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O1877 Sigma

Ochratoxin A

from Petromyces albertensis, ≥98% (HPLC)

Synonym: N-[(3R)-(5-Chloro-8-hydroxy-3-methyl-1-oxo-7-isochromanyl)carbonyl]-L-phenylalanine

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics N-S, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   PREMIUM
biological source   from Petromyces albertensis
assay   ≥98% (HPLC)
form   powder
impurities   Benzene, free
solubility   ethanol: soluble
storage temp.   2-8°C

Description

Biochem/physiol Actions

Ochratoxin A is a mycotoxin found in food that is nephrotoxic and carcinogenic in the kidney and induces differentiation in cloned renal cell lines. Increases endoplasmic reticulum ATP-dependent Ca2+ pump activity.

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Ochratoxin A

from Aspergillus ochraceus, reference material

Ochratoxin A solution

10 μg/mL in acetonitrile, analytical standard

Ochratoxin A solution

50 μg/mL in benzene: acetic acid (99:1), analytical standard

Zearalenone

fungal mycotoxin

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
Hazard Codes (Europe) 
T+
Risk Statements (Europe) 
Safety Statements (Europe) 
28-36/37-45
RIDADR 
UN 3462 6.1 / PGII
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

DNA Damage and Repair

Damage to cellular DNA is involved in mutagenesis and the development of cancer. The DNA in a human cell undergoes several thousand to a million damaging events per day, generated by both external (e...
BioFiles 2007, 2.4, 20.
Keywords: AGE, Alkylations, Apoptosis, Applications, Biochemistry, Cancer, Carcinogens, Catalysis, Clinical, DNA replication, Deaminations, Environmental, Error, Events, Gene expression, Metabolites, Methylations, Mutagens, Oxidations, Polymorphisms, Rearrangements, Recombination, Sequences, Substitutions, Transcription, Type

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Peer-Reviewed Papers

References

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Effect of superoxide dismutase and catalase on the nephrotoxicity induced by subchronical administration of ochratoxin A in rats. Baudrimont, I., et al. Toxicology 89, 101-111, (1994)

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Ochratoxin A-induced stimulation of extracellular signal-regulated kinases 1/2 is associated with Madin-Darby canine kidney-C7 cell dedifferentiation. Schramek, H., et al. J. Pharmacol. Exp. Ther. 283, 1460-1468, (1997)

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Effects of ochratoxin A on DNA repair in cultures of rat hepatocytes and porcine urinary bladder epithelial cells. Dorrenhaus, A., and Follmann, W. Arch. Toxicol. 71, 709-713, (1997)

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Characterization of an ochratoxin-A-dedifferentiated and cloned renal epithelial cell line. Gekle, M., et al. Toxicol. Appl. Pharmacol. 152, 282-291, (1998)

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Sex- and strain-specific expression of cytochrome P450s in ochratoxin A-induced genotoxicity and carcinogenicity in rats. Pfohl-Leszkowicz, A., et al. Mol. Carcinog. 23, 76-85, (1998)

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Low Doses Of Ochratoxin A Upregulate The Protein Expression Of Organic Anion Transporters Oat1, Oat2, Oat3 And Oat5 In Rat Kidney Cortex. Zlender, V., et al. Toxicol. Appl. Pharmacol. 239, 284-96, (2009)

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Induction of free radicals in hepatocytes, mitochondria and microsomes of rats by ochratoxin A and its analogs. Hoehler, D., et al. Biochim. Biophys. Acta 1357, 225-233, (1997)

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Peritubular transport of ochratoxin A by single rabbit renal proximal tubules. Welborn, J.R., et al. J. Am. Soc. Nephrol. 9, 1973-1982, (1998)

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Ochratoxin A secretion in primary cultures of rabbit renal proximal tubule cells. Groves, C.E., et al. J. Am. Soc. Nephrol. 10, 13-20, (1999)

