exogenously applied p-coumaric acid inhibited root growth and increased the total lignin content in both wild-type and less-lignin mutants. These effects appeared to diminish the symptoms of HH and suggest an important role for lignin in HH.

Introduction: Sulfur dioxide has been traditionally used in winemaking as an effective preservative even though it often has negative taste- and health-related effects on consumers, particularly when used in excess. Furthermore, it can induce both SO2-related resistance and SO2-related viable but not culturable (VBNC) states in different wine yeast and bacteria species. Currently, the replacement of sulfur dioxide with plant-derived compounds, used as food bio-preservatives, has been proposed in winemaking at the laboratory scale as a green and healthier alternative. Purpose: To replace sulfur dioxide with p-coumaric acid, a plant-derived phenolic compound, in winemaking on an industrial scale in order to produce a safe, natural wine that is more sustainable, authentic and healthier. Methods: Both sulfur dioxide- and p-coumaric acid-treated wine was made in parallel at a winery on an industrial scale (into two 10,000 L stainless steel tanks) using the same quantity of the same grape variety (10,000 kg of Lemnos Island organic white wine grapes, Muscat of Alexandria) during the harvest of 2019 and following the same oenological procedures. The influence of p-coumaric acid on wine properties and quality was compared with that of sulfur dioxide under the same conditions after 3 months of storage in a bottle. To this end, several analytical parameters of wine related to oenological, microbiological, antioxidant, sensory and safety properties were determined according to the International Standards Organization (ISO) and International Organization of Vine and Wine (OIV) official analytical methods for both wine samples. Results: In general, there were no significant differences observed in stability, microbiological, antioxidant and oenological profiles due to sulfur dioxide replacement with p-coumaric acid, while the sensory profile was slightly ameliorated. Significance: This replacement technology resulted in a suitable green alternative to sulfur dioxide and could be easily applied to the wine industry in order to guarantee high-quality green products.

The present paper developed a new enzymatic biosensor whose support is a screen-printed electrode based on carbon nanofibers modified with cobalt phthalocyanine and laccase (CNF-CoPc-Lac/SPE) to determine the p-coumaric acid (PCA) content by cyclic voltammetry and square wave voltammetry. Sensor modification was achieved by the casting and cross-linking technique, using glutaraldehyde as a reticulation agent. The biosensor’s response showed the PCA redox processes in a very stable and sensitive manner. The calibration curve was developed for the concentration range of p-coumaric acid of 0.1–202.5 μM, using cyclic voltammetry and chronoamperometry. The biosensor yielded optimal results for the linearity range 0.4–6.4 μM and stood out by low LOD and LOQ values, i.e., 4.83 × 10−7 M and 1.61 × 10−6 M, respectively. PCA was successfully determined in three phytoproducts of complex composition. The results obtained by the voltammetric method were compared to the ones obtained by the FTIR method. The amount of p-coumaric acid determined by means of CNF-CoPc-Lac/SPE was close to the one obtained by the standard spectrometric method.

In situ poloxamer-based gels are increasingly being explored as ocular drug delivery carriers to extend the release of active substances, thereby enhancing bioavailability. The objective of this study was to develop thermally stable in situ gels incorporating balsam poplar bud extract, propolis extract, and p -coumaric acid solution and to evaluate the physicochemical parameters of these gelified eye drops. This research assessed the compatibility of poloxamer-based eye drops with active components, their physicochemical properties, stability post-sterilization and during storage, and the release profiles of the active compounds. Fifteen eye drop formulations were prepared and categorized into three groups based on active components. One of the active components was propolis extract. As an alternative to propolis, eye drops containing the plant precursor, balsam poplar bud extract, were developed. The third group's active component was p -coumaric acid, a dominant phenolic acid in propolis and balsam poplar bud extracts. The study reported phenolic contents of 76.63 CAE mg/g for propolis and 83.25 CAE mg/g for balsam poplar bud aqueous extracts, with balsam poplar bud extracts showing higher SPF values (14.0) compared to propolis (12.7), while p -coumaric acid solution exhibited the highest SPF values (25.5). All eye drops were transparent, with pH values meeting the requirements for ocular drops. Formulations containing 8-10% poloxamer 407 met the criteria for in situ gels. All formulations remained stable for 90 days. Conclusion: The study results indicate that the formulated gels possess suitable physicochemical properties, are resistant to applied autoclaving conditions, and exhibit an extended release of active compounds with an increase in poloxamer content.

