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Prenylated cinnamic acid derivatives are the bioactive components of Brazilian green propolis (BGP). The effect of other botanical components on the pharmacokinetic profiles of these derivatives remains relatively unexplored. In the present study, we investigated the influence of several herbal extracts (turmeric, ginkgo leaf, coffee fruit, soybean, and gotu kola) on the plasma concentrations of cinnamic acid derivatives after BGP consumption. When the herbal extracts were co-administered with BGP in the clinical study, the area under the curve (AUC) values of artepillin C and drupanin, the major BGP components in plasma, were significantly increased by 1.7- and 1.5-fold, respectively, compared to those after BGP administration alone. Among the herbal extracts administered to rats, turmeric extract increased the AUC. Furthermore, a bidirectional transport assay suggested that artepillin C and drupanin are substrates of breast cancer resistance protein (BCRP), a drug elimination transporter. These results suggest that curcumin-containing turmeric extract may increase the plasma concentrations of artepillin C and drupanin via BCRP. Our findings enabled us to estimate the food-herb and herb-herb interactions in vivo in foods and herbal medicines containing cinnamic acid derivatives and prenylated compounds.

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Candida spp., causes invasive fungal infections, especially in immune-compromised patients and the propensity of antifungal resistance against azole-based drugs need to be addressed. This study is thus aimed to characterize the anticandidal effect of the cinnamic acid extracted from the barks of Cinnamomum cassia. Five species of Fluconazole-resistant Candida sp. were retrieved from the department repertoire. The extraction of CA was performed by three different methods followed by silica gel column chromatography. Eluant was subjected to FTIR and XRD analysis for confirmation. The anticandidal activity of the CA was checked by the agar disc diffusion method and the MIC and MFC were determined. The anti-biofilm effect of CA was assessed using the CLSM technique followed by the biocompatibility check using MTT assay in normal HGF cell lines. CA was best extracted with the hot maceration method using ethanol with a maximum yield of 6.73 mg. Purification by column chromatography was achieved using benzene, acetic acid, and water (6:7:3) mobile phase. CA was confirmed by FTIR with absorption peaks and by XDR based on strong intensity. CA was found to possess promising anticandidal activity at 8 µg/mL with MIC and MFC values determined as 0.8 µg/mL and 0.08 µg/mL respectively. Antibiofilm activity by CLSM analysis revealed biofilm inhibition and was biocompatible at 8.5 µg/ml concentrations in HGF cell lines until 24 h. The study findings conclude that CA is the best alternative to treat candidal infection warranting further experimental preclinical studies.

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Aedes aegypti serves as the primary vector for viruses like dengue, Chikungunya, Zika, and yellow fever, posing a significant public health challenge in Brazil. Given the absence of approved vaccines for these diseases, effective mosquito control becomes paramount in preventing outbreaks. However, currently available chemical insecticides face issues related to toxicity and the emergence of resistance, necessitating the exploration of new active compounds. Drawing inspiration from natural products, we identified the 1,3-benzodioxole group as a key pharmacophore associated with insecticidal activity. Therefore, this study aimed to synthesize and assess the larvicidal activity of 1,3-benzodioxole acids against Ae. aegypti, as well as their toxicity in mammals. Among the compounds evaluated, 3,4-(methylenedioxy) cinnamic acid (compound 4) demonstrated larvicidal activity. It exhibited LC50 and LC90 values of 28.9 ± 5.6 and 162.7 ± 26.2 µM, respectively, after 24 h of exposure. For reference, the positive control, temephos, displayed both LC50 and LC90 values below 10.94 µM. These findings underline the significance of the 3,4-methylenedioxy substituent on the aromatic ring and the presence of a double bond in the aliphatic chain for biological activity. Furthermore, compound 4 exhibited no cytotoxicity towards human peripheral blood mononuclear cells, even at concentrations up to 5200 µM. Lastly, in mice treated with 2000 mg kg-1, compound 4 showed mild behavioral effects and displayed no structural signs of toxicity in vital organs such as the kidney, liver, spleen, and lungs.

