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Enterolactone, coumaric acid and vitexin are polyphenolic compounds present in a variety of fruits, vegetables, cereals and plants. These bioactive compounds are in high demand due to their antioxidant property in various tissues and organs. The purpose of this study was to develop a simultaneous extraction method, an aqueous two‐phase extraction (ATPE) method, that would enable the extraction of these compounds from Hypoxis iridifolia. This environmentally friendly extraction method only applied water and ethanol as extraction solvents for these analytes from the plant matrix. After phase separation, the analytes were salted‐out from the aqueous phase into the organic phase with the aid of a chaotrope (NaCl) or kosmotrope (Na2CO3). Thereafter, the analytes were withdrawn by a micro‐pipette for analysis on the high‐performance liquid chromatography–photodiode array detector. Optimization was conducted using a central composite design, where three parameters were examined which involved percentage ethanol, centrifugation time and salt type. Generally, the optimized conditions for extraction were an ethanol percentage of 100% and a centrifugation time of 10 min, which yielded concentrations of 2942, 23,823 and 8881 mg kg−1 for enterolactone, vitexin and coumaric acid, respectively, in the presence of a kosmotrope. The optimized conditions of extraction in the presence of chaotrope were an ethanol percentage of 66% and a centrifugation time of 10 min with concentrations of 6727, 20,833 and 8618 mg kg−1 for enterolactone, vitexin and coumaric acid, respectively. The ATPE method involving Na2CO3 was a better extractant of all the compounds studied relative to that of NaCl. The superior extraction capability of Na2CO3 in ATPE could serve as a prototype for the development of efficient extraction methods to meet the high demand for medicinal compounds derived from natural products. [ABSTRACT FROM AUTHOR]

• An effective recovery of antioxidants was obtained from breweŕs spent grain. • A comparison among chemical, enzymatic and hydrothermal hydrolysis was conducted. • The highest ferulic acid yield was 7.2 g FA/kg BSG for the hydrothermal treatment. • Alkaline hydrolysis showed the lowest operating costs: €34.5/kg FA at 100 kgBSG/m3. Brewers' spent grain (BSG) is the main byproduct from the brewing industry, which accounts for 85 % of the total waste generated during beer production. This lignocellulosic material is traditionally used as livestock feed and sold at a low price. However, BSG can be used as a low-cost feedstock for the production of bioactive molecules and chemicals precursors, upgrading the value of this byproduct. In this context, BSG is a promising feedstock for the extraction of antioxidants like ferulic acid (FA) and p-coumaric acid (p -Cu). The effectiveness of three hydrolysis treatments were evaluated for the extraction of FA and p -Cu from BSG, namely enzymatic (based on the synergistic cooperation between a feruloyl esterase and an endo -1,4-β-xylanase), alkaline and hydrothermal. The hydrothermal treatment produced the highest extraction yields (7.2 g/kgBSG and 1.4 g/kgBSG for FA and p -Cu, respectively) in a short extraction time (an hour). On the other hand, enzymatic hydrolysis extracted 4.3 g/kgBSG for FA and negligible yields for p -Cu in 4 h of incubation at 25 °C. Yields of 5.5 g/kgBSG for FA and 0.6 g/kgBSG for p -Cu were obtained in more than 5 h of alkaline treatment at 120 °C. The mass and energy balances revealed the high dependence of the operating costs on the concentration of BSG used during the extraction process, with costs of 34.5 €, 6607 € and 205.5 € per kg of FA for the chemical, enzymatic and hydrothermal extraction methods at 100 kg BSG/m3. [ABSTRACT FROM AUTHOR]

A whole-grain highland barley (WHB) diet has been recognized to exhibit the potential for alleviating hyperlipidemia, which is mainly characterized by lipids accumulation in the serum and liver. Previously, procyanidin B1 (PB) and coumaric acid (CA) from WHB were found to alleviate serum lipid accumulation in impaired glucose tolerance mice, while the effect on modulating the hepatic lipid metabolism remains unknown. In this study, the results showed the supplementation of PB and CA activated the expression of peroxisome proliferator-activated receptor α (PPARα) and the target genes of cholesterol 7-α hydroxylase (CYP7A1) and carnitine palmitoyl transferase I (Cpt1) in the liver cells of high-fat-diet (HFD)-induced diabetic C57BL/6J mice, resulting in decreases in the serum total cholesterol (TC), triglyceride (TG), and low-density lipoprotein (LDL-C) contents, and an increase in the high-density lipoprotein (HDL-C) content. High-throughput sequencing of 16S rRNA indicated that supplementation with PB and CA ameliorated the gut microbiota dysbiosis, which was associated with a reduction in the relative abundance of Ruminococcaceae and an increase in the relative abundance of Lactobacillus, Desulfovibrio, and Akkermansia. Spearman's correlation analysis revealed that these genera were closely related to obesity-related indices. In summary, the activation of PPARα expression by PB and CA from WHB was important for the alleviation of hyperlipidemia and the structural adjustment of the gut microbiota. [ABSTRACT FROM AUTHOR]

Streptococcus mutans, the primary cause of dental caries, relies on its ability to create and sustain a biofilm (dental plaque) for survival and pathogenicity in the oral cavity. This study was focused on the antimicrobial biofilm formation control and biofilm dispersal potential of Coumaric acid (CA) against Streptococcus mutans on the dentin surface. The biofilm was analyzed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay, microtiter plate assay, production of extracellular polymeric substances (EPSs), florescence microscopy (surface coverage and biomass μm2) and three-dimensional (3D) surface plots. It was observed that CA at 0.01 mg/mL reduced bacterial growth by 5.51%, whereases at 1 mg/mL, a significant (p < 0.05) reduction (98.37%) was observed. However, at 1 mg/mL of CA, a 95.48% biofilm formation reduction was achieved, while a 73.45% biofilm dispersal (after 24 h. treatment) was achieved against the preformed biofilm. The MTT assay showed that at 1 mg/mL of CA, the viability of bacteria in the biofilm was markedly (p < 0.05) reduced to 73.44%. Moreover, polysaccharide (EPS) was reduced to 24.80 μg/mL and protein (EPS) to 41.47 μg/mL. ImageJ software (version 1.54 g) was used to process florescence images, and it was observed that the biofilm mass was reduced to 213 (μm2); the surface coverage was reduced to 0.079%. Furthermore, the 3D surface plots showed that the untreated biofilm was highly dense, with more fibril-like projections. Additionally, molecular docking predicted a possible interaction pattern of CA (ligand) with the receptor Competence Stimulating Peptide (UA159sp, PDB ID: 2I2J). Our findings suggest that CA has antibacterial and biofilm control efficacy against S. mutans associated with dental plaque under tested conditions. [ABSTRACT FROM AUTHOR]

