Ferulic Acid Derivatives Research Articles

Bioassay-guided isolation and antiproliferative efficacy of extract loaded in chitosan nanoparticles and LC-QTOF-MS/MS analysis of Achillea magnifica

This study investigated the antioxidant, anti-urease, anticholinesterase, and antiproliferative activities of different extracts of A. magnifica. The active compounds were isolated from chloroform extract, which has the strongest antiproliferative and antioxidant activities. The structures of the isolated compounds (elenolic acid, luteolin, eupatilin) were examined using spectroscopic techniques (NMR, UV, HR-MS). The antioxidant and antiproliferative effects of isolated compounds showed lower biological activity than those of the chloroform extract. Therefore, chitosan nanoparticles were prepared with this extract and characterized. The cytotoxic activities of the chitosan nanoparticles were examined, and they were found to have a strong antiproliferative activity similar to that of the chloroform extract. The ethanol extract had strong anti-urease and anticholinesterase activity compared with other extracts. Therefore, phenolic compounds that might be responsible for the biological activity were analysed by LC-QTOF-MS/MS. The ferulic acid derivative, apigenin-6-C-pentoside-8-C-hexoside, apigenin 6,8-di C-hexoside, vitexin, and diosmetin 8-C-glucoside (orientin 4′-methyl ether) compounds from this plant were analysed for the first time. The results showed that the chloroform-loaded chitosan nanoparticles had a strong antiproliferative activity in breast cancer cell lines (MCF-7, MDA-MB-231) and no toxic effect on normal cell lines (L-929), which suggested that this extract might be a potential candidate as a herbal medicine that can be investigated and evaluated in future cancer studies. Additionally, the potential use of ethanol extract as an anti-urease and anticholinesterase agent was revealed.

Changes in phenolic compounds and antioxidant capacity of Andean raspberries in response to Peronospora sparsa

In Colombia, the Andean raspberry (Rubus glaucus Benth) is of large economic significance because of its use in industry and widespread consumption as a fresh fruit. However, this crop is highly susceptible to disease by Peronospora sparsa, a fungus that causes between 50 % and 70 % production loss. Plants respond to pathogen-induced damage by increasing the production of specific secondary metabolites, such as phenolic compounds, which have broad industrial applications. This work estimated the antioxidant capacity and phenolic content of healthy and Peronospora sparsa-infected Andean raspberry fruits. Antioxidant capacity was analyzed by DPPH and FRAP methods, while phenolic compounds were analyzed by high performance liquid chromatography coupled to diode array detection (HPLC-DAD). According to the DPPH method, antioxidant capacity increased from 45.9 ± 1.61 µmol TE g−1 fresh sample in healthy fruits to 67.02 ± 0.58 µmol TE g−1 fresh sample in affected fruits. The FRAP method revealed an antioxidant response difference from 5.19 ± 0.8 mmol TE 100 g−1 fresh sample in healthy fruits vs. 10.97 ± 0.27 mmol TE 100 g−1 fresh sample in affected fruits. The phenolic compound content was observed in a range of 4.14 ± 1.16 to 72.03 ± 26.68 mg GAE L−1 for healthy fruits and from 4.48 ± 1.76 to 221.89 ± 1.18 mg GAE L−1 for affected fruits. Phenolic acids were the main phenols detected, encompassing derivatives of gallic acid, chlorogenic acid, ferulic acid, ellagic acid, and p-coumaric acid. This work confirmed that the Peronospora sparsa-infected berries contained relatively more antioxidants and phenolic acid compounds than their healthy counterparts, and that this difference was likely due to a defense mechanism to cope with pathogen-induced damage.

