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Self‐assembly behaviors of special topological polymers such as 8‐figure shaped cyclic polymer are interesting, but are rarely reported so far due to the limited availability. In this work, mikto 8‐figure shaped cyclic copolymers are synthesized with cinnamic acid dimer junctions, in which both rings possess diblock PSx‐b‐PEGy structures. Their self‐assembly in water is investigated in comparison with their corresponding linear precursors. According to scanning electron microscopic (SEM) and transmission electron microscopic (TEM) observation, both of the mikto 8‐figure shaped cyclic polymers and their corresponding linear precursors can form vesicles. But those formed from the former have very smooth surfaces, while those from the linear precursors have rugous surfaces. TEM observation shows that the linear precursors form loose vesicles. The size of micelles formed from 8‐shaped cyclic copolymers is much smaller than that formed from the linear precursors. The topological structure exerts a significant influence on the solution aggregation behavior and provides broad ideas for the construction of precision solution aggregates. [ABSTRACT FROM AUTHOR]

Cinnamon, an Indigenous species, is extensively used as a folk medicine in India, China, and other parts of the world due to its therapeutic potential inherited via the latent chemical composition. The vital component presented is cinnamaldehyde, along with cinnamic acid and cinnamate, which contributes to being an anti‐inflammatory, antimicrobial, antidiabetic, and anticancer agent together with the capability to control neurological syndromes like Alzheimer's and even Parkinson's diseases. Given the importance of the anticarcinogenic properties of cinnamon on various cell strains concerning the curable effect, this review focuses on evaluating different extraction methods like steam distillation, Soxhlet extraction, microwave‐assisted extraction, and more, in addition to a summary of new technologies like gas chromatography, HPLC, DART‐MS, and NMR, etc. which paved the way in characterizing the chemical composition of cinnamon. Cinnamaldehyde showed its apoptosis through various mechanistic pathways on an adequate number of cell lines and antineoplastic potential on specific multifaceted cancerous cells, which advocates for continued research and investment in this vital area of drug discovery and suggestions for future scope. [ABSTRACT FROM AUTHOR]

Starch systems of natural antioxidants containing different starch sources (lentil, chickpea, corn, pea, and tapioca) and a variety of antioxidants (ascorbic acid, linalool, carvacrol, and cinnamic acid) are prepared using a pilot scale spray dryer. The effect of drying process on structural, morphological, and physical properties of the starch complexes is investigated. X‐ray analysis (XRD) reveals that there is a possible molecular interaction of starch with natural antioxidants. Differential Scanning Calorimetry (DSC) shows the presence of an endothermic peak ranging from 91.0 to 112.1 °C, which is most probably attributed to the dissociation temperature of starch systems. Microscopic examination shows that the spray dried particles are irregular and spherical in shape and the antioxidant molecules are uniformly distributed within the starch systems matrix. All powders have moisture content values lower than 10%. The spray dried powders exhibit high lightness (L*) values and hue angle values close to 90 implying a yellow color. Chickpea‐ascorbic acid systems exhibit the highest bulk and tapped densities values and are the most hygroscopic while tapioca‐cinnamic acid systems have the lowest ones. Principal Component Analysis (PCA) and Cluster analysis show that there is a strong relationship between the physical properties of the powders. [ABSTRACT FROM AUTHOR]

Cancer is a longstanding worldwide issue, current chemotherapeutic treatments have limited effectiveness and high toxicity. An extensive investigation has revealed a significant potential link between ITK and the development of cancer. Hence, it is recommended to prioritize investigating ITK to develop and produce novel inhibitors for treating diseases associated with T cells. In our study, we have designed and synthesized two new series of compounds, which consist of cinnamic acid, carbohydrazide, and cyclopropanamide groups in a single compound. We have developed a facile method to synthesize 20 new derivatives of two series of innovative 1‐phenyl‐N'‐(3‐phenylacryloyl)cyclopropane carbohydrazide derivatives with good yields and purity. The Synthesized derivatives are conformed by analytical techniques (FT‐IR, 1H NMR, 13C NMR, elemental analysis) and their biological evaluation data is provided. The synthesized compounds displayed favorable docking scores in comparison to the ITK inhibitor, Ibrutinib. The in vitro cancer investigation shows that these compounds have good IC50 values, causing cytotoxicity against malignant cell lines. [ABSTRACT FROM AUTHOR]

Objectives: Dental caries, a prevalent infectious disease affecting teeth, ranks highest among 328 diseases, according to a 2017 Lancet study. In demineralized human dentin, matrix metalloproteinase‐3 (MMP3) functions as a proteoglycanase, contributing to the degradation of proteoglycan components. This process exposes collagen fibrils, thereby facilitating the demineralization of the dentin matrix. Inhibiting MMP3 shows potential for preventing dental caries. Methods: The binding affinity of 20 cinnamic acid derivatives, namely cynarin, chlorogenic acid, rosmarinic acid, cinnamyl caffeate, phenethyl caffeate, N‐p‐coumaroyltyramine, caffeic acid 3‐glucoside, caffeic acid phenethyl ester, roscovitine, benzyl caffeate, o‐coumaric acid, artepillin C, caffeic acid, methyl caffeate, 2‐methylcinnamic acid, ferulic acid, drupanin, p‐coumaric acid, cinnamic acid, and sinapinic acid, to the MMP3 catalytic cleft, was assessed utilizing AutoDock 4.0. Molecular dynamics simulation was then employed to analyze the stability of backbone atoms in free MMP3, MMP3‐positive control inhibitor, and MMP3 complexed with the top‐ranked cinnamic acid over a 100 ns computer simulation. Results: Four cinnamic acids demonstrated ΔGbinding scores below −10 kcal/mol, with cynarin emerging as the most potent MMP3 inhibitor, featuring a ΔGbinding score and inhibition constant value of −15.57 kcal/mol and 3.83 pM, respectively. The MMP3–cynarin complex exhibited stability after a 50 ns computer simulation, showing a root‐mean‐square deviation of 8 Å. Conclusions: The inhibition of MMP3 by cynarin, chlorogenic acid, rosmarinic acid, and cinnamyl caffeate holds promise as a potential preventive strategy for dental caries. [ABSTRACT FROM AUTHOR]

Background: The research is aimed at exploring the potential of marigold petal tea (MPT), rich in polyphenol contents, against oxidative stress and obesity in a rat model following a high‐fat‐sugar diet (HFSD). Methods: The MPT was prepared through the customary method of decoction and was subjected to analysis for its polyphenol composition using reversed‐phase high‐performance liquid chromatography (RP‐HPLC). Two specific doses of MPT, namely, 250 and 500 mg/kg body weight (BW), were chosen for the study—referred to as MPT‐250 and MPT‐500, respectively. Result: The main phenolic acids and flavonoids identified in MPT, with concentrations exceeding 10 mg/100 mL of tea, included catechin, rutin, salicylic acid, gallic acid, sinapic acid, chlorogenic acid, cinnamic acid, and ellagic acid. The total phenolic (TP) and total flavonoid (TF) contents in MPT were measured to be 5.53 and 7.73 mg/g, respectively. Additionally, MPT demonstrated a 57.2% scavenging capacity with 2,2‐diphenyl‐1‐picrylhydrazyl radical. Notably, the administration of a higher dose (MPT‐500) showed a significant reduction in body mass index (BMI) and a 51.24% reduction in the rate of increase in BW compared to the HFSD group. The findings indicated that all the treatment groups, that is, orlistat treatment (OT), MPT‐250, and MPT‐500 groups, experienced reduced levels of serum total cholesterol (TC), triglyceride (TG), and markers of lipoproteins in contrast to the HFSD group. Moreover, MPT helped restore the levels of malondialdehyde (MDA), superoxide dismutase (SOD), and reduced glutathione (GSH), thereby demonstrating its potential in combating oxidative stress. The MPT‐500 group also displayed decreased liver and kidney weights and an improved atherogenic index when compared to the HFSD group. Conclusion: The results clearly indicate that a high dosage of MPT showed antiobesity activity which was comparable to the same effects produced by the conventional drug orlistat. [ABSTRACT FROM AUTHOR]

This study evaluates the phytotoxic potential of methanolic extracts from six Asteraceae species: Wedelia chinensis, Helianthus annuus, Cosmos bipinnatus, Tagetes erecta, Tithonia diversifolia, and Zinnia elegans. The extracts were tested at concentrations of 0.03, 0.1, 0.3, and 1.0 g/mL to assess their inhibitory effects on the radicle and hypocotyl lengths of Echinochloa crus‐galli and Echinochloa colona. The two most potent species, C. bipinnatus and T. diversifolia, were further evaluated using extracts from their roots, stems, and leaves. Among these, C. bipinnatus leaf extracts showed the most significant phytotoxicity and were tested at 20, 40, and 60 days of plant age. At 0.03 g/mL, C. bipinnatus extract inhibited the hypocotyl and radicle lengths of E. colona by 23.01% and 56.45%, and E. crus‐galli by 8.5% and 36.35%, respectively. At 1.0 g/mL, the extract inhibited the hypocotyl lengths of E. colona and E. crus‐galli by 97.54% and 88.15%, and the radicle lengths by 93.52% and 99.99%, respectively. The 60‐day‐old C. bipinnatus leaf extract exhibited the highest inhibitory effect, correlating with the identification of key allelochemicals such as cinnamic acid, caffeic acid, coumaric acid, ferulic acid, 2‐4 dimethohydroxy benzoic acid, and salicylic acid. These findings suggest that the 60‐day‐old C. bipinnatus leaf extracts have strong potential for use in the biological control of these weed species, offering a promising avenue for the development of natural herbicides. [ABSTRACT FROM AUTHOR]

