Share on Facebook Share on Twitter Email
Answers.com

citrulline

 
Dictionary: cit·rul·line   (sĭt'rə-lēn') pronunciation

n.
An amino acid, C6H13N3O3, originally isolated from watermelon, that is produced as an intermediate in the conversion of ornithine to arginine during urea formation in the liver.

[New Latin Citrullus, watermelon genus (from Medieval Latin citrullus, watermelon , from Italian dialectal citrulo , from Late Latin citrium , from Latin citrus, citron) + -INE2.]


Search unanswered questions...
Enter a question here...
Search: All sources Community Q&A Reference topics
Food and Nutrition: citrulline
Top

An amino acid formed as a metabolic intermediate, but not involved in proteins, and of no nutritional importance.

Veterinary Dictionary: citrulline
Top

An alpha amino acid involved in the urea cycle.

  • c. phosphorylase — see ornithine carbamoyl transferase.
Wikipedia: Citrulline
Top
Citrulline
Citrullin - Citrulline.svg
IUPAC name
Identifiers
CAS number 372-75-8
PubChem 9750
Properties
Molecular formula C6H13N3O3
Molar mass 175.19 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

The organic compound citrulline is an α-amino acid. Its name is derived from citrullus, the Latin word for watermelon, from which it was first isolated in 1930.[1] It has the idealized formula H2NC(O)NH(CH2)3CH(NH2)CO2H. It is a key intermediate in the urea cycle, the pathway by which mammals excrete ammonia.

Contents

Biosynthesis

Citrulline is made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39).[2] Arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with release of nitric oxide.

Function

Although citrulline is not coded for by DNA directly, several proteins are known to contain citrulline as a result of a posttranslational modification. These citrulline residues are generated by a family of enzymes called peptidylarginine deiminases (PADs), which convert arginine into citrulline in a process called citrullination or deimination. Proteins that normally contain citrulline residues include myelin basic protein (MBP), filaggrin, and several histone proteins, whereas other proteins, such as fibrin and vimentin are susceptible to citrullination during cell death and tissue inflammation.

Patients with rheumatoid arthritis often have detectable antibodies against proteins containing citrulline. Although the origin of this immune response is not known, detection of antibodies reactive with citrulline (anti-citrullinated protein antibodies) containing proteins or peptides is now becoming an important help in the diagnosis of rheumatoid arthritis.[3]

In recent studies, citrulline has been found to relax blood vessels.[4]

Sources

Citrulline in the form of citrulline malate is sold as a performance-enhancing athletic dietary supplement which was shown to reduce muscle fatigue in a preliminary clinical trial.[5]

The rind of watermelon (Citrullus lanatus) is a good natural source of citrulline.[6]

See also

References

  1. ^ Wada, M (1930). "Über Citrullin, eine neue Aminosäure im Presssaft der Wassermelone, Citrullus vulgaris Schrad.". Biochem. Zeit. 224: 420. 
  2. ^ Cox M, Lehninger AL, Nelson DR (2000). Lehninger principles of biochemistry (3rd ed.). New York: Worth Publishers. ISBN 1-57259-153-6. 
  3. ^ Coenen D, Verschueren P, Westhovens R, Bossuyt X (March 2007). "Technical and diagnostic performance of 6 assays for the measurement of citrullinated protein/peptide antibodies in the diagnosis of rheumatoid arthritis". Clin. Chem. 53 (3): 498–504. doi:10.1373/clinchem.2006.078063. PMID 17259232. http://www.clinchem.org/cgi/content/full/53/3/498. 
  4. ^ Viagra-Like Effects From Watermelon
  5. ^ Bendahan D, Mattei JP, Ghattas B, Confort-Gouny S, Le Guern ME, Cozzone PJ (Aug 2002). "Citrulline/malate promotes aerobic energy production in human exercising muscle". Br J Sports Med 36 (4): 282–9. doi:10.1136/bjsm.36.4.282. PMID 12145119. PMC 1724533. http://bjsm.bmj.com/cgi/pmidlookup?view=long&pmid=12145119. 
  6. ^ Watermelon May Have Viagra-effect

 
 

 

Copyrights:

Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved.  Read more
Food and Nutrition. A Dictionary of Food and Nutrition. Copyright © 1995, 2003, 2005 by A. E. Bender and D. A. Bender. All rights reserved.  Read more
Veterinary Dictionary. Saunders Comprehensive Veterinary Dictionary 3rd Edition. Copyright © 2007 by D.C. Blood, V.P. Studdert and C.C. Gay, Elsevier. All rights reserved.  Read more
Wikipedia. This article is licensed under the Creative Commons Attribution/Share-Alike License. It uses material from the Wikipedia article "Citrulline" Read more