Difference between revisions of "Taurine"

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<p><strong>Taurine</strong>, or <strong>2-aminoethanesulfonic acid</strong>, is an <font color="#0066cc">organic acid</font>. It is also a major constituent of <font color="#0066cc">bile</font> and can be found in the lower intestine and in small amounts in the tissues of many animals and in humans as well.<sup class="reference" id="cite_ref-0"><font color="#0066cc"><span>[</span>1<span>]</span></font></sup><sup class="reference" id="cite_ref-1"><font color="#0066cc"><span>[</span>2<span>]</span></font></sup> Taurine is a derivative of the sulfur-containing (<font color="#0066cc">sulfhydryl</font>) <font color="#0066cc">amino acid</font>, <font color="#0066cc">cysteine</font>. Taurine is one of the few known naturally occurring <font color="#0066cc">sulfonic acids</font>.</p>
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<p><strong>Taurine</strong>, or <strong>2-aminoethanesulfonic acid</strong>, is an organic acid. It is also a major constituent of bile and can be found in the lower intestine and in small amounts in the tissues of many animals and in humans as well.<sup class="reference" id="cite_ref-0"><span>[</span>1<span>]</span></sup><sup class="reference" id="cite_ref-1"><span>[</span>2<span>]</span></sup> Taurine is a derivative of the sulfur-containing (sulfhydryl) amino acid, cysteine. Taurine is one of the few known naturally occurring sulfonic acids.</p>
<p>Taurine is named after the Latin <em>taurus</em>, which means bull or ox, as it was first isolated from <font color="#0066cc">ox</font> <font color="#0066cc">bile</font> in 1827 by German scientists <font color="#0066cc">Friedrich Tiedemann</font> and <font color="#0066cc">Leopold Gmelin</font>.<sup class="reference" id="cite_ref-2"><font color="#0066cc"><span>[</span>3<span>]</span></font></sup> It is often called an amino acid, even in scientific literature,<sup class="reference" id="cite_ref-3"><font color="#0066cc"><span>[</span>4<span>]</span></font></sup><sup class="reference" id="cite_ref-4"><font color="#0066cc"><span>[</span>5<span>]</span></font></sup><sup class="reference" id="cite_ref-5"><font color="#0066cc"><span>[</span>6<span>]</span></font></sup> but as it lacks a <font color="#0066cc">carboxyl group</font> it is not strictly an amino acid.<sup class="reference" id="cite_ref-6"><font color="#0066cc"><span>[</span>7<span>]</span></font></sup> It does contain a <font color="#0066cc">sulfonate group</font> and may be called an amino sulfonic acid. Small polypeptides have been identified which contain taurine, but to date no <font color="#0066cc">aminoacyl tRNA synthetase</font> has been identified as specifically recognizing taurine and capable of incorporating it onto a <font color="#0066cc">tRNA</font>.<sup class="reference" id="cite_ref-7"><font color="#0066cc"><span>[</span>8<span>]</span></font></sup></p>
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<p>Taurine is named after the Latin <em>taurus</em>, which means bull or ox, as it was first isolated from ox bile in 1827 by German scientists Friedrich Tiedemann and Leopold Gmelin.<sup class="reference" id="cite_ref-2"><span>[</span>3<span>]</span></sup> It is often called an amino acid, even in scientific literature,<sup class="reference" id="cite_ref-3"><span>[</span>4<span>]</span></sup><sup class="reference" id="cite_ref-4"><span>[</span>5<span>]</span></sup><sup class="reference" id="cite_ref-5"><span>[</span>6<span>]</span></sup> but as it lacks a carboxyl group it is not strictly an amino acid.<sup class="reference" id="cite_ref-6"><span>[</span>7<span>]</span></sup> 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 aminoacyl tRNA synthetase has been identified as specifically recognizing taurine and capable of incorporating it onto a tRNA.<sup class="reference" id="cite_ref-7"><span>[</span>8<span>]</span></sup></p>
 
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<h2><span class="mw-headline">Biosynthesis</span></h2>
 
<h2><span class="mw-headline">Biosynthesis</span></h2>
<p>The major pathway for mammalian taurine synthesis occurs in the pancreas via the cysteine sulfinic acid pathway. In this pathway, the sulfhydryl group of <font color="#0066cc">cysteine</font> is first oxidized to cysteine sulfinic acid by the enzyme <font color="#0066cc">cysteine dioxygenase</font>. Cysteine sulfinic acid, in turn, is decarboxylated by <font color="#0066cc">sulfinoalanine decarboxylase</font> to form <font color="#0066cc">hypotaurine</font>. It is unclear whether hypotaurine is then spontaneously or enzymatically oxidized to yield taurine.</p>
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<p>The major pathway for mammalian taurine synthesis occurs in the pancreas 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 sulfinoalanine decarboxylase to form hypotaurine. It is unclear whether hypotaurine is then spontaneously or enzymatically oxidized to yield taurine.</p>
<p>Taurine in the pharmaceutical and lab setting is synthesized through a combination of cysteine, <font color="#0066cc">methionine</font>, and <font color="#0066cc">vitamin E</font>. It is naturally produced in the testicles of many mammals. <font color="#0066cc">Urban legends</font> surrounding the source of taurine have included <font color="#0066cc">bull</font> urine extract and bull semen. While it's true that taurine is found in both sources, it is not the source of taurine in the pharmaceutical or <font color="#0066cc">food industry</font>.</p>
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<p>Taurine in the pharmaceutical and lab setting is synthesized through a combination of cysteine, methionine, and vitamin E. It is naturally produced in the testicles of many mammals. Urban legends surrounding the source of taurine have included bull urine extract and bull semen. While it's true that taurine is found in both sources, it is not the source of taurine in the pharmaceutical or food industry.</p>
 
