Genomes and Genes
Summary: A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13).
- Rajeshkumar N, Kuttan R. Modulation of carcinogenic response and antioxidant enzymes of rats administered with 1,2-dimethylhydrazine by Picroliv. Cancer Lett. 2003;191:137-43 pubmed..Picroliv treated liver resembled normal liver except the presence of a few degenerating cells. Renal anatomy was not altered by DMH administration. ..
- Itoh A, Isoda K, Kondoh M, Kawase M, Kobayashi M, Tamesada M, et al. Hepatoprotective effect of syringic acid and vanillic acid on concanavalin a-induced liver injury. Biol Pharm Bull. 2009;32:1215-9 pubmed..The major phenolics in L.E.M., syringic acid and vanillic acid, were intraperitoneally injected into mice shortly before the ConA treatment. Similar to L.E.M...
- Segura A, Bünz P, D Argenio D, Ornston L. Genetic analysis of a chromosomal region containing vanA and vanB, genes required for conversion of either ferulate or vanillate to protocatechuate in Acinetobacter. J Bacteriol. 1999;181:3494-504 pubmed
- Abdelkafi S, Sayadi S, Ben Ali Gam Z, Casalot L, Labat M. Bioconversion of ferulic acid to vanillic acid by Halomonas elongata isolated from table-olive fermentation. FEMS Microbiol Lett. 2006;262:115-20 pubmed..from table-olive fermentation is the first halophilic bacterium to be shown to transform ferulic acid to vanillic acid under hypersaline conditions...
- Dhananjaya B, Nataraju A, Rajesh R, Raghavendra Gowda C, Sharath B, Vishwanath B, et al. Anticoagulant effect of Naja naja venom 5'nucleotidase: demonstration through the use of novel specific inhibitor, vanillic acid. Toxicon. 2006;48:411-21 pubmed..b>Vanillic acid selectively and specifically inhibited 5'nucleotidase activity among other enzymes present in N. naja venom...
- Thanbichler M, Iniesta A, Shapiro L. A comprehensive set of plasmids for vanillate- and xylose-inducible gene expression in Caulobacter crescentus. Nucleic Acids Res. 2007;35:e137 pubmed..Since many of these constructs are also suitable for use in other bacteria, this work provides a comprehensive collection of tools that will enrich many areas of microbiological research. ..
- Girish C, Koner B, Jayanthi S, Ramachandra Rao K, Rajesh B, Pradhan S. Hepatoprotective activity of picroliv, curcumin and ellagic acid compared to silymarin on paracetamol induced liver toxicity in mice. Fundam Clin Pharmacol. 2009;23:735-45 pubmed publisher..These active phytochemicals may be developed as drugs for the treatment of liver diseases. ..
- Kim S, Kim M, Um J, Hong S. The beneficial effect of vanillic acid on ulcerative colitis. Molecules. 2010;15:7208-17 pubmed publisherb>Vanillic acid, an oxidized form of vanillin, is a benzoic acid derivative used as a flavoring agent...
- Ashengroph M, Nahvi I, Zarkesh Esfahani H, Momenbeik F. Candida galli strain PGO6: a novel isolated yeast strain capable of transformation of isoeugenol into vanillin and vanillic acid. Curr Microbiol. 2011;62:990-8 pubmed publisher..isolated from oil-contaminated water is the first isolated yeast strain which is capable to form vanillin and vanillic acid during isoeugenol biotransformation...
- Gitzinger M, Kemmer C, Fluri D, El Baba M, Weber W, Fussenegger M. The food additive vanillic acid controls transgene expression in mammalian cells and mice. Nucleic Acids Res. 2012;40:e37 pubmed publisher..Capitalizing on control components that enable Caulobacter crescentus to metabolize vanillic acid originating from lignin degradation that occurs in its oligotrophic freshwater habitat, we have designed ..
- Huang S, Chuang H, Wu C, Yen G. Cytoprotective effects of phenolic acids on methylglyoxal-induced apoptosis in Neuro-2A cells. Mol Nutr Food Res. 2008;52:940-9 pubmed publisher..this study was to investigate the inhibitory abilities of phenolic acids (chlorogenic acid, syringic acid and vanillic acid) on methylglyoxal-induced mouse Neuro-2A neuroblastoma (Neuro-2A) cell apoptosis in the progression of ..
