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•Interaction mechanisms between three kinds of cinnamic acids and pepsin were systematically researched.•Microstructural changes in pepsin were investigated via multiple ...spectroscopies.•Three kinds of cinnamic acids combined with pepsin through static quenching mechanism.•The interaction forces between three cinnamic acids and pepsin are mainly electrostatic force and hydrogen bond.•With the increase in cinnamic acid concentration, enzyme activity of pepsin had stronger decrease.
In this work, under simulated physiological conditions (pH = 2.2, glycine hydrochloric acid buffer solution), the interactions of cinnamic acid (CA), m-hydroxycinnamic acid (m-CA) and p-hydroxycinnamic acid (p-CA) with pepsin were studied by fluorescence spectroscopy, ultraviolet–visible absorption spectroscopy, circular dichroism (CD) spectroscopy, Fourier transform infrared spectroscopy (FTIR), molecular docking and molecular dynamic simulation (MD). The spectrogram results showed that these three kinds of CA had a strong ability to quench the intrinsic fluorescence of pepsin, and the quenching effects were obvious with the increase of concentration of these three kinds of molecules. The quenching mechanism of CA, m-CA and p-CA on the fluorescence of pepsin was static quenching. In addition, a stable complex was formed between three kinds of CA with pepsin. Thermodynamic data and docking information suggested that three kinds of CA combine with pepsin were mainly driven by electrostatic force and hydrogen bond. The binding constant and the number of binding sites were determined. The interaction of CA, m-CA and p-CA with pepsin was spontaneous, and accompanied by non-radiative energy transfer. The results from CD, FTIR, UV–Vis and synchronous fluorescence spectra measurements manifested that the secondary structure of pepsin was changed by the binding of three kinds of CA. The β-sheet of pepsin increased after the interaction with three kinds of CA. The assay results of pepsin activity showed that three kinds of CA led to a decrease in pepsin activity within the investigated concentrations. Molecular docking investigation revealed the formation of polar hydrogen bonds as well as hydrophobic interactions between three kinds of CA with pepsin, and the ligand within the binding pocket of pepsin. MD results implied the formation of a stable complex between three kinds of CA and pepsin. The research suggested that cinnamic acid and its derivatives could be a potential effect on the structure and properties of digestive enzyme.
Bioactive compounds from natural sources, due to their widely-recognized benefits, have been exploited as cosmeceutical ingredients. Among them, phenolic acids emerge with a very interesting ...potential. In this context, this review analyzes hydroxycinnamic acids and their derivatives as multifunctional ingredients for topical application, as well as the limitations associated with their use in cosmetic formulations. Hydroxycinnamic acids and their derivatives display antioxidant, anti-collagenase, anti-inflammatory, antimicrobial and anti-tyrosinase activities, as well as ultraviolet (UV) protective effects, suggesting that they can be exploited as anti-aging and anti-inflammatory agents, preservatives and hyperpigmentation-correcting ingredients. Due to their poor stability, easy degradation and oxidation, microencapsulation techniques have been employed for topical application, preventing them from degradation and enabling a sustained release. Based on the above findings, hydroxycinnamic acids present high cosmetic potential, but studies addressing the validation of their benefits in cosmetic formulations are still scarce. Furthermore, studies dealing with skin permeation are scarcely available and need to be conducted in order to predict the topical bioavailability of these compounds after application.
Phenylpropanoid metabolism is one of the most important metabolisms in plants, yielding more than 8,000 metabolites contributing to plant development and plant–environment interplay. Phenylpropanoid ...metabolism materialized during the evolution of early freshwater algae that were initiating terrestrialization and land plants have evolved multiple branches of this pathway, which give rise to metabolites including lignin, flavonoids, lignans, phenylpropanoid esters, hydroxycinnamic acid amides, and sporopollenin. Recent studies have revealed that many factors participate in the regulation of phenylpropanoid metabolism, and modulate phenylpropanoid homeostasis when plants undergo successive developmental processes and are subjected to stressful environments. In this review, we summarize recent progress on elucidating the contribution of phenylpropanoid metabolism to the coordination of plant development and plant–environment interaction, and metabolic flux redirection among diverse metabolic routes. In addition, our review focuses on the regulation of phenylpropanoid metabolism at the transcriptional, post‐transcriptional, post‐translational, and epigenetic levels, and in response to phytohormones and biotic and abiotic stresses.