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<h2><span class="mw-headline">Physiological roles</span></h2>
 
<h2><span class="mw-headline">Physiological roles</span></h2>
 
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<p>Taurine is <font color="#0066cc">conjugated</font> via its amino terminal group with <font color="#0066cc">chenodeoxycholic acid</font> and <font color="#0066cc">cholic acid</font> to form the <font color="#0066cc">bile salts</font> sodium taurochenodeoxycholate and sodium taurocholate. The low <font color="#0066cc">pKa</font> (1.5) of taurine's sulfonic acid group ensures that this <font color="#0066cc">moiety</font> is negatively charged in the pH ranges normally found in the intestinal tract and thus improves the <font color="#0066cc">surfactant</font> properties of the cholic acid conjugate, which can be found in many <font color="#0066cc">energy drinks</font> today. Taurine crosses the <font color="#0066cc">blood-brain barrier</font><sup class="reference" id="cite_ref-8"><font color="#0066cc"><span>[</span>9<span>]</span></font></sup><sup class="reference" id="cite_ref-9"><font color="#0066cc"><span>[</span>10<span>]</span></font></sup><sup class="reference" id="cite_ref-10"><font color="#0066cc"><span>[</span>11<span>]</span></font></sup> and has been implicated in a wide array of physiological phenomena including inhibitory <font color="#0066cc">neurotransmission</font>,<sup class="reference" id="cite_ref-11"><font color="#0066cc"><span>[</span>12<span>]</span></font></sup> <font color="#0066cc">long-term potentiation</font> in the <font color="#0066cc">striatum</font>/<font color="#0066cc">hippocampus</font>,<sup class="reference" id="cite_ref-12"><font color="#0066cc"><span>[</span>13<span>]</span></font></sup> <font color="#0066cc">membrane stabilization</font>,<sup class="reference" id="cite_ref-13"><font color="#0066cc"><span>[</span>14<span>]</span></font></sup> feedback inhibition of <font color="#0066cc">neutrophil</font>/<font color="#0066cc">macrophage</font> <font color="#0066cc">respiratory burst</font>, <font color="#0066cc">adipose</font> tissue regulation and possible prevention of obesity,<sup class="reference" id="cite_ref-14"><font color="#0066cc"><span>[</span>15<span>]</span></font></sup><sup class="reference" id="cite_ref-15"><font color="#0066cc"><span>[</span>16<span>]</span></font></sup> calcium <font color="#0066cc">homeostasis</font>,<sup class="reference" id="cite_ref-16"><font color="#0066cc"><span>[</span>17<span>]</span></font></sup> recovery from <font color="#0066cc">osmotic shock</font>,<sup class="reference" id="cite_ref-17"><font color="#0066cc"><span>[</span>18<span>]</span></font></sup> protection against glutamate <font color="#0066cc">excitotoxicity</font><sup class="reference" id="cite_ref-18"><font color="#0066cc"><span>[</span>19<span>]</span></font></sup> and prevention of epileptic seizures.<sup class="reference" id="cite_ref-19"><font color="#0066cc"><span>[</span>20<span>]</span></font></sup> It also acts as an <font color="#0066cc">antioxidant</font> and protects against toxicity of various substances (such as <font color="#0066cc">lead</font> and <font color="#0066cc">cadmium</font>).<sup class="reference" id="cite_ref-20"><font color="#0066cc"><span>[</span>21<span>]</span></font></sup><sup class="reference" id="cite_ref-21"><font color="#0066cc"><span>[</span>22<span>]</span></font></sup><sup class="reference" id="cite_ref-22"><font color="#0066cc"><span>[</span>23<span>]</span></font></sup><sup class="reference" id="cite_ref-23"><font color="#0066cc"><span>[</span>24<span>]</span></font></sup> Additionally, supplementation with taurine has been shown to prevent oxidative stress induced by exercise.<sup class="reference" id="cite_ref-24"><font color="#0066cc"><span>[</span>25<span>]</span></font></sup></p>
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<p>Taurine is conjugated via its amino terminal group with chenodeoxycholic acid and cholic acid to form the bile salts sodium taurochenodeoxycholate and sodium taurocholate. 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, which can be found in many energy drinks today. Taurine crosses the blood-brain barrier<sup class="reference" id="cite_ref-8"><span>[</span>9<span>]</span></sup><sup class="reference" id="cite_ref-9"><span>[</span>10<span>]</span></sup><sup class="reference" id="cite_ref-10"><span>[</span>11<span>]</span></sup> and has been implicated in a wide array of physiological phenomena including inhibitory neurotransmission,<sup class="reference" id="cite_ref-11"><span>[</span>12<span>]</span></sup> long-term potentiation in the striatum/hippocampus,<sup class="reference" id="cite_ref-12"><span>[</span>13<span>]</span></sup> membrane stabilization,<sup class="reference" id="cite_ref-13"><span>[</span>14<span>]</span></sup> feedback inhibition of neutrophil/macrophage respiratory burst, adipose tissue regulation and possible prevention of obesity,<sup class="reference" id="cite_ref-14"><span>[</span>15<span>]</span></sup><sup class="reference" id="cite_ref-15"><span>[</span>16<span>]</span></sup> calcium homeostasis,<sup class="reference" id="cite_ref-16"><span>[</span>17<span>]</span></sup> recovery from osmotic shock,<sup class="reference" id="cite_ref-17"><span>[</span>18<span>]</span></sup> protection against glutamate excitotoxicity<sup class="reference" id="cite_ref-18"><span>[</span>19<span>]</span></sup> and prevention of epileptic seizures.<sup class="reference" id="cite_ref-19"><span>[</span>20<span>]</span></sup> It also acts as an antioxidant and protects against toxicity of various substances (such as lead and cadmium).<sup class="reference" id="cite_ref-20"><span>[</span>21<span>]</span></sup><sup class="reference" id="cite_ref-21"><span>[</span>22<span>]</span></sup><sup class="reference" id="cite_ref-22"><span>[</span>23<span>]</span></sup><sup class="reference" id="cite_ref-23"><span>[</span>24<span>]</span></sup> Additionally, supplementation with taurine has been shown to prevent oxidative stress induced by exercise.<sup class="reference" id="cite_ref-24"><span>[</span>25<span>]</span></sup></p>
<p>It is believed that prematurely born infants lack the enzymes needed to convert <font color="#0066cc">cystathionine</font> to <font color="#0066cc">cysteine</font> and may therefore become deficient in taurine. Thus, taurine is thought to be a dietary essential nutrient in these individuals 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 beneficial, or even necessary.<sup class="reference" id="cite_ref-25"><font color="#0066cc"><span>[</span>26<span>]</span></font></sup></p>
