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14-September-2008 10:43:22 - Carnitine Carnitine Systematic IUPAC name 3-Hydroxy-4-trimethylammonio-butanoate Identifiers CAS number 541-15-1 ATC code A16AA01 PubChem 10917 DrugBank APRD01070 Chemical data Formula C7H15NO3 Mol. mass 161.199 g/mol Pharmacokinetic data Bioavailability 10% Protein binding None Metabolism slightly Half life ? Excretion Urine 95% Therapeutic considerations Pregnancy cat. ? Legal status Routes oral and iv Carnitine is a quaternary ammonium compound biosynthesized from the amino acids lysine and methionine.1 In living cells, it is required for the transport of fatty acids from the cytosol into the mitochondria during the breakdown of lipids or fats for the generation of metabolic energy. It is often sold as a nutritional supplement. Carnitine was originally found as a growth factor for mealworms and labeled vitamin Bt. Carnitine exists in two stereoisomers: its biologically active form is L-carnitine, while its enantiomer, D-carnitine, is biologically inactive.2 Contents 1 Production 2 Role in fatty acid metabolism 3 Effects on bone mass 4 Antioxidant effects 5 Effects on diabetes 6 Food sources 7 Other sources 8 As a weight loss supplement 9 See also 10 References 11 External links Production In animals, carnitine is biosynthesized primarily in the liver and kidneys from the amino acids lysine or methionine.3 Vitamin C ascorbic acid is essential to the synthesis of carnitine. During growth or pregnancy the requirement of carnitine might exceed its natural production.citation needed Role in fatty acid metabolism Carnitine transports long-chain acyl groups from fatty acids into the mitochondrial matrix, so that they can be broken down through β-oxidation to acetate to obtain usable energy via the citric acid cycle. In some organisms such as fungi, the acetate is used in the glyoxylate cycle for gluconeogenesis and formation of carbohydrates. Fatty acids must be activated before binding to the carnitine molecule to form acyl-carnitine. The free fatty acid in the cytosol is attached with a thioester bond to coenzyme A CoA. This reaction is catalyzed by the enzyme fatty acyl-CoA synthetase and driven to completion by inorganic pyrophosphatase. The acyl group on CoA can now be transferred to carnitine and the resulting acyl-carnitine transported into the mitochondrial matrix. This occurs via a series of similar steps: Acyl-CoA is conjugated to carnitine by carnitine acyltransferase I palmitoyltransferase located on the outer mitochondrial membrane Acyl-carnitine is shuttled inside by a carnitine-acylcarnitine translocase Acyl-carnitine is converted to acyl-CoA by carnitine acyltransferase II palmitoyltransferase located on the inner mitochondrial membrane. The liberated carnitine returns to the cytosol. Human genetic disorders such as primary carnitine deficiency, carnitine palmitoyltransferase I deficiency, carnitine palmitoyltransferase II deficiency and carnitine-acylcarnitine translocase deficiency affect different steps of this process.4 Carnitine acyltransferase I undergoes allosteric inhibition as a result of malonyl-CoA, an intermediate in fatty acid biosynthesis, in order to prevent futile cycling between β-oxidation and fatty acid synthesis. Click to enlarge Effects on bone mass In the course of human aging, carnitine concentration in cells diminishes affecting fatty acid metabolism in various tissues. Particularly adversely affected are bones which require continuous reconstructive and metabolic functions of osteoblasts for maintenance of bone mass. There is a close correlation between changes in plasma levels of osteocalcin and osteoblast activity and a reduction in osteocalcin plasma levels is an indicator of reduced osteoblast activity,5 which appears to underlie osteoporosis in elderly subjects and in postmenopausal women. Administration of a carnitine mixture or propionyl-L-carnitine is capable of increasing serum osteocalcin concentrations of animals thus treated, whereas serum osteocalcin levels tend to decrease with age in control animals.6 Antioxidant effects The carnitines exert a substantial antioxidant action, thereby providing a protective effect against lipoperoxidation of phospholipid membranes and against oxidative stress induced at the myocardial and endothelial cell level. 