tenuazonic acid

Summary

Summary: 3-Acetyl-5-sec-butyl-4-hydroxy-3-pyrrolin-2-one. A metabolite found in a strain of the fungus Alternaria tenuis Auct. which functions as an antibiotic with antiviral and antineoplastic properties, and may also act as a mycotoxin.

Top Publications

  1. Shephard G, Thiel P, Sydenham E, Vleggaar R, Marasas W. Reversed-phase high-performance liquid chromatography of tenuazonic acid and related tetramic acids. J Chromatogr. 1991;566:195-205 pubmed
    A reversed-phase high-performance liquid chromatographic system for the determination of the fungal toxin, tenuazonic acid, (5S,8S)-3-acetyl-5-sec.-butyltetramic acid, is described...
  2. Motta S, Valente Soares L. Survey of Brazilian tomato products for alternariol, alternariol monomethyl ether, tenuazonic acid and cyclopiazonic acid. Food Addit Contam. 2001;18:630-4 pubmed
    Alternariol (AOH), alternariol monomethyl ether (AME) and tenuazonic acid (TEA) are secondary metabolites of Alternaria species...
  3. Muller M. [Toxin-producing ability of molds of the genus Alternaria]. Zentralbl Mikrobiol. 1992;147:207-13 pubmed
    ..50 isolates were studied to produce tenuazonic acid (TeA). The strains were isolated from CCM-maize and stored hay...
  4. Ganzle M, Vogel R. Contribution of reutericyclin production to the stable persistence of Lactobacillus reuteri in an industrial sourdough fermentation. Int J Food Microbiol. 2003;80:31-45 pubmed
    ..reuteri in sourdough. Because reutericyclin is produced in active concentrations during sourdough fermentations, it is a suitable candidate for use as natural preservative. ..
  5. Blunden G, Roch O, Rogers D, Coker R, Bradburn N, John A. Mycotoxins in food. Med Lab Sci. 1991;48:271-82 pubmed
    ..Compounds discussed include the aflatoxins, cyclopiazonic acid, tenuazonic acid, the trichothecenes, zearalenone, wortmannin, fumonisins B1 and B2, patulin, ochratoxin A, diplodiatoxin and ..
  6. Gross M, Curtui V, Ackermann Y, Latif H, Usleber E. Enzyme immunoassay for tenuazonic acid in apple and tomato products. J Agric Food Chem. 2011;59:12317-22 pubmed publisher
    The Alternaria mycotoxin tenuazonic acid was derivatized with succinic anhydride and conjugated to keyhole limpet hemocyanin (KLH) and to horseradish peroxidase (HRP), respectively...
  7. Wu X, Cherian P, Lee R, Hurdle J. The membrane as a target for controlling hypervirulent Clostridium difficile infections. J Antimicrob Chemother. 2013;68:806-15 pubmed publisher
    ..difficile infections. ..
  8. Asam S, Liu Y, Konitzer K, Rychlik M. Development of a stable isotope dilution assay for tenuazonic acid. J Agric Food Chem. 2011;59:2980-7 pubmed publisher
    A stable isotope dilution assay (SIDA) for the Alternaria mycotoxin tenuazonic acid was developed...
  9. Oviedo M, Ramirez M, Barros G, Chulze S. Effect of environmental factors on tenuazonic acid production by Alternaria alternata on soybean-based media. J Appl Microbiol. 2009;107:1186-92 pubmed publisher
    ..995-0.90), temperature (5, 18, 25 and 30 degrees C), time of incubation (7-35 days) and their interactions on tenuazonic acid (TA) production on 2% soybean-based agar by two Alternaria alternata strains isolated from soybean in ..

More Information

Publications60

  1. Schwab C, Ganzle M. Effect of membrane lateral pressure on the expression of fructosyltransferases in Lactobacillus reuteri. Syst Appl Microbiol. 2006;29:89-99 pubmed
    ..The induction of glycosyltransferases by membrane stress indicates a protective role of fructans and FOS to lactobacilli exposed to physical and chemical environmental stressors. ..