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<p>It is believed that prematurely born infants lack the enzymes needed to convert cystathionine to cysteine and may therefore become deficient in taurine. Thus, taurine is thought to be a dietary essential nutrient in these individuals 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 beneficial, or even necessary.<sup class="reference" id="cite_ref-25"><span>[</span>26<span>]</span></sup></p>
<p>There is also evidence that taurine is beneficial for adult human <font color="#0066cc">blood pressure</font> and possibly, the alleviation of other cardiovascular ailments (in humans suffering essential <font color="#0066cc">hypertension</font>, taurine supplementation resulted in measurable decreases in blood pressure).<sup class="reference" id="cite_ref-26"><font color="#0066cc"><span>[</span>27<span>]</span></font></sup> In a recent 2008 study, taurine has been shown to reduce the secretion of <font color="#0066cc">apolipoprotein B100</font> and lipids in HepG2 cells.<sup class="reference" id="cite_ref-27"><font color="#0066cc"><span>[</span>28<span>]</span></font></sup> High concentrations of serum lipids and apolipoprotein B100 (essential structural component of <font color="#0066cc">VLDL</font> and <font color="#0066cc">LDL</font>) are major risk factors of <font color="#0066cc">atherosclerosis</font> and <font color="#0066cc">coronary heart disease</font>. Hence, it is possible that taurine supplementation is beneficial for the prevention of these diseases. In a 2003 study, Zhang et al. have demonstrated the hypocholesterolemic (blood cholesterol-lowering) effect of dietary taurine in young overweight adults. Furthermore, they reported that body weight also reduced significantly in the taurine supplemented group.<sup class="reference" id="cite_ref-28"><font color="#0066cc"><span>[</span>29<span>]</span></font></sup> These findings are consistent with animal studies.<sup class="reference" id="cite_ref-29"><font color="#0066cc"><span>[</span>30<span>]</span></font></sup> Taurine has also been shown to help people with <font color="#0066cc">congestive heart failure</font> by increasing the force and effectiveness of heart-muscle contractions.<sup class="reference" id="cite_ref-30"><font color="#0066cc"><span>[</span>31<span>]</span></font></sup></p>
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<p>There is also evidence that taurine is beneficial for adult human blood pressure and possibly, the alleviation of other cardiovascular ailments (in humans suffering essential hypertension, taurine supplementation resulted in measurable decreases in blood pressure).<sup class="reference" id="cite_ref-26"><span>[</span>27<span>]</span></sup> In a recent 2008 study, taurine has been shown to reduce the secretion of apolipoprotein B100 and lipids in HepG2 cells.<sup class="reference" id="cite_ref-27"><span>[</span>28<span>]</span></sup> High concentrations of serum lipids and apolipoprotein B100 (essential structural component of VLDL and LDL) are major risk factors of atherosclerosis and coronary heart disease. Hence, it is possible that taurine supplementation is beneficial for the prevention of these diseases. In a 2003 study, Zhang et al. have demonstrated the hypocholesterolemic (blood cholesterol-lowering) effect of dietary taurine in young overweight adults. Furthermore, they reported that body weight also reduced significantly in the taurine supplemented group.<sup class="reference" id="cite_ref-28"><span>[</span>29<span>]</span></sup> These findings are consistent with animal studies.<sup class="reference" id="cite_ref-29"><span>[</span>30<span>]</span></sup> Taurine has also been shown to help people with congestive heart failure by increasing the force and effectiveness of heart-muscle contractions.<sup class="reference" id="cite_ref-30"><span>[</span>31<span>]</span></sup></p>
<p>Taurine levels were found to be significantly lower in <font color="#0066cc">vegans</font> than in a control group on a standard American diet. Plasma taurine was 78% of control values, and urinary taurine 29%.<sup class="reference" id="cite_ref-31"><font color="#0066cc"><span>[</span>32<span>]</span></font></sup></p>
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<p>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 29%.<sup class="reference" id="cite_ref-31"><span>[</span>32<span>]</span></sup></p>
<p>In the cell, taurine keeps potassium and magnesium inside the cell while keeping excessive sodium out. In this sense it works like a diuretic. But unlike prescription diuretics, it is not a cellular poison. Because it aids the movement of potassium, sodium, and calcium in and out of the cell, taurine has been used as a supplementation for epileptics as well as for people who have uncontrollable facial twitches.<sup class="reference" id="cite_ref-32"><font color="#0066cc"><span>[</span>33<span>]</span></font></sup></p>
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<p>In the cell, taurine keeps potassium and magnesium inside the cell while keeping excessive sodium out. In this sense it works like a diuretic. But unlike prescription diuretics, it is not a cellular poison. Because it aids the movement of potassium, sodium, and calcium in and out of the cell, taurine has been used as a supplementation for epileptics as well as for people who have uncontrollable facial twitches.<sup class="reference" id="cite_ref-32"><span>[</span>33<span>]</span></sup></p>
<p>According to animal studies, taurine produces <font color="#0066cc">anxiolytic</font> effect and may act as a modulator or anti-anxiety agent in the central nervous system.<sup class="reference" id="cite_ref-33"><font color="#0066cc"><span>[</span>34<span>]</span></font></sup><sup class="reference" id="cite_ref-34"><font color="#0066cc"><span>[</span>35<span>]</span></font></sup><sup class="reference" id="cite_ref-35"><font color="#0066cc"><span>[</span>36<span>]</span></font></sup></p>
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<p>According to animal studies, taurine produces anxiolytic effect and may act as a modulator or anti-anxiety agent in the central nervous system.<sup class="reference" id="cite_ref-33"><span>[</span>34<span>]</span></sup><sup class="reference" id="cite_ref-34"><span>[</span>35<span>]</span></sup><sup class="reference" id="cite_ref-35"><span>[</span>36<span>]</span></sup></p>