SUMMARY: The conquest of land posed severe problems to plants which they had to cope with by adapting biosynthetic capacities. Adaptations to respond to UV irradiation, water loss, pathogen and herbivore defense, and the earth's pull were essential. Chemical compounds alleviating these problems can be synthesized by the phenylpropanoid pathway, the core of which are three enzymes: phenylalanine ammonia‐lyase (PAL), cinnamic acid 4‐hydroxylase, and 4‐coumaric acid coenzyme A‐ligase (4CL). The genomes of model organisms, Chara braunii as aquatic alga and the two bryophytes Physcomitrium patens and Marchantia polymorpha, were searched for sequences encoding PAL and 4CL and selected sequences heterologously expressed in Escherichia coli for biochemical characterization. Several possible isoforms were identified for both enzymes in Marchantia polymorpha and Physcomitrium patens, while only one or two isoforms could be retrieved for Chara braunii. Active forms of both enzymes were found in all three organisms, although the catalytic efficiencies varied in a wide range. l‐Phenylalanine was accepted as best substrate by all PAL‐like enzymes, despite annotations in some cases suggesting different activities. The substrate spectrum of 4CLs was more diverse, but caffeic and/or 4‐coumaric acids generally were the best‐accepted substrates. Our investigations show that PAL and 4CL, important enzymes for the formation of phenolic compounds, are present and active in extant charophytes and bryophytes as model organisms for the conquest of land. Significance Statement: Upon terrestrialization, plants have profited from an effective phenylpropanoid metabolism enabling them to cope with stressors on land. Essential enzymes, phenylalanine ammonia‐lyase, and 4‐coumaric acid coenzyme A‐ligase are present and active in the charophyte Chara braunii (shown for the first time) and the bryophytes Marchantia polymorpha and Physcomitrium patens and have been characterized on molecular and biochemical levels. [ABSTRACT FROM AUTHOR]

The phenylpropanoid pathway is one of the plant metabolic pathways most prominently linked to the transition to terrestrial life, but its evolution and early functions remain elusive. Here, we show that activity of the t -cinnamic acid 4-hydroxylase (C4H), the first plant-specific step in the pathway, emerged concomitantly with the CYP73 gene family in a common ancestor of embryophytes. Through structural studies, we identify conserved CYP73 residues, including a crucial arginine, that have supported C4H activity since the early stages of its evolution. We further demonstrate that impairing C4H function via CYP73 gene inactivation or inhibitor treatment in three bryophyte species—the moss Physcomitrium patens, the liverwort Marchantia polymorpha and the hornwort Anthoceros agrestis —consistently resulted in a shortage of phenylpropanoids and abnormal plant development. The latter could be rescued in the moss by exogenous supply of p -coumaric acid, the product of C4H. Our findings establish the emergence of the CYP73 gene family as a foundational event in the development of the plant phenylpropanoid pathway, and underscore the deep-rooted function of the C4H enzyme in embryophyte biology. Synopsis: The phenylpropanoid pathway is assumed to represent a key plant metabolic adaptation associated with terrestrial life, and processes about 30% of all photosynthetic carbon on Earth. This study highlights the importance of the evolutionary co-emergence of the CYP73 gene family, which encodes t -cinnamic acid 4-hydroxylase (C4H) enzymes, in establishing this pathway in a land plant's ancestor. The CYP73 gene family emerged in an ancestor of land plants and has subsequently been conserved. The CYP73 gene family encodes C4H, the first plant-specific enzyme in the phenylpropanoid pathway, from the earliest stages of its evolution. Alteration of C4H function via CYP73 gene inactivation or inhibitor treatment consistently disrupts phenylpropanoid synthesis and development in land plants. This paper shows that the t -cinnamic acid 4-hydroxylase activity emerged with the CYP73 gene family in a common ancestor of all land plants. [ABSTRACT FROM AUTHOR]

A pre‐clinical toxicological evaluation of herbal medicines is necessary to identify any underlying health‐associated side effects, if any. BPGrit is an Ayurveda‐based medicine prescribed for treating hypertensive conditions. High‐performance liquid chromatography‐based analysis revealed the presence of gallic acid, ellagic acid, coumarin, cinnamic acid, guggulsterone E, and guggulsterone Z in BPGrit. For sub‐acute toxicity analysis of BPGrit, male and female Sprague–Dawley rats were given repeated oral gavage at 100, 300, and 1000 mg/kg body weight/day dosages for 28 days, followed by a 14‐day recovery phase. No incidences of mortality, morbidity, or abnormal clinical signs were observed in BPGrit‐treated rats throughout the study period. Also, the body weight and food consumption habits of the experimental animals did not change during the study duration. Hematological, biochemical, and histopathological analysis did not indicate any abnormal changes occurring in the BPGrit‐treated rats up to the highest tested dose of 1000 mg/kg body weight/day. Finally, the study established the "no‐observed‐adverse‐effect level" for BPGrit at >1000 mg/kg body weight/day in Sprague–Dawley rats. BPGrit, an Ayurvedic polyherbal medicine prescribed to hypertensive patients, was evaluated for sub‐acute toxicity Sprague–Dawley rats over a period of 28 days, with a 14‐day recovery phase. Presence of several beneficial phytochemicals was observed in BPGrit using high‐performance liquid chromatography analysis. Repeated oral gavage of BPGrit in male and female animals did not induce mortality, morbidity, or abnormal clinical, biochemical, hematological, or histological signs. Based on these observations, the "no‐observed‐adverse‐effect level" for BPGrit was established at >1000 mg/kg body weight/day. [ABSTRACT FROM AUTHOR]

The novel cinnamic acid (CA) (H4‐CA, H5‐CA, and H7‐CA) and caffeic acid (KA) (H4‐KA, H5‐KA, and H7‐KA) hemorphin analogs have recently been synthesized and their trans isomers have been tested for antiseizure and antinociceptive activity. In the present study, the cis forms of these compounds were tested and compared with their trans isomers in seizure and nociception tests in mice. The cis‐H5‐CA and H7‐CA compounds showed efficacy against psychomotor seizures, whereas the trans isomers were ineffective. Both the cis and trans KA isomers were ineffective in the 6‐Hz test. In the maximal electroshock (MES) test, the cis isomers showed superior antiseizure activity to the trans forms of CA and KA conjugates, respectively. The suppression of seizure propagation by cis‐H5‐CA and the cis‐H5‐KA was reversed by a kappa opioid receptor (KOR) antagonist. Naloxone and naltrindole were not effective. The cis‐isomers of CA conjugates and cis‐H7‐KA produced significantly stronger antinociceptive effects than their trans‐isomers. The cis‐H5‐CA antinociception was blocked by naloxone in the acute phase and by naloxone and KOR antagonists in the inflammatory phase of the formalin test. The antinociception of the KA conjugates was not abolished by opioid receptor blockade. None of the tested conjugates affected the thermal nociceptive threshold. The results of the docking analysis also suggest a model‐specific mechanism related to the activity of the cis‐isomers of CA and KA conjugates in relation to opioid receptors. Our findings pave the way for the further development of novel opioid‐related antiseizure and antinociceptive therapeutics. [ABSTRACT FROM AUTHOR]

The pressure response of crystalline trans‐cinnamic acid is studied by means of Raman spectroscopy up to 6 GPa. Pressure application causes the reversible shift of all the observed Raman peaks to higher frequencies and changes in their relative intensities, with the intermolecular vibrational modes being by far more sensitive to pressurization compared to the intramolecular ones. The present high‐pressure Raman data indicate the structural stability of the trans‐cinnamic acid crystal and molecular conformation up to the highest pressure attained in the experiments, the importance of the hydrogen bonding, as well as the considerable strengthening of the intermolecular interactions at elevated pressures. [ABSTRACT FROM AUTHOR]

This work demonstrates the oxidative cross‐coupling of cinnamic acids with toluene using FeCl3 immobilized on a covalent organic framework (COF) pore wall, resulting in the synthesis of 1,3‐arylpropene derivatives. This iron‐based heterogeneous catalytic system affords the desired products in moderate yields ranging from 51 % to 65 %. Investigations using COFs with varying pore sizes indicate that larger pores facilitate the reaction, suggesting a spatial requirement for this transformation within the catalyst. The correlation between pore size and reaction efficiency provides insights into developing tailored catalysts to match the spatial requirements of the transformation. This version emphasizes the novelty of the study and the synthesis of 1,3‐arylpropene derivatives. It also clarifies that the iron‐based heterogeneous catalytic system is responsible for the reaction. Additionally, it provides a more detailed explanation of the findings regarding pore size and spatial requirements. [ABSTRACT FROM AUTHOR]

