Search Results (58)

The tolerance of the fall armyworm (Spodoptera frugiperda) to plant-derived secondary compounds gradually increases with instars. Therefore, even if plant-based additives are applied at early stages, such as the second or third instar, they may have a differential impact on the ecofriendly control of S. frugiperda. In this study, S. frugiperda larvae were exposed to vanillic acid or sinapic acid at the second and third instar, and physiological and growth parameters were measured. The results showed that the effects of vanillic acid treatment on S. frugiperda were similar at the different instars. They can significantly affect the larval carboxylesterase, glutathione S-transferase, and mixed-function oxidase activities. By reducing larval food intake, food conversion, and utilization efficiency while increasing the food consumption rate, it inhibits weight accumulation. This leads to a significant extension of the development of both the larval and pupal stages, and the adult longevity was reduced. Treatment with sinapic acid at the second instar extended the negative effects on the pupal duration of S. frugiperda when compared to treatment at the third instar, but did not affect adult longevity. Therefore, vanillic acid treatment at the second or third instar stage, can play an important role in the ecofriendly control process of S. frugiperda. The results of this study are of great significance for integrated pest management. Full article

The Moroccan coastline has been the focus of attention for researchers studying the national algal flora, with the aim of preserving these invaluable natural resources. Since the year 2000, these resources have stimulated great interest in the creation of new drugs, as well as their integration into food supplements and foods. Therefore, this study aims to explore the phytochemistry of a series of extracts derived from Caulerpa prolifera. To ensure better extraction of the various metabolites present, two extraction methods, namely maceration and the Soxhlet method, were employed using solvents of varying polarity (hexane, ethyl acetate, methanol, and water). The chemical composition of the extracts was analyzed using GC-MS for fatty acids and HPLC-DAD for phenolic compounds. Antioxidant activity was evaluated using DPPH and β-carotene bleaching assays, while antidiabetic potential was assessed by in vitro inhibition of α-amylase and α-glucosidase. In addition, Molecular docking models were employed to assess the interaction between the bioactive molecules and the human pancreatic α-amylase and α-glucosidase enzymes. Vanillin, p-coumaric acid, sinapic acid, 7,3′,4′-flavon-3-ol, and kaempferol were the most abundant phenolic compounds. Anti-diabetic and antioxidant effects were highly significant. Full article

Alzheimer’s disease (AD) is the most common neurodegenerative disease which has a rather complex pathophysiology. During its course, several neurotransmitter neuronal systems get affected such as acetylcholinergic, glutamatergic, gamma-aminobutyric acid (GABA)ergic systems, etc. Such complex physiology requires a sophisticated approach to pharmaceutical management. Therefore, multi-target drugs seem to be an appealing solution. In the present study, we designed and synthesized a hybrid molecule—N-sinapoylamide of memantine, whose parent molecules memantine (MEM) and sinapic acid have been shown in vivo to impact glutamatergic, acetylcholinergic, and GABA-ergic systems, respectively. In silico comparative testing of these molecules was performed, their patterns of interaction with the target enzymes or molecular complexes were analyzed, and some of the mechanisms of action were proposed. Consequently, in vivo testing was performed on a scopolamine mice model of AD and the results overly confirm part of the in silico findings. Therefore, the hybrid molecule (N-Sinapoyl-memantine) seems to be a potent candidate for further evaluation in the management of AD. Full article