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We synthesized seven (Z)-benzylidene-2-(E)-styryloxazol-5(4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 µM, showed an affinity (Ki) from 2 to 198 µM, and an IC50 from 9 to 246 µM. Molecular docking studies revealed that all binding moieties are involved in the non-covalent interactions with hAChE for all compounds. In addition, in silico pharmacokinetic analysis was carried out to predict the compounds' blood-brain barrier (BBB) permeability. The most potent inhibitor of hAChE significantly improved cognitive impairment in a modified Y-maze test (5 µmol/kg) and an Object Recognition Test (10 µmol/kg). Our results can help the rational design of hAChE inhibitors to work as potential candidates for treating cognitive disorders.

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Leishmaniasis is a group of infectious diseases caused by protozoan parasites that belong to the genus Leishmania. Currently, there is no human vaccine, and the available treatments are associated with toxicity, high cost, and the emergence of resistant strains. These factors highlight the need to identify new antileishmanial candidates. In this study, we synthesized twenty-four methoxylated cinnamides containing 1,2,3-triazole fragments and evaluated their antileishmanial activity against the Leishmania braziliensis species, which is the main etiological agent responsible for American Tegumentary Leishmaniasis (ATL). The cinnamides were synthetically prepared using nucleophilic acyl substitution and copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. The compounds were characterized using infrared, nuclear magnetic resonance, and high-resolution mass spectrometry techniques. We performed preliminary studies to evaluate the biological activity of these compounds against L. braziliensis promastigotes and axenic amastigotes. Compound 28, N-((1-(7-(diethylamino)-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazole-4-yl) methyl)-3,4-dimethoxy cinnamide, demonstrated relevant antileishmanial activity with low toxicity in murine cells. The selectivity index values for this compound were superior compared with data obtained using amphotericin B. Furthermore, this cinnamide derivative reduced the infection percentage and number of recovered amastigotes in L. braziliensis-infected macrophages. It also induced an increase in reactive oxygen species production, depolarization of the mitochondrial potential, and disruption of the parasite membrane. Taken together, these findings suggest that this synthetic compound holds potential as an antileishmanial candidate and should be considered for future studies in the treatment of ATL.

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Lung cancer is the leading cause of cancer mortality worldwide, and malignant melanomas are highly lethal owing to their elevated metastatic potential. Despite improvements in therapeutic approaches, cancer treatments are not completely effective. Thus, new drug candidates are continuously sought. We synthesized mono- and di-methoxylated cinnamic acid esters and investigated their antitumor potential. A cell viability assay was performed to identify promising substances against A549 (non-small-cell lung cancer) and SK-MEL-147 (melanoma) cells. (E)-2,5-dimethoxybenzyl 3-(4-methoxyphenyl)acrylate (4m), a monomethoxylated cinnamic acid derivative, was identified as the lead antitumor compound, and its antitumor potential was deeply investigated. Various approaches were employed to investigate the antiproliferative (clonogenic assay and cell cycle analysis), proapoptotic (annexin V assay), and antimigratory (wound-healing and adhesion assays) activities of 4m on A549 cells. In addition, western blotting was performed to explore its mechanism of action. We demonstrated that 4m inhibits the proliferation of A549 by promoting cyclin B downregulation and cell cycle arrest at G2/M. Antimigratory and proapoptotic activities of 4m on A549 were also observed. The antitumor potential of 4m involved its ability to modulate the mitogen-activated protein kinases/extracellular signal-regulated kinase (MAPK/ERK) signaling pathway once phosphorylated-ERK expression was considerably reduced in response to treatment. Our findings demonstrate that 4m is a promising anticancer drug candidate.