Based on the strong coordination ability of substituted imines towards transition metals of different oxidation states, the coordination of the HL imine ligand with the Cu2+ ion to form the Cu–bis–imine complex was achieved in 2:1 molar ratios. Their structures were confirmed with various spectroscopic tools. Heterogeneously, CuL2 was successfully appended on ZnO@TiO2 nanoparticles, as the less harmful materials, within the deprotonated p‐hydroxy chain of the bonded ligand in CuL2. The surface and internal structural morphologies of ZnO@TiO2@CuL2 were analyzed using X‐ray diffraction (XRD), field‐emission scanning electron microscopy (FESEM), high‐resolution transmission electron microscopy (HRTEM), energy‐dispersive X‐ray spectroscopy (EDS), and infrared (IR) spectroscopy, in addition to thermogravimetric analysis (TGA). The catalytic behavior of both catalysts, CuL2 (the homogeneous catalyst) and ZnO@TiO2@CuL2 (the heterogeneous catalyst), was examined in the benzyl alcohol redox protocols using H2O2 for their optimization. α,β‐Cinnamic acid decarboxylative bromination in the presence of potassium bromide and H2O2 in water was studied with both catalysts, in which (2‐bromovinyl)benzene was the chemoselective product. Both Cu catalysts displayed appreciable catalytic effectiveness for the oxidation protocols and the decarboxylative bromination reactions. CuL2 recorded less required time for optimization than that of the heterogeneous catalyst. The catalytic effectiveness of CuL2 was less promoted than that of ZnO@TiO2@CuL2. Despite the less performance in yield of benzaldehyde for the oxidation protocols with ZnO@TiO2@CuL2, ZnO@TiO2@CuL2 had more recycling than its homogeneous counterpart, with seven to three times, respectively. [ABSTRACT FROM AUTHOR]

BACKGROUND: Muffins are delightful baked food products that have earned a prominent place in the daily diet of a majority of people around the world. The incorporation of microgreens juice powder (MJP) into muffins boosts their nutritional value. The influence of the incorporation of wheatgrass, fenugreek and basil MJP at 1.5% and 3.0% levels on the nutritional composition, physical properties, pasting, sensory, textural and phenolic profile of functional muffins was evaluated. RESULTS: The results indicated a significant increase in the protein content, ash content, dietary fiber and total phenolic content of MJP incorporated muffins. The incorporation of MJP to the muffins led to a gradual reduction in the L*, a* and b* values. Baking characteristic such as bake loss decreased significantly as a result of MJP incorporation. Furthermore, the incorporation of various MJPs resulted in a significant decrease in the peak viscosity of the flour‐MJP blends. Regarding texture, the hardness and chewiness of the muffins increased progressively with an increase in the level of MJP incorporation. The highest hardness (10.15 N) and chewiness (24.45 mJ) were noted for 3% fenugreek MJP incorporated muffins (FK 3.0). The sensory score of MJP incorporated muffins was acceptable and satisfactory. Additionally, 3% basil MJP incorporated muffins (BL 3.0) marked the dominant presence of majority of the detected phenolic acids such as ferulic acid, sinapic acid, chlorogenic acid, caffeic acid, quercetin, cinnamic acid, isothymosin and rosamarinic acid. The highest concentration of p‐coumaric acid (11.95 mg kg−1), vanillic acid (26.07 mg kg−1) and kaempferol (8.04 mg kg−1) was recorded for FK 3.0 muffin. CONCLUSION: MJP incorporated muffins revealed the pool of phenolic acids and the reduced bake loss is of industrial interest. The present study concludes that wheatgrass, fenugreek and basil MJP can be incorporated by up to 3% into baked products as a source of functional ingredients for health benefits. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

In this work, the optimum process conditions and kinetics of the green synthesis of isobutyl cinnamate using deep eutectic solvents (DESs) as catalysts were investigated. Isobutyl cinnamate is a spice with low toxicity and is widely used in the food industry. However, there is a lack of reports on its green synthesis. Three DESs were prepared by adjusting the mixing ratio of choline chloride (ChCl) and p‐toluenesulfonic acid (PTSA). Response surface methodology with Box‐Behnken design (RSM‐BBD) was used to optimize the process parameters of the esterification of cinnamic acid with isobutanol. The effects of catalyst loading, stirring speed, cinnamic acid/isobutanol molar ratio, and temperature on the conversion of cinnamic acid over time were evaluated. Using ChCl‐PTSA as a catalyst, the kinetics data and chemical equilibrium constants of the esterification were determined at a temperature range of 353.15–383.15 K. The pseudo‐homogeneous (PH) model based on activity was then adopted to describe the kinetics of the reaction, and the relative deviations between the experimental values and the calculated ones by PH model are less than 5.5%. Thermodynamic data (ΔrH0, ΔrS0, ΔrG0) for the esterification reaction was calculated as well. In addition, the results of six consecutive cycles of the catalyst showed that ChCl‐PTSA has good stability and recyclability. [ABSTRACT FROM AUTHOR]

With the development of green chemistry, PVC thermal stabilizers should be developed in the direction of non‐toxic, environmental protection, and high efficiency. This study utilized natural Cinnamic acid to successfully synthesize an eco‐friendly and high‐performance cinnamate‐intercalated calcium aluminum hydrotalcite through the coprecipitation method. The structure of CaAl‐cinnamate‐LDHs was analyzed via XRD, IR, SEM, and thermogravimetric analyses. The CaAl‐cinnamate‐LDHs/PVC sample was thoroughly investigated using multiple techniques, including tests, such as oven aging, thermogravimetric analysis, Congo red analysis, and conductivity analysis. Compared with the commercial thermal stabilizers CaSt2/ZnSt2 and CaAl‐CO3‐LDHs, CaAl‐cinnamate‐LDHs demonstrated superior initial whiteness and exceptional long‐term thermal stability, it did not completely blacken until 120 min. Dynamic mechanical analysis showed that the addition of CaAl‐cinnamate‐LDHs could improve the plasticizing performance of PVC. CaAl‐cinnamate‐LDHs also had a synergistic effect with ZnSt2, with a static thermal stabilization time of up to 40.5 min. Through HCl absorption experiments to investigate the thermal stabilization mechanism, the results showed that CaAl‐cinnamate‐LDHs can effectively absorb HCl released during PVC degradation. Highlights: By utilizing natural organic Cinnamic acid, Calcium nitrate, and Aluminum nitrate as raw materials, all from a wide range of sources, the reaction process eliminated the need for toxic solvents and a large number of chemicals.The preparation process of CaAl‐cinnamate‐LDHs was simple and the reaction time was short.Comprehensive tests showcased the exceptional long‐term thermal stability of the CaAl‐cinnamate‐LDHs/PVC sample.The addition of CaAl‐cinnamate‐LDHs can improve the plasticizing property of PVC.The mechanism of CaAl‐cinnamate‐LDHs was capable of absorbing HCl released during PVC degradation. [ABSTRACT FROM AUTHOR]

BACKGROUND: Melons (Cucumis melo L.) are among the most commonly consumed fruits but they are highly susceptible to mechanical damage and rot during storage and transportation. New processed products are needed to avoid postharvest fruit loss and to increase health benefits. Fermentation is an effective means of utilizing the nutrients and improving flavor. RESULTS: Fermented melon juice (MJ) was prepared using three potential probiotics Lactiplantibacillus plantarum CICC21824 (LP), Lactiplantibacillus plantarum GB3‐2 (LG), and Lactiplantibacillus pentosus XZ‐34 (LX). The nutrition, flavor characteristics, and digestive properties of different fermented MJs were compared. The results demonstrated that, in comparison with mono‐fermentation, mixed fermentation by LG and LX could increase the level of organic acids and phenolic acids. Correspondingly, antioxidant capacity was improved significantly and positively correlated with p‐coumaric acid and cinnamic acid content. The production of alcohols and acids was more strongly enhanced by mixed culture fermentation, whereas mono‐fermentation reduced the content of esters, especially ethyl acetate and isopropyl acetate. Aldehydes and ketones increased significantly in fermented MJ, and damascenone and heptanal could be the characteristic aroma compounds. CONCLUSION: Mixed fermented MJ provides more beneficial phytochemicals, better flavor, and stronger antioxidant properties than mono‐fermentation. © 2024 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

