Citrinin

Citrinin[1]
IUPAC name	(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.

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

1. ^ Merck Index, 11th Edition, 2329.
2. ^ 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