<p>Taurine is necessary for normal skeletal muscle functioning. This was shown by a 2004 study,<sup class="reference" id="cite_ref-36"><font color="#0066cc"><span>[</span>37<span>]</span></font></sup> using mice with a genetic taurine deficiency. They had a nearly complete depletion of skeletal and cardiac muscle taurine levels. These mice had a reduction of more than 80% of exercise capacity compared to control mice. The authors expressed themselves as &quot;surprised&quot; that cardiac function showed as largely normal (given various other studies about effects of taurine on the heart).</p>
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<p>Taurine is necessary for normal skeletal muscle functioning. This was shown by a 2004 study,<sup class="reference" id="cite_ref-36"><span>[</span>37<span>]</span></sup> using mice with a genetic taurine deficiency. They had a nearly complete depletion of skeletal and cardiac muscle taurine levels. These mice had a reduction of more than 80% of exercise capacity compared to control mice. The authors expressed themselves as &quot;surprised&quot; that cardiac function showed as largely normal (given various other studies about effects of taurine on the heart).</p>
<p>Studies have shown that taurine can influence (and possibly reverse) defects in nerve blood flow, motor nerve conduction velocity, and nerve sensory thresholds in experimental diabetic neuropathic rats.<sup class="reference" id="cite_ref-PubMed_16624563_37-0"><font color="#0066cc"><span>[</span>38<span>]</span></font></sup><sup class="reference" id="cite_ref-PubMed_11259114_38-0"><font color="#0066cc"><span>[</span>39<span>]</span></font></sup> In another study on diabetic rats, taurine significantly decreased weight and decreased <font color="#0066cc">blood sugar</font> in these animal models.<sup class="reference" id="cite_ref-Japanese_rats_39-0"><font color="#0066cc"><span>[</span>40<span>]</span></font></sup> Likewise, a 2008 study demonstrated that taurine administration to diabetic rabbits resulted in 30% decrease in serum glucose levels.<sup class="reference" id="cite_ref-40"><font color="#0066cc"><span>[</span>41<span>]</span></font></sup> According to the single study on human subjects, daily administration of 1.5g taurine had no significant effect on insulin secretion or insulin sensitivity.<sup class="reference" id="cite_ref-41"><font color="#0066cc"><span>[</span>42<span>]</span></font></sup> However it is possible that an effect may occur at higher dosages. There is evidence that taurine may exert a beneficial effect in preventing diabetes-associated <font color="#0066cc">microangiopathy</font> and tubulointerstitial injury in <font color="#0066cc">diabetic nephropathy</font>.<sup class="reference" id="cite_ref-42"><font color="#0066cc"><span>[</span>43<span>]</span></font></sup><sup class="reference" id="cite_ref-43"><font color="#0066cc"><span>[</span>44<span>]</span></font></sup> Taurine acts as a glycation inhibitor. Studies have shown that taurine treated diabetic rats had a decrease in the formation of <font color="#0066cc">advanced glycation end products</font> (AGEs) and AGEs content.<sup class="reference" id="cite_ref-44"><font color="#0066cc"><span>[</span>45<span>]</span></font></sup><sup class="reference" id="cite_ref-45"><font color="#0066cc"><span>[</span>46<span>]</span></font></sup></p>
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<p>Studies have shown that taurine can influence (and possibly reverse) defects in nerve blood flow, motor nerve conduction velocity, and nerve sensory thresholds in experimental diabetic neuropathic rats.<sup class="reference" id="cite_ref-PubMed_16624563_37-0"><span>[</span>38<span>]</span></sup><sup class="reference" id="cite_ref-PubMed_11259114_38-0"><span>[</span>39<span>]</span></sup> In another study on diabetic rats, taurine significantly decreased weight and decreased blood sugar in these animal models.<sup class="reference" id="cite_ref-Japanese_rats_39-0"><span>[</span>40<span>]</span></sup> Likewise, a 2008 study demonstrated that taurine administration to diabetic rabbits resulted in 30% decrease in serum glucose levels.<sup class="reference" id="cite_ref-40"><span>[</span>41<span>]</span></sup> According to the single study on human subjects, daily administration of 1.5g taurine had no significant effect on insulin secretion or insulin sensitivity.<sup class="reference" id="cite_ref-41"><span>[</span>42<span>]</span></sup> However it is possible that an effect may occur at higher dosages. There is evidence that taurine may exert a beneficial effect in preventing diabetes-associated microangiopathy and tubulointerstitial injury in diabetic nephropathy.<sup class="reference" id="cite_ref-42"><span>[</span>43<span>]</span></sup><sup class="reference" id="cite_ref-43"><span>[</span>44<span>]</span></sup> Taurine acts as a glycation inhibitor. Studies have shown that taurine treated diabetic rats had a decrease in the formation of advanced glycation end products (AGEs) and AGEs content.<sup class="reference" id="cite_ref-44"><span>[</span>45<span>]</span></sup><sup class="reference" id="cite_ref-45"><span>[</span>46<span>]</span></sup></p>
<p>Lately, cosmetic compositions containing taurine have been introduced, possibly due to its <font color="#0066cc">antifibrotic</font> properties. It has been shown that taurine acts as a <font color="#0066cc">TGFB1</font> inhibitor.<sup class="reference" id="cite_ref-46"><font color="#0066cc"><span>[</span>47<span>]</span></font></sup> It also helps to maintain skin hydration.<sup class="reference" id="cite_ref-47"><font color="#0066cc"><span>[</span>48<span>]</span></font></sup></p>
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<p>Lately, cosmetic compositions containing taurine have been introduced, possibly due to its antifibrotic properties. It has been shown that taurine acts as a TGFB1 inhibitor.<sup class="reference" id="cite_ref-46"><span>[</span>47<span>]</span></sup> It also helps to maintain skin hydration.<sup class="reference" id="cite_ref-47"><span>[</span>48<span>]</span></sup></p>
<p>Taurine is also used in some contact lens solutions.<sup class="reference" id="cite_ref-48"><font color="#0066cc"><span>[</span>49<span>]</span></font></sup></p>
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<p>Taurine is also used in some contact lens solutions.<sup class="reference" id="cite_ref-48"><span>[</span>49<span>]</span></sup></p>
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<h2><span class="mw-headline">Taurine and cats</span></h2>
 
