Citrinin
From Wikipedia, the free encyclopedia
| Citrinin[1] | |
|---|---|
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| IUPAC name | (3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid |
| Other names | Citrinin Antimycin |
| Identifiers | |
| CAS number | [] |
| SMILES | O=C2C(C(O)=O)=C(O)C1=CO[C@H](C)[C@@H](C)C1=C2C |
| Properties | |
| Molecular formula | C13H14O5 |
| Molar mass | 250.24 |
| Appearance | Lemon-yellow needles |
| Melting point |
175 °C (decomp.) |
| Solubility in water | Insoluble |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Citrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are used in the production of human foods such as grain, cheese, sake and red pigments.
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[edit] Toxicity
Citrinin acts as a nephrotoxin in all species in which it has been tested, but its acute toxicity varies.[2] It causes mycotoxic nephropathy in livestock and has been implicated as a cause of Balkan nephropathy and yellow rice fever in humans.
Citrinin is used as a reagent in biological research. It induces mitochondrial permeability pore opening and inhibits respiration by interfering with complex I of the respiratory chain.
[edit] Citrinin producers
Citrinin is produced by a variety of fungi including:
- Aspergillus niveus
- Aspergillus ochraceus
- Aspergillus oryzae
- Aspergillus terreus
- Monascus ruber
- Monascus purpureus
- Penicillium citrinum
- Penicillium camemberti
[edit] Notes
- ^ Merck Index, 11th Edition, 2329.
- ^ Bennett, J. W.; Klich, M. Mycotoxins. Clinical Microbiology Reviews (2003), 16(3), 497-516.
[edit] References
- E.J. Da Lozzo et al. J. Biochem. Mol. Toxicol. 1998 12 291
- G.M. Chagas et al. J. Appl. Toxicol. 1995 15 91