Construction of cinnamic acids derived β-cyclodextrins and their emodin-based inclusions with enhanced water solubility, excellent antioxidant and antibacterial activities

β-Cyclodextrin (β-CD) is a natural macromolecule which has been regarded as a promising biomaterial and drug carrier. However, the poor water solubility and less functions of β-CD severely hinder its potential applications. Herein, we modified the β-CD with three cinnamic acid derivatives (ADs) of ferulic acid (FA), p-coumaric acid (p-CA) and caffeic acid (CA) by sulfonylation, amination and amidation. The resulted β-CD-ADs are β-CD-FA, β-CD-p-CA and β-CD-CA, which were confirmed by proton nuclear magnetic resonance (1H NMR) and high resolution mass spectrometry (HRMS). Compared to β-CD, the β-CD-ADs show enhanced water solubility (>600 mg/mL) and excellent antioxidant property in scavenging DPPH radicals. Furthermore, the inclusion complex of between emodin (ED) and β-CD-ADs were prepared and characterized by 1H NMR, fluorescence spectroscopy, X-ray diffraction (XRD) and differential scanning calorimetry (DSC). The ED/β-CD-ADs inclusions had antioxidant activity because of chemical modification of cinnamic acid derivatives, especially for ED/β-CD-CA, which had the highest DPPH radical scavenging rate. The three ED/β-CD-ADs inclusions showed excellent antibacterial activity against S. aureus with the bactericidal rates beyond 97 %. Additionally, the ED/β-CD-ADs inclusions exhibited good blood compatibility by in-vitro hemolysis assay. This work provides an efficient way to modify β-CD with enhanced water solubility and more functional that could facilitate the application of β-CD in medicine and cosmetic.

QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP STUDY OF ESTER-BASED FERULIC ACID DERIVATIVES AGAINST CERVICAL CANCER CELL (HELA)

Quantitative structure-activity relationship (QSAR) has been studied for ferulic acid derivatives to determine the QSAR model able to predict anticancer. As the subject of this research was a set of experimentally calculated IC50 value data of 6 ferulic acid derivatives against cervical cancer cells (HELA).
 QSAR analysis was based on multilinear regression calculation on fitting subset using log (1/IC50) as the dependent variable, and dipole moment, partition coefficient in the n-octanol/water, and atomic net charges of the aromatic carbons as independent variables. The values of the descriptors were
 obtained from semiempirical PM3 quantum mechanic calculation. The relationship between log (1/IC50) and the descriptors was described by the result in the QSAR model. The QSAR model for ferulic acid derivatives against HELA cell lineswas developed with the statistical parameters of R=0.998; R2=0.999; SE=0.00857; and F=394. The calculated log (1/IC50) using QSAR Hansch Model for ferulic acid derivatives have excellent agreement with experimental data of Log (1/IC50).

Fluorinated-antioxidant derivatives with improved pharmacological activity: a theoretical study

It has become obvious that fluorinated drugs have a significant role in medicinal applications. In this study, the fluorination of ferulic acid (FA) antioxidant was investigated using density functional theory calculations. We have explored the most important chemical properties of FA that affects the pharmacological activity of antioxidant. We found that the intramolecular hydrogen bonding and charge transfers of the FA were influenced by fluorine substitution. Our results also reveal that the fluorination altered the stability, solubility and molecular polarity of the FA. Moreover, our results show that the electronic spectra of fluorinated derivatives of FA exhibit the red and blue shifts toward higher and lower wavelengths, respectively, compared to the original FA. Our calculations show that the free energy transfer of fluorinated derivatives of the FA in water was negative that it meant that the designed molecules dissolving in aqueous phase occurred simultaneously. We also found that the fluorination can increase the first hyperpolarizability of the FA. Our results present an efficient strategy to improve the nonlinear optical responses of the antioxidants. Consequently, the results of present study show that the fluorination of FA could be considered as a promising strategy to design useful drugs with better pharmacological properties. Fluorination is an effective strategy to improve pharmacological activity of frulic acid antioxidant. Communicated by Ramaswamy H. Sarma

Chemical Characterization and Bioactive Properties of Different Extracts from Fibigia clypeata, an Unexplored Plant Food.

