Veratric Acid Research Articles

Veratric acid alleviates liver ischemia/reperfusion injury by activating the Nrf2 signaling pathway

Oxidative stress following liver ischemia/reperfusion (I/R) is an important pathological mechanism responsible for liver injury. Veratric acid (VA) is a phenolic benzoic acid that has been reported to have antioxidant properties. However, whether VA has protective effects against liver I/R injury remains unclear. In the present study, a mouse liver I/R injury model was established. VA was administered intragastrically for one week before liver I/R. Biochemical indicators, histological analysis, cell apoptosis, oxidative stress, and pathway proteins were tested to evaluate the protective effects of VA on liver I/R injury. Furthermore, a mouse AML12 hepatocyte hypoxia/reoxygenation (H/R) model was used to explore the underlying mechanism. VA alleviated liver I/R injury, as manifested by decreased alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, liver necrotic area, oxidative stress, and hepatocyte apoptosis. VA pretreatment increased the expression of Nrf2 and its downstream antioxidant proteins heme oxygenase-1 (HO-1) and NADPH quinone oxidoreductase 1 (NQO-1). In addition, VA pretreatment increased AML12 cell activity and decreased oxidative stress; it also decreased the apoptosis induced by H/R. Moreover, the protective effect of VA on hepatocytes was related to the activation of the Nrf2 signaling pathway, and to increases in the Nrf2, HO-1, and NQO-1 protein expression. The inhibition of Nrf2 with ML385 offseted VA-mediated protection in AML12 cells. In conclusion, these results suggest that VA protects the liver from oxidative stress and apoptosis induced by liver I/R injury by activating the Nrf2 signaling pathway.

Bioactive Compounds in Sarcocornia and Arthrocnemum, Two Wild Halophilic Genera from the Iberian Peninsula.

(1) Background: this study describes bioactive compounds in the following halophytes: Sarcocornia (S. alpini, S. pruinosa, and S. perennis) and Arthrocnemum (A. macrostachyum). The material comes from: coastal marshes in Tinto River, Guadiana River, and some interior provinces from the Iberian Peninsula. (2) Methods: the techniques used were Folin–Ciocalteu, GC-MS, and ESI-MS/MS. (3) Results: Five phenolic acids were found in Sarcocornia: trans-cinnamic, salicylic, veratric, coumaric, and caffeic acids. In addition, in Arthronemum, ferulic acid was also detected. The obtained flavonoids were cyanidin-3-O-arabinoside, luteolin-7-glucoside, dihydroquercetin, and p-coumaroyl-glucoside. They also presented fatty acids, such as palmitic, linoleic, and oleic acids in Sarcocornia, while palmitic, linolenic, and stearic acids were the main fatty acids in A. macrostachyum. (4) Conclusions: the high diversity of the compounds identified confirms the relation between nutritional interest and salt tolerance in halophytes.

Emerging Role of Dermal White Adipose Tissue in Modulating Hair Follicle Development During Aging.

Hair follicle stem cells are extensively reprogrammed by the aging process, manifesting as diminished self-renewal and delayed responsiveness to activating cues, orchestrated by both intrinsic microenvironmental and extrinsic macroenvironmental regulators. Dermal white adipose tissue (dWAT) is one of the peripheral tissues directly adjacent to hair follicles (HFs) and acts as a critical macroenvironmental niche of HF. dWAT directly contributes to HF aging by paracrine signal secretion. However, the altered interrelationship between dWAT and HF with aging has not been thoroughly understood. Here, through microdissection, we separated dWAT from the skin of aged mice (18 months) and young mice (2 months) in telogen and depilation-induced anagen for transcriptome comparing. Notably, compared with young dWAT, aberrant inflammatory regulators were recapitulated in aging dWAT in telogen, including substantial overexpressed inflammatory cytokines, matrix metalloproteinases, and prostaglandin members. Nonetheless, with anagen initiation, inflammation programs were mostly abolished in aging dWAT, and instead of which, impaired collagen biosynthesis, angiogenesis, and melanin synthesis were identified. Furthermore, we confirmed the inhibitory effect on hair growth of CXCL1, one of the most significantly upregulated inflammation cytokines in aging dWAT. Besides this, we also identified the under-expressed genes related to Wnt signaling fibroblast growth factor family members and increased BMP signaling in aging dWAT, further unraveling the emerging role of dWAT in aging HFs malfunction. Finally, we proved that relieving inflammation of aging dWAT by injecting high-level veratric acid stimulated HF regenerative behavior in aged mice. Concomitantly, significantly decreased TNF-a, CCL2, IL-5, CSF2, and increased IL10 in dWAT was identified. Overall, the results elaborated on the complex physiological cycling changes of dWAT during aging, providing a basis for the potential regulatory effect of dWAT on aging HFs.