  2. Asam S, Lichtenegger M, Muzik K, Liu Y, Frank O, Hofmann T, et al. Development of analytical methods for the determination of tenuazonic acid analogues in food commodities. J Chromatogr A. 2013;1289:27-36 pubmed publisher
    Analogues of the Alternaria mycotoxin tenuazonic acid (TA, biosynthesized by the fungus from the amino acid isoleucine) derived from valine (ValTA), leucine (LeuTA), alanine (AlaTA) and phenylalanine (PheTA) were synthesized and ..
  3. Scott P. Analysis of agricultural commodities and foods for Alternaria mycotoxins. J AOAC Int. 2001;84:1809-17 pubmed
    ..alternariol monomethyl ether (AME), altenuene (ALT), altertoxins I, II, and III (ATX-I, -II, and -III), and L-tenuazonic acid (TeA)...
  4. Siegel D, Merkel S, Bremser W, Koch M, Nehls I. Degradation kinetics of the Alternaria mycotoxin tenuazonic acid in aqueous solutions. Anal Bioanal Chem. 2010;397:453-62 pubmed publisher
    The degradation kinetics of the Alternaria mycotoxin tenuazonic acid (l-TA) in aqueous buffer were studied over a period of 4 months at different pH levels (3.5 and 7.0) and temperatures (4, 25 and 40 degrees C)...
  5. Somma S, Pose G, Pardo A, Mulè G, Pinto V, Moretti A, et al. AFLP variability, toxin production, and pathogenicity of Alternaria species from Argentinean tomato fruits and puree. Int J Food Microbiol. 2011;145:414-9 pubmed publisher
    ..Most of the representative strains, belonging to each AFLP cluster, when cultured on rice, produced tenuazonic acid (up to 46,760 mg/kg), alternariol monomethyl ether (AME, up to 1860 mg/kg), and alternariol (up to 70 mg/kg)...
  6. Gänzle M, Holtzel A, Walter J, Jung G, Hammes W. Characterization of reutericyclin produced by Lactobacillus reuteri LTH2584. Appl Environ Microbiol. 2000;66:4325-33 pubmed
    ..Int. Ed. 39:2766-2768, 2000) revealed that reutericyclin is a novel tetramic acid derivative. The inhibitory activity of culture supernatant of L. reuteri LTH2584 corresponded to that of purified as well as synthetic reutericyclin. ..
  7. Combina M, Dalcero A, Varsavsky E, Chulze S. Effects of food preservatives on Alternaria alternata growth and tenuazonic acid production. Food Addit Contam. 1999;16:433-7 pubmed
    The effects of different organic acids on Alternaria alternata growth and tenuazonic acid production (TeA) were evaluated. Both TeA pure toxin solution and TeA production in solid medium were considered...
  8. Janić Hajnal E, Čolović R, Pezo L, Orcic D, Vukmirović Đ, Mastilović J. Possibility of Alternaria toxins reduction by extrusion processing of whole wheat flour. Food Chem. 2016;213:784-790 pubmed publisher
    ..20, 24g/100g), feeding rate (q=15, 20, 25kg/h), and screw speed (v=300, 390, 480rpm), on reduction rate of tenuazonic acid (TeA), alternariol (AOH) and alternariol monomethyl ether (AME), in whole wheat flour were investigated...
  9. Mikula H, Horkel E, Hans P, Hametner C, Frohlich J. Structure and tautomerism of tenuazonic acid--a synergetic computational and spectroscopic approach. J Hazard Mater. 2013;250-251:308-17 pubmed publisher
    All reasonable tautomers and rotamers of tenuazonic acid, which is considered to be of the highest toxicity amongst the Alternaria mycotoxins, were investigated by DFT calculations at different levels of theory in gas phase and in ..
  10. Antony M, Gupta K, Janardanan K, Mehrotra N. Inhibition of mouse skin tumor promotion by tenuazonic acid. Cancer Lett. 1991;61:21-5 pubmed
    b>Tenuazonic acid (TA) was topically applied to the interscapular region of Swiss albino mice at different doses before the application of 12-O-tetradecanoyl phorbol-13-acetate (TPA)...
  11. Siegel D, Rasenko T, Koch M, Nehls I. Determination of the Alternaria mycotoxin tenuazonic acid in cereals by high-performance liquid chromatography-electrospray ionization ion-trap multistage mass spectrometry after derivatization with 2,4-dinitrophenylhydrazine. J Chromatogr A. 2009;1216:4582-8 pubmed publisher
    b>Tenuazonic acid (TA) is a major Alternaria mycotoxin...