Fibigia clypeata (L.) Medik. is a poorly studied plant species belonging to the Brassicaceae family, and usually used as cress in the salads. The current investigation aimed at assessing the antioxidant potential and inhibitory activity of ethyl acetate, methanol, and aqueous extracts of F. clypeata against key enzymes targeted in the management of type II diabetes (α-amylase and α-glucosidase), Alzheimer’s disease (acetylcholinesterase and butyrylcholinesterase), and skin hyperpigmentation (tyrosinase). Cytotoxicity of the extracts was also determined using normal VERO and cancer FaDu and SCC-25 cell lines. Besides, LC-MS was employed to investigate the detailed phytochemical profiles of the extracts. The methanol extract showed potent enzyme inhibitory activity (4.87 mg galantamine equivalent/g, 3.52 mg galantamine equivalent/g, 126.80 mg kojic acid equivalent/g, and 24.68 mg acarbose equivalent/g, for acetylcholinesterase, butyrylcholinesterase, tyrosinase, and α-glucosidase, respectively) and antioxidant potential (96.52, 109.10, 154.02, and 104.85 mg trolox equivalent/g, for DPPH, ABTS, CUPRAC, and FRAP assays, respectively). Interestingly, caffeic acid-O-hexoside derivative, caffeyl alcohol O-glucopyranoside, and ferulic acid derivative were identified in all extracts. F. clypeata extracts showed no cytotoxicity towards VERO cell line and a weak cytotoxic potential against FaDu and SCC-25 cell lines. Interesting scientific evidence gathered from the present study support further investigation on F. clypeata in the view of designing and developing a novel therapeutic agent for the management of Alzheimer’s disease, type II diabetes, skin hyperpigmentation problems, as well as cancer.

Improvement of the Solubility and Evaluation of the Physical Properties of an Inclusion Complex Formed by a New Ferulic Acid Derivative and γ-Cyclodextrin.

Ferulic acid derivative 012 (FAD012) is a ferulic acid (FA) derivative. The current study prepared a solid dispersion of FAD012 and γ-cyclodextrin (γCD) and ground it using a three-dimensional ball mill (3DGM) to prepare an inclusion complex. This study also assessed the physicochemical properties such as solubility of that complex. A Job’s plot indicated that FAD012 and γCD formed an inclusion complex at a molar ratio of 1:1. Phase solubility diagrams revealed that FAD012 produced a BS diagram. According to PXRD, FAD012 produced a diffraction peak at 2θ = 7.0° and γCD produced a diffraction peak at 2θ = 9.1°. Those two peaks were not produced by the 3DGM, but new peaks (2θ = 7.3 and 16.5°) were evident. DSC patterns revealed an endothermic peak due to the melting of FAD012 at 190 °C, but no endothermic peaks were evident with the 3DGM. NIR spectra of the 3DGM indicated that the methyl group of FAD012 produced a higher peak and that the OH groups of γCD produced a higher peak. 1H-1H ROESY NMR spectra (D2O) revealed cross peaks for protons of the methyl group of FAD012 and a proton (H-3) in the cavity of γCD, so FAD012 presumably interacts with the wide opening of the γCD torus. A solubility test (25 °C) indicated that solubility improved about 5-fold for the 3DGM in comparison to the solubility of FAD012 alone (about 140 μg/mL). Based on these findings, an FAD012/γCD complex was formed by cogrinding, and its solubility improved. These observations are expected to expand the usefulness of cogrinding of FAD012 with γCD using a 3D ball mill.

Structure-based drug design of peroxisome proliferator-activated receptor gamma inhibitors: ferulic acid and derivatives

Peroxisome proliferator-activated receptor gamma (PPARγ), ligand-activated transcription factor, is a key modulator of genes considered in diabetes development as well as treatment. Adipogenesis differentiation through PPARγ, CCAAT-enhancer protein alpha (C/EBPα) is identified as a critical mechanism in fat accumulation and weight gain. Polyphenols studied against adipocyte differentiation is taken up for consistent support and drug discovery. Structure-based drug design found useful to distinguish the underlying mechanism of receptor–ligand interaction and function. In this work, phenolic acids, ferulic acid and its derivatives are used as ligands. Molecular parameters have been set to filter and sort the 34 derivatives from ZINC and PubChem databases. Besides, for affinity and activity identification, troglitazone and resveratrol co-crystallized ligands have been studied. Absorption, distribution, metabolism, elimination and toxicity, density functional theory, highest occupied molecular orbital–lowest unoccupied molecular orbital values and docking scores define the drug candidate as a potential inhibitor. Residues Ser 342 and Arg 280 bind with the ligands by forming hydrogen bonds and hydrophobic contacts. Based on the docking score, pharmacophore properties and functional energy values of the top six compounds are chosen for molecular dynamics and simulation. Consistency and stability maintained throughout the simulation up to 50 ns were observed. Free binding energy values and standard deviation of receptor and ligand calculated using molecular mechanics–generalized Born and surface area solvation method (MM_GBSA) is found significant. Therefore, ferulic acid derivatives and phenolic acids could be a potential inhibitor for adipocyte differentiation and lipid accumulation. Communicated by Ramaswamy H. Sarma

