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Citrinin



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

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
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Citrinin". A list of authors is available in Wikipedia.
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