Conjugation with Phospholipids as a Modification Increasing Anticancer Activity of Phenolic Acids in Metastatic Melanoma-In Vitro and In Silico Studies.

Phenolic acids possess many beneficial biological activities, including antioxidant and anti-inflammatory properties. Unfortunately, their low bioavailability restricts their potential medical uses, as it limits the concentration of phenolic acids achievable in the organism. The conjugation with phospholipids constitutes one of the most effective strategies to enhance compounds bioavailability in biological systems. In the present study, the conjugates of anisic (ANISA) and veratric acid (VA) with phosphatidylcholine (PC) were investigated. Since both ANISA and VA are inhibitors of tyrosinase, a melanocyte enzyme, the expression of which increases during tumorigenesis, anticancer potential of the conjugates was tested in several metastatic melanoma cell lines. The conjugates proved to be antiproliferative, apoptosis-inducing and cell-cycle-affecting agents, selective for cancerous cells and not affecting normal fibroblasts. The conjugates substituted by ANISA and VA, respectively, at both the sn-1 and sn-2 positions of PC, appeared the most promising, since they were effective against the vast majority of metastatic melanoma cell lines. Additionally, the conjugation of phenolic acids to PC increased their antioxidant activity. Molecular modeling was employed for the first time to estimate the features of the investigated conjugates relevant to their anticancer properties and membrane permeation. Again, the conjugates substituted by phenolic acid at both the sn-1 and sn-2 positions of PC seemed to be presumably most bioavailable.

The study of carboxylic acids in flowers and leaves of Veronica chamaedrys L. and Veronica teucrium L.

The aim. The genus Veronica (Veronica L.), family Plantaginaceae Juss. in the flora of Ukraine is represented by 64 species; Veronica chamaedrys L. and Veronica teucrium L. are widespread in the Kharkiv region. Plants are used in folk medicine as expectorants, anti-inflammatory, diaphoretic, anti-allergic, choleretic, antispasmodic, anticonvulsant, diuretic, sedative, wound healing and antibacterial agents. The aim of this work was to study the carboxylic acids of flowers and leaves of Veronica chamaedrys L. and flowers and leaves of Veronica teucrium L. Materials and methods. The objects of the study were flowers and leaves of Veronica chamaedrys L. and Veronica teucrium L., harvested in the flowering phase in 2018 in Kharkiv region, Ukraine. The study of carboxylic acids was performed by chromatography-mass spectrometry on a 6890N MSD/DS Agilent Technologies chromatograph with a 5973N mass spectrometric detector. Identification of acid methyl esters was performed using data from the mass spectrum library NIST 05 and Willey 2007 in combination with programs for the identification of AMDIS and NIST; also compared the retention time with the retention time of standard compounds. Results. In the flowers and leaves of Veronica teucrium L. 35 carboxylic acids were identified, the total content of which is 5.55 % and 2.93 %, respectively. 31 and 32 carboxylic acids were identified in the flowers and leaves of Veronica chamaedrys L., their total content is 5.39 % and 7.45 %, respectively. Conclusions. It is established that the flowers and leaves of Veronica chamaedrys L. are characterized by a higher content of carboxylic acids compared to the flowers and leaves of Veronica teucrium L. As chemotaxonomic markers of flowers and leaves the following compounds can be used: α-furanic acid for Veronica chamaedrys L.; veratric, 4-hydroxybenzylacetic and syringic acids for Veronica teucrium L. The obtained results will be the basis for further chemotaxonomic studies

Samnamul (Shoots of Aruncus dioicus) Inhibit Adipogenesis by Downregulating Adipocyte-Specific Transcription Factors in 3T3-L1 Adipocytes

