Summary: Salts and esters of gentisic acid.

Top Publications

  1. Ferraroni M, Matera I, Burger S, Reichert S, Steimer L, Scozzafava A, et al. The salicylate 1,2-dioxygenase as a model for a conventional gentisate 1,2-dioxygenase: crystal structures of the G106A mutant and its adducts with gentisate and salicylate. FEBS J. 2013;280:1643-52 pubmed publisher
    ..Structural data are available in the Protein Data Bank databases under the accession numbers 3NST, 3NWA, 3NVC. ..
  2. Fayos J, Bellés J, Lopez Gresa M, Primo J, Conejero V. Induction of gentisic acid 5-O-beta-D-xylopyranoside in tomato and cucumber plants infected by different pathogens. Phytochemistry. 2006;67:142-8 pubmed
    ..12, 227-235], is conjugated to xylose. Notably, this result contrasts with those previously found in other plant-pathogen interactions in which phenolics analogues of GA as benzoic or salicylic acids, are conjugated to glucose. ..
  3. Xu Y, Yan D, Zhou N. Heterologous expression and localization of gentisate transporter Ncg12922 from Corynebacterium glutamicum ATCC 13032. Biochem Biophys Res Commun. 2006;346:555-61 pubmed
    ..However, it exhibited a similar level in strain U2 containing Ncg12922 induced either by salicylate or gentisate. ..
  4. Liu T, Xu Y, Liu H, Luo S, Yin Y, Liu S, et al. Functional characterization of a gene cluster involved in gentisate catabolism in Rhodococcus sp. strain NCIMB 12038. Appl Microbiol Biotechnol. 2011;90:671-8 pubmed publisher
    ..Our study suggested that the gentisate degradation pathway was shared by both naphthalene and 3-hydroxybenzoate catabolism in this strain...
  5. Devireddy L, Hart D, Goetz D, Green M. A mammalian siderophore synthesized by an enzyme with a bacterial homolog involved in enterobactin production. Cell. 2010;141:1006-17 pubmed publisher
    ..Siderophore-depleted mammalian cells and zebrafish embryos fail to synthesize heme, an iron-dependent mitochondrial process. Our results reveal features of intracellular iron homeostasis that are conserved from bacteria through humans. ..
  6. Belicová A, Krizkova L, Nagy M, Krajcovic J, Ebringer L. Phenolic acids reduce the genotoxicity of acridine orange and ofloxacin in Salmonella typhimurium. Folia Microbiol (Praha). 2001;46:511-4 pubmed
    ..typhimurium mutagenicity. In the case of ofloxacin the antimutagenic effect of PA, FA, GA and CA is assumed to be a result of their ability to scavenge reactive oxygen species (ROS) produced by ofloxacin. ..
  7. Shen X, Jiang C, Huang Y, Liu Z, Liu S. Functional identification of novel genes involved in the glutathione-independent gentisate pathway in Corynebacterium glutamicum. Appl Environ Microbiol. 2005;71:3442-52 pubmed
    ..Based on the results obtained in this study, a GSH-independent gentisate pathway was proposed, and genes involved in this pathway were identified. ..
  8. Bellés J, Garro R, Pallas V, Fayos J, Rodrigo I, Conejero V. Accumulation of gentisic acid as associated with systemic infections but not with the hypersensitive response in plant-pathogen interactions. Planta. 2006;223:500-11 pubmed
    ..This indicates that gentisic acid could act as an additional signal to SA for the activation of plant defenses in cucumber and Gynura plants. ..
  9. Ishiyama D, Vujaklija D, Davies J. Novel pathway of salicylate degradation by Streptomyces sp. strain WA46. Appl Environ Microbiol. 2004;70:1297-306 pubmed
    ..strain WA46 degrades salicylate by a novel pathway via a CoA derivative. Two-dimensional polyacrylamide gel electrophoresis and reverse transcriptase-PCR studies indicated that salicylate induced expression of the sdg cluster. ..