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Bamboo species have traditionally been used as building material and potential source of bioactive substances, as they produce a wide variety of phenolic compounds, including flavonoids and cinnamic acid derivatives that are considered biologically active. However, the effects of growth conditions such as location, altitude, climate, and soil on the metabolome of these species still need to be fully understood. This study aimed to evaluate variations in chemical composition induced by altitudinal gradient (0-3000 m) by utilizing an untargeted metabolomics approach and mapping chemical space using molecular networking analysis. We analyzed 111 samples from 12 bamboo species collected from different altitudinal ranges using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC-QTOF-MS). We used multivariate and univariate statistical analyses to identify the metabolites that showed significant differences in the altitude environments. Additionally, we used the Global Natural Products Social Molecular Networking (GNPS) web platform to perform chemical mapping by comparing the metabolome among the studied species and the reference spectra from its database. The results showed 89 differential metabolites between the altitudinal ranges investigated, wherein high altitude environments significantly increased the profile of flavonoids. While, low altitude environments significantly boosted the profile of cinnamic acid derivatives, particularly caffeoylquinic acids (CQAs). MolNetEnhancer networks confirmed the same differential molecular families already found, revealing metabolic diversity. Overall, this study provides the first report of variations induced by altitude in the chemical profile of bamboo species. The findings may possess fascinating active biological properties, thus offering an alternative use for bamboo.

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The severity of infectious diseases associated with the resistance of microorganisms to drugs highlights the importance of investigating bioactive compounds with antimicrobial potential. Therefore, nineteen synthetic cinnamides and cinnamates having a cinnamoyl nucleus were prepared and submitted for the evaluation of antimicrobial activity against pathogenic fungi and bacteria in this study. To determine the minimum inhibitory concentration (MIC) of the compounds, possible mechanisms of antifungal action, and synergistic effects, microdilution testing in broth was used. The structures of the synthesized products were characterized with FTIR spectroscopy, 1 H-NMR, 13 C-NMR, and HRMS. Derivative 6 presented the best antifungal profile, suggesting that the presence of the butyl substituent potentiates its biological response (MIC = 626.62 µM), followed by compound 4 (672.83 µM) and compound 3 (726.36 µM). All three compounds were fungicidal, with MFC/MIC ≤ 4. For mechanism of action, compounds 4 and 6 directly interacted with the ergosterol present in the fungal plasmatic membrane and with the cell wall. Compound 18 presented the best antibacterial profile (MIC = 458.15 µM), followed by compound 9 (550.96 µM) and compound 6 (626.62 µM), which suggested that the presence of an isopropyl group is important for antibacterial activity. The compounds were bactericidal, with MBC/MIC ≤ 4. Association tests were performed using the Checkerboard method to evaluate potential synergistic effects with nystatin (fungi) and amoxicillin (bacteria). Derivatives 6 and 18 presented additive effects. Molecular docking simulations suggested that the most likely targets of compound 6 in C. albicans were caHOS2 and caRPD3, while the most likely target of compound 18 in S. aureus was saFABH. Our results suggest that these compounds could be used as prototypes to obtain new antimicrobial drugs.

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The Amazonian region of Ecuador has an extremely rich vegetal biodiversity, and its inhabitants have proven to have a millennial ancestral knowledge of the therapeutic and medicinal use of these resources. This work aimed to evaluate the chemical composition and biological activity of the essential oil obtained from the medicinal plant Clinopodium brownei (Sw.) Kuntze, which is widely spread in tropical and subtropical America. This species is traditionally used for treating respiratory and digestive diseases and is also known for its analgesic properties. Most of the molecules detected on a non-polar column were ethyl cinnamate 21.4%, pulegone 20.76%, methyl cinnamate 16.68%, caryophyllene 8.17%, ß-selinene 7.92% and menthone 7.51%, while those detected on a polar column were: pulegone 29.90%, ethyl cinnamate 18.75%, methyl cinnamate 13.82%, caryophyllene 10.0% and menthone 8.04%. The antioxidant activity by the assays, DPPH (2.2-diphenyl-1-picrylhydrazyl) and ABTS (2.2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid)), shows the following values of 50% inhibition of oxidation, IC50 DPPH 1.77 mg/mL, IC50 ABTS 0.06 mg/mL, which, compared to the essential oil of Thymus vulgaris (natural positive control), turn out to be less active. Bioautography indicates that the molecules responsible for the antioxidant activity are derived from cinnamic acid: ethyl cinnamate and methyl cinnamate, and caryophyllene. The antimicrobial activity on the nine microorganisms evaluated shows bacterial growth inhibitory concentrations ranging from 13.6 mg/mL for Staphylococcus epidermidis ATCC 14990 to 3.1 mg/mL for Candida albicans ATCC 10231; the results are lower than those of the positive control. Bioautography assigns antimicrobial activity to caryophyllene. The results indicate a very interesting activity of the essential oil and several of its molecules, validating the traditional use and the importance of this medicinal plant from Ecuador.