In this study, leaves and roots from three beetroot cultivars (cv. Albina Vereduna (white roots), cv. Burpee’s Golden (golden roots), and cv. Pablo F1 (red roots)), as well as Swiss chard leaves (also known as “rhubarb chard”, or Beta vulgaris subsp. cicla var. flavescens) were evaluated in terms of their chemical profile and bioactive properties. Roots were characterized by high carbohydrate content, which also contributed to greater energy values. In contrast, fibers were the predominant macronutrient in leaves, followed by carbohydrates. In both leaves and roots, the most abundant organic acids were quinic and oxalic, while the major free sugar was sucrose. The profile of fatty acid varied between the studied plant parts, with saturated fatty acids prevailing in root samples, while leaves exhibited higher levels of polyunsaturated fatty acids. Regarding phenolic composition, a total of 19 compounds were tentatively identified in leaves (including derivatives of vitexin, isorhamnetin, quercetin, and ferulic, sinapic, and p-coumaric acids), while the roots exhibited a less diverse composition, with a total of eight compounds identified (e.g., derivatives of ferulic, sinapic, p-coumaric and caffeic acids). A total of eight betalains were also identified, out of which seven were classified as betacyanins and one as betaxanthin. The leaves of Swiss chard presented compounds from both classes, while the roots and leaves of cv. Pablo F1 were characterized only by the presence of betacyanins, and those of cv. Burpee’s Golden only by betaxanthin. All samples exhibited relevant activity against Y. enterocolitica, L. monocytogenes, and S. aureus, although leaf samples demonstrated better antioxidant capacity. In conclusion, beetroot leaves outperformed their corresponding roots in terms of chemical composition, antioxidant, and antimicrobial activity, suggesting their high potential as nutrient-rich and functional ingredients in a diverse and well-balanced diet. Full article

Cinnamic acid and its natural derivatives were primarily used in cosmetics as fragrance materials as well as skin and hair conditioners. Nowadays, not only natural but also synthetic cinnamic acid derivatives are used as active ingredients of cosmetic formulations. They still serve as fragrance ingredients but also as active ingredients supporting the treatment of selected dermatoses such as acne vulgaris, atopic dermatitis, and hyperpigmentation. They are also commonly used in anti-aging cosmetic formulations. On the other hand, several cinnamic acid derivatives used as fragrances in cosmetic products are classified as potential allergens which can cause contact dermatitis. The main mechanisms of action proved for various cinnamic acid derivatives include antioxidant, antimicrobial, anti-inflammatory, and antimelanogenic properties. Most commonly used cinnamic acid derivatives in cosmetics products are hydroxy acids such as ferulic acid, caffeic acid, p-coumaric acid, and sinapic acid. Chemical synthesis led to several modified acids, esters, and amides, which also showed the potential to be used in cosmetic formulations. Full article

Natural alkylated hydroxy cinnamates (AHCs) isolated from medicinal plants and the thereby designed and synthesized cinnamides are derivatives of hydroxy cinnamic acids such as p-coumaric, sinapic, ferulic, and caffeic acids, which are naturally derived from human dietary sources. The pharmacological properties displayed by AHCs based on their inherent structure range include antioxidant, antimicrobial, antiplasmodial, anti-tyrosinase, Alzheimer’s and Parkinson’s disease therapy, anticancer therapy, metabolic disease therapy, and biopesticides, which have not been reviewed together. Based on their inherent antioxidant, antimicrobial, and UV absorption and their structure–activity relationships, these cinnamyl esters and amides can be used for food preservation in emulsions and oils, as sun-protective components of skin care formulations, and in many other multifunctional applications. In conclusion, the fine-tuning of the structural features such as the type of hydroxy cinnamic acid used, the length of alkyl chains for variable lipophilicity, conversion from cinnamic to propanoic for antioxidants, the increase in methoxy or the change to amino groups to increase the molar absorption coefficient and loss of absorption values, the substitution by halides or amino groups for potent biopesticides, and conversion from esters to amide bonds leads to different AHCs for biomedical, cosmetic, and agriculture applications as an emerging field of investigation that can overall provide natural, safe, biodegradable, and sustainable molecules. Full article