- Kim M, Kim S, Kim D, Jeon Y, Park S, Lee H, et al. Vanillic acid inhibits inflammatory mediators by suppressing NF-?B in lipopolysaccharide-stimulated mouse peritoneal macrophages. Immunopharmacol Immunotoxicol. 2011;33:525-32 pubmed publisherb>Vanillic acid is a benzoic acid derivative that is used as a flavoring agent. It is an oxidized form of vanillin. At present, the mechanisms by which vanillic acid exerts its anti-inflammatory effects are incompletely understood...
- Sinha S, Mehrotra J, Bala L, Jaiswal A, Dhawan B. Picroliv, the iridoid glycoside fraction of Picrorhiza kurroa, selectively augments human T cell response to mycobacterial protein antigens. Immunopharmacol Immunotoxicol. 1998;20:579-88 pubmed..The selective, antigen specific augmentation of human T cell response suggests that Picroliv could be useful as an adjunct to chemotherapy or as a short term prophylactic agent. ..
- Doimo M, Trevisson E, Airik R, Bergdoll M, Santos Ocaña C, Hildebrandt F, et al. Effect of vanillic acid on COQ6 mutants identified in patients with coenzyme Q10 deficiency. Biochim Biophys Acta. 2014;1842:1-6 pubmed publisher..In fact treatment with two hydroxylated analogues of 4-hydroxybenzoic acid, namely, vanillic acid or 3-4-hydroxybenzoic acid, restored the respiratory growth of yeast ?coq6 cells expressing the mutant huCOQ6-..
- Ghosh S, Sachan A, Sen S, Mitra A. Microbial transformation of ferulic acid to vanillic acid by Streptomyces sannanensis MTCC 6637. J Ind Microbiol Biotechnol. 2007;34:131-8 pubmed..Cultures of S. sannanensis when grown on minimal medium containing ferulic acid as sole carbon source, vanillic acid accumulation was observed in the medium as the major biotransformed product along with transient formation of ..
- Nishimura M, Ishiyama D, Davies J. Molecular cloning of streptomyces genes encoding vanillate demethylase. Biosci Biotechnol Biochem. 2006;70:2316-9 pubmed..5-kb DNA region. Expression of the vanAB genes in Streptomyces lividans 1326 resulted in in vivo demethylation of veratric acid to vanillic acid.
- Vetrano A, Heck D, Mariano T, Mishin V, Laskin D, Laskin J. Characterization of the oxidase activity in mammalian catalase. J Biol Chem. 2005;280:35372-81 pubmed..that inhibit carcinogenesis, including indole-3-carbinol, indole-3-carboxaldehyde, ferulic acid, vanillic acid, and epigallocatechin-3-gallate, were effective inhibitors of the activity of catalase oxidase...
- Rastogi R, Srivastava A, Rastogi A. Long term effect of aflatoxin B(1) on lipid peroxidation in rat liver and kidney: effect of picroliv and silymarin. Phytother Res. 2001;15:307-10 pubmed..p) -toxicated rats, while drug (picroliv and silymarin both) treatment reversed the condition to near normal levels. The effects of picroliv and silymarin were comparable. ..
- Conrad J, Vogler B, Klaiber I, Reeb S, Guse J, Roos G, et al. Vanillic acid 4-O-beta-D-(6'-O-galloyl) glucopyranoside and other constituents from the bark of Terminalia macroptera Guill.et Perr. Nat Prod Lett. 2001;15:35-42 pubmedA new phenolic glucoside gallate, vanillic acid 4-O-beta-D-(6'-O-galloyl) glucopyranoside (1) was isolated from the bark of Terminalia macroptera Guill.et Perr...
- Itoh A, Isoda K, Kondoh M, Kawase M, Watari A, Kobayashi M, et al. Hepatoprotective effect of syringic acid and vanillic acid on CCl4-induced liver injury. Biol Pharm Bull. 2010;33:983-7 pubmed..During the cultivation, phenolic compounds, such as syringic acid and vanillic acid, were produced by lignin-degrading peroxidase secreted from L. edodes mycelia...
- Chou T, Ding H, Hung W, Liang C. Antioxidative characteristics and inhibition of alpha-melanocyte-stimulating hormone-stimulated melanogenesis of vanillin and vanillic acid from Origanum vulgare. Exp Dermatol. 2010;19:742-50 pubmed publisherThe antioxidant activities of vanillin and vanillic acid isolated from Origanum vulgare are investigated. These compounds may serve as agents for antimelanogenesis...