This study aimed to extract bioactive secondary metabolites, determine volatile organic compounds, and polyphenols using GC/MS and LC/MS, and assess their total phenolic content, antimicrobial, antioxidant, and cytotoxic properties. The chemical analysis of S. cerevisiae NRLL Y‐12633 ethyl acetate extract revealed eight volatile organic components, whereas the main component was phenyl ethyl alcohol (77.39 %). On the other hand, nineteen volatile organic compounds were identified in the ethyl acetate extract of S. cerevisiae NRRL Y‐1089, whereas the most critical component was 2, 3‐butanediol (60.74 %). The most abundant phenolic acids were syringic acid (25476.46 ng/mL), and cinnamic acid (5163.76 ng/mL) in the ethyl acetate extracts of S. cerevisiae NRLL Y‐12633 and S. cerevisiae NRRL Y‐1089 respectively. Flavonoid, naringenin, was also found in the ethyl acetate extract of S. cerevisiae NRLL Y‐12633, whereas daidzein and rutin were detected in the ethyl acetate extract of S. cerevisiae NRRL Y‐1089. The total phenolic content of S. cerevisiae NRRL Y‐12633 ethyl acetate extract was found to be greater than that of S. cerevisiae NRRL Y‐1089 ethyl acetate extract. Data revealed that S. cerevisiae ethyl acetate extracts displayed antioxidant and antimicrobial activity, whereas only the ethyl acetate extract of S. cerevisiae NRRL Y‐1089 showed anticancer activity. [ABSTRACT FROM AUTHOR]

In order to develop food or tobacco usable flavour precursors, compounds 2‐hydroxypropyl benzoate (3a), propane‐1,2‐diyl dibenzoate (4a), 2‐hydroxypropyl cinnamate (3b) and propane‐1,2‐diyl (2E,2′ E)‐bis(3‐hydroxypropyl cinnamate) (4b) were synthesized by transesterification propanediol with vinyl benzoate and vinyl cinnamate under the biological enzyme Novozym435. The structures of the propanediol esters were characterized using nuclear magnetic resonance (1H NMR, 13C NMR), infrared spectroscopy (IR) and high‐resolution mass spectrometry (HRMS). The hygroscopicity and moisture retention capacity of reconstituted tobacco shreds with the synthesized propanediol were explored by 100 h hygroscopic desorption assay, model validation and low‐field nuclear magnetic resonance imaging (LF‐NMR). The results showed that the bound water content of 3a and 3b was lower than that of propanediol and higher than that of the control under both low (RH = 32%) and high (RH = 84%) humidity conditions. In addition, pyrolysis‐gas chromatography/mass spectrometry (Py‐GC/MS) technique was applied to investigate the thermal behaviour of 3a and 3b. Four and five pyrolysis products were formed by pyrolysis of 3a and 3b, respectively. The main pyrolysis products benzoic acid and cinnamic acid could be used as flavouring agents in food and tobacco. 3a and 3b had good moisture and humidity retention effects as well as uniform and sustained flavour release. The results of the study not only effectively improve the water absorbency of reconstituted tobacco and enhance the flavour, which is suitable for the storage and smoking process, but also provide a reference for the further development of new flavour moisturizers in the tobacco industry. [ABSTRACT FROM AUTHOR]

Cinnamic acid and its derivatives represent attractive building blocks for the development of pharmacological tools. A series of piperoniloyl and cinnamoyl‐based amides (6‐9 a‐f) have been synthesized and assayed against a wide panel of colorectal cancer (CRC) cells, with the aim of finding promising anticancer agents. Among all twenty‐four synthesized molecules, 7a, 7e‐f, 9c, and 9f displayed the best antiproliferative activity. The induced G1 cell cycle arrest and the increase in apoptotic cell death was seen in FACS analysis and western Blotting in the colon tumor cell lines HCT116, SW480, LoVo, and HT29, but not in the nontumor cell line HCEC. In particular, 9f overcame the resistance of HT29 cells, which have a mutant p53 and BRAF. Furthermore, 9f, amide of piperonilic acid with the 3,4‐dichlorobenzyl substituent upregulated p21, which is involved in cell cycle arrest as well as in apoptosis induction. Cinnamic acid derivatives might be potential anticancer compounds, useful for the development of promising anti‐CRC agents. [ABSTRACT FROM AUTHOR]

In this study, a hydroxyl‐rich ferrofluid was prepared by dispersing silica‐coated magnetic nanoparticles into a methyltrioctylammonium chloride‐glycerol deep eutectic solvent and then employed in the preconcentration of trace‐level of cinnamic acid derivatives (caffeic acid, p‐hydroxycinnamic acid, ferulic acid, and cinnamic acid) in traditional Chinese medicine prior to high‐performance liquid chromatography analysis. The structures of the synthesized materials were characterized by X‐ray diffraction and infrared spectroscopy. The experimental parameters affecting the extraction performance, such as deep eutectic solvent composition, dosage of ferrofluid, pH of aqueous sample solution, salt concentration, extraction time, type, and volume of desorption solvent, were studied and optimized. Under the optimum conditions, the enrichment factors of four cinnamic acid derivatives were in the range of 107–114. Low detection limits (0.2–0.9 ng/mL), good precisions (relative standard deviations 1.2%–9.5%), and satisfactory recoveries (96.0%–104.7%) were achieved. Subsequently, the possible microextraction mechanism of the proposed method was explored and elucidated. It showed that the prepared ferrofluid is easily dispersed in the aqueous sample and achieved recovery after the extraction. The developed approach is a simple, convenient, and efficient method for preconcentration and determination of cinnamic acid derivatives in complex matrices. [ABSTRACT FROM AUTHOR]

The burgeoning cellulosic ethanol industry necessitates advancements in enzymatic saccharification, effective pretreatments for lignin removal, and the cultivation of crops more amenable to saccharification. Studies have demonstrated that natural inhibitors of lignin biosynthesis can enhance the saccharification of lignocellulose, even in tissues generated several months post‐treatment. In this study, we applied daidzin (a competitive inhibitor of coniferaldehyde dehydrogenase), piperonylic acid (a quasi‐irreversible inhibitor of cinnamate 4‐hydroxylase), and methylenedioxy cinnamic acid (a competitive inhibitor of 4‐coenzyme A ligase) to 60‐day‐old crops of two conventional Brazilian sugarcane cultivars and two energy cane clones, bred specifically for enhanced biomass production. The resultant biomasses were evaluated for lignin content and enzymatic saccharification efficiency without additional lignin‐removal pretreatments. The treatments amplified the production of fermentable sugars in both the sugarcane cultivars and energy cane clones. The most successful results softened the most recalcitrant lignocellulose to the level of the least recalcitrant of the biomasses tested. Interestingly, the softest material became even more susceptible to saccharification. [ABSTRACT FROM AUTHOR]

Continuous cropping severely affects faba bean growth, mainly due to pathogen and autotoxic substance accumulation. Here, we used faba bean monocropping (M) and intercropping with wheat (I), with stress treatments of Fusarium oxysporum f. sp. fabae (FOF) alone (F) and combined with cinnamic acid (F + C), to analyze seedling growth, defense‐related enzymes, levels of resistance‐associated substances, and protein expression profiles in roots. The results showed that intercropping mitigated the inhibitory effects of FOF and cinnamic acid. FOF resulted in increased activities of defense‐related enzymes as well as levels of resistance‐associated substances. Proteomic analysis showed that 22 proteins were upregulated following FOF inoculation (M + F), and 6 proteins were downregulated after the addition of cinnamic acid (M + F + C) in monocropping plants; these proteins were mainly involved in pathways associated with carbohydrate metabolism, energy, and the cytoplasm. Comparison of monocropping and intercropping indicated that the upregulated proteins were mostly associated with stress and defense, carbohydrate transport and metabolism, maintenance of cellular homeostasis, and protein synthesis. KEGG analysis revealed that intercropping increased enrichment in pathways associated with metabolism, ribosomes, biosynthesis of secondary metabolites, proteasomes, pyruvate metabolism, and pentose and glucuronate interconversions. The results indicated that intercropping mitigated growth inhibition by FOF and cinnamic acid by increasing energy production, maintaining normal cellular functions, and promoting the synthesis of defense‐associated secondary metabolites. These findings provide a basis for further investigation into the molecular mechanisms underlying the effects of intercropping in controlling resistance to Fusarium wilt in the faba bean. [ABSTRACT FROM AUTHOR]

A reliable and efficient in vitro model is needed to screen drugs for Alzheimer's disease (AD), as many drugs are currently in the developmental stage. To address this, we developed an in vitro model using amniotic membrane‐derived mesenchymal stem cells (AM‐MSCs) to screen novel drugs for AD. We differentiated AM‐MSCs into neurons and degenerated them using beta amyloid1‐42 (Aß). We then tested AD drugs, which are commercially available such as donepezil, rivastigmine, memantine, citicoline, and two novel drugs, that is, probucol, an anti‐hyperlipidaemic drug, and NMJ‐2, a cinnamic acid analogue for their potential to protect the cells against neurodegeneration. We used gene expression and immunofluorescence staining to assess the neuroprotective ability of these drugs. We also measured the ability of these drugs to reduce lactate dehydrogenase, reactive oxygen species, and nitric oxide levels, as well as their ability to stabilize the mitochondrial membrane potential and increase acetylcholine (ACh) levels. The AD drugs and novel drugs reduced cytotoxicity and oxidative stress, stabilized mitochondrial membrane potential, and restored ACh levels. Furthermore, they reduced BACE1 expression, with a concomitant increase in the expression of cholinergic markers. This AM‐MSCs‐based AD‐like model has immense potential to be an accurate human model and an alternative to animal models for testing a large number of lead compounds in a short time. Our results also suggest that the novel drugs probucol and NMJ‐2 may protect against Aß‐induced neurodegeneration. [ABSTRACT FROM AUTHOR]