More Information


  1. Yeo C, Wong M, Feng Y, Song K, Poh C. Molecular characterization of an inducible gentisate 1,2-dioxygenase gene, xlnE, from Pseudomonas alcaligenes NCIMB 9867. Gene. 2003;312:239-48 pubmed
    ..Thus, xlnE is in fact, inducible and the constitutive activity observed under non-inducing conditions was due to its relatively high basal levels of expression. ..
  2. Fairley D, Boyd D, Sharma N, Allen C, Morgan P, Larkin M. Aerobic metabolism of 4-hydroxybenzoic acid in Archaea via an unusual pathway involving an intramolecular migration (NIH shift). Appl Environ Microbiol. 2002;68:6246-55 pubmed
    ..strain D1 involves a hydroxylation-induced intramolecular migration. To our knowledge, this is the first report of a pathway which involves such a transformation (called an NIH shift) in the domain Archaea. ..
  3. Matera I, Ferraroni M, Burger S, Scozzafava A, Stolz A, Briganti F. Salicylate 1,2-dioxygenase from Pseudaminobacter salicylatoxidans: crystal structure of a peculiar ring-cleaving dioxygenase. J Mol Biol. 2008;380:856-68 pubmed publisher
    ..or 1-hydroxy-2-naphthoate dioxygenase because of its unique ability to oxidatively cleave numerous salicylates, gentisates and 1-hydroxy-2-naphthoate with high catalytic efficiency...
  4. Lin L, Liu H, Zhou N. MhbR, a LysR-type regulator involved in 3-hydroxybenzoate catabolism via gentisate in Klebsiella pneumoniae M5a1. Microbiol Res. 2010;165:66-74 pubmed publisher
    ..beta-Galactosidase activity assays and electrophoretic mobility shift assays showed that an inverted repeat sequence site 1 (ATAACCTCCAGGTTAT, position -70 to -55) within this fragment was critical for regulation. ..
  5. Zhou N, Fuenmayor S, Williams P. nag genes of Ralstonia (formerly Pseudomonas) sp. strain U2 encoding enzymes for gentisate catabolism. J Bacteriol. 2001;183:700-8 pubmed
    ..which converts gentisate to maleylpyruvate and is also able to catalyze the oxidation of some substituted gentisates. NagL is a reduced glutathione-dependent maleylpyruvate isomerase catalyzing the isomerization of maleylpyruvate ..
  6. Holesova Z, Jakubkova M, Zavadiakova I, Zeman I, Tomaska L, Nosek J. Gentisate and 3-oxoadipate pathways in the yeast Candida parapsilosis: identification and functional analysis of the genes coding for 3-hydroxybenzoate 6-hydroxylase and 4-hydroxybenzoate 1-hydroxylase. Microbiology. 2011;157:2152-63 pubmed publisher
    ..Finally, we showed that the overexpression of MNX1 or MNX2 increases the tolerance of C. parapsilosis cells to the antifungal drug terbinafine. ..
  7. Ferraroni M, Matera I, Steimer L, Burger S, Scozzafava A, Stolz A, et al. Crystal structures of salicylate 1,2-dioxygenase-substrates adducts: A step towards the comprehension of the structural basis for substrate selection in class III ring cleaving dioxygenases. J Struct Biol. 2012;177:431-8 pubmed publisher
  8. Osboum D, Lunte C. Cellulose acetate decoupler for on-column electrochemical detection in capillary electrophoresis. Anal Chem. 2001;73:5961-4 pubmed
    ..This decoupler design combines excellent mechanical stability, effective shunting of high separation currents, and ease of manufacture. ..
  9. Wang Y, Chen H, Liao M, Ruan H, Pi H, Zhang Y. [Studies on the chemical constituents of Sarcopyramis nepalensis]. Zhong Yao Cai. 2009;32:1395-7 pubmed
    ..Compounds I , IV, V, VI, VII are isolated from this plant for the first time. ..
  10. Karagulian F, Scott Lea A, Dilbeck C, Finlayson Pitts B. A new mechanism for ozonolysis of unsaturated organics on solids: phosphocholines on NaCl as a model for sea salt particles. Phys Chem Chem Phys. 2008;10:528-41 pubmed publisher
    ..In dry polluted atmospheres, ozone-alkene reactions may lead in part to the formation of stable secondary ozonides whose chemistry, photochemistry and toxicity should be taken into account in models of such regions. ..
