Taurine
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| Taurine | |
|---|---|
| Chemical name | Taurine |
| Chemical formula | C2H7NO3S |
| Molecular mass | 125.14 g/mol |
| Melting point | 305.11 °C |
| Density | 1.734 g/cm³ (@ -173.15 °C) |
| CAS number | 107-35-7 |
| SMILES | NCCS(=O)(O)=O |
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| Disclaimer and references | |
Taurine (Latin taurus = bull, as it was first isolated from ox (Bos taurus) bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin) or 2-aminoethanesulfonic acid is an acidic chemical substance found in high abundance in the tissues of many animals (metazoa), especially sea animals. Taurine is also found in plants, fungi, and some bacterial species, but in far less abundance. Taurine is a derivative of the sulphur-containing (sulfhydryl) amino acid, cysteine. Although it is often called an amino acid, even in scientific literature,[1][2][3] it lacks a carboxyl group and therefore does not qualify as an amino acid.[4] It does contain a sulfonate group and may be called an amino sulfonic acid. Small polypeptides have been identified which contain taurine but to date no tRNA synthetase has been identified as specifically recognizing taurine and capable of charging it to a tRNA. [5]
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[edit] Biosynthesis
The major pathway for mammalian taurine synthesis occurs in the liver via the cysteine sulfinic acid pathway. In this pathway, the sulfhydryl group of cysteine is first oxidized to cysteine sulfinic acid by the enzyme cysteine dioxygenase. Cysteine sulfinic acid, in turn, is decarboxylated by cysteine sulfinic acid decarboxylase to form hypotaurine. It is unclear whether hypotaurine is then spontaneously or enzymatically oxidized to yield taurine.
[edit] Physiological roles
Taurine is conjugated via its amino terminal group with the bile acids chenodeoxycholic acid and cholic acid to form the bile salts sodium taurochenodeoxycholate and sodium taurocholate (see bile). The low pKa (1.5) of taurine's sulfonic acid group ensures that this moiety is negatively charged in the pH ranges normally found in the intestinal tract and thus improves the surfactant properties of the cholic acid conjugate.
Taurine has also been implicated in a wide array of other physiological phenomena including inhibitory neurotransmission, long-term potentiation in the striatum/hippocampus, membrane stabilization, feedback inhibition of neutrophil/macrophage respiratory bursts, adipose tissue regulation, and calcium homeostasis. The evidence for these claims, when compared against that reported for taurine's role in bile acid synthesis and osmoregulation, is relatively poor.
Prematurely-born infants who lack the enzymes needed to convert cystathionine to cysteine may become deficient in taurine. Thus, taurine is a dietary essential nutrient in these individuals and is often added to many infant formulas as a measure of prudence. There is also evidence that taurine in adult humans reduces blood pressure.[6]
Many therapeutic applications of taurine have been investigated. Conditions that taurine might be useful in treating include: cardiovascular diseases, hypercholesterolemia, epilepsy and other seizure disorders, macular degeneration, Alzheimer's disease, hepatic disorders, alcoholism, and cystic fibrosis.[7] Recent studies show that taurine supplements taken by mice on a high-fat diet reduced their overall weight. Studies have yet to be done on the effect of taurine on obesity in humans.[8]. Recent studies have also shown that taurine can influence(and possibly reverse) nerve blood flow, motor nerve conduction velocity, and nerve sensory threshold defects in experimental diabetic neuropathic rats (PMID: 16624563 & PMID: P11259114 Pubmed id's).
[edit] Taurine and animals
Taurine is essential for cat health, as they cannot synthesize the compound. The absence of taurine causes the cat's retina to slowly degenerate, causing eye problems and (eventually) irreversible blindness. This condition is called central retinal degeneration (CRD). [9] [10] In addition, taurine deficiency can cause feline dilated cardiomyopathy, and supplementation can reverse left ventricular systolic dysfunction. (Pion et al 1988) Taurine is now added to all commercial cat foods, so unless you feed your cat homemade food, a Taurine deficiency is usually not an issue.
[edit] Taurine levels in vegans
Taurine levels were found to be significantly lower in vegans than in a control group on a standard American diet. Plasma taurine was 78% of control values, and urinary taurine only 29%.[11]
[edit] Commercial uses for taurine
In recent years, taurine has become a common ingredient in energy drinks. Taurine is also often used in combination with bodybuilding supplements such as creatine and anabolic steroids. Taurine is also used in some contact solutions, such as, Complete Moisture PLUS.
[edit] References
- ^ Stapleton, PP, L O'Flaherty, HP Redmond, and DJ Bouchier-Hayes (1998). "Host defense--a role for the amino acid taurine?". Journal of Parenteral and Enteral Nutrition 22 (1): 42–48. Retrieved on 2006-08-19.
- ^ Weiss, Stephen J., Roger Klein, Adam Slivka, and Maria Wei (1982). "Chlorination of Taurine by Human Neutrophils". Journal of Clinical Investigation 70 (3): 598–607. Retrieved on 2006-08-19.
- ^ Kirk, Kiaran, and Julie Kirk (1993). "Volume-regulatory taurine release from a human lung cancer cell line". FEBS Letters 336 (1): 153–158. DOI:doi:10.1016/0014-5793(93)81630-I.
- ^ Carey, Francis A. [1987] (2006). Organic Chemistry, 6th ed., New York: McGraw Hill, 1149. ISBN 0-07-282837-4. “Amino acids are carboxylic acids that contain an amine function.”
- ^ Lahdesmaki, P (1987). "Biosynthesis of taurine peptides in brain cytoplasmic fraction in vitro.". Int J Neuroscience 37 (1-2): 79–84.
- ^ Militante, J. D., J. B. Lombardini (November 2002). "Treatment of hypertension with oral taurine: experimental and clinical studies". Amino Acids 23 (4): 381–393. DOI:10.1007/s00726-002-0212-0. Retrieved on 2006-08-22.
- ^ Birdsall, Timothy C.. Therapeutic Applications of Taurine. Retrieved on 2006-08-22.
- ^ Currently taurine is being tested as an anti-manic treatment for bipolar depression. Tsuboyama-Kasaoka, Nobuyo, Chikako Shozawa, Kayo Sano, Yasutomi Kamei, Seiichi Kasaoka, Yu Hosokawa and Osamu Ezaki (2006). "Taurine (2-Aminoethanesulfonic Acid) Deficiency Creates a Vicious Circle Promoting Obesity". Endocrinology 147 (7): 3276–3284. DOI:10.1210/en.2005-1007. Retrieved on 2006-08-22.
- ^ Taurine And Its Importance In Cat Foods. Iams Cat Nutrition Library (2004). Retrieved on 2006-08-22.
- ^ Nutrient Requirements of Cats. Nutrient Requirements of Cats, Revised Edition, 1986 (1986). Retrieved on 2006-09-10.
- ^ Laidlaw S, Shultz T, Cecchino J, Kopple J (1988) "Plasma and urine taurine levels in vegans." American Journal of Clinical Nutrition, vol. 47, pp. 660-663.