Stilbenes are a group of plant phenolic secondary metabolites, with trans-resveratrol (3,5,4′-trihydroxy-trans-stilbene) being recognized as the most prominent and studied member. Stilbenes have a great potential for use in agriculture and medicine, as they have significant activities against plant pathogens and have valuable beneficial effects on human health. In this study, we analyzed the effects of direct application of stilbenes, stilbene precursor, and stilbene-rich extract solutions to the plant foliar surface for increasing the resistance of Arabidopsis thaliana to various abiotic stresses (heat, cold, drought, and soil salinity). Exogenous treatment of A. thaliana with stilbenes (trans-resveratrol, piceid, and spruce bark extract) and phenolic precursor (p-coumaric acid or CA) during germination resulted in considerable growth retardation of A. thaliana plants: a strong delay in the root and stem length of 1-week-old seedlings (in 1.3–4.5 fold) and rosette diameter of 1-month-old plants (in 1.2–1.8 fold), while the 2-month-old treated plants were not significantly different in size from the control. Plant treatments with stilbenes and CA increased the resistance of A. thaliana to heat and, to a lesser extent, to soil salinity (only t-resveratrol and spruce extract) to drought (only CA), while cold resistance was not affected. Plant treatments with stilbenes and CA resulted in a significant increase in plant resistance and survival rates under heat, with plants showing 1.5–2.3 times higher survival rates compared to untreated plants. Thus, exogenous stilbenes and a CA are able to improve plant survival under certain abiotic stresses via specific activation of the genes involved in the biosynthesis of auxins, gibberellins, abscisic acid, and some stress-related genes. The present work provides new insights into the application of stilbenes to improve plant stress tolerance. [ABSTRACT FROM AUTHOR]

Cinnamic acid is one of the naturally occurring chemical compounds present in various plants. It is obtained by both isolation from crude drugs, and by the synthetic route. In the last 10 years, many researchers have explored cinnamic acid for its pharmacological activities. Out of this anti-microbial and anti-tubercular activities are mainly focused in this review. because of the unique structural features of cinnamic acid, various substitutions can be done. This review is an attempt to summarize the chemistry, reactions and pharmacological activities of cinnamic acid with a special focus on its anti-tubercular activity. [ABSTRACT FROM AUTHOR]

Hydroxycinnamic acids such as p-coumaric acid (CA) are chemically linked to lignin in grassy biomass with fairly labile ester bonds and therefore represent a straightforward opportunity to extract and valorize lignin components. In this work, we investigated the enzymatic conversion of CA extracted from lignocellulose to 4-vinylphenol (4VP) by expressing a microbial phenolic acid decarboxylase in Corynebacterium glutamicum, Escherichia coli, and Bacillus subtilis. The performance of the recombinant strains was evaluated in response to the substrate concentration in rich medium or a lignin liquor and the addition of an organic overlay to perform a continuous product extraction in batch cultures. We found that using undecanol as an overlay enhanced the 4VP titers under high substrate concentrations, while extracting > 97% of the product from the aqueous phase. C. glutamicum showed the highest tolerance to CA and resulted in the accumulation of up to 187 g/L of 4VP from pure CA in the overlay with a 90% yield when using rich media, or 17 g/L of 4VP with a 73% yield from CA extracted from lignin. These results indicate that C. glutamicum is a suitable host for the high-level production of 4VP and that further bioprocess engineering strategies should be explored to optimize the production, extraction, and purification of 4VP from lignin with this organism.

A whole-grain highland barley (WHB) diet has been recognized to exhibit the potential for alleviating hyperlipidemia, which is mainly characterized by lipids accumulation in the serum and liver. Previously, procyanidin B1 (PB) and coumaric acid (CA) from WHB were found to alleviate serum lipid accumulation in impaired glucose tolerance mice, while the effect on modulating the hepatic lipid metabolism remains unknown. In this study, the results showed the supplementation of PB and CA activated the expression of peroxisome proliferator-activated receptor α (PPARα) and the target genes of cholesterol 7-α hydroxylase (CYP7A1) and carnitine palmitoyl transferase I (Cpt1) in the liver cells of high-fat-diet (HFD)-induced diabetic C57BL/6J mice, resulting in decreases in the serum total cholesterol (TC), triglyceride (TG), and low-density lipoprotein (LDL-C) contents, and an increase in the high-density lipoprotein (HDL-C) content. High-throughput sequencing of 16S rRNA indicated that supplementation with PB and CA ameliorated the gut microbiota dysbiosis, which was associated with a reduction in the relative abundance of Ruminococcaceae and an increase in the relative abundance of Lactobacillus, Desulfovibrio, and Akkermansia. Spearman’s correlation analysis revealed that these genera were closely related to obesity-related indices. In summary, the activation of PPARα expression by PB and CA from WHB was important for the alleviation of hyperlipidemia and the structural adjustment of the gut microbiota.

BACKGROUND: Arabinoxylan is the main fiber component in corn and corn co‐products that are commonly included in pig diets. However, this fiber fraction is resistant to enzymatic degradation in the gastrointestinal tract of pigs. Ferulic acid and p‐coumaric acid are covalently linked to arabinoxylan, so it is likely that the majority of these hydroxycinnamic acids are excreted in feces. However, data to confirm this have not been reported. The objective of this research was therefore to quantify the ferulic and p‐coumaric acids in a diet based on corn and soybean meal (SBM) and in a diet based on corn, SBM, and distillers' dried grains with solubles, as well as in feces from pigs fed these diets. RESULTS: The concentration of bound ferulic and coumaric acids in diets was greater in the corn‐SBM‐DDGS diet and in feces from pigs fed this diet than in the corn‐SBM diet and feces from pigs fed that diet. The disappearance of free coumaric acids was greater (>85%) than that of bound phenolic acids (<50%) in both diets. The disappearance of free coumaric acid and bound ferulic acid in the intestinal tract of pigs was not different between the two diets. In contrast, disappearance of bound coumaric acid was greater (P < 0.05) in the corn‐SBM diet than in the corn‐SBM‐DDGS diet. CONCLUSION: A diet based on corn and SBM contains less hydroxycinnamic acid than a corn‐SBM‐DDGS diet but bound phenolic acids are more resistant to digestion by pigs than free phenolic acids. © 2023 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

Streptococcus mutans, the primary cause of dental caries, relies on its ability to create and sustain a biofilm (dental plaque) for survival and pathogenicity in the oral cavity. This study was focused on the antimicrobial biofilm formation control and biofilm dispersal potential of Coumaric acid (CA) against Streptococcus mutans on the dentin surface. The biofilm was analyzed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay, microtiter plate assay, production of extracellular polymeric substances (EPSs), florescence microscopy (surface coverage and biomass μm2) and three-dimensional (3D) surface plots. It was observed that CA at 0.01 mg/mL reduced bacterial growth by 5.51%, whereases at 1 mg/mL, a significant (p < 0.05) reduction (98.37%) was observed. However, at 1 mg/mL of CA, a 95.48% biofilm formation reduction was achieved, while a 73.45% biofilm dispersal (after 24 h. treatment) was achieved against the preformed biofilm. The MTT assay showed that at 1 mg/mL of CA, the viability of bacteria in the biofilm was markedly (p < 0.05) reduced to 73.44%. Moreover, polysaccharide (EPS) was reduced to 24.80 μg/mL and protein (EPS) to 41.47 μg/mL. ImageJ software (version 1.54 g) was used to process florescence images, and it was observed that the biofilm mass was reduced to 213 (μm2); the surface coverage was reduced to 0.079%. Furthermore, the 3D surface plots showed that the untreated biofilm was highly dense, with more fibril-like projections. Additionally, molecular docking predicted a possible interaction pattern of CA (ligand) with the receptor Competence Stimulating Peptide (UA159sp, PDB ID: 2I2J). Our findings suggest that CA has antibacterial and biofilm control efficacy against S. mutans associated with dental plaque under tested conditions.