The color of bracts generally turns yellow or black from green during cereal grain development. However, the impact of these phenotypic changes on photosynthetic physiology during black bract formation remains unclear. Two oat cultivars (Avena sativa L.), ‘Triple Crown’ and ‘Qinghai 444’, with yellow and black bracts, respectively, were found to both have green bracts at the heading stage, but started to turn black at the flowering stage and become blackened at the milk stage for ‘Qinghai 444’. Their photosynthetic characteristics were analyzed and compared, and the key genes, proteins and regulatory pathways affecting photosynthetic physiology were determined in ‘Triple Crown’ and ‘Qinghai 444’ bracts. The results show that the actual PSII photochemical efficiency and PSII electron transfer rate of ‘Qinghai 444’ bracts had no significant changes at the heading and milk stages but decreased significantly (p < 0.05) at the flowering stage compared with ‘Triple Crown’. The chlorophyll content decreased, the LHCII involved in the assembly of supercomplexes in the thylakoid membrane was inhibited, and the expression of Lhcb1 and Lhcb5 was downregulated at the flowering stage. During this critical stage, the expression of Bh4 and C4H was upregulated, and the biosynthetic pathway of p-coumaric acid using tyrosine and phenylalanine as precursors was also enhanced. Moreover, the key upregulated genes (CHS, CHI and F3H) of anthocyanin biosynthesis might complement the impaired PSII activity until recovered at the milk stage. These findings provide a new insight into how photosynthesis alters during the process of oat bract color transition to black.

Although Allium species are involved in bioactivity, to the best of our knowledge, there is no research on the effects of Allium senescens on drug resistance in hepatocarcinoma. Ultra-high performance liquid chromatography was used to determine the concentration of several bioactive compounds in A. senescens extract; flow cytometry, reverse transcription–quantitative polymerase chain reaction, and siRNA-mediated knockdown to estimate the levels of different markers in HepG2 cells. The quantity of p-coumaric acid in the extract was 4.7291 ± 0.06 μg/mL, and the protein of relevant evolutionary and lymphoid interest (PRELI) in the resistant cells decreased 2.1 times in the presence of p-coumaric acid. The resistant cells strongly downregulated the efflux transporters (ABCB1, ABCC2, and ABCG2) when exposed to the extract or p-coumaric acid and when PRELI was knocked down, in contrast to the influx proteins (OCT-1). Additionally, the extract induced mitochondrial apoptosis and suppressed autophagy. Consequently, the extract and p-coumaric acid attenuated drug resistance of HepG2 cells through the downregulation of PRELI, a key protein associated with the modulation of drug transporter expression, the activation of autophagy, and mitochondrial apoptosis. Our results indicate that A. senescens extract is beneficial in protecting cancer cells against drug resistance and sustaining the efficacy of sorafenib against liver cancer.

Maize is an important source of phenolic compounds, specially hydroxycinnamic acids, which are widely known for their antioxidant activity and associated health benefits. However, these effects depend on their bioaccessibility, which is influenced by the different techniques used for food processing. Several traditional products can be obtained from maize and, in Portugal, it is used for the production of an ethnic bread called broa. In order to evaluate the effect of processing on maize phenolic composition, one commercial hybrid and five open-pollinated maize flours and broas were studied. The total phenolic content and antioxidant activity were evaluated by the Folin-Ciocalteu and ORAC assays, respectively. The major phenolics, namely ferulic and p-coumaric acids (in their soluble-free, soluble-conjugated and insoluble forms), insoluble ferulic acid dimers and soluble hydroxycinnamic acid amides were quantitated. Results show that the total phenolic content, antioxidant activity and hydroxycinnamic acids resisted traditional processing conditions used in the production of broas. The content in soluble-free phenolics increased after processing, meaning that their bioaccessibility improved. Portuguese traditional broas, produced with open-pollinated maize varieties, can be considered an interesting dietary source of antioxidant compounds due to the higher content in hydroxycinnamic acids and derivatives.