  11. Horiguchi T, Shimizu K, Ogino M, Suga S, Inamasu J, Kawase T. Postischemic hypothermia inhibits the generation of hydroxyl radical following transient forebrain ischemia in rats. J Neurotrauma. 2003;20:511-20 pubmed
    ..These results suggest that inhibition of ROS production accompanied with suppression of xanthine formation is implicated in the neuroprotection of postischemic hypothermia. ..
  12. Krizkova L, Nagy M, Polonyi J, Dobias J, Belicová A, Grancai D, et al. Phenolic acids inhibit chloroplast mutagenesis in Euglena gracilis. Mutat Res. 2000;469:107-14 pubmed
    ..On the other hand, the reduction of AO-induced mutagenicity correlates with the binding capabilities of CA, PCA and FA, with the exception of GA...
  13. Park M, Jeon Y, Jang H, Ro H, Park W, Madsen E, et al. Molecular and biochemical characterization of 3-hydroxybenzoate 6-hydroxylase from Polaromonas naphthalenivorans CJ2. Appl Environ Microbiol. 2007;73:5146-52 pubmed
    ..Because nagX and an adjacent MarR-type regulatory gene are both closely related to homologues in Azoarcus species, this study raises questions about horizontal gene transfer events that contribute to operon evolution. ..
  14. Li J, Liu J, Chen Y. Matrix-assisted laser ablation production of gold cluster ions from Au-coated photonic crystals. J Mass Spectrom. 2012;47:620-6 pubmed publisher
    ..The gold-deposited photonic crystal substrates could be stored at room temperature for at least 6 months. The method is hence steady and convenient in use. ..
  15. Wang J, Jiang X, Sturm R, Li L. Combining tissue extraction and off-line capillary electrophoresis matrix-assisted laser desorption/ionization Fourier transform mass spectrometry for neuropeptide analysis in individual neuronal organs using 2,5-dihydroxybenzoic acid as a multi-func. J Chromatogr A. 2009;1216:8283-8 pubmed publisher
    ..In the mean time, the concurrent use of DHB as CE separation buffer and subsequent MALDI matrix offers improved spectral quality by eliminating the interferences from typical CE electrolyte in MALDI detection. ..
  16. Ghafouri B, Karlsson H, Mortstedt H, Lewander A, Tagesson C, Lindahl M. 2,5-Dihydroxybenzoic acid instead of alpha-cyano-4-hydroxycinnamic acid as matrix in matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for analyses of in-gel digests of silver-stained proteins. Anal Biochem. 2007;371:121-3 pubmed
  17. Huang Y, Chang H. Analysis of adenosine triphosphate and glutathione through gold nanoparticles assisted laser desorption/ionization mass spectrometry. Anal Chem. 2007;79:4852-9 pubmed
    ..The present results demonstrate the practicality of the approach for monitoring the bioactivity of cells through determinations of the concentrations of ATP and GSH. ..
  18. Lin H, Song B, Lu I, Hsu K, Liao C, Lee Y, et al. Is energy pooling necessary in ultraviolet matrix-assisted laser desorption/ionization?. Rapid Commun Mass Spectrom. 2014;28:77-82 pubmed publisher
    ..The small energy pooling rate constant for THAP indicates that the potential contribution of the energy pooling mechanism to the generation of THAP matrix primary ions should be reconsidered. ..
  19. Zaar A, Eisenreich W, Bacher A, Fuchs G. A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus. J Biol Chem. 2001;276:24997-5004 pubmed
    ..The data suggest a novel aerobic pathway of benzoate catabolism via CoA intermediates leading to beta-ketoadipyl-CoA, an intermediate of the known beta-ketoadipate pathway...
  20. Jagannadham M, Nagaraj R. Detection of peptides covalently modified with multiple fatty acids by MALDI-TOF mass spectrometry. J Pept Res. 2005;66:94-100 pubmed
    ..Conditions for obtaining good signal intensities for dipalmitoylated and N-myristoyl peptides with both HCCA and DHB as matrices were also investigated. ..