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Alterations in ATP-dependent calcium uptake by rat renal cortex microsomes following ochratoxin A administration in vivo or addition in vitro. Chong, X., and Rahimtula, A.D. Biochem. Pharmacol. 44, 1401-1409, (1992)

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Mechanism of action of ochratoxin A. Dirheimer, G., and Creppy, E.E. IARC Sci. Publ. 115, 171-186, (1991)

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A review on ochratoxin A transcriptomic studies. Vettorazzi A, van Delft J, and López de Cerain A Food Chem. Toxicol. 59, 766-83, (2013)

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Relationship between ecophysiological factors, growth and ochratoxin A contamination of dry-cured sausage based matrices. Rodríguez A, Capela D, Medina Á, et al. Int. J. Food Microbiol. 194, 71-7, (2015)

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Oxidative stress induces the biosynthesis of citrinin by Penicillium verrucosum at the expense of ochratoxin. Schmidt-Heydt M, Stoll D, Schütz P, et al. Int. J. Food Microbiol. 192, 1-6, (2015)

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A review of the diagnosis and treatment of Ochratoxin A inhalational exposure associated with human illness and kidney disease including focal segmental glomerulosclerosis. Hope JH and Hope BE J. Environ. Public Health 2012, 835059, (2012)

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The effects of different ecophysiological factors on ochratoxin A production. Khalesi M and Khatib N Environ. Toxicol. Pharmacol. 32(2), 113-21, (2011)

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Multi-component immunochromatographic assay for simultaneous detection of aflatoxin B1, ochratoxin A and zearalenone in agro-food. Li X, Li P, Zhang Q, et al. Biosens. Bioelectron. 49, 426-32, (2013)

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Ochratoxin A in feed of food-producing animals: an undesirable mycotoxin with health and performance effects. Duarte SC, Lino CM, and Pena A Vet. Microbiol. 154(1-2), 1-13, (2011)

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Femtogram ultrasensitive aptasensor for the detection of Ochratoxin A. Ma W, Yin H, Xu L, et al. Biosens. Bioelectron. 42, 545-9, (2013)

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An update on direct genotoxicity as a molecular mechanism of ochratoxin a carcinogenicity. Pfohl-Leszkowicz A and Manderville RA Chem. Res. Toxicol. 25(2), 252-62, (2012)

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A reassessment of risk associated with dietary intake of ochratoxin A based on a lifetime exposure model. Haighton LA, Lynch BS, Magnuson BA, et al. Crit. Rev. Toxicol. 42(2), 147-68, (2012)

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Label-free homogeneous FRET immunoassay for the detection of mycotoxins that utilizes quenching of the intrinsic fluorescence of antibodies. Li T, Byun JY, Kim BB, et al. Biosens. Bioelectron. 42, 403-8, (2013)

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Ochratoxin a and mitotic disruption: mode of action analysis of renal tumor formation by ochratoxin A. Mally A Toxicol. Sci. 127(2), 315-30, (2012)

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Design of PEG-aptamer two piece macromolecules as convenient and integrated sensing platform: application to the label free detection of small size molecules. Hayat A, Andreescu S, and Marty JL Biosens. Bioelectron. 45, 168-73, (2013)

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Food safety implications of ochratoxin A in animal-derived food products. Duarte SC, Lino CM, and Pena A Vet. J. 192(3), 286-92, (2012)

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Combinatorial approach of LC-MS/MS and LC-TOF-MS for uncovering in vivo kinetics and biotransformation of ochratoxin A in rat. Han Z, Zhao Z, Shi J, et al. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 925, 46-53, (2013)

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Highly sensitive ochratoxin A impedimetric aptasensor based on the immobilization of azido-aptamer onto electrografted binary film via click chemistry. Hayat A, Sassolas A, Marty JL, et al. Talanta 103, 14-9, (2013)

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Determination of aflatoxins, deoxynivalenol, ochratoxin A and zearalenone in wheat and oat based bran supplements sold in the Spanish market. Vidal A, Marín S, Ramos AJ, et al. Food Chem. Toxicol. 53, 133-8, (2013)