- Tai A, Sawano T, Ito H. Antioxidative properties of vanillic acid esters in multiple antioxidant assays. Biosci Biotechnol Biochem. 2012;76:314-8 pubmedThe antioxidative properties of vanillic acid esters were systematically evaluated by multiple assays to compare with the well-known antioxidants, vanillic acid and Trolox...
- Malaj N, De Simone B, Quartarolo A, Russo N. Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids. Food Chem. 2013;141:3614-20 pubmed publisher..50 and 3.65) corresponding to those of the major food mediums where these reactions take place (fruit juices, wine, jams etc.). ..
- Shimoni E, Baasov T, Ravid U, Shoham Y. Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants. J Biotechnol. 2003;105:61-70 pubmed..and its t-anethole blocked mutants (incapable of growing on t-anethole) converted isoeugenol to vanillin and vanillic acid; and safrole to hydroxychavicol...
- Saravanakumar M, Raja B. Effect of veratric acid on the cardiovascular risk of L-NAME-induced hypertensive rats. J Cardiovasc Pharmacol. 2012;59:553-62 pubmed publisher..Histopathology of liver and kidney and in vitro study also confirmed the biochemical findings of this study. Thus, oral administration of VA reduced hyperlipidemia related to the risk of hypertension. ..
- Luo X, Li N, Zhang Y, Liu B, Yang Z, Li Y, et al. Vanillyl nonanoate protects rat gastric mucosa from ethanol-induced injury through a mechanism involving calcitonin gene-related peptide. Eur J Pharmacol. 2011;666:211-7 pubmed publisher..The underlying mechanism is related to stimulation of CGRP release and subsequent suppression of ethanol-induced inflammatory reaction, cellular apoptosis and oxidative stress. ..
- Khallouki F, Haubner R, Ulrich C, Owen R. Ethnobotanical survey, chemical composition, and antioxidant capacity of methanolic extract of the root bark of Annona cuneata Oliv. J Med Food. 2011;14:1397-402 pubmed publisher..acid (V), vanillyl alcohol (VI), syringaldehyde (VII), 4-hydroxy-3-methoxyphenylethanol (VIII), vanillic acid (IX), 3,4-dihydroxybenzoic acid (X), syringic acid (XI), and ferulic acid (XII), along with the phytosterol ..
- Kasting G. Kinetics of finite dose absorption through skin 1. Vanillylnonanamide. J Pharm Sci. 2001;90:202-12 pubmed..The analysis shows that a three-parameter model that assigns all of the resistance to transport to diffusion through the stratum corneum is able to explain most of the significant features of VN absorption through skin. ..
- Ghasemzadeh A, Jaafar H, Rahmat A. Elevated carbon dioxide increases contents of flavonoids and phenolic compounds, and antioxidant activities in Malaysian young ginger (Zingiber officinale Roscoe.) varieties. Molecules. 2010;15:7907-22 pubmed publisher..rutin, catechin, epicatechin, kaempferol, naringenin, fisetin and morin) and phenolic acid (gallic acid, vanillic acid, ferulic acid, tannic acid, cinnamic acid and salicylic acid), and antioxidant activities in different parts ..
- Jiang H, Martin J, Okot Kotber M, Seib P. Color of whole-wheat foods prepared from a bright-white hard winter wheat and the phenolic acids in its coarse bran. J Food Sci. 2011;76:C846-52 pubmed publisher..The lightness (L*) values of coarse wheat brans correlated positively with their levels of bound protocatechuic (r?= 0.72,?P?< 0.01) and?p-hydroxybenzoic acids (r?= 0.75,?P?< 0.01). ..
- Sun X, Wu H, Fu A, Zhang P. [Chemical constituents of Trichosanthes kirilowii Maxim]. Yao Xue Xue Bao. 2012;47:922-5 pubmed..1), 5-hydroxymethyl-2-furfural (2), chrysoeriol (3), 4'-hydroxyscutellarin (4), vanillic acid (5), alpha-spinasterol (6), beta-D-glucopyranosyl-a-spinasterol (7), stigmast-7-en-3beta-ol (8), and adenosine ..
