|1725411, 1725412 R, 1725413 S|
|RTECS number||CF1934200 S|
|Molar mass||174.20 g·mol−1|
|Melting point||260 °C; 500 °F; 533 K|
|Boiling point||368 °C (694 °F; 641 K)|
|14.87 g/100 mL (20 °C)|
|Solubility||slightly soluble in ethanol
insoluble in ethyl ether
|232.8 J K−1 mol−1 (at 23.7 °C)|
|250.6 J K−1 mol−1|
Std enthalpy of
|−624.9–−622.3 kJ mol−1|
Std enthalpy of
|−3.7396–−3.7370 MJ mol−1|
|GHS signal word||WARNING|
LD50 (Median lethal dose)
|5110 mg/kg (rat, oral)|
Related alkanoic acids
|Supplementary data page|
|Refractive index (n),
Dielectric constant (εr), etc.
|UV, IR, NMR, MS|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Arginine (//, abbreviated as Arg or R) is an α-amino acid. It was first isolated in 1886. The L-form is one of the 20 most common natural amino acids. At the level of molecular genetics, in the structure of the messenger ribonucleic acid mRNA, CGU, CGC, CGA, CGG, AGA, and AGG, are the triplets of nucleotide bases or codons that code for arginine during protein synthesis. Arginine was first isolated from a lupin seedling extract in 1886 by the Swiss chemist Ernst Schultze.
In mammals, arginine is classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Preterm infants are unable to synthesize or create arginine internally, making the amino acid nutritionally essential for them. Most healthy people do not need to supplement with arginine because their body produces sufficient amounts.
- 1 Sources
- 2 Function
- 3 Structure
- 4 Research
- 5 See also
- 6 References
- 7 External links
Arginine is a conditionally essential amino acid, meaning that whether or not it is required to be healthy is conditional on the health status or life cycle of the individual. The biosynthetic pathway, however, does not produce sufficient arginine, and some must still be consumed through diet.Individuals with poor nutrition or certain physical conditions may be advised to increase their intake of foods containing arginine. Arginine is found in a wide variety of foods, including:
- Animal sources
- dairy products (e.g., cottage cheese, ricotta, milk, yogurt, whey protein drinks), beef, pork (e.g., bacon, ham), gelatin, poultry (e.g. chicken and turkey light meat), wild game (e.g. pheasant, quail), seafood (e.g., halibut, lobster, salmon, shrimp, snails, tuna)
- Plant sources
- wheat germ and flour, lupins, buckwheat, granola, oatmeal, peanuts, nuts (coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazelnuts, pinenuts), seeds (pumpkin, sesame, sunflower), chickpeas, cooked soybeans, Phalaris canariensis (canaryseed or alpiste)
Arginine is synthesized from citrulline in arginine and proline metabolism by the sequential action of the cytosolic enzymes argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL). In terms of energy, this is costly, as the synthesis of each molecule of argininosuccinate requires hydrolysis of adenosine triphosphate (ATP) to adenosine monophosphate (AMP), i.e., two ATP equivalents. In essence, taking an excess of arginine gives more energy by saving ATPs that can be used elsewhere.
Citrulline can be derived from multiple sources:
- from arginine via nitric oxide synthase (NOS)
- from ornithine via catabolism of proline or glutamine/glutamate
- from asymmetric dimethylarginine (ADMA) via DDAH
On a whole-body basis, synthesis of arginine occurs principally via the intestinal–renal axis, wherein epithelial cells of the small intestine, which produce citrulline primarily from glutamine and glutamate, collaborate with the proximal tubule cells of the kidney, which extract citrulline from the circulation and convert it to arginine, which is returned to the circulation. As a consequence, impairment of small bowel or renal function can reduce endogenous arginine synthesis, thereby increasing the dietary requirement.
Synthesis of arginine from citrulline also occurs at a low level in many other cells, and cellular capacity for arginine synthesis can be markedly increased under circumstances that also induce iNOS. Thus, citrulline, a coproduct of the NOS-catalyzed reaction, can be recycled to arginine in a pathway known as the citrulline-NO or arginine-citrulline pathway. This is demonstrated by the fact that, in many cell types, citrulline can substitute for arginine to some degree in supporting NO synthesis. However, recycling is not quantitative because citrulline accumulates along with nitrate and nitrite, the stable end-products of NO, in NO-producing cells.
The roles of arginine include:
- Precursor for the synthesis of nitric oxide (NO) Non-L-arginine derived NO can be generated by the nitrate-nitrite-nitric oxide pathway that is monitored through saliva testing.
- Reduces healing time of injuries (particularly bone)
- Quickens repair time of damaged tissue
- Helps decrease blood pressure in clinical hypertensive subjects NO-mediated decrease in blood pressure is influenced by both the L-arginine-dependent nitric oxide synthase pathway and non-L-arginine or alternative pathway through nitrate-rich foods such as beets and spinach.
