Citrinin

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Citrinin[1]
Citrinin structure.svg
Names
IUPAC name
(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acid
Other names
Antimycin
Identifiers
CAS number 518-75-2 YesY
ChEMBL ChEMBL510139 N
ChemSpider 10222475 N
Jmol-3D images Image
KEGG C16765 N
PubChem 54680783
UNII 3S697X6SNZ N
Properties
C13H14O5
Molar mass 250.25 g·mol−1
Appearance Lemon-yellow needles
Melting point 175 °C (347 °F; 448 K) (decomposes)
Insoluble
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

Citrinin is a mycotoxin originally isolated in 1931 by Hetherington and Raistrick from a culture of Penicillium citrinum.[2] It has since been found to be produced by a variety of other fungi that are found or used in the production of human foods, such as grain, cheese, sake, and red pigments. Citrinin has also been found in commercial red yeast rice supplements.[3]

Toxicity[edit]

Citrinin acts as a nephrotoxin in all species in which it has been tested, but its acute toxicity varies.[4] 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 III of the respiratory chain.

Citrinin can permeate through the human skin.[5] Although no significant health risk is expected after dermal contact in agricultural or residential environments, dermal exposure should nevertheless be limited.

Citrinin producers[edit]

Citrinin is produced by a variety of fungi, including:

References[edit]

  1. ^ Merck Index, 11th Edition, 2329.
  2. ^ Hetherington, A. C.; Raistrick, H. (1931). "On the Production and Chemical Constitution of a New Yellow Colouring Matter, Citrinin, Produced from Glucose by Penicillium citrinum Thom". Philosophical Transactions of the Royal Society B: Biological Sciences 220 (468–473): 269–95. doi:10.1098/rstb.1931.0025. ISSN 0962-8436. 
  3. ^ Gordon, R. Y.; Cooperman, T.; Obermeyer, W.; Becker, D. J. (2010). "Marked Variability of Monacolin Levels in Commercial Red Yeast Rice Products: Buyer Beware!". Archives of Internal Medicine 170 (19): 1722–7. doi:10.1001/archinternmed.2010.382. PMID 20975018. 
  4. ^ Bennett, J. W.; Klich, M. (2003). "Mycotoxins". Clinical Microbiology Reviews 16 (3): 497–516. doi:10.1128/CMR.16.3.497-516.2003. PMC 164220. PMID 12857779. 
  5. ^ Boonen, J.; Malysheva, S. V.; Taevernier, L.; Diana di Mavungu, J.; de Saeger, S.; de Spiegeleer, B. (2012). "Human skin penetration of selected model mycotoxins". Toxicology 301 (1–3): 21–32. doi:10.1016/j.tox.2012.06.012. PMID 22749975. 
  6. ^ "Citrinin". Fermentek.