Adipocyte-specific transcription factors and antioxidants are considered the best target of obesity. Aruncus dioicus var. kamtschaticus (A. dioicus, Samnamul) is easily available owing to edible and inexpensive. However, the anti-adipogenic effects of the underlying mechanism of A. dioicus extract (ADE) have not yet been reported. In the present study, we evaluate anti-adipogenic pathway in 3T3-L1 adipocytes, antioxidant activities and quantified phenolics using high-performance liquid chromatography of ADE. The results revealed ADE had reduced adipocyte differentiation (0.72-fold vs. MDI (media of differentiation) control), triglyceride (TG; 0.50-fold vs. MDI control, p < 0.001), and total cholesterol contents (0.77-fold vs. MDI control) by regulating adipocyte-specific transcription factors (C/EBPα, PPARγ, and SREBP1) and their downstream mRNA (AdipoQ, Ap2, SREBP1-c, and FAS) levels. Furthermore, ADE has higher total phenol and flavonoid contents and scavenging assay in the DPPH and ABTS+. In particularly, ADE contains chlorogenic acid (7.04 mg/kg), caffeic acid (20.14 mg/kg), ferulic acid (1.74 mg/kg), veratric acid (29.31 mg/kg), cinnamic acid (4.70 mg/kg), and quercetin (4.18 mg/kg). In conclusion, since these phenols, especially quercetin, in the ADE appear to reduce differentiation, TG and cholesterol content by regulating adipocyte-specific transcription factors in adipocytes, ADE has the potential to be developed into a new antioxidant and anti-obesity therapeutics.

Screening of Allelochemicals in Miscanthus sacchariflorus Extracts and Assessment of Their Effects on Germination and Seedling Growth of Common Weeds.

There is increasing interest in the application of bioherbicides because they are less destructive to the global ecosystem than synthetic herbicides. Research has focused on reducing the dependence upon synthetic herbicides by substituting them with environmentally and economically sustainable bioproducts. Allelopathic phytochemicals may be an efficient method for controlling weeds, benefitting both the environment and human health. This study addressed the allelopathic potential of Miscanthus sacchariflorus (MS) extracts on the germination, plant growth, biomass, and biochemical parameters (electrolyte leakage, photosynthetic pigments, and antioxidant enzyme activities) of weeds using laboratory and field experiments. Liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) showed the presence of 22 phenolic compounds, including Orientin, Luteolin, Veratric acid, Chlorogenic acid, Protocatechuic acid, p-Coumaric acid, and Ferulic acid. Leaf extracts of M. sacchariflorus either completely suppressed or partially reduced seed germination and affected the development of weed seedlings (root and shoot length), in a dose-dependent manner. Aqueous extracts of M. sacchariflorus reduced the fresh weight and dry weight, affected the photosynthetic pigment content (chlorophylls, carotenoids), influenced the electrolyte ion leakage, and stimulated the activity of antioxidant enzymes in a species-specific manner. Pearson’s correlation analysis showed that the phenolic compound composition of M. sacchariflorus correlated with the variables tested, indicating that the phytochemicals present in the plant extracts of M. sacchariflorus are a potential source of bio-herbicides.

Bioanalytical Method Development and Validation of Veratraldehyde and Its Metabolite Veratric Acid in Rat Plasma: An Application for a Pharmacokinetic Study.

A simple, sensitive, and rapid UHPLC-MS/MS method was developed for the simultaneous determination of veratraldehyde and its metabolite veratric acid in rat plasma. Cinnamaldehyde was used as an internal standard (IS) and the one-step protein precipitation method with 0.2% formic acid in acetonitrile (mobile phase B) was used for the sample extraction. Reversed C18 column (YMC-Triart C18 column, 50 mm × 2.0 mm, 1.9 µm) was used for chromatographic separation and was maintained at 30 °C. The total run time was 4.5 min and the electrospray ionization in positive mode was used with the transition m/z 167.07 → 139.00 for veratraldehyde, m/z 183.07 → 139.00 for veratric acid, and m/z 133.00 → 55.00 for IS. The developed method exhibited good linearity (r2 ≥ 0.9977), and the lower limits of quantification ranged from 3 to 10 ng/mL for the two analytes. Intra-day precision and accuracy parameters met the criteria (within ±15%) during the validation. The bioanalytical method was applied for the determination of veratraldehyde and veratric acid in rat plasma after oral and percutaneous administration of 300 and 600 mg/kg veratraldehyde. Using the analytical methods established in this study, we can confirm the absorption and metabolism of veratraldehyde in rats for various routes.