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Zinc protects HepG2 cells against the oxidative damage and DNA damage induced by ochratoxin A. Zheng J, Zhang Y, Xu W, et al. Toxicol. Appl. Pharmacol. 268(2), 123-31, (2013)

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Microfluidic channel with embedded SERS 2D platform for the aptamer detection of ochratoxin A. Galarreta BC, Tabatabaei M, Guieu V, et al. Anal. Bioanal. Chem 405(5), 1613-21, (2013)

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Simultaneous determination of aflatoxin B(1) and ochratoxin A in licorice roots and fritillary bulbs by solid-phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry. Wang L, Wang Z, Gao W, et al. Food Chem. 138(2-3), 1048-54, (2013)

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Functional characterization of the polyketide synthase gene required for ochratoxin A biosynthesis in Penicillium verrucosum. Abbas A, Coghlan A, O'Callaghan J, et al. Int. J. Food Microbiol. 161(3), 172-81, (2013)

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Metabolic pathways of ochratoxin A. Wu Q, Dohnal V, Huang L, et al. Curr. Drug Metab. 12(1), 1-10, (2011)

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An aptasensing platform for simultaneous detection of multiple analytes based on the amplification of exonuclease-catalyzed target recycling and DNA concatemers. Jiang L, Peng J, Yuan R, et al. Analyst 138(17), 4818-22, (2013)

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Endocrine disrupting effects of ochratoxin A at the level of nuclear receptor activation and steroidogenesis. Frizzell C, Verhaegen S, Ropstad E, et al. Toxicol. Lett. 217(3), 243-50, (2013)

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Structural variation governs substrate specificity for organic anion transporter (OAT) homologs. Potential remote sensing by OAT family members. Gregory Kaler et al J. Biol. Chem. 282, 23841-53, (2007)

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Immunochemical methods for ochratoxin A detection: a review. Meulenberg EP Toxins (Basel.) 4(4), 244-66, (2012)

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Quercetin modulates OTA-induced oxidative stress and redox signalling in HepG2 cells - up regulation of Nrf2 expression and down regulation of NF-κB and COX-2. Ramyaa P, Krishnaswamy R, and Padma VV Biochim. Biophys. Acta 1840(1), 681-92, (2014)

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In vitro study on the effect of Saccharomyces cerevisiae strains on growth and mycotoxin production by Aspergillus carbonarius and Fusarium graminearum. Armando MR, Dogi CA, Poloni V, et al. Int. J. Food Microbiol. 161(3), 182-8, (2013)

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Screening interaction between ochratoxin A and aptamers by fluorescence anisotropy approach. Geng X, Zhang D, Wang H, et al. Anal. Bioanal. Chem 405(8), 2443-9, (2013)

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Effects of p53 knockout on ochratoxin A-induced genotoxicity in p53-deficient gpt delta mice. Hibi D, Kijima A, Suzuki Y, et al. Toxicology 304, 92-9, (2013)

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Sampling of cereals and cereal-based foods for the determination of ochratoxin A: an overview. Tittlemier SA, Varga E, Scott PM, et al. Food Addit. Contam. Part A. Chem. Anal. Control. Expo. Risk Assess. 28(6), 775-85, (2011)

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Simultaneous determination of bisphenol A, aflatoxin B1, ochratoxin A, and patulin in food matrices by liquid chromatography/mass spectrometry. Song W, Li C, and Moezzi B Rapid Commun. Mass Spectrom. 27(6), 671-80, (2013)

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Comparative proteomics and physiological characterization of Arabidopsis thaliana seedlings in responses to Ochratoxin A. Wang Y, Hao J, Zhao W, et al. Plant Mol. Biol. 82(4-5), 321-37, (2013)

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Producers and important dietary sources of ochratoxin A and citrinin. Ostry V, Malir F, and Ruprich J Toxins (Basel.) 5(9), 1574-86, (2013)