<h2><span class="mw-headline">Taurine and cats</span></h2>
<p>Taurine is an essential dietary requirement for feline health, as cats cannot synthesize the compound. The absence of taurine causes a cat's <font color="#0066cc">retina</font> to slowly degenerate, causing eye problems and (eventually) irreversible blindness &mdash; a condition known as <font color="#0066cc">central retinal degeneration</font> (CRD),<sup class="reference" id="cite_ref-49"><font color="#0066cc"><span>[</span>50<span>]</span></font></sup><sup class="reference" id="cite_ref-50"><font color="#0066cc"><span>[</span>51<span>]</span></font></sup> as well as hair loss and tooth decay. It was discovered in 1987 that taurine deficiency can also cause <font color="#0066cc">feline dilated cardiomyopathy</font>.<sup class="reference" id="cite_ref-51"><font color="#0066cc"><span>[</span>52<span>]</span></font></sup> Unlike CRD, the condition is reversible with supplementation. Taurine is now a requirement of the <font color="#0066cc">Association of American Feed Control Officials</font> (AAFCO) and any dry or wet food product labeled approved by the AAFCO should have a minimum of 0.1% taurine in dry food and 0.2% in wet food.<sup class="reference" id="cite_ref-52"><font color="#0066cc"><span>[</span>53<span>]</span></font></sup></p>
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<p>Taurine is an essential dietary requirement for feline health, as cats cannot synthesize the compound. The absence of taurine causes a cat's retina to slowly degenerate, causing eye problems and (eventually) irreversible blindness &mdash; a condition known as central retinal degeneration (CRD),<sup class="reference" id="cite_ref-49"><span>[</span>50<span>]</span></sup><sup class="reference" id="cite_ref-50"><span>[</span>51<span>]</span></sup> as well as hair loss and tooth decay. It was discovered in 1987 that taurine deficiency can also cause feline dilated cardiomyopathy.<sup class="reference" id="cite_ref-51"><span>[</span>52<span>]</span></sup> Unlike CRD, the condition is reversible with supplementation. Taurine is now a requirement of the Association of American Feed Control Officials (AAFCO) and any dry or wet food product labeled approved by the AAFCO should have a minimum of 0.1% taurine in dry food and 0.2% in wet food.<sup class="reference" id="cite_ref-52"><span>[</span>53<span>]</span></sup></p>
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<h2><span class="mw-headline">Taurine and bird development</span></h2>
 
