Methyl Vanillate

Gamma Irradiation Promotes the Growth Rate of Thai Pigmented Rice As Well As Inducing the Accumulation of Bioactive Compounds and Carbohydrate Hydrolyzing Enzymes Inhibitors (alpha-Glucosidase and alpha-Amylase) under Salt Conditions.[Pubmed:38188088]

Prev Nutr Food Sci. 2023 Dec 31;28(4):463-470.

Rice contains many bioactive compounds that perform various biological activities. Some of these compounds have been identified as alpha-glucosidase and alpha-amylase inhibitors, including guaiacol, vanillin, Methyl Vanillate, vanillic acid, syringic acid, and 2-pentyl furan. In this study, we assessed the growth rate, photosynthetic pigment content, phenolic content, and flavonoid content of gamma-irradiated Thai pigmented rice. Bioactive components of gamma-irradiated rice that had been subjected to salt treatment were also investigated. The findings showed that production of photosynthetic pigments, which are associated with plant growth, was induced by low gamma exposure. Phenolic and flavonoid content of rice was increased after gamma irradiation at 5 to 1,000 Gy. Both gamma irradiation and the salt conditions changed the quantity of vanillin, Methyl Vanillate, and vanillic acid in the rice. However, at a salt concentration of 40 mM, the salt stress had more of an effect than the gamma dosage. However, the high concentrations of Methyl Vanillate and vanillic acid detected in the rice under salt conditions were ameliorated by gamma irradiation. Guaiacol served as the substrate of guaiacol peroxidase for catalyzed reactive oxygen species, as evidenced by the observation that the guaiacol content of rice decreased between increased gamma dosages. A gamma dose of 40 to 1,000 Gy resulted in the production of syringic acid. Under salt stress, syringic acid buildup was also seen to be ameliorated by gamma irradiation. In comparison to salt conditions, particularly for 20 mM salt, gamma irradiation had less of an impact on the 2-pentyl furan in rice.

Bimetallic polyoxometalates catalysts for efficient lignin depolymerization: Unlocking valuable aromatic compounds from renewable feedstock.[Pubmed:37827421]

Int J Biol Macromol. 2023 Dec 31;253(Pt 6):127363.

Lignin, a complex and abundant polymer present in lignocellulosic biomass, holds immense potential as a renewable source for the production of valuable aromatic compounds. However, the efficient depolymerization of lignin into these compounds remains a formidable challenge. Here, we present a promising solution by harnessing polyoxometalates (POMs) catalysts, which exhibit improved catalytic performance and selectivity. We synthesized a series of Ni(x)Co(y)@POMs catalysts (POMs: CsPW or CsPMo) and explored their application in the depolymerization of pine lignin, aiming to investigate the influence of different metal species and doping ratios of POMs on catalytic performance. Through meticulous optimization of reaction conditions, we achieved significant yields of valuable aromatic compounds, including Methyl Vanillate, vanillin, and 4-hydroxy-3-methoxyacetophenone. Furthermore, the Ni(0.75)Co(0.75)@CsPMo catalyst demonstrated exceptional efficacy in catalyzing the cracking process of C-C and/or C-O bonds in a beta-O-4 dimer model compound. Notably, our catalyst exhibited outstanding stability over five cycles, underscoring its suitability as an effective heterogeneous catalyst for cyclic lignin depolymerization. This study sheds light on the potential of POMs-based catalysts for advancing lignin valorization and offers new avenues for sustainable biomass conversion into valuable chemicals.

Optimization and Validation of a Method to Determine Enolones and Vanillin Derivatives in Wines-Occurrence in Spanish Red Wines and Mistelles.[Pubmed:37241968]

Molecules. 2023 May 22;28(10):4228.