- Monnappa A, Lee S, Mitchell R. Sensing of plant hydrolysate-related phenolics with an aaeXAB::luxCDABE bioreporter strain of Escherichia coli. Bioresour Technol. 2013;127:429-34 pubmed publisher..These results demonstrate that this bioreporter maintains its sensitivity even with hydrolysate samples and that it can be potentially applied within biofuel industries to detect phenolics present within plant hydrolysates. ..
- Qiao L, Ye X, Sun Y, Ying J, Shen Y, Chen J. Sonochemical effects on free phenolic acids under ultrasound treatment in a model system. Ultrason Sonochem. 2013;20:1017-25 pubmed publisher..Five phenolic acids (protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, p-coumaric acid, and ferulic acid) proved to be stable, while two others (caffeic acid and sinapic acid) were ..
- Jakopic J, Slatnar A, Mikulic Petkovsek M, Veberic R, Stampar F, Bavec F, et al. Effect of different production systems on chemical profiles of dwarf French bean (Phaseolus vulgaris L. cv. Top Crop) pods. J Agric Food Chem. 2013;61:2392-9 pubmed publisher..the lowest levels of glucose and sucrose and the highest levels of catechin, procyanidin dimers, and a vanillic acid derivative...
- Morawski B, Segura A, Ornston L. Substrate range and genetic analysis of Acinetobacter vanillate demethylase. J Bacteriol. 2000;182:1383-9 pubmed..In one instance, phenotypic reversion failed to produce a protein with the original wild-type sequence. In this example, constraints favoring certain nucleotide substitutions appear to be imposed at the DNA level. ..
- Yu J, Song Y, Cheng Y. [Quantitative determination of vanillic acid in rhizoma Picrorhizae by TLC-scanning]. Zhongguo Zhong Yao Za Zhi. 1999;24:102-3, 126-7 pubmedTo establish a method to determine the content of vanillic acid in Rhizoma Picrorhizae.
- Zhang Y, Yue X, Zhang Z. [Study on the interactions between four components in Ligusticum chuanxiong rhizome and acceptors on cardiac muscle membrane]. Zhongguo Zhong Yao Za Zhi. 2004;29:660-2 pubmed..Tetramethylpyrazine, vanillic and chrysophol can all combine with cardiac muscle membrane acceptors, while ferulic acid can not; tetramethylpyrazine probably acts on a acceptor and vanillic acts on beta1 acceptor. ..
- Dwivedi V, Khan A, Vasco A, Fatima N, Soni V, Dangi A, et al. Immunomodulator effect of picroliv and its potential in treatment against resistant Plasmodium yoelii (MDR) infection in mice. Pharm Res. 2008;25:2312-9 pubmed publisher..The activation of host immune system can increase the efficacy of chloroquine for suppression of drug resistant malaria infection in BALB/c mice. ..
- Garcia F, Pivel J, Guerrero A, Brieva A, Martinez Alcazar M, Caamano Somoza M, et al. Phenolic components and antioxidant activity of Fernblock, an aqueous extract of the aerial parts of the fern Polypodium leucotomos. Methods Find Exp Clin Pharmacol. 2006;28:157-60 pubmed..Phenolic compounds were identified as 3,4-dihydroxybenzoic acid, 4-hydroxybenzoic acid, vanillic acid, caffeic acid, 4-hydroxycinnamic acid, 4-hydroxycinnamoyl-quinic acid, ferulic acid, and five chlorogenic acid ..
- Chaudhry M, Huang Y, Shen X, Poetsch A, Jiang C, Liu S. Genome-wide investigation of aromatic acid transporters in Corynebacterium glutamicum. Microbiology. 2007;153:857-65 pubmed publisher..Thus the functionally identified NCgl2326 belongs to a novel type of benzoate transporters. Attempts to identify the phenotype of a hydK/ncgl2953 mutant failed, so the function of ncgl2953 remains unclear...
- Engelmann T, Kaufmann F, Diekert G. Isolation and characterization of a veratrol:corrinoid protein methyl transferase from Acetobacterium dehalogenans. Arch Microbiol. 2001;175:376-83 pubmed..MTIver catalyzed the demethylation of veratrol, 3,4-dimethoxybenzoate, 2-methoxyphenol, and 3-methoxyphenol. Vanillate (3-methoxy-4-hydroxybenzoate), 2-methoxybenzoate, or 4-methoxybenzoate could not serve as substrates. ..