Preliminary bioassay-guided fractionation was performed to identify cytotoxic compounds from Hechtia glomerata, a plant that is used in Mexican ethnomedicine. Organic and aqueous extracts were prepared from H. glomerata’s leaves and evaluated against two cancer cell lines. The CHCl3/MeOH (1:1) active extract was fractionated, and the resulting fractions were assayed against prostate adenocarcinoma PC3 and breast adenocarcinoma MCF7 cell lines. Active fraction 4 was further analyzed by high-performance liquid chromatography–quadrupole time-of-flight–mass spectrometry analysis to identify its active constituents. Among the compounds that were responsible for the cytotoxic effects of this fraction were flavonoids, phenolic acids, and aromatic compounds, of which p-coumaric acid (p-CA) and its derivatives were abundant. To understand the mechanisms that underlie p-CA cytotoxicity, a microarray assay was performed on PC3 cells that were treated or not with this compound. The results showed that mitogen-activated protein kinases (MAPKs) that regulate many cancer-related pathways were targeted by p-CA, which could be related to the reported effects of reactive oxygen species (ROS). A molecular docking study of p-CA showed that this phenolic acid targeted these protein active sites (MAPK8 and Serine/Threonine protein kinase 3) at the same binding site as their inhibitors. Thus, we hypothesize that p-CA produces ROS, directly affects the MAPK signaling pathway, and consequently causes apoptosis, among other effects. Additionally, p-CA could be used as a platform for the design of new MAPK inhibitors and re-sensitizing agents for resistant cancers.

AMP-activated protein kinase (AMPK) plays a crucial role in the regulation of energy homeostasis in both peripheral metabolic organs and the central nervous system. Recent studies indicated that p-Coumaric acid (CA), a hydroxycinnamic phenolic acid, potentially activated the peripheral AMPK pathway to exert beneficial effects on glucose metabolism in vitro. However, CA’s actions on central AMPK activity and whole-body glucose homeostasis have not yet been investigated. Here, we reported that CA exhibited different effects on peripheral and central AMPK activation both in vitro and in vivo. Specifically, while CA treatment promoted hepatic AMPK activation, it showed an inhibitory effect on hypothalamic AMPK activity possibly by activating the S6 kinase. Furthermore, CA treatment enhanced hypothalamic leptin sensitivity, resulting in increased proopiomelanocortin (POMC) expression, decreased agouti-related peptide (AgRP) expression, and reduced daily food intake. Overall, CA treatment improved blood glucose control, glucose tolerance, and insulin sensitivity. Together, these results suggested that CA treatment enhanced hypothalamic leptin signaling and whole-body glucose homeostasis, possibly via its differential effects on AMPK activation.

Pharmacological efficiency of active compounds is largely determined by their membrane permeability. Thus, identification of drug-membrane interactions seems to be a crucial element determining drug-like properties of chemical agents. Yet, knowledge of this issue is still lacking. Since chemoprevention based on natural compounds such as cinnamic acid (CinA), p-coumaric acid (p-CoA) and ferulic (FA) is becoming a strong trend in modern oncopharmacology, determination of physicochemical properties of these anticancer compounds is highly important. Here, electrophoretic light scattering and impedance spectroscopy were applied to study the effects of these phenolic acids on electrical properties of bilayers formed from 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC), 1,2-diacyl-sn-glycero-3-phospho-l-serine (PS) or DOPC-PS mixture. After phenolic acid treatment, the negative charge of membranes increased in alkaline pH solutions, but not in acidic ones. The impedance data showed elevated values of both the electrical capacitance and the electrical resistance. We concluded that at acidic pH all tested compounds were able to solubilize into the membrane and permeate it. At neutral and alkaline pH, the CinA could be partially inserted into the bilayers, whereas p-CoA and FA could be anchored at the bilayer surface. Our results indicate that the electrochemical methods might be crucial for predicting pharmacological activity and bioavailability of phenolic acids.