Understanding the chemical nature of wine aroma demands accurate quantitative determinations of different odor-active compounds. Quantitative determinations of enolones (maltol, furaneol, homofuraneol, and sotolon) and vanillin derivatives (vanillin, Methyl Vanillate, ethyl vanillate, and acetovanillone) at low concentrations are complicated due to their high polarity. For this reason, this paper presents an improved and automated version for the accurate measure of these common trace wine polar compounds (enolones and vanillin derivatives). As a result, a faster and more user-friendly method with a reduction of organic solvents and resins was developed and validated. The optimization of some stages of the solid phase extraction (SPE) process, such as washing with an aqueous solution containing 1% NaHCO(3) at pH 8, led to cleaner extracts and solved interference problems. Due to the polarity of these type of compounds, an optimization of the large volume injection was also carried out. Finally, a programmable temperature vaporization (PTV) quartz glass inlet liner without wool was used. The injector temperature was raised to 300 degrees C in addition to applying a pressure pulse of 180 kPa for 4 min. Matrix effects were solved by the use of adequate internal standards, such as ethyl maltol and 3',4'-(methylenedioxy)acetophenone. Method figures of merit were highly satisfactory: good linearity (r(2) > 0.98), precision (relative standard deviation, RSD < 10%), high recovery (RSD > 89%), and low detection limits (<0.7 mug/L). Enolones and vanillin derivatives are associated with wine aging. For this reason, the methodology was successfully applied to the quantification of these compounds in 16 Spanish red wines and 12 mistelles. Odor activity values (OAV) indicate that furaneol should be considered an aroma impact odorant in red wines and mistelles (OAV > 1) while homofuraneol and sotolon could also produce changes in their aroma perceptions (0.1 < OAV < 1).

Methyl vanillate for inhibiting the proliferation, migration, and epithelial-mesenchymal transition of ovarian cancer cells via the ZEB2/Snail signaling pathway.[Pubmed:37180664]

Transl Cancer Res. 2023 Apr 28;12(4):828-836.

BACKGROUND: Globally, ovarian cancer is the leading cause of female reproductive-related death, with a 5-year survival rate below 50%. Conventional therapies, such as cancer cell reduction and paclitaxel chemotherapy, have strong toxicity and are prone to drug resistance. Thus, the development of alternatives for the treatment of ovarian cancer is urgently needed. Methyl Vanillate is a principal component of Hovenia dulcis Thunberg. It is known that several cancer cells are inhibited by Methyl Vanillate; however, whether Methyl Vanillate can inhibit the proliferation and migration of ovarian cancer cells still needs to be further studied. METHODS: In this study, cell counting kit 8 (CCK8) was used to examine the effects of methyl vanillic acid on the proliferation of SKOV3 cell lines and human ovarian surface epithelial cell (HOSEpiC) lines. Wound healing and transwell assays were used to determine the effect of Methyl Vanillate on cell migration. The expression of epithelial-mesenchymal transition (EMT) marker proteins (E-cadherin and vimentin), transcription factors (Snail and ZEB2), and skeletal proteins (F-actin) were evaluated with Western blotting. F-actin was detected by immunofluorescence assay. RESULTS: The proliferation and migration of SKOV3 cells were dose-dependently inhibited by Methyl Vanillate, but HOSEpiC cells were not inhibited by low concentrations of Methyl Vanillate. Western blotting analyses revealed a significant decrease in the expression of vimentin and a significant increase in the expression of E-cadherin in SKOV3 cells treated with Methyl Vanillate. This finding indicated that EMT inhibition was induced by the vanillate. Furthermore, Methyl Vanillate inhibited the expression of transcription factors (Snail and ZEB2) in SKOV3 cells as well as cytoskeletal F-actin assembly. CONCLUSIONS: Methyl Vanillate plays an important role in inhibiting EMT and cell proliferation and the migration of ovarian cancer, likely via the inhibition of the ZEB2/Snail signaling pathway. Consequently, Methyl Vanillate may be a promising therapeutic drug for ovarian cancer.

An efficient metal-organic framework-based drug delivery platform for synergistic antibacterial activity and osteogenesis.[Pubmed:36878070]

J Colloid Interface Sci. 2023 Jun 15;640:521-539.