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Genipa americana L. is a plant widely used by folk medicine for the prevention and as an aid in the treatment of various diseases. In this work, we evaluated the anti-glycant and antioxidant activities of genipap fruit juice, as well as the influence of different temperatures (-6 °C and -80 °C) on the preservation of phenolic compounds. Purified extract from G. americana showed anti-glycant activity reducing the formation of fructosamine by up to 53% and recovered viability of cells under oxidative stress induced by H2O2. HPLC/UV-Vis analysis identified cinnamic acid as a bioactive substance and possibly responsible for the biological activities described above. Taken together, these results indicate that G. americana is a rich source of cinnamic acid with appreciable antioxidant and anti-glycant potential.

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Cinnamic acid derivatives, which are dietary phenolic compounds, are attracting attention for their health benefits. Artepillin C, drupanin, baccharin, and p-coumaric acid are major cinnamic acid derivatives in Brazilian green propolis (BGP) used as functional food materials. To investigate the metabolism of these cinnamic acid derivatives, each compound was administered to rats, and their metabolic profiles were compared with those administered with BGP. Artepillin C is metabolized to hydroxylated metabolites (capillartemisin A), as well as glucuronide. Drupanin sulfate, glucuronide, and hydroxylated form were detected in plasma both after ingestion of drupanin and its 3-phenylpropionic acid ester (baccharin). p-Coumaric acid underwent sulfation, but not glucuronidation. These results reveal that the metabolic pathways of cinnamic acid derivatives in rats comprise ester hydrolysis and hydroxylation, as well as phase-II conjugation. Our findings may provide significant information for estimating the potential activity of various cinnamic acid derivatives derived from functional food materials.

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(E)-Cinnamaldehyde is very active against Meloidogyne incognita but has low persistence in soil. To circumvent this problem, esters of cinnamic acid were evaluated as a substitute for (E)-cinnamaldehyde. The best results under assays with M. incognita second-stage juveniles (J2) were obtained for the methyl esters of (E)-p-fluoro- (13), (E)-p-chloro- (14), and (E)-p-bromocinnamic acid (15), which showed lethal concentrations to 50% (LC50) J2 of 168, 95, and 216 µg/mL, respectively. Under the same conditions, the LC50 values for the nematicides carbofuran and fluensulfone were 160 and 34 µg/mL, respectively. Substances 13-15 were also active against nematode eggs, which account for most of the M. incognita population in the field. According to an in silico study, substances 13-15 can act against the nematode through inhibition of histone deacetylase. Therefore, esters 13-15 and histone deacetylase are potentially useful for the rational design of new nematicides for the control of M. incognita.

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Melanoma is the most aggressive skin cancer, and its incidence has continued to rise during the past decades. Conventional treatments present severe side effects in cancer patients, and melanoma can be refractory to commonly used anticancer drugs, which justify the efforts to find new potential anti-melanoma drugs. An alternative to promote the discovery of new pharmacological substances would be modifying chemical groups from a bioactive compound. Here we describe the synthesis of seventeen compounds derived from cinnamic acid and their bioactivity evaluation against melanoma cells. The compound phenyl 2,3-dibromo-3-phenylpropanoate (3q) was the most effective against murine B16-F10 cells, as observed in cytotoxicity and cell migration assays. Simultaneously, this compound showed low cytotoxic activity on non-tumor cells. At the highest concentration, the compound 3q was able to trigger apoptosis, whereas, at lower concentrations, it affected the cell cycle and melanoma cell proliferation. Furthermore, cinnamate 3q impaired cell invasion, adhesion, colonization, and actin polymerization. In conclusion, these results highlight the antiproliferative and antimetastatic potential of cinnamic acid derivatives on melanoma.