  21. Giacomelli C, Miranda F, Gonçalves N, Spinelli A. Antioxidant activity of phenolic and related compounds: a density functional theory study on the O-H bond dissociation enthalpy. Redox Rep. 2004;9:263-9 pubmed
    ..These findings suggested that the antioxidant activity evaluation of phenolic and related compounds must take into consideration the characteristics of each particular compound. ..
  22. Liu S, Cheung E, Ziegler M, Rajopadhye M, Edwards D. (90)Y and (177)Lu labeling of a DOTA-conjugated vitronectin receptor antagonist useful for tumor therapy. Bioconjug Chem. 2001;12:559-68 pubmed
    ..2-7.8 and heating at 50-100 degrees C for 5-10 min), the minimum amount of SU015 required to achieve 95% RCP for RP697 is approximately 25 microg for 20 mCi of (90)YCl(3) corresponding to a SU015:(90)Y ratio of approximately 30:1. ..
  23. Khan W, Prithiviraj B, Smith D. Photosynthetic responses of corn and soybean to foliar application of salicylates. J Plant Physiol. 2003;160:485-92 pubmed
    ..These compounds do not alter chlorophyll content. In some cases treatment with these compounds resulted in increased leaf areas and plant dry mass, however, plant height and root length were not affected. ..
  24. Tan C, Yeo C, Khoo H, Poh C. Replacement of tyrosine 181 by phenylalanine in gentisate 1,2-dioxygenase I from Pseudomonas alcaligenes NCIMB 9867 enhances catalytic activities. J Bacteriol. 2005;187:7543-5 pubmed
    ..The specific mutation conferred a 13-fold higher catalytic efficiency (k(cat)/Km) on Y181F towards 3-methylgentisate than that of the wild-type enzyme...
  25. Madeira P, Florêncio M. Flavonoid-matrix cluster ions in MALDI mass spectrometry. J Mass Spectrom. 2009;44:1105-13 pubmed publisher
    ..All ion compositions were attributed taking into account high accuracy mass measurements and tandem mass spectrometry experiments. ..
  26. Schnöll Bitai I, Ullmer R, Hrebicek T, Rizzi A, Lacik I. Characterization of the molecular mass distribution of pullulans by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry using 2,5-dihydroxybenzoic acid butylamine (DHBB) as liquid matrix. Rapid Commun Mass Spectrom. 2008;22:2961-70 pubmed publisher
    ..In particular, the average value of the distributions, M(w), and the polydispersity were obtained with predicted uncertainties of between 3 and 15% depending on the width of the distribution and the mass of the polymers. ..
  27. Lee H, Kim J, Lee S, Park M, Lee K, Madsen E, et al. Gentisate 1,2-dioxygenase, in the third naphthalene catabolic gene cluster of Polaromonas naphthalenivorans CJ2, has a role in naphthalene degradation. Microbiology. 2011;157:2891-903 pubmed publisher
    ..The HGT hypothesis was discounted by noting that the nagI3 allele of strain CJ2 did not share high sequence identity with its homologues in Polaromonas sp. JS666 and L. cholodnii SP-6...
  28. Gidden J, Liyanage R, Durham B, Lay J. Reducing fragmentation observed in the matrix-assisted laser desorption/ionization time-of-flight mass spectrometric analysis of triacylglycerols in vegetable oils. Rapid Commun Mass Spectrom. 2007;21:1951-7 pubmed
  29. Deng H, Fang Y. Aspirin metabolites are GPR35 agonists. Naunyn Schmiedebergs Arch Pharmacol. 2012;385:729-37 pubmed publisher
    ..Salicyluric acid, the main metabolite of aspirin, was also active. These results suggest that the GPR35 agonist activity of certain aspirin metabolites may contribute to the clinical features of aspirin. ..
  30. Obata T, Yamanaka Y. Glibenclamide, an antagonist of ATP sensitive K+ channels, blocks free radical generation in the rat myocardium. Neurosci Lett. 1998;257:57-9 pubmed
    ..v. injection, the elevation of DHBA was not observed. These results suggest that openings of cardiac K(ATP) channel by depolarization evokes .OH generation via xanthine oxidase reaction. ..
