Citrinin

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Citrinin[1]
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	[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	250.24
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

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 1 Toxicity 2 Citrinin producers 3 Notes 4 References

[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

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