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Approximately 11.4 million tonnes of solid by-products and an increased amount of waste water will be generated during the 2020/21 coffee harvest. There are currently no truly value-adding uses for these potentially environmentally threatening species. This work presents the most wide-ranging chemical investigation of coffee by-products collected from farms to factories, including eight never previously investigated. Twenty compounds were found for the first time in coffee by-products including the bioactive neomangiferin, kaempferol-3-O-rutinoside, lup-20(29)-en-3-one and 3,4-dimethoxy cinnamic acid. Five by-products generated inside a factory showed caffeine (53.0-17.0 mg.g-1) and/or chlorogenic acid (72.9-10.1 mg.g-1) content comparable to coffee beans, while mature leaf from plant pruning presented not only high contents of both compounds (16.4 and 38.9 mg.g-1, respectively), but also of mangiferin (19.4 mg.g-1) besides a variety of flavonoids. Such by-products are a source of a range of bioactive compounds and could be explored with potential economic and certainly environmental benefits.

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Multi-response optimization of hot pressurized liquid extraction (HPLE) was applied for the first time to obtain maqui (Aristotelia chilensis [Mol.] Stuntz) leaf extracts. The total polyphenol content (TPC), the antioxidant capacity (AC) as well as the total polyphenol purity of the maqui leaf extracts were accurately predicted (RSD < 8%) at the evaluated extraction scales. The optimum HPLE conditions that prioritized TPC and AC equally (OPT1) recovered ~3 times more TPC (205.14 mg GAE/g leaves) than maqui leaf extracts obtained by maceration, while the extract that prioritized purity over TPC and AC presented the highest purity (36.29%) and an EC50 ~3 times lower than currently reported values. It was found by multi-response optimization that maqui leaves and HPLE are among the best natural sources and extraction techniques, respectively, to recover protocatechuic acid, quercetin, and catechin.

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AIM: Hydroxycinnamic acids their derivatives have various pharmacological properties. The hydroxycinnamic acid derivatives, methyl cinnamate, trans-cinnamic, and p-coumaric acids have been the object of study in the treatment of skin wounds. However, it is unclear whether these derivatives exert a direct beneficial effect on fibroblast function. In this study, we evaluated the effects of methyl cinnamate, trans-cinnamic, and p-coumaric acids on fibroblast migration in vitro. MATERIALS AND METHODS: NIH 3T3 and L929 fibroblast cell lines were exposed to each drug at several concentrations and the effect on cell viability, cell cycle, and extracellular matrix production were assessed by MTT assay, flow cytometry, and immunofluorescence staining, respectively. The effect on cell migration was examined using scratch assay. RESULTS: The results showed that hydroxycinnamic acid derivatives not affect cell viability, but increase fibroblast migration in the in vitro scratch-wound healing assay. They also induced an increase in S and G2/M phases accompanied by a decrease in the G0/G1 phase of the cell cycle. The cell proliferation inhibitor mitomycin C abolished the effect induced by p-coumaric acid and methyl cinnamate, indicating that only the trans-cinnamic acid stimulated migration. A transwell migration assay confirmed that trans-cinnamic acid-treated fibroblasts exhibited increased migration compared with untreated cells. trans-Cinnamic acid-induced fibroblast migration was decreased by PKA inhibitor and p38-MAPK inhibitor but not by JNK inhibitor. Additionally, trans-cinnamic acid-treated fibroblasts showed an increase in the production of laminin and collagen type I. CONCLUSION: Our study showed that trans-cinnamic acid improves fibroblast migration and modulates extracellular matrix synthesis, indicating its potential for accelerating the healing process.

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Fungal infections remain a high-incidence worldwide health problem that is aggravated by limited therapeutic options and the emergence of drug-resistant strains. Cinnamic and benzoic acid amides have previously shown bioactivity against different species belonging to the Candida genus. Here, 20 cinnamic and benzoic acid amides were synthesized and tested for inhibition of C. krusei ATCC 14243 and C. parapsilosis ATCC 22019. Five compounds inhibited the Candida strains tested, with compound 16 (MIC = 7.8 µg/mL) producing stronger antifungal activity than fluconazole (MIC = 16 µg/mL) against C. krusei ATCC 14243. It was also tested against eight Candida strains, including five clinical strains resistant to fluconazole, and showed an inhibitory effect against all strains tested (MIC = 85.3-341.3 µg/mL). The MIC value against C. krusei ATCC 6258 was 85.3 mcg/mL, while against C. krusei ATCC 14243, it was 10.9 times smaller. This strain had greater sensitivity to the antifungal action of compound 16. The inhibition of C. krusei ATCC 14243 and C. parapsilosis ATCC 22019 was also achieved by compounds 2, 9, 12, 14 and 15. Computational experiments combining target fishing, molecular docking and molecular dynamics simulations were performed to study the potential mechanism of action of compound 16 against C. krusei. From these, a multi-target mechanism of action is proposed for this compound that involves proteins related to critical cellular processes such as the redox balance, kinases-mediated signaling, protein folding and cell wall synthesis. The modeling results might guide future experiments focusing on the wet-lab investigation of the mechanism of action of this series of compounds, as well as on the optimization of their inhibitory potency.