<h2><span class="mw-headline">Taurine and bird development</span></h2>
<p>Recent research has provided evidence that taurine is essential in early bird development of <font color="#0066cc">passerines</font>. Many passerines, regardless of spider availability, seek out many taurine-rich spiders to feed their young particularly in their youngest stages of life. Researchers later compared the behaviors and development of birds fed a taurine-supplemented diet to a control diet and found that juveniles that were fed taurine-rich diets as neonates were much larger risk takers and more adept at spatial learning tasks.<sup class="reference" id="cite_ref-Arnold2007_53-0"><font color="#0066cc"><span>[</span>54<span>]</span></font></sup></p>
+
<p>Recent research has provided evidence that taurine is essential in early bird development of passerines. Many passerines, regardless of spider availability, seek out many taurine-rich spiders to feed their young particularly in their youngest stages of life. Researchers later compared the behaviors and development of birds fed a taurine-supplemented diet to a control diet and found that juveniles that were fed taurine-rich diets as neonates were much larger risk takers and more adept at spatial learning tasks.<sup class="reference" id="cite_ref-Arnold2007_53-0"><span>[</span>54<span>]</span></sup></p>
<p><font color="#0066cc"></font></p>
+
<p>&nbsp;</p>
 
<h2><span class="mw-headline">Synthesis and production</span></h2>
 
<h2><span class="mw-headline">Synthesis and production</span></h2>
<p>In 1993, approximately 5,000&ndash;6,000 t. of taurine was produced; 50% for pet food manufacture, 50% in pharmaceutical applications.<sup class="reference" id="cite_ref-kirk_54-0"><font color="#0066cc"><span>[</span>55<span>]</span></font></sup> Synthetic taurine is obtained from <font color="#0066cc">isethionic acid</font> (2-hydroxyethanesulfonic acid), which in turn is obtained from the reaction of <font color="#0066cc">ethylene oxide</font> with aqueous <font color="#0066cc">sodium bisulfite</font>.<sup class="reference" id="cite_ref-55"><font color="#0066cc"><span>[</span>56<span>]</span></font></sup> Another approach is the reaction of <font color="#0066cc">aziridine</font> with <font color="#0066cc">sulfurous acid</font>. This leads directly to taurine.<sup class="noprint Template-Fact"><span title="This claim needs references to reliable sources since January 2008" style="WHITE-SPACE: nowrap">[<em><font color="#0066cc">citation needed</font></em>]</span></sup></p>
+
<p>In 1993, approximately 5,000&ndash;6,000 t. of taurine was produced; 50% for pet food manufacture, 50% in pharmaceutical applications.<sup class="reference" id="cite_ref-kirk_54-0"><span>[</span>55<span>]</span></sup> Synthetic taurine is obtained from isethionic acid (2-hydroxyethanesulfonic acid), which in turn is obtained from the reaction of ethylene oxide with aqueous sodium bisulfite.<sup class="reference" id="cite_ref-55"><span>[</span>56<span>]</span></sup> Another approach is the reaction of aziridine with sulfurous acid. This leads directly to taurine.<sup class="noprint Template-Fact"><span title="This claim needs references to reliable sources since January 2008" style="WHITE-SPACE: nowrap">[<em>citation needed</em>]</span></sup></p>
 
<p>&nbsp;</p>
 
<p>&nbsp;</p>
 
<h2><span class="mw-headline">As a functional food</span></h2>
 
<h2><span class="mw-headline">As a functional food</span></h2>
<p>Taurine is used as a <font color="#0066cc">functional food</font> in many <font color="#0066cc">energy drinks</font> and <font color="#0066cc">energy products</font><sup class="reference" id="cite_ref-56"><font color="#0066cc"><span>[</span>57<span>]</span></font></sup> Despite being present in many energy foods, it has not been proven to be energy-giving. A study of mice hereditarily unable to transport taurine suggests that it is needed for proper maintenance and functioning of <font color="#0066cc">skeletal muscles</font>.<sup class="reference" id="cite_ref-57"><font color="#0066cc"><span>[</span>58<span>]</span></font></sup> Additionally, it has been proven effective in removing fatty liver deposits in humans, preventing liver disease, and reducing <font color="#0066cc">cirrhosis</font> in rats.<sup class="reference" id="cite_ref-58"><font color="#0066cc"><span>[</span>59<span>]</span></font></sup><sup class="reference" id="cite_ref-59"><font color="#0066cc"><span>[</span>60<span>]</span></font></sup></p>
+
<p>Taurine is used as a functional food in many energy drinks and energy products<sup class="reference" id="cite_ref-56"><span>[</span>57<span>]</span></sup> Despite being present in many energy foods, it has not been proven to be energy-giving. A study of mice hereditarily unable to transport taurine suggests that it is needed for proper maintenance and functioning of skeletal muscles.<sup class="reference" id="cite_ref-57"><span>[</span>58<span>]</span></sup> Additionally, it has been proven effective in removing fatty liver deposits in humans, preventing liver disease, and reducing cirrhosis in rats.<sup class="reference" id="cite_ref-58"><span>[</span>59<span>]</span></sup><sup class="reference" id="cite_ref-59"><span>[</span>60<span>]</span></sup></p>
<p><font color="#0066cc"></font></p>
+
<p>&nbsp;</p>
 
<h2><span class="mw-headline">References</span></h2>
 
<h2><span class="mw-headline">References</span></h2>
 
<div class="references-small references-column-count references-column-count-2" style="-moz-column-count: 2; column-count: 2">
 
<div class="references-small references-column-count references-column-count-2" style="-moz-column-count: 2; column-count: 2">
 
<ol class="references">
 
<ol class="references">
    <li id="cite_note-0"><strong><a title="" href="http://en.wikipedia.org/wiki/Taurine#cite_ref-0"><font color="#0066cc">^</font></a>
+
    <li id="cite_note-0"><strong><a title="" href="http://en.wikipedia.org/wiki/Taurine#cite_ref-0">^</a></strong> <cite class="" id="
 
</ol>
 
</ol>
 
</div>
 
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Latest revision as of 01:32, 14 March 2009

Taurine, or 2-aminoethanesulfonic acid, is an organic acid. It is also a major constituent of bile and can be found in the lower intestine and in small amounts in the tissues of many animals and in humans as well.[1][2] Taurine is a derivative of the sulfur-containing (sulfhydryl) amino acid, cysteine. Taurine is one of the few known naturally occurring sulfonic acids.

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.[3] It is often called an amino acid, even in scientific literature,[4][5][6] but as it lacks a carboxyl group it is not strictly an amino acid.[7] 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 aminoacyl tRNA synthetase has been identified as specifically recognizing taurine and capable of incorporating it onto a tRNA.[8]

 

 

Biosynthesis

The major pathway for mammalian taurine synthesis occurs in the pancreas 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 sulfinoalanine decarboxylase to form hypotaurine. It is unclear whether hypotaurine is then spontaneously or enzymatically oxidized to yield taurine.