The importance of the valorization of industrial by-products has led to increasing research into their reuse. In this research, the innovative by-product okara oat flour, derived from the vegetable beverage industry, was studied. Oat okara sourdough was also produced and evaluated. The microbiological identification and typing involved bacterial and yeast isolates from both flour and sourdough. Untargeted metabolomics allowed the identification of biomarkers of fermented flour, such as phenolic classes, post-fermentation metabolites, fatty acids, and amino acids. The microorganisms most found were Weissella confusa, Enterococcus faecium, Pediococcus pentosaceus, and Pichia kudriavzevii, while Saccharomyces cerevisiae appeared only at the end of the sourdough’s back-slopping. Untargeted metabolomics identified a total of 539 metabolites, including phenolic compounds, lipids, amino acids, and organic acids. An increase in polyphenols released from the food matrix was detected, likely because of the higher bio-accessibility of phenolic metabolites promoted by microbial fermentation. Fermentation led to an increase in isoferulic acid, p-coumaric acid, sinapic acid, and a decrease in amino acids, which can be attributed to the metabolism of lactic acid bacteria. Some key markers of the fermentation process of both lactic acid bacteria and yeast were also measured, including organic acids (lactate, succinate, and propionate derivatives) and flavor compounds (e.g., diacetyl). Two bioactive compounds, such as gamma-aminobutyric acid and 3-phenyl-lactic acid had accumulated at the end of fermentation. Taken together, our findings showed that oat okara flour can be considered an excellent raw material for formulating more sustainable and functional foods due to fermentation promoted by autochthonous microbiota. Full article

This review discusses the development and applications of bioconjugates derived from natural hydroxycinnamic acids (HCA), such as coumaric, sinapic, ferulic, and caffeic acids, combined with various biomaterials. These bioconjugates offer a range of benefits including antioxidant properties, UV protection, customized hydrophilic–lipophilic balance, improved safety, solubility, emolliency, biocompatibility, biodegradability, and targeted delivery for biomedical, cosmetic, and food applications. The increasing demand for natural products in the biomedical, cosmetic, and food industries has led to the exploration of these hydroxycinnamic acids and their derivatives. We discuss the synthesis and modification of hydroxycinnamic acids with biomaterials such as ω-hydroxy fatty acids, castor and lesquerella oils, glycerol, isosorbides, and synthetic polyethylene glycol to form functional phenolipids for biomedical, sunscreen, and skincare applications. Encapsulation techniques with β-cyclodextrins and modification of polymeric supports like polysaccharides and starch are discussed for enhancing bioavailability and solubility and targeted delivery. The fine-tuned development of bioconjugates from hydroxycinnamic acids using glycerol to modify the hydrophilic–lipophilic balance, substitution by water-soluble carboxylic acid groups, vegetable oil-based phenolipids, polysaccharides, and PEGylation provide enhanced dual functionalities and offer a promising avenue for creating effective products across various applications. Full article

Petit vert (scientific name: Brassica oleracea var. gemmifera DC. × Brassica oleracea var. acephala DC.) is a new variety of vegetable created by crossbreeding kale and brussel sprouts (Brassica oleracea species). The present study aimed to identify biologically active compounds in extracts of the outer leaves of Petit vert by purification and to examine their biological activities. The dried and powdered outer leaves of Petit vert were extracted, fractionated, and purified to isolate active compounds. Mass spectrometry (MS) was used to identify the compounds, and nuclear magnetic resonance (NMR) spectroscopy was performed to elucidate their structures. The compounds isolated from Petit vert leaves were glycosides that contained kaempferol, quercetin (flavonol), or sinapic acid (phenylpropanoid). Glucose uptake in cultured C2C12 murine myoblasts in the absence of insulin was significantly increased by these compounds, kaempferol, sinapic acid, and ferulic acid, while uptake in the presence of insulin was also significantly increased by compounds 3 and 4, kaempferol, and sinapic acid. The effect was not necessarily concentration-dependent, and some agents decreased the glucose uptake at higher concentrations. The present study reports for the first time the isolation of five compounds containing sinapic acid from the outer leaves of Petit vert and their stimulation of glucose uptake in cultured C2C12 murine myoblasts. The results obtained herein suggest the potential of these compounds to effectively attenuate hyperglycemia and maintain muscle strength by promoting glucose metabolism in muscle cells. Full article