Design, synthesis & biological evaluation of ferulic acid-based small molecule inhibitors against tumor-associated carbonic anhydrase IX

Carbonic anhydrase IX (CAIX) is an emerging drug target for hypoxia associated cancers. To identify potent and selective inhibitors of CAIX, a small library of ferulic acid (FA) derivatives bearing triazole moiety has been designed, synthesized and evaluated against different human CA isoforms (CAII, CAVA & CAIX). Though most of the compounds showed CAIX inhibition in the micromolar range, compound 7i selectively inhibits CAIX in the nanomolar range (IC50 = 24 nM). In silico analysis revealed binding of 7i with the catalytically important amino acid residues of CAIX. Further, cell-based studies indicate that 7i inhibits the activity of CAIX, decreases the epithelial to mesenchymal transitions, induces apoptosis, inhibits cell migration and colonization potential of cancer cells. Taken together, these results emphasized the use of 7i as a prospective pharmacological lead molecule in CAIX targeted anticancer therapeutics.

Antigenotoxic, Anti-photogenotoxic, and Antioxidant Properties of Polyscias filicifolia Shoots Cultivated In Vitro.

Traditional medicinal plants are an important source of active compounds with potential antimutagenic activity. Polyscias filicifolia Bailey (Araliaceae) is a South Asian traditional herb used as an adaptogenic and cardiac drug. Extracts of P. filicifolia contain a wide range of biologically active compounds like phenolic acids and triterpenoid saponins. In the present study. antigenotoxic potential of three naturally occurring phenolic acids and extracts of P. filicifolia growing in vitro with the addition of elicitors was evaluated against direct (4-nitroquinoline-N-oxide (4NQO) and mitomycin C (MMC)) and indirect mutagens (2-aminoanthracene (2AA)). The evaluation was made using a bacterial umu-test. Moreover, the ability to prevent photogenotoxicity induced by chlorpromazine (CPZ) under UVA irradiation was measured. The phytochemical profiling of examined extracts revealed the presence of numerous compounds with the prevelance of chlorogenic, caffeic, and ferulic acid derivatives; however, saponin fractions were also determined. The antioxidant potential of extracts strictly correlated with their composition. The tested extracts exhibited high antigenotoxic activity if the assay was performed with 2AA and metabolic activation. Moreover, the extracts slightly decreased the MMC-induced genotoxicity. However, an increase of the genotoxic effect was observed in the assay performed with 4NQO. In addition, photo-antigenotoxic activity was observed. In our study, phenolic acids exhibited lower activity than the extracts.

Umbelliprenin as a novel component of the phytochemical pool from Artemisia spp

Plants belonging to Artemisia spp. are known to biosynthesize a wide panel of 3,3-dimethylallyl- and sesquiterpenyl- substituted coumarins. In this short communication we applied a novel extraction methodology based on the use of subcritical butane under a counter-current mode to further characterize the presence of selected biologically active oxyprenylated phenylpropanoids, namely coumarins and ferulic acid derivatives, in extracts deriving from aerial parts of Artemisia vulgaris L. (commonly known as “common mugwort”) (Asteraceae). In the mean time, we assessed the efficiency of the above mentioned extractive methodology with other routes like maceration and ultrasounds and microwaves-based methods using absolute EtOH as the solvents. UHPLC analysis coupled to UV/Vis detection revealed that, among the 5 pure chemical standard assayed, only umbelliprenin (7-farnesyloxycoumarin) was recorded, while boropinic acid, 4′-geranyloxyferulic acid, 7-isopentenyloxycoumarin, and auraptene were not detected. The best extractive yield (0.18 %) was obtained after extaction with subcritical butane. The presence of umbelliprenin in Artemisia plant species has been reported herein for the first time. This coumarin may represent the biosynthetic precursors of sesquiterpenyloxycoumarins with more complex structures typically found in this genus.