Stilbenes are a group of plant phenolic secondary metabolites, with trans-resveratrol (3,5,4′-trihydroxy-trans-stilbene) being recognized as the most prominent and studied member. Stilbenes have a great potential for use in agriculture and medicine, as they have significant activities against plant pathogens and have valuable beneficial effects on human health. In this study, we analyzed the effects of direct application of stilbenes, stilbene precursor, and stilbene-rich extract solutions to the plant foliar surface for increasing the resistance of Arabidopsis thaliana to various abiotic stresses (heat, cold, drought, and soil salinity). Exogenous treatment of A. thaliana with stilbenes (trans-resveratrol, piceid, and spruce bark extract) and phenolic precursor (p-coumaric acid or CA) during germination resulted in considerable growth retardation of A. thaliana plants: a strong delay in the root and stem length of 1-week-old seedlings (in 1.3–4.5 fold) and rosette diameter of 1-month-old plants (in 1.2–1.8 fold), while the 2-month-old treated plants were not significantly different in size from the control. Plant treatments with stilbenes and CA increased the resistance of A. thaliana to heat and, to a lesser extent, to soil salinity (only t-resveratrol and spruce extract) to drought (only CA), while cold resistance was not affected. Plant treatments with stilbenes and CA resulted in a significant increase in plant resistance and survival rates under heat, with plants showing 1.5–2.3 times higher survival rates compared to untreated plants. Thus, exogenous stilbenes and a CA are able to improve plant survival under certain abiotic stresses via specific activation of the genes involved in the biosynthesis of auxins, gibberellins, abscisic acid, and some stress-related genes. The present work provides new insights into the application of stilbenes to improve plant stress tolerance.

By acting as mechanoreceptors, osteocytes can be stimulated by a mechanical orthodontic force to detect changes in blood flow in the bone canaliculi and respond by signaling osteoblasts and stimulating osteoclast development, which leads to bone resorption. Periodontal ligament (PDL) and alveolar bone renewal are necessary for optimal orthodontic tooth movement. Hibiscus sabdariffa flower may have the potential to improve alveolar bone regeneration in dentistry since it possesses anti-inflammatory, pro-osteogenic, pro-angiogenic, and anti-osteoclastogenic properties. Aim: To evaluate the molecular docking of bioactive compounds in H. sabdariffa flower Anthocyanins, trimethylgossypentin-coumaric acid, Quarcetin-3'-O-glucoside on bone remodeling biomarkers through an in silico study. The ADMET (absorption, distribution, metabolism, excretion, and toxicity) prediction of the chemical constituents of H. sabdariffa flowers was carried out. Anthocyanins, 3,4,7'-trimethylgossypentin coumaric acid, and quercetin-3'-O-glucoside make up the chemical composition of the Roselle flower. The target proteins used were heat shock protein (HSP)-10, HSP-70, receptor activator nuclear kappa beta (RANK), RANK-Ligand (RANKL), osteoprotegrin (OPG), vascular endothelial growth factor (VEGF), fibroblast growth factor-2 (FGF-2), matrix metalloproteinase-9 (MMP-9), nuclear factor kappa beta (NFKB), tumor necrosis factor-a (TNF-a), runt related transcription factor-2 (RUNX2), Osterix, nuclear factor associated T-cells1 (NFATc1), tartate resistant acid phosphatase (TRAP), & collagen type 1a1 (Coll1A1) through molecular docking. Quarcetin-3'-O-glucosidein H. sabdariffa flower has a high binding affinity to osterix, FGF-2, and HSP-70 but not MMP-9 and TNF-α. Quarcetin-3'-O-glucosidein H. sabdariffa flower enhance bone regeneration through elevation of osteoblastogenesis but not osteoclastogenesis biomarker as documented in silico. [ABSTRACT FROM AUTHOR]

Objective: Due to the high side effects of commonly used drugs and according to the pharmacological properties reported for coumaric acid (CA), this study was designed to determine the impact of CA on acetic acid-induced colitis in rats, considering its possible anti-inflammatory, antioxidant, and anti-apoptotic properties. Materials and methods: Forty-eight male Wistar rats were divided into 6 equal groups (n = 8). Colitis was induced by acetic acid intrarectally. CA in three different doses (50, 100, and 150 mg/kg) was administrated for 5 days. Finally, the macroscopic and histopathological changes in the colon tissue were examined. The expression of inflammatory and apoptotic genes, including NF-κB, TNF-α, INOS, IL-1β, IL-6, TLR4, Caspase-3, Caspase-8, Bax, Bcl-2 was assessed. In addition, changes in the levels of catalase (CAT), superoxide dismutase (SOD), malondialdehyde (MDA), nitrite, and total antioxidant capacity (TAC) were measured in the colon tissue. Results: Colitis led to a decrease in TAC and the activity levels of CAT and SOD and an increase in the expression of inflammatory and apoptotic genes, MDA, and nitrite levels in the colon. Colitis was also associated with edema and severe damage to the epithelium, infiltration of inflammatory cells, and the presence of ulcers and necrosis in the colon tissue. CA significantly improved the inflammation, oxidative stress, apoptosis, and histopathological indices caused by acetic acid-induced colitis on the colon. Conclusion: It is concluded that CA probably exerts its positive effects in the management of colitis, through its anti-inflammatory, antioxidant, and anti-apoptotic properties. [ABSTRACT FROM AUTHOR]

Alpha-amylase (α-amylase) is a key player in the management of diabetes and its related complications. This study was intended to have an insight into the binding of caffeic acid and coumaric acid with α-amylase and analyze the effect of these compounds on the formation of advanced glycation end-products (AGEs). Fluorescence quenching studies suggested that both the compounds showed an appreciable binding affinity towards α-amylase. The evaluation of thermodynamic parameters (ΔH and ΔS) suggested that the α-amylase-caffeic/coumaric acid complex formation is driven by van der Waals force and hydrogen bonding, and thus complexation process is seemingly specific. Moreover, glycation and oxidation studies were also performed to explore the multitarget to manage diabetes complications. Caffeic and coumaric acid both inhibited fructosamine content and AGE fluorescence, suggesting their role in the inhibition of early and advanced glycation end-products (AGEs). However, the glycation inhibitory potential of caffeic acid was more in comparison to p-coumaric acid. This high antiglycative potential can be attributed to its additional –OH group and high antioxidant activity. There was a significant recovery of 84.5% in free thiol groups in the presence of caffeic acid, while coumaric attenuated the slow recovery of 29.4% of thiol groups. In vitro studies were further entrenched by in silico studies. Molecular docking studies revealed that caffeic acid formed six hydrogen bonds (Trp 59, Gln 63, Arg 195, Arg 195, Asp 197 and Asp 197) while coumaric acid formed four H-bonds with Trp 59, Gln 63, Arg 195 and Asp 300. Our studies highlighted the role of hydrogen bonding, and the ligands such as caffeic or coumaric acid could be exploited to design antidiabetic drugs. [ABSTRACT FROM AUTHOR]