Taurine in the pharmaceutical and lab setting is synthesized through a combination of cysteine, methionine, and vitamin E. It is naturally produced in the testicles of many mammals. Urban legends surrounding the source of taurine have included bull urine extract and bull semen. While it's true that taurine is found in both sources, it is not the source of taurine in the pharmaceutical or food industry.

 

Physiological roles

 

Taurine is conjugated via its amino terminal group with chenodeoxycholic acid and cholic acid to form the bile salts sodium taurochenodeoxycholate and sodium taurocholate. 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, which can be found in many energy drinks today. Taurine crosses the blood-brain barrier[9][10][11] and has been implicated in a wide array of physiological phenomena including inhibitory neurotransmission,[12] long-term potentiation in the striatum/hippocampus,[13] membrane stabilization,[14] feedback inhibition of neutrophil/macrophage respiratory burst, adipose tissue regulation and possible prevention of obesity,[15][16] calcium homeostasis,[17] recovery from osmotic shock,[18] protection against glutamate excitotoxicity[19] and prevention of epileptic seizures.[20] It also acts as an antioxidant and protects against toxicity of various substances (such as lead and cadmium).[21][22][23][24] Additionally, supplementation with taurine has been shown to prevent oxidative stress induced by exercise.[25]

It is believed that prematurely born infants lack the enzymes needed to convert cystathionine to cysteine and may therefore become deficient in taurine. Thus, taurine is thought to be a dietary essential nutrient in these individuals 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 beneficial, or even necessary.[26]

There is also evidence that taurine is beneficial for adult human blood pressure and possibly, the alleviation of other cardiovascular ailments (in humans suffering essential hypertension, taurine supplementation resulted in measurable decreases in blood pressure).[27] In a recent 2008 study, taurine has been shown to reduce the secretion of apolipoprotein B100 and lipids in HepG2 cells.[28] High concentrations of serum lipids and apolipoprotein B100 (essential structural component of VLDL and LDL) are major risk factors of atherosclerosis and coronary heart disease. Hence, it is possible that taurine supplementation is beneficial for the prevention of these diseases. In a 2003 study, Zhang et al. have demonstrated the hypocholesterolemic (blood cholesterol-lowering) effect of dietary taurine in young overweight adults. Furthermore, they reported that body weight also reduced significantly in the taurine supplemented group.[29] These findings are consistent with animal studies.[30] Taurine has also been shown to help people with congestive heart failure by increasing the force and effectiveness of heart-muscle contractions.[31]

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 29%.[32]

In the cell, taurine keeps potassium and magnesium inside the cell while keeping excessive sodium out. In this sense it works like a diuretic. But unlike prescription diuretics, it is not a cellular poison. Because it aids the movement of potassium, sodium, and calcium in and out of the cell, taurine has been used as a supplementation for epileptics as well as for people who have uncontrollable facial twitches.[33]

According to animal studies, taurine produces anxiolytic effect and may act as a modulator or anti-anxiety agent in the central nervous system.[34][35][36]

Taurine is necessary for normal skeletal muscle functioning. This was shown by a 2004 study,[37] using mice with a genetic taurine deficiency. They had a nearly complete depletion of skeletal and cardiac muscle taurine levels. These mice had a reduction of more than 80% of exercise capacity compared to control mice. The authors expressed themselves as "surprised" that cardiac function showed as largely normal (given various other studies about effects of taurine on the heart).

Studies have shown that taurine can influence (and possibly reverse) defects in nerve blood flow, motor nerve conduction velocity, and nerve sensory thresholds in experimental diabetic neuropathic rats.[38][39] In another study on diabetic rats, taurine significantly decreased weight and decreased blood sugar in these animal models.[40] Likewise, a 2008 study demonstrated that taurine administration to diabetic rabbits resulted in 30% decrease in serum glucose levels.[41] According to the single study on human subjects, daily administration of 1.5g taurine had no significant effect on insulin secretion or insulin sensitivity.[42] However it is possible that an effect may occur at higher dosages. There is evidence that taurine may exert a beneficial effect in preventing diabetes-associated microangiopathy and tubulointerstitial injury in diabetic nephropathy.[43][44] Taurine acts as a glycation inhibitor. Studies have shown that taurine treated diabetic rats had a decrease in the formation of advanced glycation end products (AGEs) and AGEs content.[45][46]

Lately, cosmetic compositions containing taurine have been introduced, possibly due to its antifibrotic properties. It has been shown that taurine acts as a TGFB1 inhibitor.[47] It also helps to maintain skin hydration.[48]

Taurine is also used in some contact lens solutions.[49]

 

Taurine and cats

Taurine is an essential dietary requirement for feline health, as cats cannot synthesize the compound. The absence of taurine causes a cat's retina to slowly degenerate, causing eye problems and (eventually) irreversible blindness — a condition known as central retinal degeneration (CRD),[50][51] as well as hair loss and tooth decay. It was discovered in 1987 that taurine deficiency can also cause feline dilated cardiomyopathy.[52] Unlike CRD, the condition is reversible with supplementation. Taurine is now a requirement of the Association of American Feed Control Officials (AAFCO) and any dry or wet food product labeled approved by the AAFCO should have a minimum of 0.1% taurine in dry food and 0.2% in wet food.[53]

 