Characterization of 6-bromoferulic acid as a novel common-use matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.

Ferulic acid (FA) is a standard matrix used for analyzing proteins. In this study, the ability of a halogenated FA to serve as an effective MALDI matrix was investigated. Various halogenated FAs were synthesized, and the characteristics and performance of each were compared with those of the standard matrices α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydrobenzoic acid (DHBA). The abilities of 6-bromoferulic acid (6-BFA), ferulic acid (FA), and eight other halogenated FA derivatives to ionize eight synthetic peptides were examined. Absorption measurements, MM2 structure optimizations, and proton affinity (PA) calculations were also performed for 6-BFA and FA. The suitabilities of these compounds as matrices for matrix-assisted laser desorption/ionization (MALDI) for lipids, sugar chains, polymers, cyanocobalamin, synthetic peptides, and tryptic peptides originating from two types of serum proteins were also tested. The 6-position of FA was found to be the best site for introducing a bromine because the generated compound allowed facile detection of cyanocobalamin and several peptides. 6-BFA exhibited good sensitivity for large peptides (3-5 kDa) and peptides containing acidic amino acids or proline. 6-BFA was also shown to be a suitable matrix for tandem mass spectrometry (MS/MS) analysis when using MALDI time-of-flight (TOF) mass spectrometry (MS) with a quadrupole ion trap (QIT) system. The properties of 6-BFA as a MALDI matrix differed from those of DHBA and CHCA. 6-BFA appears to be a useful matrix for de novo sequencing using MALDI-QIT-TOF-MS.

Propolis Consumption Reduces Nosema ceranae Infection of European Honey Bees (Apis mellifera).

Nosema ceranae is a widespread obligate intracellular parasite of the ventriculus of many species of honey bee (Apis), including the Western honey bee Apis mellifera, in which it may lead to colony death. It can be controlled in A. mellifera by feeding the antibiotic fumagillin to a colony, though this product is toxic to humans and its use has now been banned in many countries, so in beekeeping, there exists a need for alternative and safe products effective against N. ceranae. Honeybees produce propolis from resinous substances collected from plants and use it to protect their nest from parasites and pathogens; propolis is thought to decrease the microbial load of the hive. We hypothesized that propolis might also reduce N. ceranae infection of individual bees and that they might consume propolis as a form of self-medication. To test these hypotheses, we evaluated the effects of an ethanolic extract of propolis administered orally on the longevity and spore load of experimentally N. ceranae-infected worker bees and also tested whether infected bees were more attracted to, and consumed a greater proportion of, a diet containing propolis in comparison to uninfected bees. Propolis extracts and ethanol (solvent control) increased the lifespan of N. ceranae-infected bees, but only propolis extract significantly reduced spore load. Our propolis extract primarily contained derivatives of caffeic acid, ferulic acid, ellagic acid and quercetin. Choice, scan sampling and food consumption tests did not reveal any preference of N. ceranae-infected bees for commercial candy containing propolis. Our research supports the hypothesis that propolis represents an effective and safe product to control N. ceranae but worker bees seem not to use it to self-medicate when infected with this pathogen.

Tributyltin(IV) ferulate, a novel synthetic ferulic acid derivative, induces autophagic cell death in colon cancer cells: From chemical synthesis to biochemical effects