(1) Background: Verticillium wilt (VW) of hop is a devastating disease caused by the soil-borne fungi Verticillium nonalfalfae and Verticillium dahliae. As suggested by quantitative trait locus (QTL) mapping and RNA-Seq analyses, the underlying molecular mechanisms of resistance in hop are complex, consisting of preformed and induced defense responses, including the synthesis of various phenolic compounds. (2) Methods: We determined the total polyphenolic content at two phenological stages in roots and stems of 14 hop varieties differing in VW resistance, examined the changes in the total polyphenols of VW resistant variety Wye Target (WT) and susceptible Celeia (CE) on infection with V. nonalfalfae, and assessed the antifungal activity of six commercial phenolic compounds and total polyphenolic extracts from roots and stems of VW resistant WT and susceptible CE on the growth of two different V. nonalfalfae hop pathotypes. (3) Results: Generally, total polyphenols were higher in roots than stems and increased with maturation of the hop. Before flowering, the majority of VW resistant varieties had a significantly higher content of total polyphenols in stems than susceptible varieties. At the symptomatic stage of VW disease, total polyphenols decreased in VW resistant WT and susceptible CE plants in both roots and stems. The antifungal activity of total polyphenolic extracts against V. nonalfalfae was higher in hop extracts from stems than those from roots. Among the tested phenolic compounds, only p-coumaric acid and tyrosol markedly restricted fungal growth. (4) Conclusions: Although the correlation between VW resistance and total polyphenols content is not straightforward, higher levels of total polyphenols in the stems of the majority of VW resistant hop varieties at early phenological stages probably contribute to fast and efficient activation of signaling pathways, leading to successful defense against V. nonalfalfae infection.

Maize is one of the most interesting dietary sources of hydroxycinnamic acids, widely known for their beneficial health effects, namely antioxidant properties. This work aims to identify hydroxycinnamic acids and their derivatives in broa, a Portuguese traditional ethnic maize bread, and corresponding maize flours. Soluble and insoluble phenolic fractions of diverse maize flours and corresponding broas were prepared and analysed by HPLC-DAD-MS/MS (high-performance liquid chromatography coupled with diode array detector and tandem mass spectrometry). Besides free hydroxycinnamic acids, mainly ferulic and p-coumaric acids, several structural isomers and stereoisomers of insoluble ferulic acid dehydrodimers (n = 18) and trimers (n = 11), were also identified. Hydroxycinnamic acid amides consisting of coumaroyl and feruloyl conjugates (n = 22) were present in both soluble and insoluble fractions of maize flours and breads, in different isomeric forms. A new compound was putatively identified as bis-N,N′-diferuloyl putrescine. Additionally, more complex and insoluble hydroxycinnamic acid amides, derived from ferulic acid dehydrodimers (n = 47) and trimers (n = 18), were also putatively identified for the first time, suggesting that hydroxycinnamic acid amides are also linked to maize cell walls. Since hydroxycinnamic derivatives were not only identified in maize flours, but also in broas, they can contribute to the antioxidant properties and beneficial health effects of maize-based foods.

Brettanomyces bruxellensis is regarded as the main spoilage microorganism in the wine industry, owing to its production of off-flavours. It is difficult to eradicate owing to its high tolerance of adverse environmental conditions, such as low nutrient availability, low pH, and high levels of ethanol and SO2. In this study, the production of volatile phenols and the growth kinetics of isolates from various regions of Chile were evaluated under stressful conditions. Through randomly amplified polymorphic DNA (RAPD) analysis, 15 strains were identified. These were grown in the presence of p-coumaric acid, a natural antimicrobial and the main precursor of off-flavours, and molecular sulfur dioxide (mSO2), an antimicrobial synthetic used in the wine industry. When both compounds were used simultaneously, there were clear signs of an improvement in the fitness of most of the isolates, which showed an antagonistic interaction in which p-coumaric acid mitigates the effects of SO2. Fourteen strains were able to produce 4-vinylphenol, which showed signs of phenylacrylic acid decarboxylase activity, and most of them produced 4-ethylphenol as a result of active vinylphenol reductase. These results demonstrate for the first time the serious implications of using p-coumaric acid, not only for the production of off-flavours, but also for its protective action against the toxic effects of SO2.

p-Coumaric acid (pCA) and trans-ferulic acid (TFA) were co-crystallised with 2-amino-4-picoline (2A4MP) and 2-amino-6-picoline (2A6MP) producing organic salts of (pCA−)(2A4MP+) (1), (pCA̶ )(2A6MP+) (2) and (TFA̶ )(2A4MP+)·( 3 2 H2O) (3). For salt 3, water was included in the crystal structure fulfilling a bridging role. pCA formed a 1:1 salt with 2A4MP (Z’ = 1) and a 4:4 salt with 2A6MP (Z’ = 4). The thermal stability of the salts was determined using differential scanning calorimetry (DSC). Salt 2 had the highest thermal stability followed by salt 1 and salt 3. The salts were also characterised using Fourier transform infrared (FTIR) spectroscopy. Hirshfeld surface analysis was used to study the different intermolecular interactions in the three salts. Solvent-assisted grinding was also investigated in attempts to reproduce the salts.

