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Chemical Compound Review

Citrullin     2-amino-5- (aminocarbonylamino)pentanoic acid

Synonyms: citrulina, DL-Citrulline, D-Cit-OH, Citrulline,(l), SGCUT00061, ...
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Disease relevance of citrulline


Psychiatry related information on citrulline

  • RESULTS: Plasma citrulline concentration was lower (P < 0.001) in patients with villous atrophy (24 +/- 13 micromol/L) than in healthy subjects (40 +/- 10 micromol/L) and patients with anorexia nervosa (39 +/- 9 micromol/L) [6].

High impact information on citrulline


Chemical compound and disease context of citrulline


Biological context of citrulline


Anatomical context of citrulline


Associations of citrulline with other chemical compounds


Gene context of citrulline

  • Competitive inhibition studies, measurement of citrulline uptake, and lack of complementation in gap1- strains indicated that the human cDNA genes code for proteins that prevent GAP repression by ammonium [29].
  • The conversion of L-arginine to L-citrulline, a relatively specific measure of NOS activity, was easily measured and inducible in fractionated HAECs, and > 90% of all L-arginine conversion was blocked by the NOS inhibitor, N omega-amino-L-arginine (L-NAA) [30].
  • The peptide inhibited formation of L-citrulline by eNOS and nNOS with IC(50) values of 10.6 +/- 0.4 microM and 7.1 +/- 0.6 microM, respectively [31].
  • A general amino acid permease cDNA (AAP2) was isolated from Arabidopsis by complementation of a yeast mutant defective in citrulline uptake [32].
  • A greater increase on iNOS activity (fmol [3H] citrulline/min/microg protein) and a lesser increase in calcium/calmodulin-dependent NOS activity (cNOS) were observed in the obstructed renal medulla [33].