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In this paper, two types of photo/thermal dual and programmable staged responsive shape memory PAEK are fabricated. On one side, photosensitive cinnamic acid (CA) is grafted onto shape memory poly(aryl ether ketone) (PAEK) chains to obtain PEAK‐CA with photo/thermal response. On the other hand, PAEK/CA composites are prepared via a facile physical blending as comparison. Both PAEK‐CA and PAEK/CA materials exhibit the excellent heat‐triggered (recovery ratio over 91.8%) and photo‐responsive shape memory effect (recovery ratio over 76.5%). More interestingly, the staged shape fixity and shape recovery behaviors can be realized by combining independent photo/heat responsive shape memory behaviors. Take the PAEK/CA for example, the irradiation with λ of 365 nm can be used for shape fixity, and shape recovery can be triggered by heating. Meanwhile, the fixation of the temporary shape of the sample can also be realized by heating–cooling process, and then the irradiation with λ of 365 nm is used for shape recovery. These photo/thermal dual and staged responsive shape memory PAEK materials could be widely utilized in fields of soft robots, smart actuators, and deformable devices. [ABSTRACT FROM AUTHOR]

Development of tough, reusable adhesives is important, but remains a major challenge, especially in water. A tough reusable adhesive that resets entirely to its virgin condition when needed is reported using caffeic acid. Here, caffeic acid is employed as adhesive moiety to achieve such the functions due to its dual characteristics: an adhesive moiety from mussel‐inspired catechol and a photo‐reversible crosslink from cinnamic acid. Adhesion involves a two‐step process. First, the caffeic acid‐functionalized polymer is applied to the adherend, followed by UV irradiation (peak wavelength of light‐emitting diode, λP: 365 nm) to form a durable pre‐applied adhesive (PAA) layer through crosslinking among the caffeic acid moieties. Second, thermal activation of the PAA layer ensures repeated adhesion to a variety of adherends (Reuse‐Many mode). The cyclic dimer of the caffeic acid moiety is de‐crosslinked by UV irradiation at λP: 254 nm. This allows the complete removal of the adhesive residues from the adherends when the adhesive is no longer needed (Reset‐On demand mode). Furthermore, using magnetic nanoparticles, the caffeic acid‐functionalized polymer can be activated remotely under water by magnetic induction heating. This study paves the way for the rational design of bio‐inspired adhesives that outperform nature using plant‐derived raw materials. [ABSTRACT FROM AUTHOR]

Elevated CO2 (eCO2) is one of the climate changes that may benefit plant growth under emerging soil contaminants such as heavy metals. In this regard, the morpho‐physiological mechanisms underlying the mitigating impact of eCO2 on beryllium (Be) phytotoxicity are poorly known. Hence, we investigated eCO2 and Be interactive effects on the growth and metabolism of two species from different groups: cereal (oat) and legume (alfalfa). Be stress significantly reduced the growth and photosynthetic attributes in both species, but alfalfa was more susceptible to Be toxicity. Be stress induced reactive oxygen species (ROS) accumulation by increasing photorespiration, subsequently resulting in increased lipid and protein oxidation. However, the growth inhibition and oxidative stress induced by Be stress were mitigated by eCO2. This could be explained, at least partially, by the increase in organic acids (e.g., citric acid) released into the soil, which subsequently reduced Be uptake. Additionally, eCO2 reduced cellular oxidative damage by reducing photorespiration, which was more significant in alfalfa plants. Furthermore, eCO2 improved the redox status and detoxification processes, including phytochelatins, total glutathione and metallothioneins levels, and glutathione‐S‐transferase activity in both species, but to a greater extend in alfalfa. In this context, eCO2 also stimulated anthocyanin biosynthesis by accumulating its precursors (phenylalanine, coumaric acid, cinnamic acid, and naringenin) and key biosynthetic enzymes (phenylalanine ammonia‐lyase, cinnamate hydroxylase, and coumarate:CoA ligase) mainly in alfalfa plants. Overall, this study explored the mechanistic approach by which eCO2 alleviates the harmful effects of Be. Alfalfa was more sensitive to Be stress than oats; however, the alleviating impact of eCO2 on Be stress was more pronounced in alfalfa. [ABSTRACT FROM AUTHOR]

Ephedra herba is a conventional Chinese medicine to treat cold, fever, asthma, edema, and lung diseases in the clinic. At present, most pharmacokinetic studies focus on the pharmacokinetic process of alkaloids in normal animals. However, the non‐alkaloid components are also active. In addition, the pharmacokinetic studies under pathological state make more sense for clarifying the material basis of efficacy. In this study, a sensitive and rapid ultra‐high‐performance–tandem mass spectrometry method was developed and applied to determine nine bioactive components (ephedrine, pseudoephedrine, methylephedrine, (+)‐catechin, epicatechin, vitexin, vicenin‐2, cinnamic acid, and ferulic acid) in normal, common cold and nephrotic syndrome rats after the oral administration of Ephedra herba. Compared to the normal group, except for ferulic acid, the exposure levels of the other eight components were significantly increased and the plasma clearance clearly declined in common cold rats. Similarly, the exposure levels of seven components other than cinnamic acid and ferulic acid were also significantly augmented and the plasma clearance decreased significantly in nephrotic syndrome rats. In brief, the pathological conditions of the common cold and nephrotic syndrome could lead to alterations in the pharmacokinetics profiles of the nine components, which provide a reference for further exploration of the pharmacodynamics basis of Ephedra herba. [ABSTRACT FROM AUTHOR]

Ethyl acetate fraction column chromatographic analysis was used to isolate eleven compounds (numerically tagged 1–10) from Cassia occidentalis L. in this study. Two unique metabolites, including a neolignan compound designated as occidentalignan I (9) and a flavonoidal glycoside, chrysin-7-O-α-L-rhamnopyranosyl (10), were identified, while silybin A (8) was the first flavonolignan to be isolated from the Fabaceae family. Four compounds, including β-sitosterol-3-O-β-D-glucopyranoside (1), stigmasterol-3-O-β-D-glucopyranoside (2), betulinic acid (3), and vanillic acid (4) were isolated from C. occidentalis for the first time. In addition, four known compounds, cinnamic acid (5), p-hydroxybenzoic acid (6), β- resorcylic acid (7), and citric acid (11), were also detected. The in-vitro cytotoxicity assessment of the methanolic extract of C. occidentalis on seven cancer cell lines, including A-549, Colo-205, Huh-7, HCT-116, PANC-1, SKOV-3, and BNL, demonstrated its selective potent cytotoxicity on lung cancer cells without affecting normal BNL cells. In contrast, the methanolic extract showed moderate activity on Colo-205 and Huh-7 and nearly no activity on HCT-116, PANC-1, and SKOV-3 cell lines. These results suggest that the methanolic extract of C. occidentalis is an excellent candidate with potential antiproliferative activity against lung cancer; however, further studies are necessary to clarify its mechanism of action. [ABSTRACT FROM AUTHOR]

BACKGROUND: The chemical composition, phenylalanine ammonia‐lyase (PAL), polyphenol oxidase (PPO) and peroxidase (POD) activity of the three main Portuguese elderberry cultivars were determined for the first time through five stages of maturation, in different harvesting years, to gain a deeper understanding of the effect of climatic conditions and enzymatic activity involved in the synthesis and degradation of phenolic compounds on the final quality of elderberries. RESULTS: Simple sugar and anthocyanin content increased with maturation but total acidity and flavonoids content decreased, and cinnamic acids did not show a clear trend. Climatic conditions seem to have a decisive influence on the elderberry maturation, namely the total number of hot (>30 °C) days. The PAL, PPO, and POD activity can explain the differences observed in elderberry phenolic content. CONCLUSION: These results highlighted the influence of climatic conditions in each harvesting season on elderberry development and quality. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

