Taurine, or 2-aminoethanesulfonic acid, is an organic compound that is widely distributed in animal tissues. It is a major constituent of bile and can be found in the large intestine, and accounts for up to 0.1% of total human body weight. Taurine is named after the Latin taurus which means bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin. It was discovered in human bile in 1846 by Edmund Ronalds. Taurine has many biological roles, such as conjugation of bile acids, antioxidation, osmoregulation, membrane stabilization, and modulation of calcium signaling. It is essential for cardiovascular function, and development and function of skeletal muscle, the retina, and the central nervous system. Taurine is an unusual example of a naturally occurring sulfonic acid. Chemical and biochemical features Taurine exists as a zwitterion H3N+CH2CH2SO3-, as verified by X-ray crystallography.
The sulfonic acid has a low pKa ensuring that it is fully ionized to the sulfonate at the pH's found in the intestinal tract. Synthesis Synthetic taurine is obtained by the ammonolysis of isethionic acid, which in turn is obtained from the reaction of ethylene oxide with aqueous sodium bisulfite. A direct approach involves the reaction of aziridine with sulfurous acid. In 1993, about 5,000–6,000 tons of taurine were produced for commercial purposes: 50% for pet food and 50% in pharmaceutical applications. As of 2010, China alone has more than 40 manufacturers of taurine. Most of these enterprises employ the ethanolamine method to produce a total annual production of about 3,000 tons. In the laboratory taurine can be produced by alkylation of ammonia with bromoethanesulfonate salts. Biosynthesis Taurine is naturally derived from cysteine.
Mammalian taurine synthesis occurs in the pancreas via the cysteine sulfinic acid pathway. In this pathway, cysteine is first oxidized to its sulfinic acid, catalyzed by the enzyme cysteine dioxygenase. Cysteine sulfinic acid, in turn, is decarboxylated by sulfinoalanine decarboxylase to form hypotaurine. Hypotaurine is enzymatically oxidized to yield taurine by hypotaurine dehydrogenase. Taurine is also produced by the transsulfuration pathway, which converts homocysteine into cystathionine. The cystathionine is then converted to hypotaurine by the sequential action of three enzymes: cystathionine gamma-lyase, cysteine dioxygenase, and cysteine sulfinic acid decarboxylase. Hypotaurine is then oxidized to taurine as described above.
Oxidative degradation of cysteine to taurine Nutritional significance Taurine occurs naturally in fish and meat. The mean daily intake from omnivore diets was determined to be around 58 mg and to be low or negligible from a strict vegan diet. In another study, taurine intake was estimated to be generally less than 200 mg/day, even in individuals eating a high-meat diet. According to a third study, taurine consumption was estimated to vary between 40 and 400 mg/day.
The availability of taurine is affected depending on how the food is prepared, with raw diets retaining the most taurine, and baking or boiling resulting in the greatest taurine loss. 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 was 29%. Prematurely born infants are believed to lack the enzymes needed to convert cystathionine to cysteine, and may, therefore, become deficient in taurine.
Taurine is present in breast milk, and has been added to many infant formulas, as a measure of prudence, since the early 1980s. However, this practice has never been rigorously studied, and as such it has yet to be proven to be necessary, or even beneficial. Energy drinks Taurine is an ingredient in energy drinks. Many contain 1000 mg per serving, and some as much as 2000 mg. The addition of taurine is used as a nervous system depressant. Physiological functions Taurine is essential for cardiovascular function and development and function of skeletal muscle, the retina, and the central nervous system. It is a biosynthetic precursor to the bile salts sodium taurochenodeoxycholate and sodium taurocholate.
Taurine functions as an antioxidant, suppressing the toxicity of hypochlorite and hypobromite produced physiologically. Taurine reacts with these halogenating agents to form N-chloro- and N-bromotaurine, which are less toxic than their precursors hypohalides. Role in nutrition and cardiovascular health Taurine has been shown to reduce the secretion of apolipoprotein B100 and lipids in HepG2 cells. High concentrations of serum lipids and apolipoprotein B100 are major risk factors of atherosclerosis and coronary heart disease. Hence, taurine supplementation is possibly beneficial for the prevention of these diseases.
Role in the muscular system Taurine is necessary for normal skeletal muscle functioning. Mice with a genetic taurine deficiency had a nearly complete depletion of skeletal and cardiac muscle taurine levels and a reduction of more than 80% of exercise capacity compared to control mice. Taurine can influence defects in nerve blood flow, motor nerve conduction velocity, and nerve sensory thresholds in experimental diabetic neuropathic rats. Pharmacology Taurine crosses the blood–brain barrier and has been implicated in a wide array of physiological phenomena including inhibitory neurotransmission, long-term potentiation in the striatum/hippocampus, membrane stabilization, feedback inhibition of neutrophil/macrophage respiratory burst, adipose tissue regulation and possible prevention of obesity, calcium homeostasis, recovery from osmotic shock, protection against glutamate excitotoxicity, and prevention of epileptic seizures.
According to the single study on human subjects, daily administration of 1.5 g of taurine had no significant effect on insulin secretion or insulin sensitivity. There is evidence that taurine may exert a beneficial effect in preventing diabetes-associated microangiopathy and tubulointerstitial injury in diabetic nephropathy. According to animal studies, taurine produces an anxiolytic effect and may act as a modulator or antianxiety agent in the central nervous system by activating the glycine receptor. Taurine acts as a glycation inhibitor. Taurine-treated diabetic rats had a decrease in the formation of advanced glycation end products and AGEs content. The United States Department of Agriculture has found a link between cataract development and lower levels of vitamin B6, folate, and taurine in the diets of the elderly.
Other uses In cosmetics and contact lens solutions Since the 2000s cosmetic compositions containing taurine have been introduced, possibly due to its antifibrotic properties. It has been shown to prevent the damaging effects of TGFB1 to hair follicles. It also helps to maintain skin hydration. Taurine is also used in some contact lens solutions. Derivatives Taurine is used in the preparation of the anthelmintic drug netobimin . Taurolidine Taurocholic acid and tauroselcholic acid Tauromustine 5-Taurinomethyluridine and 5-taurinomethyl-2-thiouridine are modified uridines in mitrochondrial tRNA. Tauryl is the functional group attaching at the sulfur, 2-aminoethylsulfonyl. Taurino is the functional group attaching at the nitrogen, 2-sulfoethylamino. See also Homotaurine, precursor to acamprosate Taurates, a substance group.