Bone implants for clinical application should be endowed with antibacterial activity, biocompatibility, and even osteogenesis-promoting properties. In this work, metal-organic framework (MOF) based drug delivery platform was used to modify titanium implants for improved clinical applicability. Methyl Vanillate@Zeolitic Imidazolate Framework-8 (MV@ZIF-8) was immobilized on the polydopamine (PDA) modified titanium. The sustainable release of the Zn(2+) and MV causes substantial oxidative damage to Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus). The increased reactive oxygen species (ROS) significantly up-regulates the expression of oxidative stress and DNA damage response genes. Meanwhile, the structural disruption of lipid membranes caused by the ROS, the damage caused by Zinc active sites and the damage accelerated by the MV are both involved in inhibiting bacterial proliferation. The up-regulated expression of the osteogenic-related genes and proteins indicated that the MV@ZIF-8 could effectively promote the osteogenic differentiation of the human bone mesenchymal stem cells (hBMSCs). RNA sequencing and Western blotting analysis revealed that the MV@ZIF-8 coating activates the canonical Wnt/beta-catenin signaling pathway through the regulation of tumor necrosis factor (TNF) pathway, thereby promoting the osteogenic differentiation of the hBMSCs. This work demonstrates a promising application of the MOF-based drug delivery platform in bone tissue engineering.

Inhibitory potential of phenolic compounds of Thai colored rice (Oryza sativa L.) against alpha-glucosidase and alpha-amylase through in vitro and in silico studies.[Pubmed:35620810]

J Sci Food Agric. 2022 Nov;102(14):6718-6726.

BACKGROUND: This study investigated the inhibitory efficiency of phenolic compounds content Methyl Vanillate, syringic acid and vanillic acid against alpha-glucosidase and alpha-amylase. The phenolic compound contents of 10 Thai colored rice cultivars were also determined, and the relationship between the inhibitory efficiency of colored rice extract with Methyl Vanillate, syringic acid and vanillic acid was evaluated. RESULTS: The results revealed that the inhibition efficiency of Methyl Vanillate, syringic acid and vanillic acid was higher against alpha-glucosidase than against alpha-amylase. Inhibitory activity of vanillic acid against alpha-glucosidase and alpha-amylase was highest, with IC(50) of 0.100 +/- 0.01 and 0.130 +/- 0.02 mmol L(-1) , respectively. Docking study showed strong binding by three hydrogen bonds and four hydrogen bonds between vanillic acid with the amino acid in the binding site of alpha-glucosidase and alpha-amylase, respectively. Inhibition modes of these phenolic compounds were defined as a mixed type inhibition against alpha-glucosidase. Highest phenolic compound contents of Methyl Vanillate, syringic acid and vanillic acid were obtained from methanol extracts of all rice cultivars. The methanol extracts of all colored rice cultivars such as Khao Leum Pua also showed the highest inhibition potential against alpha-glucosidase and alpha-amylase. The results indicated that these phenolic compound contents were closely related to the inhibition potential of colored rice extracts against alpha-glucosidase and alpha-amylase. CONCLUSION: Our results suggest that rice, especially colored rice cultivars, has the source of phenolic compounds. Moreover, the phenolic compounds had the greatest source of natural inhibitor against alpha-glucosidase and alpha-amylase. (c) 2022 Society of Chemical Industry.

Induced circular dichroism as a tool to monitor the displacement of ligands between albumins.[Pubmed:35597161]

Spectrochim Acta A Mol Biomol Spectrosc. 2022 Oct 5;278:121374.