  12. Hofstetter S, Winter R, McMullen L, Gänzle M. In situ determination of Clostridium endospore membrane fluidity during pressure-assisted thermal processing in combination with nisin or reutericyclin. Appl Environ Microbiol. 2013;79:2103-6 pubmed publisher
    ..Pressure (200 MPa) stabilized membrane order. Reutericyclin and nisin exhibit divergent effects on heat- and pressure-induced spore inactivation and membrane fluidity. ..
  13. Schwarz C, Kreutzer M, Marko D. Minor contribution of alternariol, alternariol monomethyl ether and tenuazonic acid to the genotoxic properties of extracts from Alternaria alternata infested rice. Toxicol Lett. 2012;214:46-52 pubmed publisher
    ..of secondary metabolites with alternariol (AOH), alternariol monomethyl ether (AME), altenuene (ALT) and tenuazonic acid (TA) as the major mycotoxins with respect to quantity...
  14. Schrader T, Cherry W, Soper K, Langlois I, Vijay H. Examination of Alternaria alternata mutagenicity and effects of nitrosylation using the Ames Salmonella test. Teratog Carcinog Mutagen. 2001;21:261-74 pubmed
    ..ALT), Alternariol (AOH), Alternariol Monomethyl Ether (AME), Altertoxin I (ATX I), Tentoxin (TENT), Tenuazonic Acid (TA), and Radicinin (RAD) using the Ames Salmonella strains TA98 and TA100...
  15. Chen S, Yin C, Strasser R, Govindjee -, Yang C, Qiang S. Reactive oxygen species from chloroplasts contribute to 3-acetyl-5-isopropyltetramic acid-induced leaf necrosis of Arabidopsis thaliana. Plant Physiol Biochem. 2012;52:38-51 pubmed publisher
    ..Thus, 3-AIPTA-triggered leaf necrosis of Arabidopsis was found to be a result of direct oxidative injury from the chloroplast-originated ROS burst initiated by the inhibition of normal photosynthetic electron transport. ..
  16. Ozcelik S, Ozcelik N, Beuchat L. Toxin production by Alternaria alternata in tomatoes and apples stored under various conditions and quantitation of the toxins by high-performance liquid chromatography. Int J Food Microbiol. 1990;11:187-94 pubmed
    ..A high-performance liquid chromatography method was developed to quantitate tenuazonic acid (TeA), alternariol (AOH), alternariol methyl ether (AME), and altenuene (ALT)...
  17. Dobretsov S, Teplitski M, Bayer M, Gunasekera S, Proksch P, Paul V. Inhibition of marine biofouling by bacterial quorum sensing inhibitors. Biofouling. 2011;27:893-905 pubmed publisher
    ..coli pSB401 and the LasR-based reporter E. coli pSB1075. Midpacamide and tenuazonic acid were toxic to the tested reporters...
  18. Jeong Y, Moloney M. Synthesis of and tautomerism in 3-acyltetramic acids. J Org Chem. 2011;76:1342-54 pubmed publisher
    ..The tautomeric equilibrium of these 3-acyltetramic acids in solution was found to strongly depend on the nitrogen substituent group (R(1)) rather than the 3-acyl group. ..
  19. Zhao J, Guo L, Zeng H, Yang X, Yuan J, Shi H, et al. Purification and characterization of a novel antimicrobial peptide from Brevibacillus laterosporus strain A60. Peptides. 2012;33:206-11 pubmed publisher
    ..contains eleven amino acid residues, L-Y-K-L-V-K-V-V-L-N-M, and a choline connected to the N-terminal and a tenuazonic acid modified of the C-terminal...
  20. Moss M. Fungi, quality and safety issues in fresh fruits and vegetables. J Appl Microbiol. 2008;104:1239-43 pubmed publisher
    ..The significance of the mycotoxins patulin, ochratoxin and tenuazonic acid will be reviewed.
  21. Marfori E, Kajiyama S, Fukusaki E, Kobayashi A. Phytotoxicity of the tetramic acid metabolite trichosetin. Phytochemistry. 2003;62:715-21 pubmed
    ..FDA-PI staining, to determine cell viability, indicated that cells of the trichosetin-treated roots were mostly dead. ..