Taurine and bird development

Recent research has provided evidence that taurine is essential in early bird development of passerines. Many passerines, regardless of spider availability, seek out many taurine-rich spiders to feed their young particularly in their youngest stages of life. Researchers later compared the behaviors and development of birds fed a taurine-supplemented diet to a control diet and found that juveniles that were fed taurine-rich diets as neonates were much larger risk takers and more adept at spatial learning tasks.[54]

 

Synthesis and production

In 1993, approximately 5,000–6,000 t. of taurine was produced; 50% for pet food manufacture, 50% in pharmaceutical applications.[55] Synthetic taurine is obtained from isethionic acid (2-hydroxyethanesulfonic acid), which in turn is obtained from the reaction of ethylene oxide with aqueous sodium bisulfite.[56] Another approach is the reaction of aziridine with sulfurous acid. This leads directly to taurine.[citation needed]

 

As a functional food

Taurine is used as a functional food in many energy drinks and energy products[57] Despite being present in many energy foods, it has not been proven to be energy-giving. A study of mice hereditarily unable to transport taurine suggests that it is needed for proper maintenance and functioning of skeletal muscles.[58] Additionally, it has been proven effective in removing fatty liver deposits in humans, preventing liver disease, and reducing cirrhosis in rats.[59][60]

 

References

  1. ^ Bouckenooghe T, Remacle C, Reusens B (2006). "Is taurine a functional nutrient?". Curr Opin Clin Nutr 9 (6): 728–733. 
  2. ^ Brosnan J, Brosnan M (2006). "The sulfur-containing amino acids: an overview.". J Nutr 136 (6 Suppl): 1636S–1640S. PMID 16702333. 
  3. ^ F. Tiedemann, L. Gmelin (1827). "Einige neue Bestandtheile der Galle des Ochsen". Annalen der Physik 85 (2): 326–337. doi:10.1002/andp.18270850214. 
  4. ^ 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. doi:10.1177/014860719802200142. PMID 9437654. http://jpen.aspenjournals.org/cgi/content/abstract/22/1/42. Retrieved on 2006-08-19. 
  5. ^ 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. doi:10.1172/JCI110652. PMID 6286728. http://www.pubmedcentral.nih.gov/articlerender.fcgi?artid=370261. Retrieved on 2006-08-19. 
  6. ^ Kirk, Kiaran; and Julie Kirk (1993). "Volume-regulatory taurine release from a human heart cancer cell line". FEBS Letters 336 (1): 153–158. doi:10.1016/0014-5793(93)81630-I. 
  7. ^ Carey, Francis A. (2006) [1987]. Organic Chemistry (6th ed. ed.). New York: McGraw Hill. pp. 1149. ISBN 0-07-282837-4. "Amino acids are carboxylic acids that contain an amine function." 
  8. ^ Lahdesmaki, P (1987). "Biosynthesis of taurine peptides in brain cytoplasmic fraction in vitro.". Int J Neuroscience 37 (1-2): 79–84. doi:10.3109/00207458708991804. 
  9. ^ Urquhart N, Perry TL, Hansen S, Kennedy J. Passage of taurine into adult mammalian brain. Journal of Neurochemistry 1974 May;22(5):871-2.
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  38. ^ Li F, Abatan OI, Kim H, Burnett D, Larkin D, Obrosova IG, Stevens MJ (2006 Jun). "Taurine reverses neurological and neurovascular deficits in Zucker diabetic fatty rats.". Neurobiology of Disease 22 (3): 669–676. doi:10.1016/j.nbd.2006.01.012. PMID 16624563. 
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  47. ^ Collin C, Gautier B, Gaillard O, Hallegot P, Chabane S, Bastien P, Peyron M, Bouleau M, Thibaut S, Pruche F, Duranton A, Bernard BA. Protective effects of taurine on human hair follicle grown in vitro(1). International Journal of Cosmetic Science 2006 Aug;28(4):289-98.
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  52. ^ Myocardial failure in cats associated with low plasma taurine: a reversible cardiomyopathy
  53. ^ AAFCO
  54. ^ Arnold, K.E.; Ramsay, S.L.; Donaldson, C.; Adam, A. (2007). "Parental prey selection affects risk-taking behaviour and spatial learning in avian offspring" (PDF). Proceedings of the Royal Society B: Biological Sciences 274 (1625): 2563–2569. doi:10.1098/rspb.2007.0687. http://www.journals.royalsoc.ac.uk/index/M820008244125737.pdf. Retrieved on 2008-03-26. 
  55. ^ Tully, Paul S. Sulfonic Acids. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. Published online 2000. doi:10.1002/0471238961.1921120620211212.a01
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  57. ^ This Ain't No Wine Cooler, John Cloud, Time Magazine, July 17, 2008
  58. ^ U. Warskulat, U. Flogel, C. Jacoby, H.-G. Hartwig, M. Thewissen, M. W. Merx, A. Molojavyi, B. Heller-Stilb, J. Schrader and D. Haussinger (2004). "Taurine transporter knockout depletes muscle taurine levels and results in severe skeletal muscle impairment but leaves cardiac function uncompromised". Faseb J.: 03–0496fje. doi:10.1096/fj.03-0496fje. PMID 14734644. 
  59. ^ M. D. J. Kerai, Catherine J. Waterfield, S. H. Kenyon, D. S. Asker, J. A. Timbrell Taurine: Protective properties against ethanol-induced hepatic steatosis and lipid peroxidation during chronic ethanol consumption in rats Amino Acids Volume 15, Numbers 1-2 / March, 1998
  60. ^ McCall, Becky (2005-12-28). "The ultimate hangover cure?". bbc.co.uk. http://news.bbc.co.uk/1/hi/magazine/4563760.stm. Retrieved on 2008-09-01.