Directly Microwave-Accelerated Cleavage of C-C and C-O Bonds of Lignin by Copper Oxide and H2 O2.

Model erythro, phenolic, and nonphenolic lignin β-O-4 dimer compounds are treated with copper oxide and H2 O2 at the electronic field maximum position of a single-mode 2.45 GHz microwave system equipped with a cavity resonator. The products obtained through microwave heating and oil-bath heating with the same reaction vessel and temperature profile are quantitatively compared. Dimer degradation is found to proceed through consecutive elementary reactions. The phenolic dimer is dehydroxylated and this is followed by the spontaneous cleavage of Cα -Cβ and C-O-C bonds to produce guaiacol, vanillin, and vanillic acid. The reaction of the nonphenolic dimer produces veratric acid, veratraldehyde, and guaiacol. Microwave irradiation accelerates cleavage of the side chain and the oxidation of vanillin to vanillic acid. However, no acceleration of veratraldehyde oxidation to veratric acid or aromatic ring cleavage to produce dicarboxylic acids is observed. The selective acceleration of elementary reactions during the degradation of model lignin compounds indicates that microwaves interact with reaction intermediates that are sensitive to electromagnetic waves.

Enzymatic Synthesis of O-Methylated Phenophospholipids by Lipase-Catalyzed Acidolysis of Egg-Yolk Phosphatidylcholine with Anisic and Veratric Acids

Lipase-catalyzed acidolysis reactions of egg-yolk phosphatidylcholine (PC) with anisic (ANISA) and veratric (VERA) acids were investigated to develop a biotechnological method for the production of corresponding biologically active O-methylated phenophospholipids. Screening experiments with four commercially available immobilized lipases indicated that the most effective biocatalyst for the incorporation of ANISA into phospholipids was Novozym 435. None of the tested enzymes were able to catalyze the synthesis of PC structured with VERA. The effects of different solvents, substrate molar ratios, temperature, enzyme loading, and time of the reaction on the process of incorporation of ANISA into the phospholipids were evaluated in the next step of the study. The mixture of toluene/chloroform in the ratio 9:1 (v/v) significantly increased the incorporation of ANISA into PC. The acidolysis reaction was carried out using the selected binary solvent system, 1/15 substrate molar ratio PC/ANISA, 30% (w/w) enzyme load, and temperature of 50 °C afforded after 72 h anisoylated lysophosphatidylcholine (ANISA-LPC) and anisoylated phosphatidylcholine (ANISA-PC) in isolated yields of 28.5% and 2.5% (w/w), respectively. This is the first study reporting the production of ANISA-LPC and ANISA-PC via a one-step enzymatic method, which is an environmentally friendly alternative to the chemical synthesis of these biologically active compounds.

Polycaprolactone/polyvinylpyrrolidone coaxial electrospun fibers containing veratric acid-loaded chitosan nanoparticles for bone regeneration

Veratric acid (3,4-dimethoxy benzoic acid) (VA) is a hydrophobic phenolic phytocompound possessing therapeutic potential, but it has not been reported as actuating bone regeneration to date. Furthermore, delivery of hydrophobic compounds is often impeded in the body, thus depreciating their bioavailability. In this study, VA was found to have osteogenic potential and its sustained delivery was facilitated through a nanoparticle-embedded coaxial electrospinning technique. Polycaprolactone/polyvinylpyrrolidone (PCL/PVP) coaxial fibers were electrospun, encasing VA-loaded chitosan nanoparticles (CHS-NP). The fibers showed commendable physiochemical and material properties and were biocompatible with mouse mesenchymal stem cells (mMSCs). When mMSCs were grown on coaxial fibers, VA promoted these cells towards osteoblast differentiation as was reflected by calcium deposits. The mRNA expression of Runx2, an important bone transcriptional regulator, and other differentiation markers such as alkaline phosphatase, collagen type I, and osteocalcin were found to be upregulated in mMSCs grown on the PCL/PVP/CHS-NP-VA fibers. Overall, the study portrays the delivery of the phytocompound, VA, in a sustained manner to promote bone regeneration.