The distributing basics of the moderate structure found in geometry, charge distribution, and ability to form multiple H-bonds make arginine ideal for binding negatively charged groups. For this reason, arginine prefers to be on the outside of the proteins, where it can interact with the polar environment.
Incorporated in proteins, arginine can also be converted to citrulline by PAD enzymes. In addition, arginine can be methylated by protein methyltransferases.
Arginine is the immediate precursor of nitric oxide (NO), urea, ornithine, and agmatine; is necessary for the synthesis of creatine; and can also be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine), citrulline, and glutamate. As a precursor of nitric oxide, arginine may have a role in the treatment of some conditions where vasodilation is required. The presence of asymmetric dimethylarginine (ADMA), a close relative, inhibits the nitric oxide reaction; therefore, ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium.
Treatment of dentin hypersensitivity
Arginine (8%) in dental products (e.g., toothpaste) provides effective relief from sensitive teeth by depositing a dentin-like mineral, containing calcium and phosphate, within the dentin tubules and in a protective layer on the dentin surface.
Treatment of herpes simplex virus
Possible increased risk of death after supplementation following heart attack
A clinical trial found that patients taking an L-arginine supplement following a heart attack found no change in the heart's vascular tone or decrease in the symptoms of congestive heart failure (the heart's ability to pump). In fact, six more patients that were taking L-arginine died than those taking a placebo, resulting in early termination of the study with the recommendation that the supplement not be used by heart attack patients.
With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments, and thus imparts basic chemical properties to arginine. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized, enabling the formation of multiple H-bonds.
Intravenously-administered arginine stimulates the secretion of growth hormone, and is used in growth hormone stimulation tests. Two studies have found that oral arginine supplementation is also effective at increasing resting GH levels. The first study found that oral preparations of arginine are effective at increasing growth hormone levels. In fact, the 9-gram dose resulted in mean peak GH levels of 6.4 (+/- 1.3) µg/L versus placebo levels of 2.9 (+/- 0.7). Another study found similar results. It included resting versus exercise and oral L-arginine versus oral placebo. The authors concluded that "Oral arginine alone (7 g) stimulated GH release, but a greater GH response was seen with exercise alone. The combined effect of arginine before exercise attenuates the GH response… GH production: Ex > Arg+Ex > Arg > placebo" suggesting against supplementing with arginine alone prior to exercise if the goal is to raise GH levels, but concurring with the previous study that oral L-arginine increases GH on days free of significant exercise. In contrast to these two studies that found increased resting GH due to oral arginine supplementation, a third study did not find increase in resting GH levels from oral supplementation. In that study, oral preparations of L-arginine were ineffective at increasing growth hormone levels despite being effective at increasing plasma levels of L-arginine.
High blood pressure
Intravenous infusion of arginine reduces blood pressure in patients with hypertension as well as normal subjects.
A meta-analysis showed that L-arginine reduces blood pressure with pooled estimates of 5.4/2.7 mmHg for SBP/DBP.
Supplementation with L-arginine reduces diastolic blood pressure and lengthens pregnancy for women with gestational hypertension, including women with high blood pressure as part of pre-eclampsia. It does not lower systolic blood pressure or improve the baby's weight at birth.
- IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. Archived from the original on 29 May 2007. Retrieved 2007-05-17.
- "Drugs and Supplements Arginine". http://www.mayoclinic.org/. Retrieved 15 January 2015.
- Saini, Rashmi; Badole, Sachin L.; Zanwar, Anand A. (2013). "Arginine Derived Nitric Oxide: Key to Healthy Skin". In Watson, Ronald Ross; Zibadi, Sherma. Bioactive Dietary Factors and Plant Extracts in Dermatology. Nutrition and Health. pp. 73–82. doi:10.1007/978-1-62703-167-7_8. ISBN 978-1-62703-166-0.
- Tapiero H, Mathé G, Couvreur P, Tew KD (November 2002). "L-Arginine". (review). Biomedicine & Pharmacotherapy 56 (9): 439–445. doi:10.1016/s0753-3322(02)00284-6.
- Wu G, Jaeger LA, Bazer FW, Rhoads JM (Aug 2004). "Arginine deficiency in preterm infants: biochemical mechanisms and nutritional implications". (review). The Journal of Nutritional Biochemistry 15 (8): 442–51. doi:10.1016/j.jnutbio.2003.11.010. PMID 15302078.
- Morris SM (Oct 2004). "Enzymes of arginine metabolism". (review). The Journal of Nutrition 134 (10 Suppl): 2743S–2747S; discussion 2765S–2767S. PMID 15465778.
- Stechmiller JK, Childress B, Cowan L (Feb 2005). "Arginine supplementation and wound healing". (review). Nutrition in Clinical Practice 20 (1): 52–61. doi:10.1177/011542650502000152. PMID 16207646.
- Witte MB, Barbul A (2003). "Arginine physiology and its implication for wound healing". (review). Wound Repair and Regeneration 11 (6): 419–23. doi:10.1046/j.1524-475X.2003.11605.x. PMID 14617280.