Ferulic acid (FA) is a natural phenolic phytochemical that has low toxicity and exhibits therapeutic effects against various diseases, behaving as an antioxidant. FA also displays modest antitumor properties that have been reported at relatively high concentrations. With the aim of improving the anti-tumor efficacy of FA, we synthesized the novel compound tributyltin(IV) ferulate (TBT-F). The coordination environment at the tin center was investigated spectroscopically. Following synthesis, chemical characterization and computational analysis, we evaluated TBT-F effects in colon cancer cells. The results showed that TBT-F, at nanomolar range concentrations, was capable of reducing the viability of HCT116, HT-29 and Caco-2 colon cancer cells. On the other hand, FA was completely inefficacious at the same treatment conditions. Cell viability reduction induced by TBT-F was associated with G2/M cell cycle arrest, increase in membrane permeabilization and appearance of typical morphological signs. TBT-F-induced cell death seemed not to involve apoptotic or necroptotic markers whereas autophagic vacuoles appearance and increase in LC3-II and p62 autophagic proteins were observed after treatment with the compound. The autophagy inhibitor bafylomicin A1 markedly prevented the effect of TBT-F on colon cancer cells, thus indicating that autophagy is triggered as a cell death process.Taken together, our results strongly suggest that the novel ferulic derivative TBT-F is a promising therapeutic agent for colon cancer since it is capable of triggering autophagic (type-II) cell death that may be important in case of resistance to classic apoptosis.

Identification and quantitative determination of feruloyl-glucoside from hairy root cultures of Turbinicarpus lophophoroides (Werderm.) Buxb. & Backeb. (Cactaceae)

Transformed hairy root cultures have become an alternative for the biosynthesis of plant secondary metabolites with biological activities. In this present work, the effects of liquid Murashige and Skoog (MS) and Gamborg B5 (B5) medium on kinetic behavior, biomass and phenolic metabolite production were analyzed in Turbinicarpus lophophoroides (Werderm.) Buxb. & Backeb. hairy root cultures. Liquid MS medium showed the highest biomass production (13.67 g L−1 dry weight) after 77 d of culture. For B5 medium, highest biomass was achieved sooner, at day 56, but with lower total biomass (8.10 g L−1 dry weight). After isolation, structural elucidation of the major compound present in T. lophophoroides hairy roots was determined by nuclear magnetic resonance and mass spectral analysis. As a result, a ferulic acid derivative (feruloyl-glucoside) was isolated from T. lophophoroides hairy roots and reported for the first time. Quantitative analysis indicated that feruloyl-glucoside was the major phenolic metabolite at 56 d of growth in MS medium (2.7267 ± 0.041 mg g−1 dry weight L−1) and at 7 and 35 d in B5 medium (2.6328 ± 0.108 and 2.4372 ± 0.026 mg g−1 dry weight L−1, respectively). The feruloyl-glucoside was not detected in untransformed roots (control). The present results suggested the potential of T. lophophoroides hairy roots culture for the production of this phenolic glycoside.

Identification of hydroxycinnamic acid derivatives of selected canadian and foreign commercial beer extracts and determination of their antioxidant properties

Phenolic compounds in beer are derived from grains and hops during processing and production. Thus, the total phenolic content (TPC) of beer extracts, from selected Canadian and foreign commercial, and laboratory produced beers were examined and ranged from 3.72 ± 0.23 to 13.73 ± 0.49 mg GAE/100 mL beer. The total flavonoid content (TFC) of the same beer extracts varied from 0.82 ± 0.02 to 5.28 ± 0.04 mg CE/100 mL beer. Of particular interest were the hydroxycinnamic acids (HCAs) and derivatives in beer extracts because of their antioxidant properties. Main HCAs and a key derivative of ferulic acid, 4-vinylguaiacol (4-VG), were identified in beer extracts by high performance liquid chromatography (HPLC). Significant variations in TPC, TFC, HCAs and 4-VG content were observed among the beer extracts. Antioxidant activities of beer extracts, determined by radical scavenging and ferric-reducing assays, were positively correlated (p < 0.05) with TPC, TFC, and 4-VG but observed negative correlation with individual HCAs (p > 0.05). The positive correlation of 4-VG with ABTS radical cation scavenging and reducing power assays is reported first time. These findings suggest that phenolic compounds and a key derivative of the hydroxycinnamic acid, 4-VG, may have the protective role in the beer as an antioxidant.

Hydrophilic Glyceryl Ferulates Preparation Catalyzed by Free Lipase B from Candida antartica.