Analytical, diagnostic and therapeutic context of citrulline


  1. Arginine, an indispensable amino acid for patients with inborn errors of urea synthesis. Brusilow, S.W. J. Clin. Invest. (1984) [Pubmed]
  2. L-arginine abrogates salt-sensitive hypertension in Dahl/Rapp rats. Chen, P.Y., Sanders, P.W. J. Clin. Invest. (1991) [Pubmed]
  3. Arginine, citrulline, and nitric oxide metabolism in end-stage renal disease patients. Lau, T., Owen, W., Yu, Y.M., Noviski, N., Lyons, J., Zurakowski, D., Tsay, R., Ajami, A., Young, V.R., Castillo, L. J. Clin. Invest. (2000) [Pubmed]
  4. Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Crenn, P., Coudray-Lucas, C., Thuillier, F., Cynober, L., Messing, B. Gastroenterology (2000) [Pubmed]
  5. Increased nitric oxide synthesis in ulcerative colitis. Middleton, S.J., Shorthouse, M., Hunter, J.O. Lancet (1993) [Pubmed]
  6. Plasma citrulline: A marker of enterocyte mass in villous atrophy-associated small bowel disease. Crenn, P., Vahedi, K., Lavergne-Slove, A., Cynober, L., Matuchansky, C., Messing, B. Gastroenterology (2003) [Pubmed]
  7. Histone deimination antagonizes arginine methylation. Cuthbert, G.L., Daujat, S., Snowden, A.W., Erdjument-Bromage, H., Hagiwara, T., Yamada, M., Schneider, R., Gregory, P.D., Tempst, P., Bannister, A.J., Kouzarides, T. Cell (2004) [Pubmed]
  8. Long-term treatment of girls with ornithine transcarbamylase deficiency. Maestri, N.E., Brusilow, S.W., Clissold, D.B., Bassett, S.S. N. Engl. J. Med. (1996) [Pubmed]
  9. Middle T antigen-transformed endothelial cells exhibit an increased activity of nitric oxide synthase. Ghigo, D., Arese, M., Todde, R., Vecchi, A., Silvagno, F., Costamagna, C., Dong, Q.G., Alessio, M., Heller, R., Soldi, R., Trucco, F., Garbarino, G., Pescarmona, G., Mantovani, A., Bussolino, F., Bosia, A. J. Exp. Med. (1995) [Pubmed]
  10. Erythrocyte stages of Plasmodium falciparum exhibit a high nitric oxide synthase (NOS) activity and release an NOS-inducing soluble factor. Ghigo, D., Todde, R., Ginsburg, H., Costamagna, C., Gautret, P., Bussolino, F., Ulliers, D., Giribaldi, G., Deharo, E., Gabrielli, G., Pescarmona, G., Bosia, A. J. Exp. Med. (1995) [Pubmed]
  11. Hypotension and reduced nitric oxide-elicited vasorelaxation in transgenic mice overexpressing endothelial nitric oxide synthase. Ohashi, Y., Kawashima, S., Hirata, K., Yamashita, T., Ishida, T., Inoue, N., Sakoda, T., Kurihara, H., Yazaki, Y., Yokoyama, M. J. Clin. Invest. (1998) [Pubmed]
  12. The late phase of ischemic preconditioning is abrogated by targeted disruption of the inducible NO synthase gene. Guo, Y., Jones, W.K., Xuan, Y.T., Tang, X.L., Bao, W., Wu, W.J., Han, H., Laubach, V.E., Ping, P., Yang, Z., Qiu, Y., Bolli, R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  13. Dysregulation of C/EBP{alpha} by mutant Huntingtin causes the urea cycle deficiency in Huntington's disease. Chiang, M.C., Chen, H.M., Lee, Y.H., Chang, H.H., Wu, Y.C., Soong, B.W., Chen, C.M., Wu, Y.R., Liu, C.S., Niu, D.M., Wu, J.Y., Chen, Y.T., Chern, Y. Hum. Mol. Genet. (2007) [Pubmed]
  14. The citrulline biosynthetic operon, argC-F, and a ribose transport operon, rbs, from Bacillus subtilis are negatively regulated by Spo0A. O'Reilly, M., Woodson, K., Dowds, B.C., Devine, K.M. Mol. Microbiol. (1994) [Pubmed]
  15. Genetic factors affecting recovery of nonpoint mutations in the region of a gene coding for ornithine transcarbamylase: involvement of both the F factor in its chromosomal state and the recA gene. Jessop, A.P., Glansdorff, N. Genetics (1980) [Pubmed]
  16. The flux of arginine after ischemia-reperfusion in the rat kidney. Prins, H.A., Nijveldt, R.J., Gasselt, D.V., van Kemenade, F., Teerlink, T., van Lambalgen, A.A., Rauwerda, J.A., van Leeuwen, P.A. Kidney Int. (2002) [Pubmed]
  17. Plasma arginine and citrulline kinetics in adults given adequate and arginine-free diets. Castillo, L., Chapman, T.E., Sanchez, M., Yu, Y.M., Burke, J.F., Ajami, A.M., Vogt, J., Young, V.R. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  18. Differential regulation of inducible nitric oxide synthase by fibroblast growth factors and transforming growth factor beta in bovine retinal pigmented epithelial cells: inverse correlation with cellular proliferation. Goureau, O., Lepoivre, M., Becquet, F., Courtois, Y. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  19. Purification of a soluble isoform of guanylyl cyclase-activating-factor synthase. Schmidt, H.H., Pollock, J.S., Nakane, M., Gorsky, L.D., Förstermann, U., Murad, F. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  20. l-Citrulline and l-arginine supplementation retards the progression of high-cholesterol-diet-induced atherosclerosis in rabbits. Hayashi, T., Juliet, P.A., Matsui-Hirai, H., Miyazaki, A., Fukatsu, A., Funami, J., Iguchi, A., Ignarro, L.J. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  21. Effects of transition metals on nitric oxide synthase catalysis. Perry, J.M., Marletta, M.A. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  22. Hepatocytes produce nitrogen oxides from L-arginine in response to inflammatory products of Kupffer cells. Curran, R.D., Billiar, T.R., Stuehr, D.J., Hofmann, K., Simmons, R.L. J. Exp. Med. (1989) [Pubmed]
  23. L-citrulline recycling in opossum internal anal sphincter relaxation by nonadrenergic, noncholinergic nerve stimulation. Rattan, S., Chakder, S. Gastroenterology (1997) [Pubmed]
  24. Agmatine, a bioactive metabolite of arginine. Production, degradation, and functional effects in the kidney of the rat. Lortie, M.J., Novotny, W.F., Peterson, O.W., Vallon, V., Malvey, K., Mendonca, M., Satriano, J., Insel, P., Thomson, S.C., Blantz, R.C. J. Clin. Invest. (1996) [Pubmed]
  25. Nitric oxide mediates norepinephrine-induced prostaglandin E2 release from the hypothalamus. Rettori, V., Gimeno, M., Lyson, K., McCann, S.M. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  26. Endothelial cellular senescence is inhibited by nitric oxide: Implications in atherosclerosis associated with menopause and diabetes. Hayashi, T., Matsui-Hirai, H., Miyazaki-Akita, A., Fukatsu, A., Funami, J., Ding, Q.F., Kamalanathan, S., Hattori, Y., Ignarro, L.J., Iguchi, A. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  27. The metabolism of L-arginine and its significance for the biosynthesis of endothelium-derived relaxing factor: cultured endothelial cells recycle L-citrulline to L-arginine. Hecker, M., Sessa, W.C., Harris, H.J., Anggård, E.E., Vane, J.R. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  28. Nitric oxide as a mediator of oxidant lung injury due to paraquat. Berisha, H.I., Pakbaz, H., Absood, A., Said, S.I. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  29. Isolation of a gene encoding a chaperonin-like protein by complementation of yeast amino acid transport mutants with human cDNA. Segel, G.B., Boal, T.R., Cardillo, T.S., Murant, F.G., Lichtman, M.A., Sherman, F. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  30. Human polymorphonuclear leukocytes lack detectable nitric oxide synthase activity. Yan, L., Vandivier, R.W., Suffredini, A.F., Danner, R.L. J. Immunol. (1994) [Pubmed]
  31. Interaction of endothelial and neuronal nitric-oxide synthases with the bradykinin B2 receptor. Binding of an inhibitory peptide to the oxygenase domain blocks uncoupled NADPH oxidation. Golser, R., Gorren, A.C., Leber, A., Andrew, P., Habisch, H.J., Werner, E.R., Schmidt, K., Venema, R.C., Mayer, B. J. Biol. Chem. (2000) [Pubmed]
  32. Differential expression of two related amino acid transporters with differing substrate specificity in Arabidopsis thaliana. Kwart, M., Hirner, B., Hummel, S., Frommer, W.B. Plant J. (1993) [Pubmed]
  33. H+-ATPase activity on unilateral ureteral obstruction: interaction of endogenous nitric oxide and angiotensin II. Valles, P.G., Manucha, W.A. Kidney Int. (2000) [Pubmed]
  34. Citrulline is an essential constituent of antigenic determinants recognized by rheumatoid arthritis-specific autoantibodies. Schellekens, G.A., de Jong, B.A., van den Hoogen, F.H., van de Putte, L.B., van Venrooij, W.J. J. Clin. Invest. (1998) [Pubmed]
  35. Lysinuric protein intolerance. Basolateral transport defect in renal tubuli. Rajantie, J., Simell, O., Perheentupa, J. J. Clin. Invest. (1981) [Pubmed]
  36. Neuronal nitric oxide synthase alternatively spliced forms: prominent functional localizations in the brain. Eliasson, M.J., Blackshaw, S., Schell, M.J., Snyder, S.H. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  37. Citrullinemia: prenatal diagnosis of an affected fetus. Fleisher, L.D., Harris, C.J., Mitchell, D.A., Nadler, H.L. Am. J. Hum. Genet. (1983) [Pubmed]
  38. Expression of the human argininosuccinate synthetase gene in hamster transferents. Hudson, L.D., Erbe, R.W., Jacoby, L.B. Proc. Natl. Acad. Sci. U.S.A. (1980) [Pubmed]
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