- Mayer M, Narbad A, Parr A, Parker M, Walton N, Mellon F, et al. Rerouting the plant phenylpropanoid pathway by expression of a novel bacterial enoyl-CoA hydratase/lyase enzyme function. Plant Cell. 2001;13:1669-82 pubmed..accumulation of novel metabolites, including the glucosides and glucose esters of 4-hydroxybenzoic acid and vanillic acid and the glucosides of 4-hydroxybenzyl alcohol and vanillyl alcohol...
- Phan V, Nguyen T, Minh C, Nguyen H, Nguyen H, Nguyen P, et al. Two new C-glucosyl benzoic acids and flavonoids from Mallotus nanus and their antioxidant activity. Arch Pharm Res. 2010;33:203-8 pubmed publisher..Their structures were established on the basis of spectral and chemical evidence. Their antioxidant activities were shown to depend on the number of hydroxyl groups, and the location and species of sugar moiety...
- Chang C, Hsieh Y, Shih I, Hsu S, Wang K. The formation and control of disinfection by-products using chlorine dioxide. Chemosphere. 2000;41:1181-6 pubmedIn this study, chlorine dioxide (ClO2) was used as an alternative disinfectant with vanillic acid, p-hydroxybenzoic acid, and humic acid as the organic precursors in a natural aquatic environment...
- Chen S, Ma D, Ge W, Buswell J. Induction of laccase activity in the edible straw mushroom, Volvariella volvacea. FEMS Microbiol Lett. 2003;218:143-8 pubmed..In solid-state systems, only low levels of laccase are detectable during the vegetative growth phase but enzyme activity increases sharply at the onset of fruiting and during sporophore development. ..
- Reenilä I, Rauhala P. Simultaneous analysis of catechol-O-methyl transferase activity, S-adenosylhomocysteine and adenosine. Biomed Chromatogr. 2010;24:294-300 pubmed publisherNovel HPLC method utilizing UV-detection was developed to analyse catechol-O-methyltransferase (COMT) products, vanillic acid and isovanillic acid, S-adenosylhomocysteine (SAH) and adenosine formed from dihydroxybenzoic acid and S-..
- Tsujiyama S, Ueno M. Formation of 4-vinyl guaiacol as an intermediate in bioconversion of ferulic acid by Schizophyllum commune. Biosci Biotechnol Biochem. 2008;72:212-5 pubmed..This was then oxidized to vanillin and vanillic acid. This result indicates that S. commune distinguished ferulic acid from lignins and metabolized it specifically. ..
- Tang Z, Zhou Y, Zeng Y, Zang S, He P, Fang Y. Determination of active ingredients of Ilex Purpurea Hassk and its medicinal preparations by capillary electrophoresis with electrochemical detection. J Pharm Biomed Anal. 2006;40:484-9 pubmed..The method has been successfully applied to the analysis of real sample, with satisfactory results. ..
- Mishra S, Sachan A, Sachan S. Production of natural value-added compounds: an insight into the eugenol biotransformation pathway. J Ind Microbiol Biotechnol. 2013;40:545-50 pubmed publisher..The present review focuses on eugenol biotransformation by microorganisms resulting in the formation of various value-added products such as ferulic acid, coniferyl alcohol, vanillin and vanillic acid.
- Huo C, Wang B, Liang H, Zhao Y, Lin W. [Study on chemical constituents of mangrove Acanthus ilcifolius]. Zhongguo Zhong Yao Za Zhi. 2006;31:2052-4 pubmed..2), phenylethyl-O-beta-D-glucopyranoside (3), acteoside (4), isoacteoside (5), benzyl-O-beta-D-glucopyranoside (6) and vanillic acid (7) were obtained. 1, 3, 6 and 7 were obtained from the genus for the first time.
- Lessmeier L, Hoefener M, Wendisch V. Formaldehyde degradation in Corynebacterium glutamicum involves acetaldehyde dehydrogenase and mycothiol-dependent formaldehyde dehydrogenase. Microbiology. 2013;159:2651-62 pubmed publisher..glutamicum to external stress by free formaldehyde in its habitat and for growth with natural substrates like vanillate, which are metabolized with concomitant release of formaldehyde. ..