Enterolactone, coumaric acid and vitexin are polyphenolic compounds present in a variety of fruits, vegetables, cereals and plants. These bioactive compounds are in high demand due to their antioxidant property in various tissues and organs. The purpose of this study was to develop a simultaneous extraction method, an aqueous two-phase extraction (ATPE) method, that would enable the extraction of these compounds from Hypoxis iridifolia . This environmentally friendly extraction method only applied water and ethanol as extraction solvents for these analytes from the plant matrix. After phase separation, the analytes were salted-out from the aqueous phase into the organic phase with the aid of a chaotrope (NaCl) or kosmotrope (Na 2 CO 3 ). Thereafter, the analytes were withdrawn by a micro-pipette for analysis on the high-performance liquid chromatography-photodiode array detector. Optimization was conducted using a central composite design, where three parameters were examined which involved percentage ethanol, centrifugation time and salt type. Generally, the optimized conditions for extraction were an ethanol percentage of 100% and a centrifugation time of 10 min, which yielded concentrations of 2942, 23,823 and 8881 mg kg -1 for enterolactone, vitexin and coumaric acid, respectively, in the presence of a kosmotrope. The optimized conditions of extraction in the presence of chaotrope were an ethanol percentage of 66% and a centrifugation time of 10 min with concentrations of 6727, 20,833 and 8618 mg kg -1 for enterolactone, vitexin and coumaric acid, respectively. The ATPE method involving Na 2 CO 3 was a better extractant of all the compounds studied relative to that of NaCl. The superior extraction capability of Na 2 CO 3 in ATPE could serve as a prototype for the development of efficient extraction methods to meet the high demand for medicinal compounds derived from natural products., Competing Interests: Tebogo Mphatlalala Mokgehle declares that he has no competing interests. Rangani Tracy Lukheli declares that she has no competing interests. Nikita Tawanda Tavengwa declares that he has no competing interests., (© 2024 The Author(s). Analytical Science Advances published by Wiley‐VCH GmbH.)

Abstract Hydroxycinnamic acids such as p-coumaric acid (CA) are chemically linked to lignin in grassy biomass with fairly labile ester bonds and therefore represent a straightforward opportunity to extract and valorize lignin components. In this work, we investigated the enzymatic conversion of CA extracted from lignocellulose to 4-vinylphenol (4VP) by expressing a microbial phenolic acid decarboxylase in Corynebacterium glutamicum, Escherichia coli, and Bacillus subtilis. The performance of the recombinant strains was evaluated in response to the substrate concentration in rich medium or a lignin liquor and the addition of an organic overlay to perform a continuous product extraction in batch cultures. We found that using undecanol as an overlay enhanced the 4VP titers under high substrate concentrations, while extracting > 97% of the product from the aqueous phase. C. glutamicum showed the highest tolerance to CA and resulted in the accumulation of up to 187 g/L of 4VP from pure CA in the overlay with a 90% yield when using rich media, or 17 g/L of 4VP with a 73% yield from CA extracted from lignin. These results indicate that C. glutamicum is a suitable host for the high-level production of 4VP and that further bioprocess engineering strategies should be explored to optimize the production, extraction, and purification of 4VP from lignin with this organism.

Coumaric acid (CouH), an antioxidant molecule assimilated by food consumption, was intercalated into layered double hydroxide (LDH) nanocarrier, having zinc and aluminium ions in the layers (LDH-Cou), to evaluate its pharmacological activity through in vitro and in vivo assays in mice. Therefore, the following tests were performed: coumarate delivery in saline solution, fibroblasts' cell viability using neutral red, peritonitis induced by carrageenan, formalin test, acetic-acid-induced writhing, and tail-flick assay, for the non-intercalated CouH and the intercalated LDH-Cou system. Furthermore, different pharmacological pathways were also investigated to evaluate their possible anti-inflammatory and antinociceptive mechanisms of action, in comparison to traditionally used agents (morphine, naloxone, caffeine, and indomethacin). The LDH-Cou drug delivery system showed more pronounced anti-inflammatory effect than CouH but not more than that evoked by the classic non-steroidal anti-inflammatory drug (NSAID) indomethacin. For the analgesic effect, according to the tail-flick test, the treatment with LDH-Cou expressively increased the analgesia duration (p < 0.001) by approximately 1.7–1.8 times compared to CouH or indomethacin. Thus, the results pointed out that the LDH-Cou system induced in vivo analgesic and anti-inflammatory activities and possibly uses similar mechanisms to that observed for classic NSAIDs, such as indomethacin. [ABSTRACT FROM AUTHOR]

Biosynthesis of Amaryllidaceae alkaloids (AA) starts with the condensation of tyramine with 3,4-dihydroxybenzaldehyde. The latter derives from the phenylpropanoid pathway that involves modifications of trans -cinnamic acid, p -coumaric acid, caffeic acid, and possibly 4-hydroxybenzaldehyde, all potentially catalyzed by hydroxylase enzymes. Leveraging bioinformatics, molecular biology techniques, and cell biology tools, this research identifies and characterizes key enzymes from the phenylpropanoid pathway in Leucojum aestivum. Notably, we focused our work on trans -cinnamate 4-hydroxylase (Lae C4H) and p -coumaroyl shikimate/quinate 3ʹ-hydroxylase (Lae C3′H), two key cytochrome P450 enzymes, and on the ascorbate peroxidase/4-coumarate 3-hydroxylase (Lae APX/C3H). Although Lae APX/C3H consumed p -coumaric acid, it did not result in the production of caffeic acid. Yeasts expressing Lae C4H converted trans -cinnamate to p- coumaric acid, whereas Lae C3′H catalyzed specifically the 3-hydroxylation of p -coumaroyl shikimate, rather than of free p -coumaric acid or 4-hydroxybenzaldehyde. In vivo assays conducted in planta in this study provided further evidence for the contribution of these enzymes to the phenylpropanoid pathway. Both enzymes demonstrated typical endoplasmic reticulum membrane localization in Nicotiana benthamiana adding spatial context to their functions. Tissue-specific gene expression analysis revealed roots as hotspots for phenylpropanoid-related transcripts and bulbs as hubs for AA biosynthetic genes, aligning with the highest AAs concentration. This investigation adds valuable insights into the phenylpropanoid pathway within Amaryllidaceae, laying the foundation for the development of sustainable production platforms for AAs and other bioactive compounds with diverse applications. [Display omitted] • Study of cinnamate 4-hydroxylase (C4H) & p -coumaroyl 3′-hydroxylase (C3′H) enzymes. • Characterization of Leucojum aestivum C4H & C3′H unveils their substrate specificity. • Elucidate the roles of Lae C4H & Lae C3′H in Amaryllidaceae alkaloids (AA) biosynthesis. • Their ER-membrane localization provides insights into their cellular dynamics. • Tissue-specific expression analysis reveals bulbs as hotspots for AA-related transcripts. [ABSTRACT FROM AUTHOR]

Objectives. Cinnamic acid derivatives belong to a large class of phenolic compounds, which are widely distributed in plants and have high potential for use in the medical and industrial fields. They have various useful practical properties, e.g., antioxidant, anti-inflammatory, antiplatelet, and anti-melanogenic properties. Hydroxycinnamic acids are of particular interest as phenylpropanoids, which are the starting compounds of lignin. The aim of this work was to study the electronic structure and analyze the reactivity of the simplest representatives of phenylpropanoids formed during the biosynthesis of the coumaric (p-hydroxycinnamic), caffeic (3,4-dihydroxycinnamic), ferulic (3-methoxy-4-hydroxycinnamic), sinapic (3,5-dimethoxy-4- hydroxycinnamic), and 3,4-dimethoxycinnamic acids. These acids are the biogenetic precursors of most other phenolic compounds (coumarins, melanins, lignins, and flavonoids) and are found in almost all higher plants.Methods. Calculations with full optimization of the geometric parameters were performed using the original Hartree–Fock theory and hybrid density functional method. All calculations were performed using the Firefly program. Results. A comparative quantum chemical calculation of the geometric parameters of hydroxycinnamic acid molecules was conducted via two methods, and the values of the charges on atoms according to Mulliken were determined. It was found that with the addition of hydroxyl and methoxy substituents at the meta and para positions relative to the carboxyl fragment, the electron density shifts toward the benzene ring, and the symmetry of the molecule decreases. Additionally, in these structures, there is π,π-conjugation of the carboxyl fragment of the –СН=СНСООН molecule with the aromatic ring, which significantly affects the geometric configuration of the molecule. The maximum positive charge is concentrated on the C9 atom, while the maximum negative charge is on the oxygen atoms belonging to the methoxy substituents and the hydroxyl group, which confirms the role of oxygen atoms in the chemical transformations of acids. Conclusions. Two different methods were used to calculate the geometric, electronic, and energy parameters and electrophilicity indices of the studied hydroxycinnamic acids in the gas phase. The obtained values were consistent (within the limits of error) with the experimental data as well as the results described in earlier works’ calculations by other methods.