The use of vegetable oils and their derivatives for polymer synthesis has been a major focus in recent years due to their universal availability, low production costs and biodegradability. In this study, the enzymatic synthesis of oligoesters of ricinoleic acid obtained from castor oil combined with three aromatic natural derivatives (cinnamyl alcohol, sinapic acid, and caffeic acid) was investigated. The formation of the reaction products was demonstrated by FT-IR, MALDI-TOF MS and NMR spectroscopy and for the oligo (ricinoleyl)-caffeate the thermal properties and biodegradability in sweet water were analyzed and a rheological characterization was performed. The successful enzymatic synthesis of oligoesters from ricinoleic acid and aromatic monomers using lipases not only highlights the potential of biocatalysis in green chemistry but also contributes to the development of sustainable and biodegradable methods for synthesizing products with potential applications as cosmetic ingredients. Full article

Degenerative conditions, such as neurodegenerative disorders (Alzheimer’s disease (AD), Parkinson’s disease (PD)) and cardiovascular diseases, are complex, multifactorial disorders whose pathophysiology has not been fully elucidated yet. As a result, the available treatment options cannot eliminate these diseases radically, but only alleviate the symptoms. Both inflammatory processes and oxidation are key factors in the development and evolution of neurodegeneration, while acetylcholinesterase inhibitors are the most used therapeutic options against AD. In this work, following the multi-targeting compound approach, we designed and synthesized a series of proline and gamma-aminobutyric acid (GABA) amides with various acidic moieties that possess an antioxidant and/or anti-inflammatory potency. Proline is the pharmacophore of nootropic drugs (e.g., piracetam) used for memory improvement, while GABA is the main inhibitory neurotransmitter in the central nervous system. The designed molecules were subjected to a preliminary screening of their bioactivity in antioxidant and anti-inflammatory assays, as well as against acetylcholinesterase. Most of the synthesized compounds could inhibit lipid peroxidation (IC₅₀ as low as 8 μΜ) and oxidative protein glycation (inhibition of up to 48%) and reduce the 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH). In addition, all of the compounds were moderate inhibitors of lipoxygenase (LOX) (up to 46% at 100 μΜ) and could decrease carrageenan-induced paw edema in rats by up to 55%. Finally, some of the compounds were moderate acetylcholinesterase inhibitors (IC₅₀ as low as 219 μΜ). The results confirmed the design rationale, indicating that the compounds could be further optimized as multi-targeting molecules directed against degenerative conditions. Full article

Staphylococcus epidermidis, a component of human microbiota, may also cause life-threatening opportunistic infections. These are becoming increasingly common infections associated with the implantation of various implants. Due to the exhaustion of antibiotic resources, new substances with antimicrobial activity are being sought. The present study examined the antibacterial effect of cinnamic acid and its derivatives and their combinations with β-lactam antibiotics on the growth of Staphylococcus epidermidis strains isolated from vascular infections. The data obtained during the research indicated that cinnamic acid and its derivatives, sinapic acid, ferulic acid, and p-coumaric acid, have weak antibacterial activity (MIC values at the level of 2048 and 4096 mg/L). The combination of cinnamic acid and its derivatives with β-lactam antibiotics increases the effectiveness of their action and may demonstrate various pharmacological effects depending on the established cutoff. Full article

Berberis vulgaris L. (Berberidaceae) is a shrub that has been widely used in European folk medicine as an anti-inflammatory and antimicrobial agent. The purpose of our study was to elucidate the mechanisms of the chemopreventive action of the plant’s methanolic root extract (BVR) against colon cancer cells. Studies were conducted in human colon adenocarcinoma cell lines (LS180 and HT-29) and control colon epithelial CCD841 CoN cells. According to the MTT assay, after 48 h of cell exposure, the IC₅₀ values were as follows: 4.3, 46.1, and 50.2 µg/mL for the LS180, HT-29, and CCD841 CoN cells, respectively, showing the greater sensitivity of the cancer cells to BVR. The Cell Death Detection ELISAPLUS kit demonstrated that BVR induced programmed cell death only against HT-29 cells. Nuclear double staining revealed the great proapoptotic BVR properties in HT-29 cells and subtle effect in LS180 cells. RT-qPCR with the relative quantification method showed significant changes in the expression of genes related to apoptosis in both the LS180 and HT-29 cells. The genes BCL2L1 (126.86–421.43%), BCL2L2 (240–286.02%), CASP3 (177.19–247.83%), and CASP9 (157.99–243.75%) had a significantly elevated expression, while BCL2 (25–52.03%) had a reduced expression compared to the untreated control. Furthermore, in a panel of antioxidant tests, BVR showed positive effects (63.93 ± 0.01, 122.92 ± 0.01, and 220.29 ± 0.02 mg Trolox equivalents (TE)/g in the DPPH•, ABTS•+, and ORAC assays, respectively). In the lipoxygenase (LOX) inhibition test, BVR revealed 62.60 ± 0.87% of enzyme inhibition. The chemical composition of BVR was determined using a UHPLC-UV-CAD-MS/MS analysis and confirmed the presence of several known alkaloids, including berberine, as well as other alkaloids and two derivatives of hydroxycinnamic acid (ferulic and sinapic acid hexosides). The results are very promising and encourage the use of BVR as a comprehensive chemopreventive agent (anti-inflammatory, antioxidant, and pro-apoptotic) in colorectal cancer, and were widely discussed alongside data from the literature. Full article

