Ochratoxin A

Ochratoxin A
IUPAC name N-​{[(3R)-​5-​chloro-​8-​hydroxy-​3-​methyl-​1-​oxo-​3,​4-​dihydro-​1H-​isochromen-​7-​yl]​carbonyl}-​L-​phenylalanine
Other names (R)-N- [(5-Chloro- 3,4-dihydro- 8-hydroxy- 3-methyl- 1-oxo- 1H-2-benzopyran-7-yl) -carbonyl]- L- phenylalanine (-)-N- [(5-Chloro- 8-hydroxy- 3-methyl- 1-oxo- 7-isochromanyl) carbonyl]- 3-phenylalanine
Identifiers
CAS number	303-47-9 Y
PubChem	442530
ChemSpider	390954 Y
KEGG	C09955 Y
ChEBI	CHEBI:7719 Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](NC(=O)c1c(O)c2c(c(Cl)c1)C[C@H](OC2=O)C)Cc3ccccc3
InChI InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1 Y Key: RWQKHEORZBHNRI-BMIGLBTASA-N Y InChI=1/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15+/m1/s1 Key: RWQKHEORZBHNRI-BMIGLBTABQ
Properties
Molecular formula	C20H18ClNO6
Molar mass	403.81 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ochratoxin A, a toxin produced by Aspergillus ochraceus, Aspergillus carbonarius and Penicillium verrucosum, is one of the most abundant food-contaminating mycotoxins in the world.^[1] Human exposure occurs mainly through consumption of improperly stored food products,^[2] particularly contaminated grain and pork products, as well as coffee^[3], wine grapes ^[4] and dried grapes. The toxin has been found in the tissues and organs of animals, including human blood and breast milk.^[5] Ochratoxin A toxicity has large species- and sex-specific differences.^[3]

Impact on human and animal health

Carcinogenicity

Ochratoxin A is potentially carcinogenic to humans (Group 2B). Ochratoxin A has been shown to be weakly mutagenic, possibly by induction of oxidative DNA damage.^[6]

There is sufficient evidence in experimental animals for the carcinogenicity of ochratoxin A. Ochratoxin A was tested for carcinogenicity by oral administration in mice and rats. It increased the incidence of hepato-cellular (Hepatic tumor) tumours in mice of each sex and produced renal-cell adenomas and carcinomas in male mice and in rats of each sex.

Immuno suppression and immunotoxicity

Ochratoxin A can cause immunosuppression and immunotoxicity in animals.^[1] The toxin's immunosuppressant activity in animals may include depressed antibody responses, reduced size of immune organs (such as the thymus, spleen, and lymph nodes), changes in immune cell number and function, and altered cytokine production.^[1] Immunotoxicity probably results from cell death following apoptosis and necrosis, in combination with slow replacement of affected immune cells due to inhibition of protein synthesis.^[1]

Potential link to Balkan endemic nephropathy

A number of descriptive studies have suggested a correlation between exposure to ochratoxin A and Balkan endemic nephropathy, and have found a correlation between the geographical distribution of Balkan endemic nephropathy and a high incidence of, and mortality from, urothelial urinary tract tumours.^[7] However, there is currently insufficient information to conclusively link ochratoxin A to Balkan endemic nephropathy.^[8] The toxin may require synergistic interactions with predisposing genotypes or other environmental toxicants to induce Balkan endemic nephropathy.^[9]

Food animal industry impact

Ochratoxin-contaminated feed has its major economic impact on the poultry industry. Chickens, turkeys and ducklings are susceptible to this toxin. Clinical signs of avian ochratoxicosis are similar to other toxins and generally involve reduction in weight gains, poor feed conversion, reduced egg production, poor egg shell quality and kidney poisoning.^{[citation needed]}

Acute toxicity does not seem to constitute a problem in cattle.^{[citation needed]}

See also

• Ochratoxin

References

1. ^ ^{a b c d} Al-Anati L, Petzinger E (2006). "Immunotoxic activity of ochratoxin A". J. Vet. Pharmacol. Ther. 29 (2): 79–90. doi:10.1111/j.1365-2885.2006.00718.x. PMID 16515661. 
2. ^ Pfohl-Leszkowicz A, Manderville RA (2007). "Ochratoxin A: An overview on toxicity and carcinogenicity in animals and humans". Mol Nutr Food Res 51 (1): 61–99. doi:10.1002/mnfr.200600137. PMID 17195275. 
3. ^ ^{a b} O'Brien E, Dietrich DR (2005). "Ochratoxin A: the continuing enigma". Crit. Rev. Toxicol. 35 (1): 33–60. doi:10.1080/10408440590905948. PMID 15742902. 
4. ^ Blesa J, Soriano JM, Moltó JC, Mañes J (2006). "Factors affecting the presence of ochratoxin A in wines". Critical reviews in food science and nutrition 46 (6): 473–8. doi:10.1080/10408390500215803. PMID 16864140. 
5. ^ Clark HA, Snedeker SM (2006). "Ochratoxin a: its cancer risk and potential for exposure". Journal of toxicology and environmental health. Part B, Critical reviews 9 (3): 265–96. doi:10.1080/15287390500195570. PMID 16621780. 
6. ^ Palma N, Cinelli S, Sapora O, Wilson SH, Dogliotti E (2007). "Ochratoxin A-Induced Mutagenesis in Mammalian Cells Is Consistent with the Production of Oxidative Stress". Chemical Research in Toxicology 20 (7): 1031–1037. doi:10.1021/tx700027j. PMC 2367102. PMID 17567156. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2367102. 
7. ^ Castegnaro M, Canadas D, Vrabcheva T, Petkova-Bocharova T, Chernozemsky IN, Pfohl-Leszkowicz A (2006). "Balkan endemic nephropathy: role of ochratoxins A through biomarkers". Mol Nutr Food Res 50 (6): 519–29. doi:10.1002/mnfr.200500182. PMID 16715544. 
8. ^ Long DT, Voice TC (2007). "Role of exposure analysis in solving the mystery of Balkan endemic nephropathy". Croat. Med. J. 48 (3): 300–11. PMC 2080532. PMID 17589972. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2080532. 
9. ^ Abouzied MM, Horvath AD, Podlesny PM, et al. (2002). "Ochratoxin A concentrations in food and feed from a region with Balkan Endemic Nephropathy". Food additives and contaminants 19 (8): 755–64. doi:10.1080/02652030210145036. PMID 12227939. 

External links

• Detailed information about mycotoxins