Arginine was discovered by Ernst Schulze, a Swiss chemist who first isolated it from a lupine seedling extract back in 1886. Later on, in 1895, this amino acid was recognized as a component of casein and appeared to be widely distributed in various food and feed.
Chemical structure of Arginine
Chemical and physical properties of Arginine
IUPAC Name: (2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acid
Symbol: Three-letter code - Arg. One-letter code - R
Molecular Weight (Molar Mass): 174.20096 g/mol
Formula: C6H14N4O2
Canonical SMILES: C(CC(C(=O)O)N)CN=C(N)N
Isomeric SMILES: C(C[C@@H](C(=O)O)N)CN=C(N)N
InChIKey Identifier: ODKSFYDXXFIFQN-SMLZDNMQDI
CAS Number: 74-79-3
MDL Number: MFCD00002635
Melting point: 223 °C
RNA codons: CGU, CGC, CGA, CGG; AGA, AGG
Solubility in water: 148,7 g/L (20 °C); pKa - 2,17; pKb - 9,04
Rf value in n-butanol/acetic acid/water = 12:3:5 - 0.20
2D Molfile: Get the molfile
3D PDB file: Get the PDB file
Other names: (S)-2-Amino-5-guanidinopentanoic acid; L-(+)-Arginine; S-(+)-Arginine
Benefits of L-Arginine
You can benefit from Arginine in different ways. For example, it plays an important role in the cell division and in the immune functioning. In addition, it helps healing wounds, release hormones, and remove ammonia from your body. This amino acid is proved to be a precursor of nitric oxide, which, as you know, causes a blood vessel relaxation. Therefore, through the nitric oxide (NO) it becomes a mediator in different biological systems. In addition, Arginine is an intermediate in the urea cycle, cleaved into ornithine and urea.
Arginine may be useful under many body conditions, including colds, high blood pressure, migraines, congestive heart failure, and even erectile dysfunction, male infertility and sexual dysfunction in women. Many people use Arginine in order to boost up the immune system and to improve the athletic performance - this amino acid is known for aiding in bodybuilding. The others use it to faster recover after surgery.
Researches have been performed to prove that Arginine is effective for managing the inflammation of the bladder. This amino acid is also known to be effective in relieving leg cramping and weakness, both conditions caused by blocked arteries (intermittent claudication). Besides, Arginine can improve kidney function in kidney transplant patients who take cyclosporine. Finally, taking an additional amount of Arginine combined with ribonucleic acid and eicosapentaenoic acid will help reduce recovery time and protect you against infection. That is why this amino acid is known for promoting wound healing after surgery.
A number of independent studies revealed that an increasing intake of food containing Arginine may help ease symptoms of angina and improve blood vessel functioning in ill people. Meanwhile, NIH points out that the scale has not yet been developed to rate the effectiveness of Arginine in relieving cold, migraines, dementia, and high blood pressure, as well as male infertility.
Argininemia
Argininemia is a rare inherited disorder caused by a deficiency of the enzyme arginase, which is essential for breaking down the amino acid arginine. This condition leads to high levels of arginine in the blood. Symptoms typically appear in early childhood and may include poor growth, developmental delays, spasticity, seizures, and intellectual disability. Argininemia is an autosomal recessive disorder, meaning both copies of the gene in each cell must have mutations for the condition to be expressed. Treatment often involves dietary management to restrict arginine intake and medications to remove excess nitrogen. Early diagnosis and intervention are crucial for managing symptoms and improving quality of life.
Food Sources
Arginine is considered a semi-essential amino acid, meaning that while the body can produce arginine on its own, there are circumstances where dietary intake becomes important. Here are some food sources rich in arginine.
Meat and Poultry
• Turkey: Turkey is a particularly good source of arginine.
• Chicken: Chicken, especially lean cuts, contains a decent amount of arginine.
Seafood
• Tuna: Tuna and other fish are good sources of arginine.
• Salmon: Salmon is not only rich in omega-3 fatty acids but also contains arginine.
Nuts and Seeds
• Almonds: Almonds are a great source of arginine and provide a range of other nutrients.
• Peanuts: Peanuts and peanut butter are also good sources of arginine.
• Sunflower Seeds: Sunflower seeds contain arginine and are a healthy snack option.
Legumes
• Soybeans: Soybeans and soy products, such as tofu and soy milk, are rich in arginine.
• Lentils: Lentils are a good plant-based source of arginine.
Dairy Products
• Dairy foods, such as yogurt and milk, contain arginine.
Grains
• Oats: Oats and oat-based products contain arginine.
• Wheat Germ: Wheat germ is a nutrient-rich part of the wheat kernel and is a good source of arginine.
Chocolate
Dark chocolate contains arginine, among other beneficial compounds. However, it's essential to consume it in moderation due to its calorie and sugar content.
Fruits
Watermelon: Watermelon is known to have higher levels of arginine compared to some other fruits.
It's important to note that the levels of arginine can vary in different foods, and individual dietary requirements may differ. While these foods contribute to arginine intake, it's also advisable to maintain a balanced diet to ensure you're getting all the essential nutrients your body needs.
As with any nutrient, it's best to obtain arginine from a varied and balanced diet rather than relying solely on specific foods. If you have specific health concerns or conditions, it's always a good idea to consult with a healthcare professional or a registered dietitian for personalized advice.