High melting point and hydrophilicity of phenolic acids limit their application in lipophilic environments such as fat‐containing cosmetics and foods. The esterification of the carboxyl group with fatty and aromatic alcohols has been considered as an effective way to enhance the lipophilicity of phenolic acids and thus enable better location of the antioxidant moiety into membranes and interface of emulsion systems where oxidation is expected to occur. Therefore, this study aims to evaluate the catalytic properties of six solid acids (HND‐34, HND‐6, HND‐580, HND‐2, HND‐8 and HND‐26) for the synthesis of benzyl cinnamate. Results show that HND‐26 was the most effective solid acid to catalyse the esterification reaction of cinnamic acid with benzyl alcohol. By using response surface methodology, the influence of key experimental factors on the yield of benzyl cinnamate was investigated and the maximum yield (95.1%) was obtained under the optimized conditions (58°C, cinnamic acid/benzyl alcohol 1:20 (mol/mol), HND‐26 loading 13.8% and 25 hours). The activation energy of cinnamic acid conversion with benzyl alcohol was 30.3 kJ/mol. Obtained results provide a cost‐effective way of green synthesis of benzyl cinnamate and highlights the potential applications of HND‐26 as an efficient catalyst for the production of phenolic acid esters with broad usage in cosmetic industry. [ABSTRACT FROM AUTHOR]

Background and Aims: Liver fibrosis is an excessive wound‐healing response governed by activated hepatic stellate cells (HSCs). To date, there is no drug available for liver fibrosis. Although ferulic acid (FA) has multiple pharmacological functions, its anti‐hepatic fibrosis activity is weak. Based on the activity modification of the FA structure, we synthesized a series of phenylacrylic derivatives and found a superior compound, FA11. In this study, we investigated its antifibrotic effect and mechanism. Methods: Activated HSC and CCl4‐induced mouse liver fibrosis were established and followed by FA11 treatment. Cell viability was measured by CCK‐8 assay. Apoptosis and cell cycle analysis were conducted by flow cytometry. Western blot and Real‐time qPCR were used to examine the expression of fibrotic and M1/M2‐type macrophages markers. Degree of liver fibrosis was shown by histological staining. Results: In vitro, FA11 inhibited TGF‐β1‐induced LX‐2 proliferation and led to apoptosis and cycle arrest. Furthermore, elevation of fibrotic markers in TGF‐β1‐induced LX‐2 and primary activated HSC was reversed by FA11. In vivo, FA11 administration alleviated collagen deposition and blocked HSC activation and epithelial‐mesenchymal transition (EMT). Additionally, FA11 reduced macrophage infiltration in fibrotic liver and prevented macrophage polarization to a profibrotic phenotype. Meanwhile, the systemic toxicity of CCl4 was also ameliorated by FA11. Mechanistically, FA11 reversed the phosphorylation of canonical and noncanonical TGF‐β1 signalling, as well as FGFR1 signalling. Conclusions: We reported an oral phenylacrylic acid derivative, FA11, which showed excellent antifibrotic activity and was expected to be an anti‐hepatic fibrosis candidate. [ABSTRACT FROM AUTHOR]

Herein, the successful development of a metal‐free, solution [2 + 2] photopolymerization of natural cinnamic acid‐derived bisolefinic monomers is reported, which is enabled by a strategy based on direct triplet state access via energy transfer catalysis. 2,2'‐Methoxythioxanthone has been identified as an effective organic photocatalyst for the [2 + 2] photopolymerization in solution, which can be excited by visible light and activate the biscinnamate monomers via triplet energy transfer. This method features its metal‐free conditions, visible light utilization, solution polymerization, and abundant biomass‐based feedstock, as well as processable polymer products, which is different from the rigid, insoluble products obtained from solid‐state photopolymerization. This solution polymerization method also shows a good compatibility to monomer structures; cinnamic acid‐derived bisolefinic monomers with different linkers, including diamine, natural diol, and bisphenol, can all readily undergo [2 + 2] photopolymerization, and be transformed into colorless, sustainable polymers. [ABSTRACT FROM AUTHOR]

In this study, ultrasound-assisted extraction (UAE) was used for the extraction of bioactive compounds from eggplant peels (EPP) and conditions were optimized by using response surface methodology (RSM). Methanol concentrations (60%, 70%, and 80%), time (30 min, 45 min, and 60 min), and temperature (30°C, 45°C, and 60°C) were selected as independent extraction parameters, whereas total anthocyanin content (TAC), DPPH inhibition, and total phenolic content (TPC) were response variables. The optimal extraction was at 45°C for 45 min of extraction time with 70% solvent which corresponded to TAC, TPC, and DPPH inhibition values of 7.94 mg/g, 7.03 mg GAE/g, and 94.8%, respectively. The optimized EPP extract was chemically characterized by a Fourier-transform infrared spectrometer (FTIR), high-performance liquid chromatography (HPLC), and a gas chromatography mass spectrometer (GCMS). The optimized extract was further evaluated for antioxidant and anticancer potential. For antioxidant and anticancer potential, the corresponding IC50 values of the EPP extract were 243.2 μg/ml and 1.52–1.99 mg/ml, respectively. Furthermore, the EPP extract significantly inhibited the migratory ability of cancer cells in a dose-dependent manner. Major components identified in the EPP extract were chlorogenic acid (261.76 mg/kg), benzoic acid (184.41 mg/kg), syringic acid (78.48 mg/kg), p-coumaric acid (49.59 mg/kg), cinnamic acid (32.17 mg/kg), quercetin (5.24 mg/kg), sinapic acid (5.14 mg/kg), and gallic acid (4.34 mg/kg). The EPP extract-enriched ice-cream showed high antioxidant potential and consumer acceptability than the blank ice-cream formulation. The EPP extract, due to its antioxidant and anticancer potential, can be used in the formulation of functional food products. [ABSTRACT FROM AUTHOR]

Comprehensive Summary: The chemistry of alkoxy radicals was extensively explored during the period of 1960s to 1990s, but it has remained dormant for the past few decades. Recently, alkoxy radicals attract the attentions again, because new methods for generating alkoxy radical species have emerged. These newly developed methods are mainly based on the photolysis by visible light under mild conditions, thus allowing for new transformations of the carbon‐centered radical species that are generated from the β‐scission or hydrogen abstraction of the alkoxy radicals. Herein, we demonstrate that the alkoxy radicals derived from cyclic hemiacetals can be generated through visible‐light‐induced electron transfer with sodium iodide and triphenylphosphine as the catalyst. The alkoxy radicals subsequently undergo β‐scission to generate carbon‐centered radicals, which are trapped by cinnamic acids, aryl alkenes, vinylboronic acid and silyl enol ether to deliver the corresponding C—C bond forming products. This catalytic method for ring‐opening alkenylation reaction of cyclic hemiacetal derivatives under visible‐light irradiation conditions demonstrates the compatibility of the visible light‐promoted alkoxy radical generation method with various carbon radical trapping processes. This work opens up new possibilities for the application of alkoxy radicals in organic synthesis. [ABSTRACT FROM AUTHOR]

A series of novel piperazine based cinnamic acid bearing coumarin derivatives were designed and synthesized by piperazine based cinnamic acids esterification with 4‐hydroxycoumarin and characterized by various spectral techniques like infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass. The novel bioactive compounds (7a‐7m) screen their potential against different bacterial and fungal strains. Compound 7g (minimum inhibitory concentration [MIC] = 12.5 µg/ml) exhibited potent antibacterial activity against Escherichia coli strain. Compounds 7d, 7f, 7g, 7k, 7l, and 7m showed potent antibacterial activity against all bacterial strains. Compounds 7a, 7g, 7h, 7k, 7l, and 7m exhibited potent antifungal activity against all fungal strains. Furthermore, a molecular docking study revealed that compounds 7d, 7f, 7g, and 7k could bind to the active site of E. coli DNA gyrase subunit B protein and form hydrogen bonding with crucial amino acid residues Arg136 in the active sites. Comprehensively, our study recommends that 7d, 7f, 7g, and 7k could be a promising lead for developing more efficient antimicrobial drug candidates and DNA gyrase inhibitors. [ABSTRACT FROM AUTHOR]

Cervical cancer is one of the most aggressive and important cancer types in the female population, due to its low survival rate. Actually, the search for new bioactive compounds, like gallic and cinnamic acid, is one of the most employed options to finding a treatment. In the present study, 134 phenolic compounds with cytotoxic activity over HeLa cell line were used to generate a descriptive (R2 ${{R}^{2}}$ =0.76) and predictive (Q2 ${{Q}^{2}}$ =0.69 and Qext2 ${{Q}_{{\rm e}{\rm x}{\rm t}}^{2}}$ =0.62) QSAR model. Structural, electronic, steric, and hydrophobic features are represented as different molecular descriptors in our QSAR model. From this model, nine gallate‐cinnamate ester derivatives (N1–N9) were designed and synthesized. Furthermore, in vitro cytotoxic activity was evaluated against HeLa and non‐tumorigenic cells. Derivatives N6, N5, N1, and N9 were the most active molecules with IC50ExpHeLa values from 7.26 to 11.95 μM. Finally, the binding of the synthesized compounds to the colchicine binding site on tubulin was evaluated by molecular docking as a possible action mechanism. N1, N5 and N6 can be considered as templates for the design of new cervical anticancer compounds. [ABSTRACT FROM AUTHOR]