Plant development and plant‐environment interactions are modulated by phenylpropanoid metabolism, which is regulated by transcriptional, post‐transcriptional, post‐translational, and epigenetic mechanisms, and responds to phytohormones and biotic and abiotic stresses.
Hydroxycinnamic acids (HCAs) are important natural phenolic compounds present in high concentrations in fruits, vegetables, cereals, coffee, tea and wine. Many health beneficial effects have been ...acknowledged in food products rich in HCAs; however, food processing, dietary intake, bioaccessibility and pharmacokinetics have a high impact on HCAs to reach the target tissue in order to exert their biological activities. In particular, metabolism is of high importance since HCAs' metabolites could either lose the activity or be even more potent compared to the parent compounds. In this review, natural sources and pharmacokinetic properties of HCAs and their esters are presented and discussed. The main focus is on their metabolism along with biological activities and health benefits. Special emphasis is given on specific effects of HCAs' metabolites in comparison with their parent compounds.
Summary
Grass cell walls have hydroxycinnamic acids attached to arabinosyl residues of arabinoxylan (AX), and certain BAHD acyltransferases are involved in their addition. In this study, we ...characterized one of these BAHD genes in the cell wall of the model grass Setaria viridis. RNAi silenced lines of S. viridis (SvBAHD05) presented a decrease of up to 42% of ester‐linked p‐coumarate (pCA) and 50% of pCA‐arabinofuranosyl, across three generations. Biomass from SvBAHD05 silenced plants exhibited up to 32% increase in biomass saccharification after acid pre‐treatment, with no change in total lignin. Molecular dynamics simulations suggested that SvBAHD05 is a p‐coumaroyl coenzyme A transferase (PAT) mainly involved in the addition of pCA to the arabinofuranosyl residues of AX in Setaria. Thus, our results provide evidence of p‐coumaroylation of AX promoted by SvBAHD05 acyltransferase in the cell wall of the model grass S. viridis. Furthermore, SvBAHD05 is a promising biotechnological target to engineer crops for improved biomass digestibility for biofuels, biorefineries and animal feeding.
Significance Statement
A BAHD acyltransferase gene was studied, and it was demonstrated that its suppression causes reduction of ester‐linked p‐coumaric acid in the cell walls of Setaria viridis. RNAi silenced lines had higher biomass digestibility with no alteration in the biomass production. Molecular dynamics simulation reinforced the evidence that SvBAHD05 is mainly responsible for the incorporation of p‐coumaric acid onto arabinoxylan, the main hemicellulose in grass cell walls.
Tyramine-derived hydroxycinnamic acid amines (HCAAT) are naturally occurring group of secondary metabolites present in various plant genera, such as Allium, Cannabis, Lycium, Polyganotum and Solanum. ...It belongs to the neutral, water-insoluble compounds and plays a role in plant growth, development and defence mechanism. The past two decades have seen a shift in the study of HCAAT from its role in plants to its potent biological activities. This review highlights the sources, roles in plants, biosynthetic pathways, metabolic engineering and chemical synthesis of HCAAT. The biological properties of HCAAT remain the focus in this paper, including antioxidant, anti-inflammatory, anti-cancer, anti-diabetic, anti-melanogenesis and neuroprotective properties. The effects of food processing and technology on HCAAT are also discussed. Given the current research gap, this review proposes future directions on the study of HCAAT, as well as its potential applications in food and pharmaceutical industry.