The induction of chirality in a ligand can be a powerful analytical tool for studying protein-ligand interactions. Here, we advanced by applying the technique to monitor the inversion of the induced circular dichroism (ICD) spectrum when ligands move between human and bovine serum albumin proteins (HSA and BSA). ICD experiments were performed using dimers of Methyl Vanillate (DVT) and vanillin (DVN). The sign and spectra shape were dependent on the albumin type. DVN presented a positive maximum in 312 nm when complexed with HSA and a negative one in BSA. It was possible to induce and follow the time-dependent displacement of the ligand from BSA (2.2 x 10(6) M(-1)) to HSA (6.6 x 10(5) M(-1)) via ICD inversion. The Molecular Mechanics Generalized Born Surface Area approach was used to calculate the binding free energy of the conformers, and a dissociation pathway for each system was proposed using Umbrella Sampling calculations. Four energy minima dihedral angle conformers were identified, and the corresponding CD spectra were calculated using the quantum chemistry approach. Then, weighted spectra for the conformationally accessible conformers were obtained based on each conformer's Boltzmann probability distribution. In conclusion, the methodology described in the manuscript might be helpful in monitoring the movement of ligands between proteins that they bind.

The dimerization of methyl vanillate improves its effect against breast cancer cells via pro-oxidant effect.[Pubmed:35523312]

Chem Biol Interact. 2022 Jul 1;361:109962.

Phenolic phytochemicals are a group of organic compounds with potent antioxidant features but can also act as powerful pro-oxidants. These characteristics are effective in reducing metastatic potential in cancer cells, and this effect has been associated with reactive oxygen species (ROS). Methyl Vanillate (MV) and its dimer, methyl divanillate (DMV), are potent antioxidants. In the present study, we investigated the effects of MV and DMV on breast cancer cell lines MCF-7 and MDA-MB-231 and compared the results using the non-tumor cell line HB4a. Our results indicated that the compounds performed a pro-oxidant action, increasing the generation of ROS. DMV decreased the viability cell, showing a higher apoptotic effect and inhibition of proliferation than MV on both cell lines, with significant differences between groups (p < 0.05). Some modulation of NOX4, NOX5, and DUOX were observed, but the results did not correlate with the intracellular production of ROS. The dimer showed more effectivity and pro-oxidant effect than MV, impacting cell line MCF-7 in higher extension than MDA-MB-231. In conclusion, and corroborating with reported works, the dimerization of natural phenolic compounds was associated with improved beneficial biological effects as a potential cytotoxic agent to tumor cells.

The anthelmintic drug niclosamide induces GSK-beta-mediated beta-catenin degradation to potentiate gemcitabine activity, reduce immune evasion ability and suppress pancreatic cancer progression.[Pubmed:35115509]

Cell Death Dis. 2022 Feb 3;13(2):112.

Niclosamide, a cell-permeable salicylanilide, was approved by the Food and Drug Administration for its anthelmintic efficiency. A growing body of evidence in recent years suggests that niclosamide exhibits potential tumor-suppressive activity. However, the role and molecular mechanism of niclosamide in pancreatic cancer remain unclear. In this study, niclosamide inhibited proliferation of pancreatic cancer cells (PCCs), induced apoptosis via the mitochondrial-mediated pathway, and suppressed cell migration and invasion by antagonizing epithelial-to-mesenchymal transition. Also, niclosamide inhibited tumor growth and metastasis in pancreatic cancer xenograft mouse models. Mechanistically, niclosamide exerted these therapeutic effects via targeting beta-catenin. Niclosamide did not reduce beta-catenin mRNA expression in PCCs, but significantly downregulated its protein level. Moreover, niclosamide induced beta-catenin phosphorylation and protein degradation. Interestingly, niclosamide also induced GSK-3beta phosphorylation, which is involved in the ubiquitination degradation of beta-catenin. Pharmacological activation of beta-catenin by Methyl Vanillate and beta-catenin overexpression abolished the inhibitory effects of niclosamide. Furthermore, niclosamide potentiated the antitumor effect of the chemotherapy drug gemcitabine and reduced the ability of cancer immune evasion by downregulating the expression levels of PD-L1, which is involved in T cell immunity. Thus, our study indicated that niclosamide induces GSK-beta-mediated beta-catenin degradation to potentiate gemcitabine activity, reduce immune evasion ability, and suppress pancreatic cancer progression. Niclosamide may be a potential therapeutic candidate for pancreatic cancer.