Comparison of microwave and high‐pressure processing on bound phenolic composition and antioxidant activities of sorghum hull

SummaryThe influence of microwave boiling (MB treated 5, 10 and 15 s was abbreviated as MB5, MB10 and MB15, respectively) and high‐pressure boiling (HB processed 10, 20 and 30 min was denoted as HB10, HB20 and HB30, respectively) processing on the composition and content of bound phenolic substances of sorghum hull and their antioxidant capacity were evaluated. Nine bound phenolic profiles were identified by HPLC‐ESI‐MS/MS, including syringic acid, veratric acid, p‐hydroxybenzonic acid, caffeic acid, sinapic alcohol, ascorbic acid, prenylnaringenin and luteolin. Compared with traditional hot water processing (HP treated 10, 30 and 50 min was abbreviated as HP10, HP30 and HP50, respectively), the content of free procyanidins and total phenolics of sorghum hull treated with HB increased by 35.92–58.87% and 6.20–18.70%, respectively. Sorghum hull treated with HB20 possessed the highest ABTS (ABTS radical scavenging capacity) and FRAP (ferric ion reducing antioxidant power) among all treatment groups.

Furofuranone Lignans from Leucophyllum ambiguum.

Eight furofuranone lignans with an endo,endo relationship between the oxygen atoms, an exo,exo relationship between the aryl groups, and a chair,chair conformation (1-4 and 6-9), in addition to the α-amino acid (3S)-hydroxy-3',4'-dimethoxy-L-phenylalanine (5), veratric acid (10), and β-sitosterol (11), were isolated from the powdered and defatted air-dried aerial parts of Leucophyllum ambiguum. Four of these lignans, ciquitins A-D, 1-4, were isolated for the first time as natural products. The structures of these compounds were established based on their spectrometric/spectroscopic data. Additionally, single-crystal X-ray crystallography confirmed the structure of ciquitin A (1), and derivatization with (9S)-naproxen and X-ray diffraction crystallography data established its absolute configuration. Ciquitins A (1) and B (2) possess a 9-hydroxy group; this chemical characteristic grants these species conformational isomerism not seen in the other six lignans. The conformers of 1 and 2 are distinguishable via their 1H and 13C NMR spectroscopic data. This is the first report of this phenomenon, and hence, a complete assignment of the signals in both spectra of each conformer for each compound is presented. Compounds 1-9 were found to exhibit potent inhibitory activity in the 1.0 × 10-3 to 2.2 μM range against acetylcholinesterase, an enzyme directly involved in the etiology of Alzheimer's disease and senile dementia. Thus, these natural products are promising agents that are potentially useful for the treatment of neurological degeneration.

Determination of Physicochemical Properties, Fatty Acid, Tocopherol, Sterol, and Phenolic Profiles of Expeller–Pressed Poppy Seed Oils from Turkey

AbstractIn this study, the aim was to characterize the physicochemical properties and some bioactive compounds of expeller‐pressed oils of five registered poppy seed varieties (TMO–1, Ofis–8, Ofis–96, Ofis–95, Ofis–3) grown in Turkey. The amounts of total carotenoids, chlorophylls, phenols, and antioxidant activities of oils ranged between 0.08–0.24 mg 100 g−1, 0.03–9.04 mg pheophytin a kg−1, 3.41–8.57 mg gallic acid equivalent 100 g−1, and 5.60–7.33 mM Trolox equivalent 100 g−1, respectively. The most abundant fatty acid in poppy seed oils was linoleic acid (69.85–74.02%), followed by oleic acid (13.98–16.99%), and palmitic acid (8.51–9.75%). In addition, poppy seed oils were rich in β–sitosterol (133.47–153.42 mg 100 g−1), campesterol (45.36–58.60 mg 100 g−1), and δ–5–avenasterol (28.21–39.40 mg 100 g−1). High amounts of γ–tocopherol and α–tocopherol were detected. This research is the first study, which identified and quantified the polyphenol, β–carotene, and lutein compounds of expeller–pressed poppy seed oils by HPLC. Tyrosol, apigenin, syringic acid, 3–hydroxytyrosol, luteolin, p–coumaric acid, quercetin, ferulic acid, sinapic acid, and veratric acid were detected in expeller‐pressed poppy seed oils.