The current study was designed to evaluate the biological potential of bioactive compounds in the selected fractions of Trichodesma indicum. The results showed that the chloroform and ethyl acetate fractions of ethanolic extract of the whole plant T. indicum were rich in TPCs (total phenolic content) i.e 499.80 and 744.65 mg of gallic acid equivalents per g, respectively, while TFCs (total flavonoid content) were 42.48, and 55.02 mg of catechin equivalents per g, respectively. HPLC analysis confirmed the presence of phenolics i. e., chlorogenic acid (252.35 ppm), ferulic acid (92.56 ppm), caffeic acid (28.72 ppm), cinnamic acid (28.97 ppm), syringic acid (23.75 ppm), gallic acid (7.28 ppm) and flavonoids i. e. myricetin (72.1 ppm), Quercetin (57.3 ppm) in a selected fraction of T. indicum ethanolic extract. The significant potential of antioxidants was observed through ABTS, DPPH, and H2O2 methods. The highest % inhibition of inflammation was observed in ethyl acetate fraction by performing in‐vitro and in‐vivo assays, 87.57 % and 79.18 % (P<0.05) respectively. The thrombolytic activity of the T. indicum fractions was observed in the range from 9.85 % to 27.26. GC‐MS coupled with molecular docking depicted the inhibition of COX‐1 and COX‐2 by the GC‐MS‐identified compound 9,19‐Cyclolanost‐24‐en‐3‐ol, (3. Beta.)‐ (−9.6 kJ/mol). The in‐silico anti‐proliferative analysis was conducted by using BRCA1 and BRCA2 cancerous protein against GC‐MS identified compounds among which stigmasterol (−8.0 kJ/mol) was observed for high binding affinity. [ABSTRACT FROM AUTHOR]

This study was performed to compare the noncapsulated with nanoliposome‐encapsulated phenolic‐rich fraction (PRF) obtained from Rheum ribes as a dietary additive and to assess their health‐promoting potentials in the mice infected by enteropathogenic Escherichia coli (O157:H7). Upon fractionation, the ethyl acetate fraction with 46.9 ± 2.17 mg GAE/g DW was found as a highest phenolic content. The PRF successfully loaded into nanoliposome structure with a nanometer in size (193.2 nm) and spherical shape and homogeneous dispersion. The gallic acid, salicylic acid, caffeic acid, cinnamic acid, catechin, ellagic acid, and ferulic acid are bioactive phenolics present in the nanoliposome‐loaded PRF; however, the main bioactive compounds are cinnamic acid (911 μg/g DW) and ellagic acid (826 μg/g DW). The infection caused by E. coil impaired the weight gain and food intake, liver function, morpho structural characteristics of jejunum, upregulated the expression of inflammatory genes (Cox2, iNOS), downregulation of antioxidant‐related genes (SOD, GPX), and increased the ileal population of E. coil. The addition of nonencapsulated PRF and nanoliposome‐encapsulated PRF at the concentration of 10 mg TPC/kg BW/day improved these parameters although the nanoliposome‐encapsulated PRF revealed more potential as compared with the nonencapsulated PRF in improving the health parameters in mice. The higher health‐promoting activity of nanoliposome‐encapsulated PRF could be associated with its enhanced intestinal absorption, bioavailability, bioaccessibility, and bioactivity. Consequently, the nanoliposome‐encapsulated PRF could be considered as a promising phytobiotic against E. coil infection in mice. [ABSTRACT FROM AUTHOR]

The phenylpropanoid cinnamic acid (CA) is a plant metabolite that can occur under a trans‐ or cis‐form. In contrast to the proven bioactivity of the cis‐form (c‐CA), the activity of trans‐CA (t‐CA) is still a matter of debate. We tested both compounds using a submerged rice coleoptile assay and demonstrated that they have opposite effects on cell elongation. Notably, in the tip of rice coleoptile t‐CA showed an inhibiting and c‐CA a stimulating activity. By combining transcriptomics and (untargeted) metabolomics with activity assays and genetic and pharmacological experiments, we aimed to explain the underlying mechanistic processes. We propose a model in which c‐CA treatment activates proton pumps and stimulates acidification of the apoplast, which in turn leads to the loosening of the cell wall, necessary for elongation. We hypothesize that c‐CA also inactivates auxin efflux transporters, which might cause a local auxin accumulation in the tip of the coleoptile. For t‐CA, the phenotype can partially be explained by a stimulation of cell wall polysaccharide feruloylation, leading to a more rigid cell wall. Metabolite profiling also demonstrated that salicylic acid (SA) derivatives are increased upon t‐CA treatment. As SA is a known antagonist of auxin, the shift in SA homeostasis provides an additional explanation of the observed t‐CA‐mediated restriction on cell growth. [ABSTRACT FROM AUTHOR]

Diabetes‐related health issues are increasing day by day in public, and diabetic cardiomyopathy (DCM) is one serious issue among them. There is a lack of proper strategy to control and manage DCM. Here we are attempting a nutraceutical‐based approach to protect the heart from DCM. The beneficial effect of cinnamic acid (CiA), was evaluated in an experimental model of diabetes. For this, diabetic model was created by feeding male Wistar rats with a high fat, high fructose diet for 6 months and a single dose of streptozotocin (25 mg/kg bwt). Metformin was used as the positive control. The diabetic rats showed insulin resistance, myocardial injury, and a significant increase of total cholesterol, triglycerides, and LDL. Development of DCM was evident from the increased cardiac mass index, LDH, CKMB, ANP, and CRP levels in the diabetic group. There was a significant increase in the levels of cardiac hypertrophy markers like TGF‐β and β‐MHC in the hearts of diabetic rats revealing DCM. Pro‐inflammatory cytokines (TNF‐α, IL‐6) and lipid peroxides were significantly elevated in the serum of diabetic rats. Histopathology revealed inflammation and necrosis in the heart of diabetic rats confirming DCM. Oral administration of CiA (5 and 10 mg/kg bwt) prevented the development of DCM via its cardioprotective, anti‐inflammatory, anti‐dyslipidemia potential, and antidiabetic properties. Similarly, metformin (50 mg/kg bwt) has also shown protection against DCM. We conclude from this study that CiA is found to be beneficial against DCM and recommend more detailed preclinical and clinical studies to develop CiA‐based nutraceutical against DCM. [ABSTRACT FROM AUTHOR]

A series of seventeen cinnamic acid hybrids (4ai–ci) were obtained through an amidation of aminoadamantanes (amantadine, rimantadine, and memantine) with mixed anhydride generated from different substituted cinnamic acid and ethyl chloroformate. 1H NMR, 13C NMR, IR, and HRMS were used for the confirmation of the structures of the synthesized hybrids. Moreover, the antioxidant profiles of amides were estimated as per five different in vitro methods: 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid cation radical (ABTS⁺), ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC) assay, and inhibition of Fe(III)/asc induced lipid peroxidation (LP) in brain homogenate. For comparison, caffeic acid (CaffA), known as a potent naturally occurring antioxidant, was used as a reference compound in our study. The results revealed that the most prominent antioxidant activity was demonstrated by compound 4b2, with excellent CUPRAC, FRAP, scavenging ABTS+˙ potential, and inhibition of Fe/asc–induced LP, followed by 4c6 > 4a6 > CaffA > 4c5 and 4a5 > 4a7. Overall, the results suggest that the hybrids (4b2, 4c6, and 4a6) consisting of a caffeoyl moiety and lipophilic adamantane core endow the molecules with the higher antioxidant activity than their parent compound (caffeic acid), especially against LP. Thus, these promising antioxidants could have beneficial effects in various pathological conditions, where oxidative stress is implicated. [ABSTRACT FROM AUTHOR]

Soilborne Fusarium wilt is a key factor restricting the cultivation of faba bean. Intercropping faba bean and wheat effectively alleviate faba bean Fusarium wilt. This study analyzed the mechanism by which cinnamic acid promotes Fusarium wilt and the mechanism that enables intercropping alleviated Fusarium wilt. Faba beans were inoculated with Fusarium oxysporum f. sp. fabae (FOF), while the controls were not inoculated. Different concentrations of cinnamic acid were added to the inoculated plants to study the occurrence of Fusarium wilt, seedling growth, the activities of cell wall degradation enzyme (CWDESs) produced by FOF in the root, defense enzymes, total phenolics and lignin, levels of expression of the pathogenesis‐related genes (PRs) PR1, PR2, and PR10, and changes in the submicroscopic cell wall structure of the roots under monocropping and intercropping systems. Cinnamic acid increased the activities of CWDEs produced by FOF in the roots, increased the activities of phenylalanine ammonia lyase and polyphenol oxidase and the contents of total phenolics and lignin, and upregulated the levels of expression of PRs in the root, but it decreased the activity of peroxidase. Transmission electron microscopy (TEM) observations identified severe damage and disruption of the root cell walls, and numerous FOF mycelia entered the cytoplasm from the cell wall. The combination of these factors increased the occurrence of Fusarium wilt. The activities of CWDEs produced by FOF in the roots decreased by intercropping wheat with faba bean, which increased the resistance of the root cell walls to infection and decreased the Fusarium wilt. [ABSTRACT FROM AUTHOR]