Objective. The aim of this study was to determine the protective effect of p-coumaric acid (p-CA) against toluene-induced hepatotoxicity, nephrotoxicity and neurotoxicity in rats. Materials and methods. A total of 32 Sprague-Dawley male rats, 8 in each group, were used. 4 groups were formed as control, toluene, p-CA and toluene+p-CA. Animals in the control group, toluene group and p-CA group were given 0.9% NaCl, 0.9 mg/kg b.w toluene and 100 mg/kg b.w p-CA orally for 21 days, respectively. The animals in toluene+p-CA group were received p-CA for 3 days and from day 4, toluene and p-CA were applied together daily until day 25. On the 25th day, the study was terminated, blood and tissue samples were collected. Aspartate aminotransferase (AST), alanine aminotransferase (ALT) and creatinine levels in serum, glutathione peroxidase (GSH-Px) activity and malondialdehyde (MDA) and glutathione (GSH) levels in the tissue samples were determined. Results. In this study, it was determined that there were significant increases in ALT and AST activities, and creatinine levels in toluene-induced group compared to control group. Moreover, there was a decrease in the GSH-Px activities and GSH levels, and an increase in the MDA levels compared to the control group. However, in the toluene+p-CA group, significant decreases in aminotransferases activities, creatinine and MDA levels, and significant increases in GSH-Px activities and GSH levels were determined compared to the toluene group. Conclusions. It has been determined that p-CA has a protective effect against toluene-induced hepatotoxicity, nephrotoxicity and neurotoxicity.

Alpha-amylase (α-amylase) is a key player in the management of diabetes and its related complications. This study was intended to have an insight into the binding of caffeic acid and coumaric acid with α-amylase and analyze the effect of these compounds on the formation of advanced glycation end-products (AGEs). Fluorescence quenching studies suggested that both the compounds showed an appreciable binding affinity towards α-amylase. The evaluation of thermodynamic parameters (ΔH and ΔS) suggested that the α-amylase-caffeic/coumaric acid complex formation is driven by van der Waals force and hydrogen bonding, and thus complexation process is seemingly specific. Moreover, glycation and oxidation studies were also performed to explore the multitarget to manage diabetes complications. Caffeic and coumaric acid both inhibited fructosamine content and AGE fluorescence, suggesting their role in the inhibition of early and advanced glycation end-products (AGEs). However, the glycation inhibitory potential of caffeic acid was more in comparison to p-coumaric acid. This high antiglycative potential can be attributed to its additional –OH group and high antioxidant activity. There was a significant recovery of 84.5% in free thiol groups in the presence of caffeic acid, while coumaric attenuated the slow recovery of 29.4% of thiol groups. In vitro studies were further entrenched by in silico studies. Molecular docking studies revealed that caffeic acid formed six hydrogen bonds (Trp 59, Gln 63, Arg 195, Arg 195, Asp 197 and Asp 197) while coumaric acid formed four H-bonds with Trp 59, Gln 63, Arg 195 and Asp 300. Our studies highlighted the role of hydrogen bonding, and the ligands such as caffeic or coumaric acid could be exploited to design antidiabetic drugs.

Coumaric acid (CouH), an antioxidant molecule assimilated by food consumption, was intercalated into layered double hydroxide (LDH) nanocarrier, having zinc and aluminium ions in the layers (LDH-Cou), to evaluate its pharmacological activity through in vitro and in vivo assays in mice. Therefore, the following tests were performed: coumarate delivery in saline solution, fibroblasts’ cell viability using neutral red, peritonitis induced by carrageenan, formalin test, acetic-acid-induced writhing, and tail-flick assay, for the non-intercalated CouH and the intercalated LDH-Cou system. Furthermore, different pharmacological pathways were also investigated to evaluate their possible anti-inflammatory and antinociceptive mechanisms of action, in comparison to traditionally used agents (morphine, naloxone, caffeine, and indomethacin). The LDH-Cou drug delivery system showed more pronounced anti-inflammatory effect than CouH but not more than that evoked by the classic non-steroidal anti-inflammatory drug (NSAID) indomethacin. For the analgesic effect, according to the tail-flick test, the treatment with LDH-Cou expressively increased the analgesia duration (p < 0.001) by approximately 1.7–1.8 times compared to CouH or indomethacin. Thus, the results pointed out that the LDH-Cou system induced in vivo analgesic and anti-inflammatory activities and possibly uses similar mechanisms to that observed for classic NSAIDs, such as indomethacin.

Background and purpose: Rice (Oryzasativa L.) is one the most important staple food in the world. There is an increasing interest for pigmented varieties, due to their antioxidant properties. In this research, the antioxidant activities in different parts of three varieties of rice were studied. Materials and methods: White rice, brown rice, husk, and bran of Fajr, Hashemi and KB13 were extracted by maceration method using methanol as a solvent. Antioxidant capacity was assessed by three different methods. The total phenolic and flavonoid contents were also determined. Ferulic acid and p-coumaric acid were detected by High-Performance Liquid Chromatography (HPLC). Results: KB13 rice bran showed the highest amount of total phenolics (319.83 ± 15.21 mgGAE) and flavonoid contents (77.58 ± 3.8 mgQE). The Hashemi crude bran extract was significantly different from other extracts in DPPH radical scavenging activity (P

p‐Hydroxycinnamic acids (i. e., p‐coumaric, ferulic, sinapic, and caffeic acids) are phenolic compounds involved in the biosynthesis pathway of lignin. These naturally occurring molecules not only exhibit numerous attractive properties, such as antioxidant, anti‐UV, and anticancer activities, but they also have been used as building blocks for the synthesis of tailored monomers and functional additives for the food/feed, cosmetic, and plastics sectors. Despite their numerous high value‐added applications, the sourcing of p‐hydroxycinnamic acids is not ensured at the industrial scale except for ferulic acid, and their production cost remains too high for commodity applications. These compounds can be either chemically synthesized or extracted from lignocellulosic biomass, and recently their production through bioconversion emerged. Herein the different strategies described in the literature to produce these valuable molecules are discussed. [ABSTRACT FROM AUTHOR]

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Excessive pigmentation and reduced elasticity are the major skin problems that dermatologists and cosmetologists address. Compounds that inhibit melanin production might contribute to improving skin problems. In this study, we investigated whether coumaric acid- and caffeic acid-conjugated peptides might affect alpha-melanocyte stimulating hormone-induced melanin production, tyrosinase activity, and melanin synthesis-related gene expression in SK-MEL-2 human melanoma cells. Coumaric acid and caffeic acid showed no significant cytotoxicity, and they inhibited melanin production. In addition, coumaric acid- and caffeic acid-conjugated peptides suppressed tyrosinase activity more than arbutin, a known tyrosinase inhibitor. Quantitative real-time PCR (qRT-PCR) results also showed that both peptides inhibited the expression of melanin synthesis-related genes, TYR, TYRP1, TYRP2, and MITF. In particular, among the nine conjugated peptides tested, caffeic acid linked to a Gly-Gly-Gly linker and conjugated to the tripeptide, ARP, showed the greatest inhibition of gene expression in the qRT-PCR analysis. These results suggested that the inhibition of melanin exerted by coumaric acid- and caffeic acid-conjugated peptides might provide important information for the development of pigmentation-related skin diseases and cosmetic products.