Promoting Candida zemplinina adhesion on oak chips: A strategy to enhance esters and glycerol content of Montepulciano d'Abruzzo organic wines.[Pubmed:34865787]

Food Res Int. 2021 Dec;150(Pt A):110772.

In this study cell surface hydrophobicity and the ability to adhere on abiotic surfaces (polystyrene plates, stainless steel and oak chips) of 10 Candida zemplinina strains were assessed. Moreover, the impact of C. zemplinina cells adhered on oak surface on fermentation kinetics and volatile profile of Montepulciano d'Abruzzo organic wines was evaluated. All strains showed a hydrophobic nature with a certain affinity for the apolar solvents tested (hexadecane and decane). In agreement with this data strains were able to adhere on abiotic surfaces in a strain dependent way. On polystyrene plates all strains mainly grew as planktonic cells. On stainless steel surfaces sessile cells ranged from 2.6 Log CFU/mL (SB2) to 4.1 Log CFU/mL (SB8), while on oak chips were about 2 log higher ranging from 4.3 Log CFU/mL (SB8) to 6.1 Log CFU/mL (SB10). Candida zemplinina sessile state resulted in an increase of glycerol (from 6.98 g/L to 11.92 g/L) and esters amount (from 55.47 g/L to 91.5 mg/L), and a reduction of ethanol content (from 14.13% to 9.12% v/v). As for esters, Methyl Vanillate, ethyl isobutyrate, and ethyl isovalerate were present only when C. zemplinina was adhered on oak chips. This study revealed that changes of concentrations in esters and glycerol content reflected the fermentation bioactivity of yeast cells attached on oak chips. Surface-adhered behaviours should be considered in the improvement of strategies for the development of high-quality organic wines and eventually obtain novel wine styles.

White rot fungal impact on the evolution of simple phenols during decay of silver fir wood by UHPLC-HQOMS.[Pubmed:34322910]

Phytochem Anal. 2022 Mar;33(2):170-183.

INTRODUCTION: Silver fir (Abies alba Mill.) is one of the most valuable conifer wood species in Europe. Among the main opportunistic pathogens that cause root and butt rot on silver fir are Armillaria ostoyae and Heterobasidion abietinum. Due to the different enzymatic pools of these wood-decay fungi, different strategies in metabolizing the phenols were available. OBJECTIVE: This work explores the changes in phenolic compounds during silver fir wood degradation. METHODOLOGY: Phenols were analyzed before and after fungus inoculation in silver fir macerated wood after 2, 4 and 6 months. All samples were analyzed using high-performance liquid chromatography coupled to a hybrid quadrupole-orbitrap mass spectrometer. RESULTS: Thirteen compounds, including simple phenols, alkylphenyl alcohols, hydroxybenzoketones, hydroxycinnamaldehydes, hydroxybenzaldehydes, hydroxyphenylacetic acids, hydroxycinnamic acids, hydroxybenzoic acids and hydroxycoumarins, were detected. Pyrocatechol, coniferyl alcohol, acetovanillone, vanillin, benzoic acid, 4-hydroxybenzoic acid and vanillic acid contents decreased during the degradation process. Methyl Vanillate, ferulic acid and p-coumaric were initially produced and then degraded. Scopoletin was accumulated. Pyrocatechol, acetovanillone and Methyl Vanillate were found for the first time in both degrading and non-degrading wood of silver fir. CONCLUSIONS: Despite differences in the enzymatic pool, both fungi caused a significant decrease in the amounts of phenolic compounds with the accumulation of the only scopoletin. Principal component analysis revealed an initial differentiation between the degradation activity of the two fungal species during degradation, but similar phenolic contents at the end of wood degradation.

