Ochratoxin A
Names | |
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IUPAC name
N-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carbonyl]-L-phenylalanine
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Systematic IUPAC name
(2S)-2-[(3R)-5-Chloro-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-7-carboxamido]-3-phenylpropanoic acid | |
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 | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.005.586 |
IUPHAR/BPS |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C20H18ClNO6 | |
Molar mass | 403.813 |
Melting point | 169 °C (336 °F; 442 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ochratoxin A—a
Impact on human and animal health
Carcinogenicity
Ochratoxin A is potentially
The evidence in experimental animals is sufficient to indicate carcinogenicity of ochratoxin A. It was tested for
Neurotoxicity
Ochratoxin A has a strong affinity for the brain, especially the cerebellum (Purkinje cells), ventral mesencephalon, and hippocampal structures.[13] The affinity for the hippocampus could be relevant to the pathogenesis of Alzheimer's disease, and subchronic administration to rodents induces hippocampal neurodegeneration. Ochratoxin causes acute depletion of striatal dopamine, which constitutes the bed of Parkinson's disease, but it did not cause cell death in any of brain regions examined.[14] Teams from Zheijiang Univ. and Kiel Univ. hold that ochratoxin may contribute to Alzheimer's and to Parkinson's diseases. Nonetheless, their study was performed in vitro and may not extrapolate to humans.[15] The developing brain is very susceptible to ochratoxin, hence the need for caution during pregnancy.[16]
Immunosuppression and immunotoxicity
Ochratoxin A can cause
Potential link to nephropathies
Balkan endemic nephropathy (BEN), a slowly progressive renal disease, appeared in the middle of the 20th century, highly localized around the Danube, but only hitting certain households. Patients over the years develop kidney failure that requires dialysis or transplantation. The initial symptoms are those of a tubulointerstitial
Other nephropathies, although not responding to the "classical" definition of BEN, may be linked to ochratoxin. Thus, this could in certain circumstances be the case for focal segmental
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 generally involve reduction in weight gains, poor feed conversion, reduced egg production, and poor egg shell quality.[25] Economic losses occur also in swine farms, linked to nephropathy and costs for the disposal of carcasses.
Toxicity does not seem to constitute a problem in cattle, as the rumen harbors protozoa that hydrolyze OTA.[26] However, contamination of milk is a possibility.[citation needed]
Dietary guidelines
Source | Median in μg/kg of food |
Median in ng/kg of food |
Weight in kg |
Diet 1 | Diet 1+ |
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Liquorice extract | 26.30 | 26,300 | |||
Ginger | 5.50 | 5,500 | 0.005 | 27.50 | |
Nutmeg | 2.27 | 2,265 | 0.005 | 11.33 | |
Paprika | 1.32 | 1,315 | 0.005 | 6.58 | |
Pig liver | 1.10 | 1,100 | |||
Ginseng | 1.10 | 1,100 | |||
Raisins dry | 0.95 | 950 | 0.1 | 95.00 | |
Pig kidney | 0.80 | 800 | 0.2 | 160 | |
Liquorice confectionery | 0.17 | 170 | |||
Coffee | 0.13 | 125 | 0.3 | 37.50 | |
Cereals | 0.09 | 87.5 | 0.5 | 43.75 | |
Peanuts | 0.08 | 79 | 0.2 | 15.80 | |
Wine | 0.05 | 50 | 0.5 | 25 | |
Pulses | 0.05 | 49.5 | 0.5 | 24.75 | |
Beer | 0.05 | 49 | |||
Salami | 0.05 | 49 | 0.3 | 14.70 | |
Total in ng | 286.11 | 461.91 |
Gender | Weight in kg |
Tolerable OTA in ng |
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male | 86 | 430 |
female | 74 | 370 |
Although ochratoxin A is not held as of today as responsible for renal cell carcinoma (RCC), the most frequent renal cancer, it is frequently written that dietary pattern might decrease or increase the risk of RCC. A Uruguayan case-control study [29] correlates intake of meat with occurrence of RCC. A very large prospective cohort in Sweden [30] explores correlations between RCC occurrence, diets rich in vegetables and poultry (so-called "healthy diets"), and diets rich in meat (especially processed meat: salami, black pudding). The thesis defended is that more fruit and vegetables might have a protective role. Fruit (except raisins and dried fruit) are very poor in ochratoxin, and processed meat can be rich in ochratoxin.
Dermal exposure
Ochratoxin A can permeate through the human skin.[31] Although no significant health risk is expected after dermal contact in agricultural or residential environments, skin exposure to ochratoxin A should nevertheless be limited.
Genetic resistance
In 1975, Woolf et al.[32] proposed that the inherited disorder phenylketonuria protects against ochratoxin A poisoning through the production of high levels of phenylalanine. Ochratoxin is a competitive inhibitor of phenylalanine in the phenylalanyl-tRNA-synthetase-catalyzed reaction thus preventing protein synthesis, which can be reversed by introducing phenylalanine, which is in excess in PKU individuals.[33]
See also
References
- ^ PMID 16515661.
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- PMID 3862905.
- ^ Gary A. Boorman. "Toxicology and Carcinogenesis studies of Ochratoxin A in F344/N rats". National Toxicology Program, May 1989, NTP TR 358.
- PMID 17580155.
- PMID 17110534.
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- ^ Fink-Gremmels J. (29 June – 1 July 2005). "Conclusions from the workshops on Ochratoxin A in Food: recent developments and significance". Organized by ILSI Europe in Baden (Austria).
- PMID 970130.
- PMID 22253638. Article ID 835059.
- .
- PMID 22069661.
- ^ Scientific Panel on Contaminants in the Food Chain (2006). "Opinion of the Scientific Panel on Contaminants in the Food Chain on a request from the Commission related to Ochratoxin A in Food, Question N° EFSA-Q-2005-154, Adopted on 4 April 2006". The EFSA Journal. 365: 1–56.
- ^ Codex Alimentarius Commission (1999). "Codex Committee on Food Additives and Contaminants, Position paper on ochratoxin A, Thirty-first Session, The Hague, The Netherlands, 22-26 March 1999" (PDF). Joint FAO/WHO Food Standards Programme: 1–9. Archived from the original (PDF) on 2017-05-18.
- PMID 9820187.
- PMID 15987861.
- PMID 22749975.
- S2CID 970755.
- PMID 30258868.
External links
- Media related to Ochratoxin A at Wikimedia Commons