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Chemical modifications in the chitosan structure may result in obtaining a new material with improved chemical properties, such as an ability to encapsulate lipophilic compounds. This study aimed to synthesize cinnamic acid grafted chitosan nanogel to encapsulate the essential oils of Syzygium aromaticum and Cinnamomum ssp., in order to develop a material to be applied in the control of dermatophytosis caused by the fungus Microsporum canis. The cinnamic acid graft in chitosan was verified by the Attenuated Total Reflectance Fourier Transform Infrared Spectroscopy (ATR-FTIR), Solid State Nuclear Magnetic Resonance of the 13C Nucleus (13C SSNMR) and Thermal analysis coupled to mass spectrometry (TG-MS) techniques. The nanogel obtained showed affinity for the essential oils of S. aromaticum and Cinnamomum, with encapsulation efficiencies equal to 74% and 89%, respectively. When in an aqueous medium the nanogel with the encapsulated essential oils was able to form stable nanoparticles with average sizes of 176.0 ± 54.3 nm and 263.0 ± 81.4 nm. The cinnamic acid grafted chitosan nanogel showed antifungal activity in vitro against M. canis, inhibiting up to 53.96% of its mycelial growth. Complete inhibition of mycelial growth was achieved by the nanogel with encapsulated essential oils. The results found in this work demonstrated the development of a material with potential application in the control of dermatophytosis caused by the fungus M. canis.

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Cinnamic acids and their derivatives are found in abundance in fruits, vegetables, and other food products of plant origin. The trans-cinnamic and p-coumaric acids in particular have been a subject of research for the treatment of a diverse range of pathological conditions. However, it is unclear whether these derivatives exert a direct beneficial effect on the cells that play a role in regulating skin wound healing, such as fibroblasts. In this study, using in vitro scratch-wound healing assay, it was observed that treatment with trans-cinnamic acid resulted in increased migration of fibroblasts when compared with that of p-coumaric acid-treated cells, without any adverse effect on cell viability. Studies on the lipophilicity of these acids using the XLOGP3 algorithm showed that trans-cinnamic acid was more lipophilic than p-coumaric. Thus, the findings of this study indicated that the lipophilic characteristic of trans-cinnamic acid rendered it more suitable as a potential drug candidate.

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The detection of emerging contaminants in the aquatic environment, such as ibuprofen and caffeine, was studied by means of surface-enhanced Raman spectroscopy (SERS) using Ag nanoparticles (AgNPs) synthesized with ß-cyclodextrin (ßCD) as a reducing agent. The effect on the SERS signal of different molar ratios of Ag+/ßCD in the synthesis route and the aging process of AgNPs were investigated by using trans-cinnamic as a test molecule. The SERS effectiveness of these ß-cyclodextrin colloids (Ag@ßCD) was also checked and compared with that of other silver sols usually employed in SERS synthesized by using other reducing agents such as citrate, borohydride and hydroxylamine. All the synthesized SERS substrates were characterized by different techniques. The experimental results indicate that Ag@ßCD with the more diluted Ag+/ßCD molar ratio showed the best SERS signal, enabling detection at trace concentrations of 0.5 µM in the case of trans-cinnamic acid. The Ag@ßCD sols also showed the best sensitivity for detecting ibuprofen and caffeine, reaching the lowest limit of detection (0.1 mM). The proposed synthetic route for Ag@ßCD sols provides an improved SERS substrate for detecting organic pollutants with better performance than other standard silver sols.