The current work investigated the phytochemical profile of ultrasound‐assisted ethanolic extract of Morus nigra (M. nigra) fruit. FTIR analysis of M. nigra fruit extract revealed the presence of alcohols (O‐H), alkanes (C‐H stretch), alkenes (C=C), and alkynes (C≡C). The HPLC analysis quantified the quercetin, gallic acid, vanillic acid, chlorogenic acid, syringic acid, cinnamic acid, sinapic acid, and kaempferol. Furthermore, the cardioprotective activity of ethanolic extract of M. nigra fruit was investigated. Cholesterol supplementation (2%) in the daily diet and exposure to cigarette smoke (2 cigarettes twice a day) were to induce hypertension in rats. The experimental animals were categorized into four groups: G0 (negative control), G1 (positive control), G2 (standard drug), and G3 (M. nigra fruit). The fruit extract administration at 300 mg/kg BW/day orally for 2 months significantly (p <.001) enhanced the activities of serum and cardiac tissue antioxidants in hypertensive rats. Meanwhile, the fruit extract reduced the elevated serum lipid profile while significantly increasing the high‐density lipoproteins in G3 than G1 and G2. The increase in blood pressure, liver transaminases, and serum lactate dehydrogenase also reduced significantly in M. nigra fruit extract‐treated rats. Histopathological findings revealed mild normalization of cardiac myocytes with central nuclei, branching, and cross‐striations. Consequently, the M. nigra fruit extract exerted the cardioprotective potential via increasing the antioxidant enzymes and reducing the lipids, lactate dehydrogenase, liver transaminases, and blood pressure. The therapeutic potential of M. nigra fruit can be due to flavonols and phenolic acids. Practical applications: The present work quantified the Morus nigra fruit phytochemicals and its significant role in reducing lipid markers and blood pressure and improving antioxidant status in rats fed a hypercholesterolemic diet and exposed to cigarette smoke. Conclusively, the inclusion of M. nigra fruit in daily diet could improve the cardiac health of the individuals. Furthermore, the therapeutic potential of M. nigra fruit and its isolated constituents in modulating the gene expression against cardiac problems can explore after clinical trials and standardization in higher animals. [ABSTRACT FROM AUTHOR]

Summary: Shiitake mushrooms contain free phenolics (FPs) and bound phenolics (BPs). BPs embedded in mushrooms are generally neglected and underestimated. Methods of hydrolysis with acid, base and their combination in different sequences were developed to release BPs. The contents, compositions and antioxidant capacities of FPs and BPs were investigated. Results found that BPs yielded with combining base and acid hydrolysis received the highest value (25.67 mg gallic acid equivalents (GAE)/100 g dry weight (DW)), which was higher than FPs (20.62 mg GAE/100 g DW). LC‐ESI‐QqQ‐MS/MS analysis demonstrated that gallic acid, protocatechuic acid, caffeic acid, and ferulic acid presented in all BPs fractions, whereas hesperidin, luteolin, quercetin, and cinnamic acid were affected by hydrolysis methods and procedures. BPs fractions with higher phenolic content showed strong antioxidant capacities. These results demonstrate the importance of BPs and can be applied to enhance the amount and bioavailability of BPs from shiitake mushrooms and other foods. [ABSTRACT FROM AUTHOR]

SARS‐CoV‐2 has been responsible for causing 6,218,308 deaths globally till date and has garnered worldwide attention. The lack of effective preventive and therapeutic drugs against SARS‐CoV‐2 has further worsened the scenario and has bolstered research in the area. The N‐terminal and C‐terminal RNA binding domains (NTD and CTD) of SARS‐CoV‐2 nucleocapsid protein represent attractive therapeutic drug targets. Naturally occurring compounds are an excellent source of novel drug candidates due to their structural diversity and safety. Ten major bioactive compounds were identified in ethanolic extract (s) of Cinnamomum zeylanicum, Cinnamomum tamala, Origanum vulgare, and Petroselinum crispum using HPLC and their cytotoxic potential was determined against cancer and normal cell lines by MTT assay to ascertain their biological activity in vitro. To evaluate their antiviral potential, the binding efficacy to NTD and CTD of SARS‐CoV‐2 nucleocapsid protein was determined using in silico biology tools. In silico assessment of the phytocomponents revealed that most of the phytoconstituents displayed a druglike character with no predicted toxicity. Binding affinities were in the order apigenin > catechin > apiin toward SARS‐CoV‐2 nucleocapsid NTD. Toward nucleocapsid CTD, the affinity decreased as apigenin > cinnamic acid > catechin. Remdesivir displayed lesser affinity with NTD and CTD of SARS‐CoV‐2 nucleocapsid proteins than any of the studied phytoconstituents. Molecular dynamics (MD) simulation results revealed that throughout the 100 ns simulation, SARS‐CoV‐2 nucleocapsid protein NTD‐apigenin complex displayed greater stability than SARS‐CoV‐2 nucleocapsid protein NTD‐cinnamic acid complex. Hence, apigenin, catechin, apiin and cinnamic acid might prove as effective prophylactic and therapeutic candidates against SARS‐CoV‐2, if examined further in vitro and in vivo. Practical applications: Ten major bioactive compounds were identified in the extract(s) of four medicinally important plants viz. Cinnamomum zeylanicum, Cinnamomum tamala, Origanum vulgare and Petroselinum crispum using HPLC and their biological activity was also evaluated against cancer and normal cell lines. Interestingly, while all extract(s) wielded significant cytotoxicity against cancer cells, no significant toxicity was found against normal cells. The outcome of the results prompted evaluation of the antiviral potential of the ten bioactive compounds using in silico biology tools. The present study emphasizes on the application of computational approaches to understand the binding interaction and efficacy of the ten bioactive compounds from the above plants with SARS‐CoV‐2 nucleocapsid protein N‐terminal and C‐terminal RNA binding domains in preventing and/or treating COVID‐19 using in silico tools. Druglikeness and toxicity profiles of the compounds were carried out to check the therapeutic application of the components. Additionally, molecular dynamics (MD) simulation was performed to check the stability of ligand‐protein complexes. The results provided useful insights into the structural binding interaction(s) that can be exploited for the further development of potential antiviral agents targeting SARS‐CoV‐2 especially since no specific therapy is still available to combat the rapidly evolving virus and the existing treatment is more or less symptomatic which makes search for novel antiviral agents all the more necessary and crucial. [ABSTRACT FROM AUTHOR]

Summary: Chitosan (CS) derivatives, chemically modified appropriately, can be used to produce nanoparticles with good properties. In this work, using CS, hydroxypropyl CS (HPCS) and HPCS modified by cinnamic acid (HPCS‐CA) derivative as raw materials, the nanoparticles were synthesised by ion crosslinking method with tripolyphosphate. FT‐IR spectra indicated that CS and its derivatives successfully cross‐linked with TPP at the molecular level. XRD and TG results exhibited changes in crystallinity and thermal stability. The nanoparticles had narrow size distribution and were nearly spherical. The surfaces of the nanoparticles were all positively charged. The nanoparticles‐stabilised oil‐in‐water Pickering emulsions were obtained by high‐speed homogenisation. The emulsions' morphology was reported by confocal laser scanning microscopy, indicating that the Pickering emulsions were synthesised successfully. The stability of the emulsion stabilised by HPCS‐CA nanoparticles was better than that of CS and HPCS nanoparticles. Taking curcumin as the target component, its stability in Pickering emulsions was good. The Pickering emulsion stabilised by HPCS‐CA nanoparticles may be a novel bioactive compound delivery system. [ABSTRACT FROM AUTHOR]

Here we report the design, synthesis and evaluation of dihydropyrimidinones (DHPMs)‐cinnamic acids hybrids as potential anti‐cancer compounds. The synthetic route was successfully performed and the products obtained in good to excellent yields. These compounds were tested against LNCaP and PC‐3 metastatic prostate cancer cells and RWPE‐1 prostate cells. The results indicate that hybridization was effective, since the hybrids were much more cytotoxic than DHPMs and cinnamic acids evaluated separately. Compound 3 a was the most potent hybrid against PC‐3 cells (IC50 of 15.7 μM) and LNCaP cells (IC50 of 11.5 μM) and was further optimized by bioisosterism and molecular simplification strategies leading to three new analogues (5, 7 and 8). Compounds 3 a, 7 and 8 showed an antiproliferative effect against PC‐3 cells without inducing cell death nor cell cycle arrest. The mechanism of action of compound 8 was further investigated. The results indicated that compound 8 inhibits autophagic flux, and this effect could be linked to the antiproliferative activity. Moreover, in silico prediction of some molecular properties related to pharmacokinetics showed that all the hybrids meet the criteria for a drug prototype to have a good absorption and permeation for oral administration. These results highlight the potential use of DHPMs‐cinnamic acids hybrids as antiproliferative agents for further evaluation of the antitumor activity in vivo. [ABSTRACT FROM AUTHOR]