Arginine
From Wikipedia, the free encyclopedia
| L-Arginine | |
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| IUPAC name |
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| Identifiers | |
| CAS number | 74-79-3 |
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| Properties | |
| Molecular formula | C6H14N4O2 |
| Molar mass | 174.2 g mol−1 |
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| Structure and properties |
n, εr, etc. |
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Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Arginine (abbreviated as Arg or R)[1] is an α-amino acid. The L-form is one of the 20 most common natural amino acids. Its codons are CGU, CGC, CGA, CGG, AGA, and AGG. In mammals, arginine is classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to meet their requirements and thus arginine is nutritionally essential for infants. Arginine was first isolated from a lupin seedling extract in 1886 by the Swiss chemist Ernst Schultze.
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[edit] Structure
The amino acid side chain of arginine consists of a 4-carbon aliphatic straight chain, the distal end of which is capped by a complex guanidinium group. 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 de-localized, enabling the formation of multiple H-bonds.
[edit] Sources
[edit] Dietary sources
Arginine is a conditionally essential amino acid, meaning most of the time it can be manufactured by the human body, and does not need to be obtained directly through the diet. The biosynthetic pathway however does not produce sufficient arginine, and some must still be consumed through diet. Individuals who have 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[2]:
- Animal sources: dairy products (e.g. cottage cheese, ricotta, milk, yogurt, whey protein drinks), beef, pork (e.g. bacon, ham), poultry (e.g. chicken and turkey light meat), wild game (e.g. pheasant, quail), seafood (e.g. halibut, lobster, salmon, shrimp, snails, tuna)
- Vegetable sources: wheat germ and flour, buckwheat, granola, oatmeal, nuts (coconut, pecans, cashews, walnuts, almonds, Brazil nuts, hazelnuts, pinenuts, peanuts), seeds (pumpkin, sesame, sunflower), chick peas, cooked soybeans
[edit] Biosynthesis
Arginine is synthesized from citrulline by the sequential action of the cytosolic enzymes argininosuccinate synthetase (ASS) and argininosuccinate lyase (ASL). This is energetically costly, as the synthesis of each molecule of argininosuccinate requires hydrolysis of adenosine triphosphate (ATP) to adenosine monophosphate (AMP); i.e., two ATP equivalents.
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
The pathways linking arginine, glutamine, and proline are bidirectional. Thus, the net utilization or production of these amino acids is highly dependent on cell type and developmental stage.
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. Consequently, 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.[3]
[edit] Function
Arginine plays an important role in cell division, the healing of wounds, removing ammonia from the body, immune function, and the release of hormones.[citation needed] Arginine, taken in combination with proanthocyanidins[4] or yohimbine[5], has also been used as a treatment for erectile dysfunction.
The benefits and functions attributed to oral ingestion of L-arginine include:
- Precursor for the synthesis of nitric oxide (NO)
- Stimulation of the release of growth hormone.
- Improves immune function
- Reduces healing time of injuries (particularly bone)
- Quickens repair time of damaged tissue
- Reduces risk of heart disease
- Increases muscle mass
- Reduces adipose tissue body fat
- Helps improve insulin sensitivity
- Helps decrease blood pressure
- Alleviates male infertility, improving sperm production and motility
- Increases circulation throughout the body, including the sex organs
[edit] In proteins
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.
[edit] As a precursor
Arginine is the immediate precursor of 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. For being a precursor of NO, (relaxes blood vessels), arginine is used in many 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.
[edit] Treatment of herpes simplex virus
A low ratio of arginine to lysine may be of benefit in the treatment of herpes simplex virus. For more information, refer to Herpes - Treatment.
[edit] Possible increases in risk of death from heart disease
A clinical trial found that patients taking an L-arginine supplement following a heart attack didn't improve in their vascular tone or their hearts' ability to pump. In fact, more patients died who were taking L-arginine than placebo and the study was stopped early with the recommendation the supplement not be used by heart attack patients. The supplement still is widely marketed.[6][7][8]
[edit] Lung inflammation and asthma
The Mayo Clinic web page on L-arginine reports that inhalation of L-arginine can increase lung inflammation and worsen asthma. No primary source for this observation is cited, making it difficult to judge the validity and clinical significance of this effect, which only highlights how much easier it is to criticize than to create, or even to spend five minutes searching Pubmed for the reference: "Effect of inhaled L-arginine on exhaled nitric oxide in normal and asthmatic subjects."[9] Compare and contrast with lung inflammation in cystic fibrosis, a condition characterized by abnormally low NO production: "Inhaled L-arginine improves exhaled nitric oxide and pulmonary function in patients with cystic fibrosis."[10]
[edit] Growth hormone
Arginine increases the production of growth hormone.[11]
[edit] References
- ^ IUPAC-IUBMB Joint Commission on Biochemical Nomenclature. "Nomenclature and Symbolism for Amino Acids and Peptides". Recommendations on Organic & Biochemical Nomenclature, Symbols & Terminology etc. http://www.chem.qmul.ac.uk/iupac/AminoAcid/. Retrieved on 2007-05-17.
- ^ "L-Arginine Supplements Nitric Oxide Scientific Studies Food Sources". http://www.keysupplements.com/articles/L-Arginine-Supplements-Nitric-Oxide-Scientific-Studies.htm. Retrieved on 2007-02-20.
- ^
Enzymes of arginine metabolism J Nutr. 2004 Oct; 134(10 Suppl): 2743S-2747S; PMID 15465778 Free text - ^ Stanislavov, R. and Nikolova. 2003. Treatment of Erectile Dysfunction with Pycnogenol and L-arginine. Journal of Sex and Marital Therapy, 29(3): 207 – 213.
- ^ Lebret, T., Hervéa, J. M., Gornyb, P., Worcelc, M. and Botto, H. 2002. Efficacy and Safety of a Novel Combination of L-Arginine Glutamate and Yohimbine Hydrochloride: A New Oral Therapy for Erectile Dysfunction. European Urology 41(6): 608-613.
- ^ Medical College of Georgia. "Diabetes Makes It Hard For Blood Vessels To Relax." ScienceDaily 1 February 2008. 1 February 2008
- ^ Arginine Therapy in Acute Myocardial Infarction JAMA. 2006 Jan; Vol.295 #1: 58-64; PMID 16391217 Abstract
- ^ This study has been discussed in some detail in : "Reverse Heart Disease Now" by Stephen T Sinatra MD and James C Roberts MD, publ. Wiley 2006 ISBN 0-471-74704-1 at pp 111-113.
- ^ Sapienza MA, Kharitonov SA, Horvath I, Chung KF, Barnes PJ. "Effect of inhaled L-arginine on exhaled nitric oxide in normal and asthmatic subjects." Thorax. 1998 Mar;53(3):172-5.
- ^ Grasemann H, Kurtz F, Ratjen F. "Inhaled L-arginine improves exhaled nitric oxide and pulmonary function in patients with cystic fibrosis." Am J Respir Crit Care Med. 2006 Jul 15;174(2):208-12.
- ^ Alba-Roth J, Müller O, Schopohl J, von Werder K (1988). "Arginine stimulates growth hormone secretion by suppressing endogenous somatostatin secretion". J Clin Endocrinol Metab 67 (6): 1186–9. doi:10.1126/science.2237411.<br> (inactive 2008-06-25). PMID 2903866.
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