World Library  
  
Flag as Inappropriate
Email this Article

Citrinin

Article Id: WHEBN0004535954
Reproduction Date:

Title: Citrinin  
Author: World Heritage Encyclopedia
Language: English
Subject: Mycotoxin, List of MeSH codes (D03), Mycotoxicology, Penicillium, Penicillium gorlenkoanum
Collection:
Publisher: World Heritage Encyclopedia
Publication
Date:
 

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

Antimycin

Identifiers
CAS number  YesY
PubChem
ChemSpider  N
UNII  N
KEGG  N
ChEMBL  N
Jmol-3D images Image 1
Properties
Molecular formula C13H14O5
Molar mass 250.25 g mol−1
Appearance Lemon-yellow needles
Melting point 175 °C (347 °F; 448 K) (decomposes)
Solubility in water Insoluble
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N   YesY/N?)

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

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

Citrinin is produced by a variety of fungi, including:

References

  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.  
  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.  
  4. ^ Bennett, J. W.; Klich, M. (2003). "Mycotoxins". Clinical Microbiology Reviews 16 (3): 497–516.  
  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.  
  6. ^ "Citrinin".  
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.