  31. Asakawa D, Smargiasso N, De Pauw E. Discrimination of isobaric Leu/Ile residues by MALDI in-source decay mass spectrometry. J Am Soc Mass Spectrom. 2013;24:297-300 pubmed publisher
    ..MALDI-ISD with 1,5-DAN appears to be an useful method for the top-down sequencing of proteins, including discrimination of Leu and Ile near the C-terminal end. ..
  32. Joshi R, Gangabhagirathi R, Venu S, Adhikari S, Mukherjee T. Antioxidant activity and free radical scavenging reactions of gentisic acid: in-vitro and pulse radiolysis studies. Free Radic Res. 2012;46:11-20 pubmed publisher
    ..We, therefore, propose that the antioxidant and radioprotective properties of GA are exerted by its phenoxyl group. ..
  33. Niikawa M, Shin S, Nagase H. Suppressive effect of post- or pre-treatment of aspirin metabolite on mitomycin C-induced genotoxicity using the somatic mutation and recombination test in Drosophila melanogaster. Biomed Pharmacother. 2007;61:113-9 pubmed
    ..Therefore, we consider there are effective doses and/or administration timing of aspirin and MMC to prevent secondary cancer. ..
  34. Mohanakumar K, Muralikrishnan D, Thomas B. Neuroprotection by sodium salicylate against 1-methyl-4-phenyl-1,2,3, 6-tetrahydropyridine-induced neurotoxicity. Brain Res. 2000;864:281-90 pubmed
    ..The present study suggests that SA acts as a free radical scavenger in the brain and indicates its strength as a valuable neuroprotectant. ..
  35. Knochenmuss R, McCombie G, Faderl M. Ion yields of thin MALDI samples: dependence on matrix and metal substrate and implications for models. J Phys Chem A. 2006;110:12728-33 pubmed
    ..The surface-enhanced matrix photoionization model best fits the evidence, including the fluence dependence of electron emission from DHB on steel. ..
  36. Tallur P, Megadi V, Kamanavalli C, Ninnekar H. Biodegradation of p-cresol by Bacillus sp. strain PHN 1. Curr Microbiol. 2006;53:529-33 pubmed
    ..Such a bacterial strain can be used for bioremediation of environments contaminated with phenolic compounds. ..
  37. Larsen M, Thingholm T, Jensen O, Roepstorff P, Jørgensen T. Highly selective enrichment of phosphorylated peptides from peptide mixtures using titanium dioxide microcolumns. Mol Cell Proteomics. 2005;4:873-86 pubmed
    ..A putative mechanism for this intriguing effect is presented. ..
  38. Andreassen O, Ferrante R, Dedeoglu A, Albers D, Klivenyi P, Carlson E, et al. Mice with a partial deficiency of manganese superoxide dismutase show increased vulnerability to the mitochondrial toxins malonate, 3-nitropropionic acid, and MPTP. Exp Neurol. 2001;167:189-95 pubmed
    ..These findings show that a subclinical deficiency in a free radical scavenging enzyme may act in concert with environmental toxins to produce selective neurodegeneration. ..
  39. Cunha J, Campestrini F, Calixto J, Scremin A, Paulino N. The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: the role of potassium channels and vasoactive intestinal peptide receptors. Braz J Med Biol Res. 2001;34:381-8 pubmed
  40. Uhrig R, Picard M, Beyreuther K, Wiessler M. Synthesis of antioxidative and anti-inflammatory drugs glucoconjugates. Carbohydr Res. 2000;325:72-80 pubmed
    ..For the synthesis of the S-glucosides, the glycosyl donor 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose provided higher yields than the corresponding O-acetylated imidate. ..
  41. Matthews R, Beal M. Increased 3-nitrotyrosine in brains of Apo E-deficient mice. Brain Res. 1996;718:181-4 pubmed
    ..These results suggest the Apo-E may modulate oxidative stress produced by peroxynitrite. ..
  42. Ballinger J, Pygas J, Gerson B, Gulenchyn K. Stabilization of stannous pyrophosphate kits with gentisic acid. Int J Rad Appl Instrum B. 1988;15:391-3 pubmed
    ..Gentisic acid is now used routinely in the Sn:PPi kit formulation in this institution...