Cis-diammineedichloroplatinum (cisplatin) is a chemotherapeutic agent used for the treatment of several types of cancer. However, severe side-effects such as ototoxicity, nephrotoxicity and neurotoxicity restrict its use. p-Coumaric acid (PCA) is a phenol class compound obtained from various plants in nature such as grape, carrot and tomato and from beverages such as tea and beer. It was shown to have antioxidant and free radical scavenging, anti-inflammatory and neuroprotective effects. The purpose of this study was to perform a biochemical and histopathological evaluation of the protective efficacy of PCA in ototoxicity induced with cisplatin in rats. To the best of our knowledge, no previous research has investigated the protective effect of PCA against cisplatin-induced ototoxicity. 28 Wistar rats were used. The animals were randomly divided into four groups of seven members each. No drug was administered to the rats in the control group, while the cisplatin group received a single intraperitoneal dose of 10 mg/kg cisplatin. PCA was administered to the PCA group rats by the intraperitoneal route for three days at a dose of 100 mg/kg. In the cisplatin+PCA group, intraperitoneal PCA at 100 mg/kg was administered one hour after injection of 10 mg/kg intraperitoneal cisplatin for three consecutive days. Rats were sacrificed 24 h after the final drug administration. The cochlear tissues were removed and MDA levels, GPx and SOD activities were measured to evaluate the oxidative stress status and histopathological evaluation was performed to reveal cochlear damage. The results showed that PCA protects the cochlea from ototoxic effect of cisplatin. PCA is a reliable agent that provides significant biochemical and histopathological protection against cisplatin-induced ototoxicity in rats. [Med-Science 2018; 7(2.000): 373-77]

Excessive pigmentation and reduced elasticity are the major skin problems that dermatologists and cosmetologists address. Compounds that inhibit melanin production might contribute to improving skin problems. In this study, we investigated whether coumaric acid- and caffeic acid-conjugated peptides might affect alpha-melanocyte stimulating hormone-induced melanin production, tyrosinase activity, and melanin synthesis-related gene expression in SK-MEL-2 human melanoma cells. Coumaric acid and caffeic acid showed no significant cytotoxicity, and they inhibited melanin production. In addition, coumaric acid- and caffeic acid-conjugated peptides suppressed tyrosinase activity more than arbutin, a known tyrosinase inhibitor. Quantitative real-time PCR (qRT-PCR) results also showed that both peptides inhibited the expression of melanin synthesis-related genes, TYR , TYRP1 , TYRP2 , and MITF. In particular, among the nine conjugated peptides tested, caffeic acid linked to a Gly-Gly-Gly linker and conjugated to the tripeptide, ARP, showed the greatest inhibition of gene expression in the qRT-PCR analysis. These results suggested that the inhibition of melanin exerted by coumaric acid- and caffeic acid-conjugated peptides might provide important information for the development of pigmentation-related skin diseases and cosmetic products. [ABSTRACT FROM AUTHOR]

Objective: Dietary bioactive materials having anti‐inflammatory and antioxidant potentials are able to inhibit diabetes‐associated periodontal complications. Although numerous studies indicate that administration of p‐coumaric acid (p‐CA) ameliorates diabetes and diabetes‐related complications, the roles of p‐CA on periodontal tissue destruction in diabetic mice and the possible mechanisms therein are not completely understood. In this study, we evaluated whether supplementation with p‐CA protects mice against diabetes‐associated spontaneous periodontal destruction and also explored the associated mechanism therein using in vivo and in vitro experimental systems. Materials and Methods: C57BL/6 male mice were divided into sham, streptozotocin (STZ), and STZ+CA groups (n = 5/group). Sham group was intraperitoneally injected with sodium buffer, whereas other two groups were injected with the buffer containing 160 mg/kg of STZ. STZ‐induced diabetic mice received oral gavage with p‐CA (50 mg/kg) (STZ+CA group) or with buffer only (STZ group) daily for 6 weeks. The effect of p‐CA on diabetes‐associated spontaneous periodontal destruction was evaluated using μCT analysis, hematoxylin and eosin staining, tartrate‐resistant acid phosphatase staining, and immunohistochemical staining methods. The efficacies of p‐CA on cell proliferation, osteoblast differentiation, reactive oxygen species (ROS) accumulation, and antioxidant‐related marker expression were examined using human periodontal ligament fibroblasts (hPLFs) cultured under high glucose condition. Results: Streptozotocin group exhibited periodontal tissue destruction along with increased inflammation, oxidative stress, and osteoclast formation, as well as with decreased osteogenesis. However, oral administration with p‐CA protected mice against STZ‐induced periodontal destruction by inhibiting inflammation and osteoclastic activation. STZ+CA group also showed higher expression of antioxidant and osteogenic markers in periodontal tissue than did STZ group. Treatment with high glucose concentration (30 mmol/L) impaired proliferation and osteoblast differentiation of hPLFs along with cellular ROS accumulation, whereas these impairments were almost completely disappeared by supplementation with p‐CA. Conclusion: These findings demonstrate that supplementation with p‐CA inhibits diabetes‐associated spontaneous destruction of periodontal tissue by enhancing anti‐inflammatory, anti‐osteoclastogenic, and antioxidant defense systems in STZ‐treated mice. [ABSTRACT FROM AUTHOR]

[Display omitted] • Alkaline processing of spent aromatic biomass to value added products. • Efficient recovery of lignin and phenolic acids from biomass hydrolysate. • One-pot conversion of biomass derived phenolic acids to aldehydes. • Recovery of cellulose from unreacted biomass. In order to combat the environmental issues associated with the burning of spent aromatic biomass (SAB), a method for alkaline hydrolysis of SAB has been developed to afford phenolic acids, predominantly the p -coumaric acid, lignin, and cellulose. Lignin (∼15 wt%) from alkaline hydrolysate was separated by precipitation while a mixture of phenolic acids obtained was directly reacted with a green reagent, PhI(OAc) 2 , under one-pot condition to afford a mixture of p -hydroxybenzaldehyde (>90 wt%) and vanillin (<10 wt%). Unreacted biomass obtained in the process was successfully used as a substrate for the production of cellulose (∼40 wt%). The developed method exhibits potential for application on an industrial scale. [ABSTRACT FROM AUTHOR]

Background: Cutaneous melanoma is the most aggressive form of skin cancer, with the worst prognosis, and it affects a younger population than most cancers. The high metastatic index, in more advanced stages, and the high aggressiveness decrease the effectiveness of currently used therapies, such as surgical removal, radiotherapy, cryotherapy, and chemotherapy, used alone or in combination. Based on these disadvantages, research focused on alternative medicine offers great potential for therapeutic innovation. Medicinal plants represent a remarkable source of compounds for the treatment of various diseases. Methods: In this study, we investigated the tumoral behavior of melanoma under treatment with the compounds baccharin and p-coumaric acid, extracted from green propolis, in mice inoculated with B16F10 cells for 26 days. Results: A significant modulation in the number of inflammatory cells recruited to the tumor region and blood in the groups treated with the compounds was observed. In addition, a significant reduction in the amount of blood vessels and mitosis in the neoplastic area was noticed. Conclusions: Through our research, we confirmed that baccharin and coumaric acid, isolated substances from Brazilian green propolis, have a promising anticarcinogenic potential to be explored for the development of new antitumor agents, adhering to the trend of drugs with greater tolerance and biological effectiveness.

