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Citrinin
From Wikipedia, the free encyclopedia
| Citrinin[1] | |
|---|---|
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid | |
other names Citrinin Antimycin | |
| Identifiers | |
| CAS number | 518-75-2 |
| SMILES | O=C2C(C(O)=O)=C(O)C1=CO[C@H](C)[C@@H](C)C1=C2C |
| Properties | |
| Molecular formula | C13H14O5 |
| Molar mass | 250.25 g mol−1 |
| 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 references | |
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.
Contents |
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.
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
Notes
- ^ Merck Index, 11th Edition, 2329.
- ^ Bennett, J. W.; Klich, M. Mycotoxins. Clinical Microbiology Reviews (2003), 16(3), 497-516.
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
- D.Heperkan,B.E.Meriç,G.Şişmanoğlu,G.Dalkılıç,F.Güler. In: Advances in Experimental Medicine & Biology. Edited by A.D. Hocking; J.I.Pitt, R.A.Samson & U.Thrane.2006 571
- Ö.Tokuşoğlu,H.Alpas,F.Bozoğlu. Effect of High Hydrostatic Pressure (HHP) on Mycotoxin Citrinin, Major Phenolics Oleuropein, Hydroxytyrosol, and Total Antioxidant Activity in Black Table Olives. 135-26 Technical Research Paper. 2008 IFT Annual Meeting+Food Expo. June 28-July 1, New Orleans, LA, USA.2008 183