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Downregulation of Rad51 participates in OTA-induced DNA double-strand breaks in GES-1 cells in vitro. Lian H, Cui J, Wang Y, et al. Toxicol. Lett. 226(2), 214-21, (2014)

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Ochratoxin A induces karyomegaly and cell cycle aberrations in renal tubular cells without relation to induction of oxidative stress responses in rats. Taniai E, Yafune A, Nakajima M, et al. Toxicol. Lett. 224(1), 64-72, (2014)

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VeA and LaeA transcriptional factors regulate ochratoxin A biosynthesis in Aspergillus carbonarius. Crespo-Sempere A, Marín S, Sanchis V, et al. Int. J. Food Microbiol. 166(3), 479-86, (2013)

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Identification and quantification of fungi and mycotoxins from Pu-erh tea. Haas D, Pfeifer B, Reiterich C, et al. Int. J. Food Microbiol. 166(2), 316-22, (2013)

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Review. Ochratoxin A: presence in human plasma and intake estimation. Coronel MB, Sanchis V, Ramos AJ, et al. Food Sci. Technol. Int. 16(1), 5-18, (2010)

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Total synthesis and cytotoxicity evaluation of all ochratoxin A stereoisomers. Benedikt Cramer et al Bioorg. Med. Chem. 18, 343-7, (2010)

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Molecular mechanisms underlying ochratoxin A-induced genotoxicity: global gene expression analysis suggests induction of DNA double-strand breaks and cell cycle progression. Hibi D, Kijima A, Kuroda K, et al. J. Toxicol. Sci. 38(1), 57-69, (2013)

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Aptamers: a promosing tool for ochratoxin A detection in food analysis. Rhouati A, Yang C, Hayat A, et al. Toxins (Basel.) 5(11), 1988-2008, (2013)

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Toxicity of ochratoxin a and its modulation by antioxidants: a review. Sorrenti V, Di Giacomo C, Acquaviva R, et al. Toxins (Basel.) 5(10), 1742-66, (2013)

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Novel IAC-LC-ESI-MS(2) analytical set-up for ochratoxin A determination in pork. Duarte SC, Lino CM, and Pena A Food Chem. 138(2-3), 1055-61, (2013)

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Protective effect of lycopene against ochratoxin A induced renal oxidative stress and apoptosis in rats. Palabiyik SS, Erkekoglu P, Zeybek ND, et al. Exp. Toxicol. Pathol. 65(6), 853-61, (2013)

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Determination of ochratoxin A in licorice and licorice extracts by high-performance liquid chromatography coupled with fluorescence detection: collaborative study. Lerda D, Ambrosio M, Kunsagi Z, et al. J. AOAC Int. 96(2), 331-40, (2013)

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Development of nanogold-based lateral flow immunoassay for the detection of ochratoxin A in buffer systems. Moon J, Kim G, and Lee S J. Nanosci. Nanotechnol. 13(11), 7245-9, (2013)

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Deleterious effects of mycotoxin combinations involving ochratoxin A. Klarić MS, Rašić D, and Peraica M Toxins (Basel.) 5(11), 1965-87, (2013)

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Ecophysiology of Aspergillus section nigri species potential ochratoxin a producers. Astoreca AL, Magnoli CE, and Dalcero AM Toxins (Basel.) 2(11), 2593-605, (2010)

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Distribution and mycotoxigenic potential of Aspergillus section Nigri species in naturally contaminated almonds. Palumbo JD and O'Keeffe TL J. Food Prot. 76(4), 702-6, (2013)

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Multiplex real-time PCR method for detection and quantification of mycotoxigenic fungi belonging to three different genera. Vegi A and Wolf-Hall CE J. Food Sci. 78(1), M70-6, (2013)

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Control of ochratoxin A production in grapes. Ponsone ML, Chiotta ML, Palazzini JM, et al. Toxins (Basel.) 4(5), 364-72, (2012)