Three varieties of rapeseed (Castilla, California, and Nelson F1) were cultivated using medium–intensive (control), intensive, and economical (spare) technologies with different nitrogen and sulfur fertilization techniques. The antioxidant potential of rapeseeds was investigated using ABTS, FRAP, and DPPH assays. The content of total phenolic compounds was determined using the Folin–Ciocalteu phenol reagent. The profile of phenolic compounds was determined using high-performance liquid chromatography (HPLC). Diversifying fertilization in various ways influenced the content of phenolic compounds in extracts of rapeseed. In extracts from the Nelson F1 rapeseeds, intensive cultivation resulted in a lower content of phenolic compounds compared to the control group. Economic fertilization reduced the content of phenolic compounds in seeds from the California variety. HPLC chromatograms of the extracts were characterized by the presence of five (California and Castilla) and six (Nelson F1) main phenolic compounds. Two compounds were identified as sinapine and sinapic acid; others were classified as derivatives of sinapic acid. The effect of fertilization on the antioxidant activity of the seeds and their extracts varied depending on the plant variety and antioxidant assay. For the Castilla and California varieties, no differences were found in the results of the ABTS assay. The antiradical activity against ABTS^•+ of extracts from the Nelson F1 intensive and spare cultivated seeds was higher than that of extracts from control seeds. The FRAP values of extracts/seeds from the Castilla variety cultivated using different methods did not differ significantly. The results of the DPPH assay were not affected by fertilization in the case of extracts from the California and Castilla varieties. However, the extracts from spare cultivated seeds of Nelson F1 exhibited stronger antiradical activity against DPPH^•. These findings highlight the complex relationship between fertilization practices, phenolic compound accumulation, and antioxidant activity in rapeseed. Integrating varietal traits and cultivation practices is crucial for optimizing the nutritional benefits of rapeseed. Full article

Oxidative stress and hyperlipidemia are important factors for the initiation and progression of various cell degenerative pathological conditions, including cardiovascular and neurological diseases. A series of cinnamic acid-derived acids, such as ferulic acid, sinapic acid, 3,4-dimethoxycinnamic acid, p-coumaric acid, and (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylic acid, were esterified or amidated with various moieties, bearing different biological activities, and evaluated. The antioxidant and radical scavenging abilities of the compounds via inhibition of rat hepatic microsomal membrane lipid peroxidation, as well as their interaction with the stable radical 2,2-diphenyl-1-picrylhydrazyl (DPPH), were assessed. Further, their hypolipidemic activity in vivo was tested. The majority of the obtained compounds demonstrated considerable radical scavenging and antioxidant action, with a parallel decrease in Triton-induced hyperlipidemia in rats. The (E)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)acrylic acid derivative with morpholine and 4-methylpiperidine (compounds 4 and 13, respectively) significantly decreased triglycerides and total cholesterol in the plasma of hyperlipidemic rats, with an antioxidant capacity similar to that of the antioxidant Trolox. The compounds were designed to exhibit antioxidant and hypolipidemic pharmacological actions, and this succeeded for the majority of them. Thus, such agents may be of interest in conditions and diseases implicating oxidative stress and dyslipidemia. Full article