A thermostable glycosyltransferase from Paenibacillus polymyxa NJPI29: recombinant expression, characterization, and application in synthesis of glycosides.[Pubmed:34109099]

3 Biotech. 2021 Jul;11(7):314.

Glycosylation is a prominent biological mechanism, affecting the structural and functional diversity of many natural products. In this study, a novel thermostable uridine diphosphate-dependent glycosyltransferase gene PpGT1 was cloned from Paenibacillus polymyxa NJPI29 and recombinantly expressed in B. subtilis WB600. The purified PpGT1 had a molecular weight of 45 kDa, as estimated using SDS-PAGE. The PpGT1 could catalyze the glycosylation of vanillic acid, Methyl Vanillate, caffeic acid, cinnamic alcohol, and ferulic acid. Moreover, PpGT1 possessed good thermostability and retained 80% of its original activity even after 12 h of incubation at 45 degrees C. In addition, PpGT1 remained stable within a neutral to alkaline pH range as well as in the presence of metal ions. The synthesis of Methyl Vanillate 4-O-beta-D-glucoside by purified PpGT1 reached a yield 3.58 mM in a system with pH 8.0, 45 degrees C, 12 mM UDP-Glc, and 4 mM Methyl Vanillate. 3D-structure-based amino acid sequence alignments revealed that the catalytic residues and C-terminated PSPG motif were conserved. These unusual properties indicated that PpGT1 is a candidate UGT for valuable natural product industrial applications. SUPPLEMENTARY INFORMATION: The online version contains supplementary material available at 10.1007/s13205-021-02855-z.

Simple Vanilla Derivatives for Long-Lived Room-Temperature Polymer Phosphorescence as Invisible Security Inks.[Pubmed:33681812]

Research (Wash D C). 2021 Feb 16;2021:8096263.

Developing novel long-lived room-temperature polymer phosphorescence (RTPP) materials could significantly expand their application scope. Herein, a series of RTPP materials based on eight simple vanilla derivatives for security ink application are reported. Attributed to strong mutual hydrogen bonding with polyvinyl alcohol (PVA) matrix, vanilla-doped PVA films exhibit ultralong phosphorescence emission under ambient conditions observed by naked eyes, where Methyl Vanillate shows the longest emission time up to 7 s. Impressively, when vanilla-doped PVA materials are utilized as invisible security inks, and the inks not only present excellent luminescent emission stability under ambient conditions but also maintain perfect reversibility between room temperature and 65 degrees C for multiple cycles. Owing to the unique RTPP performance, an advanced anticounterfeiting data encoding/reading strategy based on handwriting technology and complex pattern steganography is developed.

Bidirectional differentiation of BMSCs induced by a biomimetic procallus based on a gelatin-reduced graphene oxide reinforced hydrogel for rapid bone regeneration.[Pubmed:33426373]

Bioact Mater. 2020 Dec 31;6(7):2011-2028.

Developmental engineering strategy needs the biomimetic composites that can integrate the progenitor cells, biomaterial matrices and bioactive signals to mimic the natural bone healing process for faster healing and reconstruction of segmental bone defects. We prepared the gelatin-reduced graphene oxide (GOG) and constructed the composites that mimicked the procallus by combining the GOG with the photo-crosslinked gelatin hydrogel. The biological effects of the GOG-reinforced composites could induce the bi-differentiation of bone marrow stromal cells (BMSCs) for rapid bone repair. The proper ratio of GOG in the composites regulated the composites' mechanical properties to a suitable range for the adhesion and proliferation of BMSCs. Besides, the GOG-mediated bidirectional differentiation of BMSCs, including osteogenesis and angiogenesis, could be activated through Erk1/2 and AKT pathway. The Methyl Vanillate (MV) delivered by GOG also contributed to the bioactive signals of the biomimetic procallus through priming the osteogenesis of BMSCs. During the repair of the calvarial defect in vivo, the initial hypoxic condition due to GOG in the composites gradually transformed into a well-vasculature robust situation with the bi-differentiation of BMSCs, which mimicked the process of bone healing resulting in the rapid bone regeneration. As an inorganic constituent, GOG reinforced the organic photo-crosslinked gelatin hydrogel to form a double-phase biomimetic procallus, which provided the porous extracellular matrix microenvironment and bioactive signals for the bi-directional differentiation of BMSCs. These show a promised application of the bio-reduced graphene oxide in biomedicine with a developmental engineering strategy.