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Susceptibility and mode of binding of the Mycobacterium tuberculosis cysteinyl transferase mycothiol ligase to tRNA synthetase inhibitors. Maria-Teresa Gutierrez-Lugo et al Bioorg. Med. Chem. Lett. 21, 2480-3, (2011)

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Effect of Robusta (Coffea canephora P.) coffee cherries quantity put out for sun drying on contamination by fungi and ochratoxin A (OTA) under tropical humid zone (Côte d'Ivoire). Kouadio IA, Koffi LB, Nemlin JG, et al. Food Chem. Toxicol. 50(6), 1969-79, (2012)

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Biocontrol activity of four non- and low-fermenting yeast strains against Aspergillus carbonarius and their ability to remove ochratoxin A from grape juice. Fiori S, Urgeghe PP, Hammami W, et al. Int. J. Food Microbiol. 189, 45-50, (2014)

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The impact of water and temperature interactions on lag phase, growth and potential ochratoxin A production by two new species, Aspergillus aculeatinus and A. sclerotiicarbonarius, on a green coffee-based medium. Akbar A and Magan N Int. J. Food Microbiol. 188, 116-21, (2014)

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Biodegradation of ochratoxin A by Pediococcus parvulus isolated from Douro wines. Abrunhosa L, Inês A, Rodrigues AI, et al. Int. J. Food Microbiol. 188, 45-52, (2014)

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The loss of the inducible Aspergillus carbonarius MFS transporter MfsA leads to ochratoxin A overproduction. Crespo-Sempere A, Martínez-Culebras PV, and González-Candelas L Int. J. Food Microbiol. 181, 1-9, (2014)

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Identification and characterization of the polyketide synthase involved in ochratoxin A biosynthesis in Aspergillus carbonarius. Gallo A, Knox BP, Bruno KS, et al. Int. J. Food Microbiol. 179, 10-7, (2014)

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The influence of salt (NaCl) on ochratoxin A biosynthetic genes, growth and ochratoxin A production by three strains of Penicillium nordicum on a dry-cured ham-based medium. Rodríguez A, Medina Á, Córdoba JJ, et al. Int. J. Food Microbiol. 178, 113-9, (2014)

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Wavelength-dependent degradation of ochratoxin and citrinin by light in vitro and in vivo and its implications on Penicillium. Schmidt-Heydt M, Cramer B, Graf I, et al. Toxins (Basel.) 4(12), 1535-51, (2012)

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First evidence of placental transfer of ochratoxin A in horses. Minervini F, Giannoccaro A, Nicassio M, et al. Toxins (Basel.) 5(1), 84-92, (2013)

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Ochratoxin A management in vineyards by Lobesia botrana biocontrol. Cozzi G, Somma S, Haidukowski M, et al. Toxins (Basel.) 5(1), 49-59, (2013)

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Role of microRNA-29b in the ochratoxin A-induced enhanced collagen formation in human kidney cells. Hennemeier I, Humpf HU, Gekle M, et al. Toxicology 324, 116-22, (2014)

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QuickTox Kit for QuickScan Ochratoxin-A. Davis AH, Roberts RW, and Ziemer W J. AOAC Int. 96(5), 1019-25, (2013)

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Apoptosis induction by OTA and TNF-α in cultured primary rat hepatocytes and prevention by silibinin. Essid E, Dernawi Y, and Petzinger E Toxins (Basel.) 4(11), 1139-56, (2012)

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Development of a stir bar sorptive extraction method for analysis of ochratoxin A in beer. Nguyen KT and Ryu D J. AOAC Int. 97(4), 1092-6, (2014)

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Occurrence of Ochratoxin A in the wild boar (Sus scrofa): chemical and histological analysis. Bozzo G, Ceci E, Bonerba E, et al. Toxins (Basel.) 4(12), 1440-50, (2012)

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[Ochratoxin A in foods for human consumption: review]. Ravelo Abreu A, Rubio Armendáriz C, Gutiérrez Fernández AJ, et al. Nutr. Hosp. 26(6), 1215-26, (2011)

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Merck 14,6740

Beil. 18,V,9,56

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