  22. Chen S, Xu X, Dai X, Yang C, Qiang S. Identification of tenuazonic acid as a novel type of natural photosystem II inhibitor binding in Q(B)-site of Chlamydomonas reinhardtii. Biochim Biophys Acta. 2007;1767:306-18 pubmed
    b>Tenuazonic acid (TeA) is a natural phytotoxin produced by Alternaria alternata, the causal agent of brown leaf spot disease of Eupatorium adenophorum...
  23. Riley R, Goeger D, Yoo H, Showker J. Comparison of three tetramic acids and their ability to alter membrane function in cultured skeletal muscle cells and sarcoplasmic reticulum vesicles. Toxicol Appl Pharmacol. 1992;114:261-7 pubmed
    ..by comparing the effects of two structurally related tetramic acids, cyclopiazonic acid imine and tenuazonic acid, with cyclopiazonic acid...
  24. Yekeler H, Bitmiş K, Ozcelik N, Doymaz M, Calta M. Analysis of toxic effects of Alternaria toxins on esophagus of mice by light and electron microscopy. Toxicol Pathol. 2001;29:492-7 pubmed
    In this study, the possible toxic effects of Alternariol Methyl Ether (AME) and Tenuazonic Acid (TeA) produced by Alternaria species on esophagus of mice were investigated by using light and electron microscopy techniques...
  25. Hofstetter S, Gebhardt D, Ho L, Gänzle M, McMullen L. Effects of nisin and reutericyclin on resistance of endospores of Clostridium spp. to heat and high pressure. Food Microbiol. 2013;34:46-51 pubmed publisher
    ..Reutericyclin did not enhance spore inactivation or DPA release. Use of nisin in combination with high pressure, thermal treatments enhanced inactivation of endospores of Clostridium spp. and may have application in foods. ..
  26. Schobert R, Jagusch C, Melanophy C, Mullen G. Synthesis and reactions of polymer-bound Ph3P=C=C=O: a quick route to tenuazonic acid and other optically pure 5-substituted tetramates. Org Biomol Chem. 2004;2:3524-9 pubmed
    ..Optically pure 5-substituted tetramates were obtained from reactions of resin-bound Ph3PCCO with alpha-ammonium esters in one step. The mycotoxin (-)-tenuazonic acid was accordingly prepared in just three steps.
  27. Lohrey L, Marschik S, Cramer B, Humpf H. Large-scale synthesis of isotopically labeled 13C2-tenuazonic acid and development of a rapid HPLC-MS/MS method for the analysis of tenuazonic acid in tomato and pepper products. J Agric Food Chem. 2013;61:114-20 pubmed publisher
    b>Tenuazonic acid is a fungal secondary metabolite that is produced by a number of Alternaria species and is therefore a natural contaminant of food and feed samples...
  28. Ganzle M, Vogel R. Studies on the mode of action of reutericyclin. Appl Environ Microbiol. 2003;69:1305-7 pubmed
    ..A comparison of reutericyclin activity with those of nisin, nigericin, and valinomycin demonstrated that reutericyclin does not form pores but selectively dissipates the transmembrane proton potential. ..
  29. Messens W, De V. Inhibitory substances produced by Lactobacilli isolated from sourdoughs--a review. Int J Food Microbiol. 2002;72:31-43 pubmed
    ..However, potent antimicrobials towards Bacilli as well as antifungal substances will have to be found using rational screening strategies and novel purification and analytical techniques. ..
  30. Chen S, Yin C, Qiang S, Zhou F, Dai X. Chloroplastic oxidative burst induced by tenuazonic acid, a natural photosynthesis inhibitor, triggers cell necrosis in Eupatorium adenophorum Spreng. Biochim Biophys Acta. 2010;1797:391-405 pubmed publisher
    b>Tenuazonic acid (TeA), a nonhost-specific phytotoxin produced by Alternaria alternata, was determined to be a novel natural photosynthesis inhibitor owning several action sites in chloroplasts...
  31. Andersen B, Smedsgaard J, Jørring I, Skouboe P, Pedersen L. Real-time PCR quantification of the AM-toxin gene and HPLC qualification of toxigenic metabolites from Alternaria species from apples. Int J Food Microbiol. 2006;111:105-11 pubmed
    ..The analyses also showed the production of tenuazonic acid, alternariols, Altenuene, altenusin and/or altertoxin I in pure culture...