Abstract Background Medicinal plants are rich source of traditional herbal medicine around the globe. Most of the plant’s therapeutic properties are due to the presence of secondary bioactive compounds. Methods The present study analyzed the High Pressure Liquid Chromatography (HPLC) fractions of Puncia granatum (peel) extracts (aqueous, chloroform, ethanol and hexane) against multidrug resistant bacterial pathogens (Acinetobacter baumannii, Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus). All the fractions having antibacterial activity was processed for bioactive compounds identification using LC MS/MS analysis. Results Among total HPLC fractions (n = 30), 4 HPLC fractions of P. granatum (peel) showed potential activity against MDR pathogens. Fraction 1 (F1) and fraction 4 (F4) collected from aqueous extract showed maximum activity against P. aeruginosa. Fraction 2 (F2) of hexane showed antibacterial activity against three pathogens, while ethanol F4 exhibited antibacterial activity against A. baumannii. The active fractions were processed for LC MS/MS analysis to identify bioactive compounds. Valoneic acid dilactone (aqueous F1 and F4), Hexoside (ethanol F4) and Coumaric acid (hexane F2) were identified as bioactive compounds in HPLC fractions. Conclusion Puncia granatum peel extracts HPLC fractions exhibited potential inhibitory activity against MDR bacterial human pathogens. Several bioactive compounds were identified from the HPLC fractions. Further characterization of these compounds may be helpful to conclude it as therapeutic lead molecules against MDR pathogens.

The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines.

Fruitlet core rot is one of the major postharvest disease of pineapple (Ananas comosus var. comosus). In the past, control strategies were designed to eliminate symptoms without addressing their causes or mechanisms, thus achieving only moderate success. In this study, (i) we focused on the anatomy of the fruitlets in the resistant “MD-2” and susceptible “Queen” pineapple cultivars; (ii) we identified the key role of the carpel margin in the infection process; (iii) we identified the key role of the sinuous layer of thick-walled cells in the inhibition of Fusarium ananatum colonization; and (iv) we linked the anatomy of the fruitlets with the phenolic content of cell walls. The fruitlet anatomy of the two cultivars was studied using X-ray, fluorescence, and multiphoton microscopy. Sepals and bracts were not perfectly fused with each other, allowing the pathogen to penetrate the fruit even after flowering. In fact, the fungi were found in the blossom cups of both cultivars but only became pathogenic in the flesh of the “Queen” pineapple fruit under natural conditions. The outer layer of the “MD-2” cavity was continuous with thick cell walls composed of ferulic and coumaric acids. The cell walls of the “Queen” blossom cup were less lignified at the extremities, and the outer layer was interspersed with cracks. The carpel margins were fused broadly in the “MD-2” pineapple, in contrast to the “Queen” pineapple. This blemish allows the fungus to penetrate deeper into the susceptible cultivar. In pineapple fruitlets, the hyphae of F. ananatum mainly progressed directly between cell walls into the parenchyma but never reached the vascular region. A layer of thick-walled cells, in the case of the resistant cultivar, stopped the colonization, which were probably the infralocular septal nectaries. Anatomical and histochemical observations coupled with spectral analysis of the hypodermis suggested the role of lignin deposition in the resistance to F. ananatum. The major phenolics bound to the cell walls were coumaric and ferulic acids and were found in higher amounts in the resistant cultivar postinoculation. The combination of fruitlet anatomy and lignification plays a role in the mechanism of host resistance to fruitlet core rot.

In this study, a model system of firm tofu (pressed gel) was prepared to study how the coagulation mechanism—acidification with glucono δ-lactone (GDL) or coagulation with magnesium sulphate (MgSO4)—affected the physical properties of the gels along with their in vitro proteolysis (or extent of proteolysis). The two types of gels were also fortified with 3.5 mM protocatechuic (PCA) and coumaric acid (CMA) to test whether they can be used as bioactive delivery systems. Texture analysis showed that all MgSO4-induced gels (fortified and control) had a higher hydration capacity and a weaker texture than the GDL-induced gels (p < 0.05). MgSO4 gels had almost double proteolysis percentages throughout the in vitro digestion and showed a significantly higher amino acid bioaccessibility than the GDL gels (essential amino acid bioaccessibility of 56% versus 31%; p < 0.05). Lastly, both gel matrices showed a similar phenolic acid release profile, on a percentage basis (~80% for PCA and ~100% for CMA). However, GDL gels delivered significantly higher masses of bioactives under simulated intestinal conditions because they could retain more of the bioactives in the gel after pressing. It was concluded that the coagulation mechanism affects both the macro- and microstructure of the soy protein pressed gels and as a result their protein digestibility. Both pressed gel matrices are promising delivery systems for bioactive phenolic acids.

Fruitlet core rot is one of the major postharvest disease of pineapple (Ananas comosus var. comosus). In the past, control strategies were designed to eliminate symptoms without addressing their causes or mechanisms, thus achieving only moderate success. In this study, (i) we focused on the anatomy of the fruitlets in the resistant "MD-2" and susceptible "Queen" pineapple cultivars; (ii) we identified the key role of the carpel margin in the infection process; (iii) we identified the key role of the sinuous layer of thick-walled cells in the inhibition of Fusarium ananatum colonization; and (iv) we linked the anatomy of the fruitlets with the phenolic content of cell walls. The fruitlet anatomy of the two cultivars was studied using X-ray, fluorescence, and multiphoton microscopy. Sepals and bracts were not perfectly fused with each other, allowing the pathogen to penetrate the fruit even after flowering. In fact, the fungi were found in the blossom cups of both cultivars but only became pathogenic in the flesh of the "Queen" pineapple fruit under natural conditions. The outer layer of the "MD-2" cavity was continuous with thick cell walls composed of ferulic and coumaric acids. The cell walls of the "Queen" blossom cup were less lignified at the extremities, and the outer layer was interspersed with cracks. The carpel margins were fused broadly in the "MD-2" pineapple, in contrast to the "Queen" pineapple. This blemish allows the fungus to penetrate deeper into the susceptible cultivar. In pineapple fruitlets, the hyphae of F. ananatum mainly progressed directly between cell walls into the parenchyma but never reached the vascular region. A layer of thick-walled cells, in the case of the resistant cultivar, stopped the colonization, which were probably the infralocular septal nectaries. Anatomical and histochemical observations coupled with spectral analysis of the hypodermis suggested the role of lignin deposition in the resistance to F. ananatum. The major phenolics bound to the cell walls were coumaric and ferulic acids and were found in higher amounts in the resistant cultivar postinoculation. The combination of fruitlet anatomy and lignification plays a role in the mechanism of host resistance to fruitlet core rot. [ABSTRACT FROM AUTHOR]