Ferulic acid (FA), 4-hydroxyl-3-methoxy-2-benzylacrylic acid, has antioxidant, anticancer and ultraviolet absorption activities. However, the low hydrophilicity of FA has limited its application. Glyceryl ferulate (FG), which is an all-natural hydrophilic derivative of FA, can be used as an antioxidant and UV filter in food and cosmetic formulations. However, the applications of FG in these fields are limited due to its low content in nature. In this work, free liquid lipase was firstly used as a catalyst for FG preparation. Several different free liquid lipases (Candida antartica lipase-B, Candida antartica lipase-A, Thermomyces lanuginosus (Lipozyme TL 100L)) were screened and compared. The effects of the transesterification parameters (time, temperature, enzyme load and substrate ratio) were optimized and evaluated by response surface methodology. A reaction thermodynamic investigation was also performed. The results showed that, among the tested free lipases, the maximum FG yield (84.8±1.5%) was achieved using free Candida antartica lipase-B. Under the optimized conditions (an atmospheric system, an enzyme load of 11.1% and a 20:1 molar ratio of glycerol to EF at 70°C for 39.5 h), the FG yield and EF conversion were 84.8±1.5% and 95.7±1.2%, respectively. The activation energies of FG formation and EF conversion were 56.4 and 58.0kJ/mol, respectively.

Lipophilic ferulic acid derivatives protect PC12 cells against oxidative damage via modulating β-amyloid aggregation and activating Nrf2 enzymes.

Ferulic acid (FA) has been shown to have a neuroprotective effect on Alzheimer's disease induced by amyloid-beta (Aβ) neurotoxicity. This work aims to ascertain the structure-activity relationship of FA and its alkyl esters (FAEs) for evaluating the antioxidant activities in PC12 cells and Aβ1-42 aggregation inhibitory activities in vitro, as well as the signaling mechanisms against oxidative stress elicited by Aβ1-42 in PC12 cells. Our data showed that alterations in the subcellular localization and cytotoxicity of FAEs caused by the lipophilicity of FA were crucial when evaluating their antioxidant capacities. Pre-treating cells with butyl ferulate (FAC4) significantly attenuated Aβ1-42-evoked intracellular ROS formation. Besides, FAC4 exhibited the highest Aβ1-42 aggregation inhibitory effectiveness. The molecular docking results showed that FAC4 binds to amide NH in Gln15 and Lys16 via a hydrogen bond. Notably, FAC4 could upregulate antioxidant defense systems by modulating the Keap1-Nrf2-ARE signaling pathway. Identification of the functions of FAEs could be useful in developing food supplements or drugs for treating AD.

Phenolic Compounds with Antioxidant Properties from Canola Meal Extracts Inhibit Adipogenesis.

The extraction of phenolic compounds from canola meal produces functional health products and renders the canola meal a more digestible animal feed. The extracted phenolics may have novel bioactivity worth investigation. In this study, several solvents were evaluated for their ability to extract phenolic compounds from canola meal: water (WE) and various 80% organic solvent/water mixtures of methanol (ME), acetone (AE), ethanol (EE), butanol (BE), chloroform (CE) and hexane (HE). The in vitro antioxidant and anti-obesity properties of various extracts were investigated. Anti-obesity properties were studied using adipogenic differentiation inhibition of a murine mesenchymal stem cell line (C3H10T1/2) and a pancreatic lipase inhibition assay. AE, ME, and BE showed significant (p < 0.05) adipogenesis and pancreatic lipase inhibitory activities and may have more pharmacological properties. AE down-regulated the gene expression of the major adipogenic transcription factor, peroxisome proliferator-activated receptor gamma (PPARγ), correlating to phenolic content in a dose-dependent manner. The chemical characterization of AE revealed the presence of sinapic acid, ferulic acid, and kaempferol derivatives as main bioactive phenols.

Novel ferulic acid and benzophenone derivatives from the flower buds of Syzygium aromaticum

Phytochemical investigation of clove resulted in the isolation of two new natural compounds, a ferulic acid derivative, sabrinic acid (1) and a benzophenone derivative (2) together with two known compounds kaempferol-3,5-dimethyl ether (3) and 4-methyl benzoic acid (4). Compounds 3 and 4 were isolated for the first time from the genus Syzygium. The structures of compounds were elucidated through modern spectroscopic techniques including 1D and 2D NMR spectroscopy.