The antioxidant activity of Psychotria carthagenensis, P. leiocarpa, P. capillacea and P. deflexa (Rubiaceae) extracts were investigated, and the concentrations of total phenolics, flavonoids, condensed tannins and flavonols were determined. The chemical compositions of the extracts were investigated using the high performance liquid chromatography (HPLC/PAD) method. We used 1,1-diphenyl-1-picrylhydrazyl free radical (DPPH), β-Carotene bleaching and 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cations to determine antioxidant activity. The ability to scavenge radical was measured in these experiments by the discoloration of the solution. Concentrations of constituents were measured spectrophotometrically. P. carthagenensis and P. capillacea exhibited the highest antioxidant activity, in the DPPH test, β-carotene bleaching and ABTS system. The highest phenolic, flavonoid, condensed tannin and flavonol concentration was found in P. carthagenensis and P. capillacea extracts. HPLC-PDA analysis of P. carthagenensis and P. capillacea revealed hydroxycinnamic acid (p-coumaric acid). This is the first report on the antioxidant properties and constituent analysis of these Psychotria extracts.

According to recent studies, the Plantaginaceae, which are traditional Chinese herbal remedies, have potential for use in viral infection treatment and cancer therapy. Linalool and p-coumaric acid are two of the biologically active compounds that can be isolated from the Plantaginaceae. This study mainly focused on investigating the bioactivity of linalool as well as the bioactivity of p-coumaric acid in terms of their cytotoxic effects on cancer cells. Whether the mechanisms of such effects are generated through apoptosis and immunoregulatory activity were also investigated. By using WST-1 analysis, it was shown that linalool and p-coumaric acid have good inhibitory effects against breast, colorectal and liver cancer cells. The IC50 values of linalool for those cancer cell types were 224 μM, 222 μM, and 290 μM, respectively, and the IC50 values of p-coumaric acid were 693 μM, 215 μM and 87 μM, respectively. Cell cycle analysis also confirmed that linalool and p-coumaric acid can lead to apoptosis. By using flow cytometry, it was determined that treatment with linalool rather than p-coumaric acid significantly increased the sub-G1 phase and that there were more cells concentrated in the G1 phase. Furthermore, by using cytokine array analysis, we found that linalool can stimulate IFN-γ, IL-13, IL-2, IL-21, IL-21R, IL-4, IL-6sR and TNF-α secretion. This demonstrated that in addition to the bidirectional regulation capabilities found in linalool, it also induces Th1 cellular immune response in T-47D cells. These results showed that linalool holds great potential for use in cancer therapy, and we believe that it could provide an alternative way to take action against tumors.

p-Coumaric acid (p-CoA), a phenolic acid belonging to the hydroxycinnamic acids family, is a compound with tentative anticancer potential. Microelectrophoretic mobility measurements conducted at various pH values of electrolyte solution were applied to study p-CoA effects on electrical properties of human glioblastoma cell membranes. The obtained results demonstrated that after the p-CoA treatment, the surface charge density of cancer cells changed in alkaline pH solutions, while no noticeable changes were observed in cell membranes incubated with p-CoA compared to control at acidic pH solutions. A four-equilibrium model was used to describe the phenomena occurring on the cell membrane surface. The total surface concentrations of both acidic and basic functional groups and their association constants with solution ions were calculated and used to define theoretical curves of membrane surface charge density versus pH. The resulting theoretical curves and the experimental data were compared to verify the reliability and validity of the adopted model. The deviation of both kinds of data obtained at a higher pH may be caused by disregarding interactions between the functional groups of cancer cells. Processes occurring in the cell membranes after their incubation with p-CoA can lead to disorders of existing equilibria, which result in changes in values of the parameters describing these equilibria.