Abstract This study was designed to co-load hydrophilic arbutin and hydrophobic coumaric acid in nano-sized multi-phase emulsion (W/O/W) using hydrocolloids and examined for its various stability and bioaccessibility parameters. The creaming stability and sensory evaluation of emulsion in Lactobacillus beverage and its release kinetics in simulated oral and gastrointestinal conditions were also studied. Results revealed that multi-phase emulsion exhibited small particle size and low polydispersity index with high zeta potential. Higher encapsulation efficiency was also observed. Moreover, the multi-phase emulsion showed good storage stability under different conditions. The multi-phase emulsion also showed controlled release of arbutin and coumaric acid in simulated conditions with increasing bioaccessibility. Stability of these compounds under unfavorable conditions was also found to be increased. Moreover, high creaming stability and sensory evaluation score of the multi-phase emulsion suggested that the formulation was capable of retaining arbutin and coumaric acid in Lactobacillus beverage without affecting its sensory properties. These results indicated that the multi-phase nano-emulsion (W/O/W) could effectively co-deliver hydrophilic arbutin and hydrophobic coumaric acid and thus could be a novel delivery method for increasing bioaccessibility of these nutraceutically important phenolic compounds. Graphical abstract Image 1 Highlights • Hydrophilic arbutin and hydrophobic coumaric acid were co-loaded in W/O/W emulsion. • The emulsion increased stability and bioaccessibility of arbutin and coumaric acid. • Sustainable release of arbutin and coumaric acid in gastrointestinal fluid. • W/O/W emulsion retained phenolics in Lactobacillus beverage as functional food. [ABSTRACT FROM AUTHOR]

Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time‐consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure‐activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. [ABSTRACT FROM AUTHOR]

The dissociation constant (pKa) of a drug is a key parameter in drug discovery and pharmaceutical formulation. The hydroxy substituent has a significant effect on the acidity of hydroxycinnamic acid. In this work, the acidic constants of coumaric acids are obtained experimentally by spectrophotometry using the chemometric method and calculated theoretically using ab initio quantum mechanical method at the HF/6‐31G* level of theory in combination with the SMD continuum solvation method. Rank annihilation factor analysis (RAFA) is an efficient chemometric technique based on the elimination of the contribution of one of the chemical components from the data matrix. RAFA cannot be performed because the pure spectrum of HA− is not available. So, two‐rank annihilation factor analysis (TRAFA) is proposed for the determination of the pKa OF H2A. A comparison between the pKa values obtained previously by TRAFA for the molecules o‐coumaric acid (4.13, 9.58), m‐coumaric acid (4.48, 10.35), and p‐coumaric acid (4.65, 9.92) makes it clear that there is good agreement between the results obtained by TRAFA and ab initio quantum mechanical method. [ABSTRACT FROM AUTHOR]

Background and purpose: Rice (Oryzasativa L.) is one the most important staple food in the world. There is an increasing interest for pigmented varieties, due to their antioxidant properties. In this research, the antioxidant activities in different parts of three varieties of rice were studied. Materials and methods: White rice, brown rice, husk, and bran of Fajr, Hashemi and KB13 were extracted by maceration method using methanol as a solvent. Antioxidant capacity was assessed by three different methods. The total phenolic and flavonoid contents were also determined. Ferulic acid and p-coumaric acid were detected by High-Performance Liquid Chromatography (HPLC). Results: KB13 rice bran showed the highest amount of total phenolics (319.83 ± 15.21 mgGAE) and flavonoid contents (77.58 ± 3.8 mgQE). The Hashemi crude bran extract was significantly different from other extracts in DPPH radical scavenging activity (P<0.001). The barn of three rice varieties showed the highest activity in nitric oxide radical scavenging activity (P<0.001). The bran of Hashemi and KB13 showed the highest amount of ferulic acid (26.21 mg/g extract) and p-Coumaric acid (3.66 mg.g extract), respectively. Conclusion: The Iranian Fajr, Hashemi and KB13 rice varieties were found to have significantly higher antioxidant activities and total phenolic and flavonoid contents compared with other foreign samples reviewed. [ABSTRACT FROM AUTHOR]

Nowadays there are still various chemical pesticides being applied in the course of ensuring plant protection. Since 2010, we have been working on the development of new, environmentally-friendly plant protection products which will provide an effective tool against pathogenic fungi and bacteria which cause disease in crop plants. The specific aim of this study was to evaluate a risk assessment for new plant protection products that have been elaborated on the basis of coniferous tree bark. Various products were tested which are extracted during the processing of wood bark from pine (Pinus sylvestris L.) and spruce (Picea abies (L.) Karst.). Ethanol extracts were formulated and applied during these experiments. Two formulations, which showed anti-fungal activity in vitro and in field trials on fruit crops (involving strawberries and raspberries) were selected for the risk assessment studies. The impact was studied of formulation treatment on crop plants and soil biological activity, and the accumulation of residues of active substances in crop plants and soil. The application of new formulations did not show any negative effect on the chlorophyll content and the chlorophyll fluorescence of plant leaves. The results showed that pine and spruce bark extract formulations contain active compounds (coumaric acid, quercetin, epicatechin, and ferulic acid) within the range of 5.1--5.9 mg kg-1 and 11.1--443.9 mg kg-1 respectively. The amount of active substances which were determined in most cases was higher in the spruce bark extract formulation when compared to the pine bark extract formulation. Our results confirmed the presence of active compounds -- epicatechin, quercetin, and coumaric acid -- in strawberry fruits which remained untreated and in those that were treated with spruce ethanol extract formulation. Untreated raspberry fruits contained all four active substances within the range of 81--5,300 ng kg-1. We observed a significant increase of coumaric acid and quercetin in raspberries after their having been treated with spruce bark extract formulation in a 2% concentration, P < 0.05, and did not find any negative impact for spruce bark extract formulations when used on soil microbial biomass. [ABSTRACT FROM AUTHOR]

The aim of this study was to analyze the profile of endogenous phenolic acids in yellow-flowered magnolias and to evaluate the effects of endogenous and exogenous phenolic acids on the in vitro rooting of three magnolia cultivars (‘Butterflies’, ‘Yellow Bird’, and ‘Elizabeth’). It has been shown that magnolia cultivars are phenolic acid-rich plants. Of the 16 phenolic acids tested, all were detected in each magnolia cultivar. The most abundant was gallic acid (max. 34,946 ng·mg−1 dry mass), followed by chlorogenic acid, ferulic acid, and caffeic acid. The amount of individual phenolic acids differed between the cultivars and media. The total phenolic production was enhanced by auxin, the main factor promoting rooting in magnolia in vitro. It has been found that the difficult-to-root ‘Butterflies’ and ‘Yellow Bird’ rooted better when they were grown on medium containing a mixture of auxins—3-indolebutyric acid (IBA) and 1-naphthaleneacetic acid (NAA)—as compared to IBA alone. The highest rooting frequency was observed for ‘Elizabeth’ (95.8%), followed by ‘Butterflies’ (46.1%) and ‘Yellow Bird’ (21.4%). In the case of ‘Yellow Bird’, the auxin treatment enhanced the leaf yellowing. The present work indicates a clear relationship between the overaccumulation of chlorogenic acid and coumaric acid in the late phase of rooting in vitro and the low rooting responses of magnolia ‘Butterflies’ and ‘Yellow Bird’. On the other hand, ‘Elizabeth’ produced more soluble sugars by 29.2% than easy-to-root ones. The biochemical status of the plantlets can influence their further ex vitro establishment, which was the highest for ‘Elizabeth’ (97.5%), followed by ‘Butterflies’ (49.9%) and ‘Yellow Bird’ (24.6%).