Anti-influenza A virus mechanism of three representative compounds from Flos Trollii via TLRs signaling pathways

Ethnopharmacological relevanceFlos Trollii is the dried flowers of Trollius chinensis. It has been used as a traditional herbal medicine for the treatment of upper respiratory tract infection, tonsillitis and pharyngitis in China for a long history. Veratric acid, vitexin, and trolline are the representative compounds of phenolic acids, flavonoids and alkaloids in this herbal medicine. All of these three compounds show antiviral activity which is related to the efficacy of Flos Trollii. Aim of the studyTo investigate the anti-influenza A virus mechanism of the three representative compounds from the perspective of regulating TLRs signaling pathways, so as to understand the relevant efficacy of Flos Trollii. Materials and methodsInfluenza A virus A/FM/1/47 (H1N1) and mouse peritoneal macrophages (RAW264.7) were used in the whole process of investigation. MTT assay was conducted to select the appropriate experimental concentrations of the three compounds on RAW264.7 cells. Western blot, RT-PCR, and ELISA assays were performed to determine the protein and mRNA expression of key factors and related inflammatory factors of TLRs signaling pathways. Griess method was employed to detect the production of NO. ResultsThe three representative compounds reduced the inflammatory factors including NO, IL-6, and TNF-α and enhanced the production of IFN-β through dynamically regulating the TLRs 3, 4 and 7 pathways. Veratric acid significantly down-regulated the protein expression of TLR3 and IRF3 as well as the mRNA expression of TBK1 and TRIF. Vitexin significantly down-regulated the protein expression of TBK1 and IRF3 as well as the mRNA expression of TLR3, TBK1, TRIF and IRF3 while up-regulated the protein expression of TLR4 and IKKα. Trolline significantly down-regulated the protein expression of TLR7 whereas significantly up-regulated the protein expression of TLR4, IKKα and TAK1. ConclusionsThe three representative compounds from Flos Trollii play their parts in anti-H1N1 viral effect through partially down-regulating TLRs 3 and 7 pathways and up-regulating TLR4 pathway. They counteract the inflammatory injury caused by excessive production of NO, IL-1, IL-6, and TNF-α induced by virus infection and enhance the production of IFN-β so as to eliminate the virus.

Development and validation of veratric acid in Tabebuia avellanedae using liquid chromatography-electrospray ionization-mass spectrometry/mass spectrometry-multiple reaction monitoring-based assay coupled with 1,1-diphenyl-2-picrylhydrazyl method

Objective: The aim of the present study is to develop a new simple, precise, and accurate liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the quantification of veratric acid in Tabebuia avellanedae Linn. Materials and Methods: The quantification of veratric acid was done using collision-induced dissociation multiple reaction monitoring scan of mass spectrometry technique. The developed method was validated according to the International Conference on Harmonization guidelines. The free radical scavenging activity was performed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. Results: The ion transitions of the precursor to the productions were principally protonated ion [M + H]+ at m/z 182.8 >139.20, 124.20, and 77.0 for veratric acid. The proposed method was validated for linearity with an excellent correlation coefficient of 0.9978. The intraday and intermediate precisions and repeatability showed the percentage relative standard deviation was