  32. Schlegel B, Schmidtke M, Dörfelt H, Kleinwächter P, Grafe U. (-)-Terpestacin and L-tenuazonic acid, inducers of pigment and aerial mycelium formation by Fusarium culmorum JP 15. J Basic Microbiol. 2001;41:179-83 pubmed
    ..Two inducers from strain Ulocladium sp. HKI 0226, the new (-)-terpestacin (1) and L-tenuazonic acid (2), were isolated. 1 inhibited syncytium formation by cells infected with respiratory syncytial virus (RSV).
  33. Julian A, Wareing P, Phillips S, Medlock V, MacDonald M, Del Río L. Fungal contamination and selected mycotoxins in pre- and post-harvest maize in Honduras. Mycopathologia. 1995;129:5-16 pubmed
    ..Moniliformin and tenuazonic acid were not detected in the samples tested...
  34. Aziz N, Farag S, Hassanin M. Effect of gamma irradiation and water activity on mycotoxin production of Alternaria in tomato paste and juice. Nahrung. 1991;35:359-62 pubmed
    Gamma-irradiation, water activity (aw) and incubation temperature were found to affect the production of tenuazonic acid (TZA) by Alternaria alternata in tomato paste and juice...
  35. Asam S, Habler K, Rychlik M. Determination of tenuazonic acid in human urine by means of a stable isotope dilution assay. Anal Bioanal Chem. 2013;405:4149-58 pubmed publisher
    The content of tenuazonic acid in human urine was determined by a stable isotope dilution assay (SIDA) that was recently developed for the analysis of food commodities and extensively re-validated for urine matrix in this study...
  36. Muller M, Lepom P. [The detection of Alternaria mycotoxins in laboratory culture]. Zentralbl Mikrobiol. 1992;147:197-206 pubmed
    ..of the Alternaria mycotoxins alternariol (AOH), alternariol monomethyl ether (AME), altenuene (ALT) and tenuazonic acid (TeA) in natural and semisynthetic laboratory cultures...
  37. Fan C, Cao X, Liu M, Wang W. Determination of Alternaria mycotoxins in wine and juice using ionic liquid modified countercurrent chromatography as a pretreatment method followed by high-performance liquid chromatography. J Chromatogr A. 2016;1436:133-40 pubmed publisher
    Alternariol (AOH), alternariol monomethyl ether (AME), and tenuazonic acid (TeA) are some of the main Alternaria mycotoxins that can be found as contaminants in food materials...
  38. Yun C, Motoyama T, Osada H. Regulatory Mechanism of Mycotoxin Tenuazonic Acid Production in Pyricularia oryzae. ACS Chem Biol. 2017;12:2270-2274 pubmed publisher
    b>Tenuazonic acid (TeA) is a mycotoxin produced by the rice blast fungus Pyricularia oryzae and some plant pathogenic fungi. We previously demonstrated that TeA is biosynthesized in P...
  39. Hurdle J, Heathcott A, Yang L, Yan B, Lee R. Reutericyclin and related analogues kill stationary phase Clostridium difficile at achievable colonic concentrations. J Antimicrob Chemother. 2011;66:1773-6 pubmed publisher
    ..difficile at concentrations that may be attained in the gastrointestinal tract. Since these agents represent novel potential treatments for C. difficile infection, further development of this compound class is warranted. ..
  40. Hurdle J, Yendapally R, Sun D, Lee R. Evaluation of analogs of reutericyclin as prospective candidates for treatment of staphylococcal skin infections. Antimicrob Agents Chemother. 2009;53:4028-31 pubmed publisher
    ..aureus superficial skin infections in mice. These data exemplify the prospect of developing reutericyclins as new topical antibiotics. ..
  41. Azcarate M, Patriarca A, Terminiello L, Fernandez Pinto V. Alternaria toxins in wheat during the 2004 to 2005 Argentinean harvest. J Food Prot. 2008;71:1262-5 pubmed
    ..produced by species of Alternaria were determined in wheat: alternariol, alternariol monomethyl ether, and tenuazonic acid. Alternariol was detected in 4 (6%) of 64 samples, with a range of 645 to 1,388 microg/kg (mean of 1,054 ..