  43. Merrill G, McConnell P, Vandyke K, Powell S. Coronary and myocardial effects of acetaminophen: protection during ischemia-reperfusion. Am J Physiol Heart Circ Physiol. 2001;280:H2631-8 pubmed
  44. Li X, Gu J, Lu S, Sun F. Melatonin attenuates MPTP-induced dopaminergic neuronal injury associated with scavenging hydroxyl radical. J Pineal Res. 2002;32:47-52 pubmed
    ..Present results suggest that melatonin can ameliorate MPTP-induced dopaminergic neuronal lesions probably, at least partially, because of its inhibition of *OH generation. ..
  45. Zeng Y, Tang Z, Wang Q, He P, Fang Y. Simultaneous determination of active ingredients in ethnomedicine Gaultheria leucocarpa var. yunnanensis and its medicinal preparation by capillary electrophoresis with electrochemical detection. J Chromatogr Sci. 2007;45:610-5 pubmed
    ..The proposed method is successfully used in the analysis of real samples after a relatively simple extraction procedure, and the assay results are satisfactory...
  46. Mank M, Stahl B, Boehm G. 2,5-Dihydroxybenzoic acid butylamine and other ionic liquid matrixes for enhanced MALDI-MS analysis of biomolecules. Anal Chem. 2004;76:2938-50 pubmed
    ..This was proven by the desialylation of sialylactose with sialidase from Clostridium perfringens in the presence of diluted aqueous DHBB and subsequent direct MALDI-MS analysis of the reaction mixture...
  47. Kjellström S, Jensen O. Phosphoric acid as a matrix additive for MALDI MS analysis of phosphopeptides and phosphoproteins. Anal Chem. 2004;76:5109-17 pubmed
    ..subtilis PrkC phosphoprotein. Finally, the mass resolution of MALDI mass spectra of intact proteins was significantly improved by using phosphoric acid in 2,5-DHB matrix. ..
  48. Mikolasch A, Niedermeyer T, Lalk M, Witt S, Seefeldt S, Hammer E, et al. Novel cephalosporins synthesized by amination of 2,5-dihydroxybenzoic acid derivatives using fungal laccases II. Chem Pharm Bull (Tokyo). 2007;55:412-6 pubmed
    ..The results show the usefulness of laccase for the synthesis of potential new antibiotics. The biological activity of the new compounds stimulates intensified pharmacological tests. ..
  49. Yeh C, Huang S, Yen G. Induction of phenolsulfotransferase expression by phenolic acids in human hepatoma HepG2 cells. J Agric Food Chem. 2005;53:4766-73 pubmed
  50. Chan T, Tang K. Analysis of a bioactive beta-(1 --> 3) polysaccharide (Curdlan) using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2003;17:887-96 pubmed
    ..MALDI analysis of the water-insoluble Curdlan portion gave number-average (Mn) and weight-average (Mw) molecular weights and polydispersity of 8000 Da, 8700 Da, and 1.10, respectively. ..
  51. Ibáñez A, Muck A, Svatos A. Dissipation of charge on MALDI-TOF polymeric chips using an electron-acceptor: analysis of proteins. J Mass Spectrom. 2007;42:634-40 pubmed
    ..This approach can be used on a wide range of nonconductive support materials. ..
  52. Chao H, Zhou N. GenR, an IclR-type regulator, activates and represses the transcription of gen genes involved in 3-hydroxybenzoate and gentisate catabolism in Corynebacterium glutamicum. J Bacteriol. 2013;195:1598-609 pubmed publisher
    ..The results reveal a new regulatory function of the IclR family in the catabolism of aromatic compounds. ..
  53. Thomadaki H, Karaliota A, Litos C, Scorilas A. Enhanced antileukemic activity of the novel complex 2,5-dihydroxybenzoate molybdenum(VI) against 2,5-dihydroxybenzoate, polyoxometalate of Mo(VI), and tetraphenylphosphonium in the human HL-60 and K562 leukemic cell lines. J Med Chem. 2007;50:1316-21 pubmed
    ..Our results suggest that the new 2,5-dihydroxybenzoate molybdenum(VI) complex may provide a valuable tool in cancer chemotherapy. ..