Previously six selected Oenococcus oeni strains (P2A, P3A, P3G, P5A, P5C and P7B) have been submitted to further characterization in order to clarify their potential as malolactic starters. ...Laboratory scale vinifications gave an insight of the most vigorous strains: both P2A and P3A strains were able to conclude malolactic fermentation (MLF) in less than 15 days. The remaining strains showed good viability and were able to successfully finish MLF in the established analysis time, except for the strain P5A, which viability was totally lost after inoculation. Also spontaneous fermentation was not initiated. None of the strains was biogenic amine producer; however, P5C strain significantly increased the concentration of volatile phenol-precursor hydroxycinnamic acids after MLF. Regarding the evolution of wine aromatic compounds, main changes were detected for both ethyl and acetate esters after MLF; however, key aromatic compounds including alcohols, terpenes or acids were also found to significantly increase. Principal component analysis classified the strains in two distinct groups, each one correlated with different key volatile compounds. P2A, P3A, P3G and P5C strains were mainly linked to esters, while P7B and the commercial strain Viniflora OENOS showed higher score for diverse compounds as hexanoic acid, β-damascenone, linalool or 2-phenylethanol. These results confirmed the specific impact of each strain on wine aroma profile, which could lead to the production of wines with individual characteristics, in which the reliability and safety of MLF is also ensured.
•No production of biogenic amines was observed after each MLF.•Strain P5C significantly increased the concentration of hydroxycinnamic acids after MLF.•Strains contribution to aroma profile modification was confirmed.•Different aroma compounds profiles were obtained depending on the analysed strain.•Main increase of aroma compounds after MLF occurred for both ethyl and acetate esters
Radical copolymerization of coumarin with
N
-vinylamides (
N
‑vinylpyrrolidone,
N
-methyl-
N
-vinylacetamide,
N
-vinylformamide) has been used to prepare copolymers of various composition with ...variable molecular weights. Subsequent reactions in their polymer chains affords water-soluble copolymers of salts of hydroxycinnamic acid and its hydrazides. The synthesized copolymers of hydroxycinnamic acid salts and hydrazides with
N
-vinylamides have low cytotoxicity and demonstrate the pronounced antiviral activity against human respiratory syncytial virus (strain A2).
Summary
Hydroxycinnamic acid amides (HCAAs) are a class of antimicrobial metabolites involved in plant defense against necrotrophic pathogens, including Alternaria brassicicola and Botrytis cinerea. ...The agmatine coumaryl transferase (AtACT) is the key enzyme that catalyzes the last reaction in the biosynthesis of HCAAs, including p‐coumaroylagmatine (CouAgm) and feruloylagmatine in Arabidopsis thaliana. However, the regulatory mechanism of AtACT gene expression is currently unknown. Yeast one‐hybrid screening using the AtACT promoter as bait isolated the key positive regulator ORA59 that is involved in jasmonic acid/ethylene (JA/ET)‐mediated plant defense responses. AtACT gene expression and HCAAs biosynthesis were synergistically induced by a combination of JA and ET. In the AtACT promoter, two GCC‐boxes function equivalently for trans‐activation by ORA59 in Arabidopsis protoplasts, and mutation of either GCC‐box abolished AtACT mRNA accumulation in transgenic plants. Site‐directed mutation analysis demonstrated that the specific Leu residue at position 228 of the ORA59 EDLL motif mainly contributed to its transcriptional activity on AtACT gene expression. Importantly, MEDIATOR25 (MED25) and ORA59 homodimer are also required for ORA59‐dependent activation of the AtACT gene. These results suggest that ORA59 and two functionally equivalent GCC‐boxes form the regulatory module together with MED25 that enables AtACT gene expression and HCAAs biosynthesis to respond to simultaneous activation of the JA/ET signaling pathways.
Significance Statement
The molecular regulatory mechanism of plant antimicrobial metabolites HCAAs biosynthesis in response to necrotrophic pathogen attack is unknown. This research reveals that the JA/ET‐responsive transcription factor ORA59 activates the expression of key enzyme gene AtACT resulting in accumulation of HCAAs, which provides important insights into the regulatory mechanism of the HCAAs‐mediated defense responses.
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