  42. Antony M, Shukla Y, Janardhanan K. Protective effect of tenuazonic acid against dimethyl benz(a)antracene-induced skin carcinogenesis in mice. Teratog Carcinog Mutagen. 2002;22:309-14 pubmed
    Anticarcinogenic potential of tenuazonic acid (TA), a mycotoxin isolated from a fungus, Alternaria alternata, on skin tumorigenesis induced by 7,12-dimethyl benz(a) antracene (DMBA) was investigated...
  43. Dacero A, Combina M, Etcheverry M, Varsavsky E, Rodriguez M. Evaluation of Alternaria and its mycotoxins during ensiling of sunflower seeds. Nat Toxins. 1997;5:20-3 pubmed
    ..The incidence of Alternaria species and the levels of alternariol and tenuazonic acid decreased as the time of ensiling increased...
  44. Lebrun M, Gaudemer F, Boutar M, Nicolas L, Gaudemer A. Ion-pair, anion-exchange and ligand-exchange high-performance liquid chromatography of tenuazonic acid and 3-acetyl 5-substituted pyrrolidine-2,4-diones. J Chromatogr. 1989;464:307-22 pubmed
    The ion-pair, ligand-exchange and anion-exchange chromatography of the fungal metabolic tenuazonic acid (TA) and its related 3-acetyl 5-substituted pyrrolidine-2,4-diones were studied...
  45. Qin J, Zhang Y, Hu L, Ma Y, Gao J. Cytotoxic metabolites produced by Alternaria no.28, an endophytic fungus isolated from Ginkgo biloba. Nat Prod Commun. 2009;4:1473-6 pubmed
    ..were elucidated as alterperylenol (1), altertoxin I (2), alternariol (3), alternariol monomethyl ether (4), tenuazonic acid (5) and its derivative (6), together with ergosterol and ergosta-4, 6, 8, 22-tetraen-3-one by means of ..
  46. Patriarca A, Azcarate M, Terminiello L, Fernandez Pinto V. Mycotoxin production by Alternaria strains isolated from Argentinean wheat. Int J Food Microbiol. 2007;119:219-22 pubmed
    ..A total of 123 strains were assayed for the production of tenuazonic acid (TA), alternariol (AOH) and alternariol monomethyl ether (AME)...
  47. Canafoglia M, Comerio R, Fernández Pinto V, Vaamonde G. [Putative mycotoxin-producing fungi isolated from alpataco (Prosopis flexuosa) fruits]. Rev Iberoam Micol. 2007;24:56-8 pubmed
    ..species with higher incidence, were screened for alternariol (AOH), alternariol monomethyl ether (AME) and tenuazonic acid (TA) production...
  48. Gänzle M. Reutericyclin: biological activity, mode of action, and potential applications. Appl Microbiol Biotechnol. 2004;64:326-32 pubmed
    ..Therefore, they could serve as a suitable model system to evaluate a possible impact of antimicrobial compounds on the intestinal microflora of humans and animals. ..
  49. Aresta A, Cioffi N, Palmisano F, Zambonin C. Simultaneous determination of ochratoxin A and cyclopiazonic, mycophenolic, and tenuazonic acids in cornflakes by solid-phase microextraction coupled to high-performance liquid chromatography. J Agric Food Chem. 2003;51:5232-7 pubmed
    ..array UV detection (LC-UV/DAD), for the simultaneous determination of cyclopiazonic acid, mycophenolic acid, tenuazonic acid, and ochratoxin A is described...
  50. Asam S, Lichtenegger M, Liu Y, Rychlik M. Content of the Alternaria mycotoxin tenuazonic acid in food commodities determined by a stable isotope dilution assay. Mycotoxin Res. 2012;28:9-15 pubmed publisher
    The Alternaria mycotoxin tenuazonic acid (TA) was quantified in fruit juices (n?=?50), cereals (n?=?12) and spices (n?=?38) using a recently developed stable isotope dilution assay (SIDA)...
  51. Ansari A, Shrivastava A. Natural occurrence of Alternaria mycotoxins in sorghum and ragi from North Bihar, India. Food Addit Contam. 1990;7:815-20 pubmed
    ..e. alternariol (AOH), alternariol methyl ether (AME), altenuene (ALT), altertoxin-1 (ATX-1) and tenuazonic acid (TA) has been investigated in sorghum (Sorghum vulgare Pers.) and ragi (Eleusine coracana Gaertn...