- Andrew PJ, Mayer B (Aug 1999). "Enzymatic function of nitric oxide synthases". (review). Cardiovascular Research 43 (3): 521–31. doi:10.1016/S0008-6363(99)00115-7. PMID 10690324.
- Gokce N (Oct 2004). "L-arginine and hypertension". (review). The Journal of Nutrition 134 (10 Suppl): 2807S–2811S; discussion 2818S–2819S. PMID 15465790.
- Rajapakse NW, De Miguel C, Das S, Mattson DL (Dec 2008). "Exogenous L-arginine ameliorates angiotensin II-induced hypertension and renal damage in rats". (primary). Hypertension 52 (6): 1084–90. doi:10.1161/HYPERTENSIONAHA.108.114298. PMC 2680209. PMID 18981330.
- Dong JY, Qin LQ, Zhang Z, Zhao Y, Wang J, Arigoni F, Zhang W (Dec 2011). "Effect of oral L-arginine supplementation on blood pressure: a meta-analysis of randomized, double-blind, placebo-controlled trials". review. American Heart Journal 162 (6): 959–965. doi:10.1016/j.ahj.2011.09.012. PMID 22137067.
- Petrou I, Heu R, Stranick M, Lavender S, Zaidel L, Cummins D, Sullivan RJ, Hsueh C, Gimzewski JK (2009). "A breakthrough therapy for dentin hypersensitivity: how dental products containing 8% arginine and calcium carbonate work to deliver effective relief of sensitive teeth". (primary). J Clin Dent 20 (1): 23–31. PMID 19489189.
- Naito T, Irie H, Tsujimoto K, Ikeda K, Arakawa T, Koyama AH (Apr 2009). "Antiviral effect of arginine against herpes simplex virus type 1". (review). International Journal of Molecular Medicine 23 (4): 495–499. doi:10.3892/ijmm_00000156. PMID 19288025.
- Romero, Maritza J.; Platt, Daniel H.; Tawfik, Huda E.; Labazi, Mohamed; El-Remessy, Azza B.; Bartoli, Manuela; Caldwell, Ruth B.; Caldwell, Robert W. (2008). "Diabetes-induced Coronary Vascular Dysfunction Involves Increased Arginase Activity". Circulation Research 102 (1): 95–102. doi:10.1161/CIRCRESAHA.107.155028. PMC 2822539. PMID 17967788. Lay summary – ScienceDaily (February 1, 2008).
- Schulman SP, Becker LC, Kass DA, Champion HC, Terrin ML, Forman S, Ernst KV, Kelemen MD, Townsend SN, Capriotti A, Hare JM, Gerstenblith G (Jan 2006). "L-arginine therapy in acute myocardial infarction: the Vascular Interaction With Age in Myocardial Infarction (VINTAGE MI) randomized clinical trial". (primary). Jama 295 (1): 58–64. doi:10.1001/jama.295.1.58. PMID 16391217.
- Alba-Roth J, Müller OA, Schopohl J, von Werder K (Dec 1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion". The Journal of Clinical Endocrinology and Metabolism 67 (6): 1186–9. doi:10.1210/jcem-67-6-1186. PMID 2903866.
- U.S. National Library of Medicine (September 2009 Growth hormone stimulation test
- Collier SR, Casey DP, Kanaley JA (Apr 2005). "Growth hormone responses to varying doses of oral arginine". (primary). Growth Hormone & IGF Research 15 (2): 136–139. doi:10.1016/j.ghir.2004.12.004. PMID 15809017.
- Forbes SC, Bell GJ, Turner AJ, Hick PE, Bland RD, Clarke TL, Harden LB (Feb 1976). "Rapid infusion of sodium bicarbonate and albumin into high-risk premature infants soon after birth: a controlled, prospective trial". (review). American Journal of Obstetrics and Gynecology 124 (3): 405–11. doi:10.1139/h11-035. PMID 21574873.
- Finsterer J (Nov 2009). "Management of mitochondrial stroke-like-episodes". (review). European Journal of Neurology 16 (11): 1178–84. doi:10.1111/j.1468-1331.2009.02789.x. PMID 19780807.
- Nakaki T, Hishikawa K, Suzuki H, Saruta T, Kato R (Sep 1990). "L-arginine-induced hypotension". (primary). Lancet 336 (8716): 696. doi:10.1016/0140-6736(90)92196-O. PMID 1975886.
- Gui S, Jia J, Niu X, Bai Y, Zou H, Deng J, Zhou R (Mar 2014). "Arginine supplementation for improving maternal and neonatal outcomes in hypertensive disorder of pregnancy: a systematic review". (review). Journal of the Renin-Angiotensin-Aldosterone System 15 (1): 88–96. doi:10.1177/1470320313475910. PMID 23435582.
|Wikimedia Commons has media related to arginine.|
- NIST Chemistry Webbook
- Mayo Clinic discussion of Arginine.
- National Institute of Health discussion of Arginine.