MASS SPECTROMETRIC CHARACTERIZATION OF PLASMA MEBEVERINE METABOLITES AND ITS SYNTHESIS

Mebeverine is a musculotropic antispasmodic drug that is widely used in the treatment of irritable bowel syndrome. As an ester of mebeverine alcohol and veratric acid, mebeverin is quickly metabolized and is practically undetectable in blood plasma. The main goal of this work was establishing the structure of the main metabolites of mebeverin in human blood plasma. The study was conducted by time-of-flight mass spectrometry (LC-IT-TOF MS), metabolites of mebeverine were extracted from plasma with acetonitrile. When comparing chromatograms of blood plasma obtained before and after drug administration, four main peaks of metabolites were detected. To establish the structure of the compounds, mass spectra of the first and second order were taken. The first-order spectra were used to calculate the metabolite formula and the structure was determined from the fragmentation spectra, as well as by comparing the fragmentation spectra of mebeverine and its proposed metabolites. The proposed compounds were synthesized, and their structure was confirmed using NMR and chromatography-mass spectrometry. Four main metabolites were found in this study: desmethylmebeverine acid (DMAC), glucuronide product of DMAC (DMAC-Glu), mebeverine acid (MAC) and mebeverine alcohol (MAL). The results complement the available literature data about the veratric acid metabolism, urine, and microsomal studies. According to the data obtained, the main metabolite of mebeverine in the blood is DMAC. The concentration of MAC after mebeverine administration is almost ten times less than DMAC, the content of MAL and DMAC-Glu is insignificant, and probably does not affect the pharmacological effect of mebeverine. Therefore, the concentration of DMAC is the main parameter to be monitored in pharmacokinetics studies.

Activity of Adesmia boronioides resinous exudate against phytopathogenic bacteria

Resinous exudate obtained from the aerial parts of Adesmia boronioides Hook.f. were evaluated to determine anti-phytopathogenic effects. Briefly, resinous exudate was obtained by dipping fresh plant material in dichloromethane; chemical composition was determined by GC–MS; and minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were evaluated against four phytopathogenic bacteria. Resinous exudate yield was 8.5% (resin/fresh plant), of which esquel-6-en-9-one (14.25%), esquel-7-en-9-one (5.86%), and veratric acid (2.59%) were the effective antibacterial compounds. Tested against Pectobacterium carotovorum subsp. carotovora, Erwinia amylovora, Bacillus subtilis, and Pseudomonas syringae, MICs and MBCs ranged from 16 to 128 µg/mL and 32–256 µg/mL, respectively. These results provide initial evidence that resinous bush A. boronioides is a new and alternative source of substances with agricultural interest.

Depolymerization of Laccase-Oxidized Lignin in Aqueous Alkaline Solution at 37 °C

Lignin depolymerization is a coveted process for the generation of high-value compounds from a low-cost feedstock. This report describes a chemoenzymatic approach for the depolymerization of lignin involving a laccase-catalyzed oxidation under ambient air at room temperature followed by a base (NaOH)-induced depolymerization in aqueous solution at 37 °C. Two-dimensional nuclear magnetic resonance heteronuclear single quantum coherence spectroscopy, gel permeation chromatography, and liquid chromatography-electrospray ionization-quadrupole-time of flight-mass spectrometry (LC-ESI-Q-TOF-MS) analysis indicated the degradation of lignin and the formation of water-soluble fractions containing guaiacol, syringol, vanillic acid, m-anisic acid, and veratric acid. Furthermore, guaiacol and veratric acid are the main final products in the chemoenzymatic decomposition of a β-O-4 model compound.

Solvent and temperature effects on the solubility of syringic, vanillic or veratric acids: Experimental, modeling and solid phase studies

The solubility of syringic acid, vanillic acid and veratric acid was measured in pure water and eleven organic solvents (methanol, ethanol, 1-propanol, 2-propanol, 2-butanone, ethyl acetate, acetonitrile, dimethylformamide, 1,2-propanediol, 1,3-propanediol and 1,3-butanediol), at 298.2 K and 313.2 K. Besides the solubility data, the melting temperatures and enthalpies of the solutes were determined by differential scanning calorimetry, while powder and single X-ray diffraction were used to resolve the solute solid structure, before and after the solubility studies.For modeling purposes, the NRTL-SAC model, also combined with the Reference Solvent Approach (RSA), and the Abraham solvation model were applied to describe the solid-liquid equilibria of the binary systems. A set of solvents was used to estimate the model parameters and afterwards, solubility predictions were carried out for binary systems not included in the correlation step. Better results were obtained using the Abraham solvation model with average relative deviations (ARD) of 15% for the correlation set and 26% for the predictions, which are more satisfactory than the results found with the NRTL-SAC model (33% for the correlation and 59% for the predictions) or the NRTL-SAC model combined with RSA (30% for the correlation and 59% for the predictions).