7 Effects on diabetes L-Carnitine improved glucose disposal among 15 patients with type II diabetes and 20 healthy volunteers.8 Glucose storage increased between both groups, but glucose oxidation increased only in the diabetic group. Finally, glucose uptake increased about 8% for both. Food sources The highest concentrations of carnitine are found in red meat and dairy products. Other natural sources of carnitine include nuts and seeds e.g. pumpkin, sunflower, sesame, legumes or pulses beans, peas, lentils, peanuts, vegetables artichokes, asparagus, beet greens, broccoli, brussels sprouts, collard greens, garlic, mustard greens, okra, parsley, kale, fruits apricots, bananas, cereals buckwheat, corn, millet, oatmeal, rice bran, rye, whole wheat, wheat bran, wheat germ and other 'health' foods bee pollen, brewer's yeast, carob.citation needed Product Quantity Carnitine Beef Steak 3.5 oz 95 mg Ground Beef 3.5 oz 94 mg Pork 3.5 oz 27.7 mg Bacon 3.5 oz 23.3 mg Tempeh half cup 19.5 mg Cod Fish 3.5 oz 5.6 mg Chicken Breast 3.5 oz 3.9 mg American Cheese 3.5 oz 3.7 mg Ice Cream 3.5 fl oz 3.7 mg Whole Milk 3.5 fl oz 3.3 mg Avocado one medium 2 mg9 Cottage Cheese 3.5 fl oz 1.1 mg Whole Wheat Bread 3.5 oz 0.36 mg Asparagus 3.5 oz 0.195 mg White Bread 3.5 oz 0.147 mg Macaroni 3.5 oz 0.126 mg Peanut Butter 3.5 oz 0.083 mg Rice cooked 3.5 oz 0.0449 mg Eggs 3.5 oz 0.0121 mg Orange Juice 3.5 fl oz 0.0019 mg Generally, 20 to 200 mg/day are ingested per day by those on an omnivorous diet, while those on a strict vegetarian or vegan diet may ingest as little as 1 mg/day.citation needed No advantage appears to exist in giving an oral dose greater than 2g at one time, since absorption studies indicate saturation at this dose.10 Other sources Other sources may be found in over-the-counter vitamins, energy drinks and various other products. Products containing L-carnitine cannot be marketed as natural health products in Canada. L-Carnitine products and supplements are not allowed to be imported into Canada Health Canada.11 As a weight loss supplement Although L-carnitine has been marketed as a weight-loss supplement, there is no scientific evidence to date to show that it improves weight loss. A recent study of moderately overweight women found that L-carnitine did not significantly alter body weight, body fat, or lean body mass. Based on the results of this one small study, claims that L-carnitine helps reduce weight are not supported at this time. 12 See also Acetylcarnitine Primary carnitine deficiency References ^ Steiber A, Kerner J, Hoppel C 2004. Carnitine: a nutritional, biosynthetic, and functional perspective. Mol. Aspects Med. 25 5-6: 455-73. doi:10.1016/j.mam.2004.06.006. PMID 15363636. ^ A. J. Liedtke, S. H. Nellis, L. F. Whitesell and C. Q. Mahar 1982. Metabolic and mechanical effects using L- and D-carnitine in working swine hearts. Heart and Circulatory Physiology 243 5: H691-H697. PMID 7137362. ^ L-Carnitine. Retrieved on 2007-06-01. ^ Olpin S 2005. Fatty acid oxidation defects as a cause of neuromyopathic disease in infants and adults. Clin. Lab. 51 5-6: 289-306. PMID 15991803. ^ Claudio Cavazza, Composition for the Prevention and Treatment of Osteoporosis due to Menopause Syndrome 2002, US Patent 6,335,038, column 4. ^ Claudio Cavazza, Composition for the Prevention and Treatment of Osteoporosis due to Menopause Syndrome 2002, US Patent 6,335,038, columns 3-4. ^ Claudio Cavazza, Composition for the Prevention and Treatment of Osteoporosis due to Menopause Syndrome 2002, US Patent 6,335,038, column 3. ^ Geltrude Mingrone, Aldo V. Greco, Esmeralda Capristo, Giuseppe Benedetti, Annalisa Giancaterini, Andrea De Gaetano, and Giovanni Gasbarrini 1999. L-Carnitine Improves Glucose Disposal in Type 2 Diabetic Patients. Journal of the American College of Nutrition 18 1: 77-82. PMID 10067662. ^ Linus Pauling Institute at Oregon State University ^ http://www.encyclopedia.com/doc/1G1-131086133.html ^ NHPD Monthly Communique, Vol. 1, Issue 1, September 2005. Retrieved on 2007-06-01. ^ University of Maryland Medical Centre, April 2002. Retrieved on 2008-05-20. External links article on Carnitine at University of Maryland Medical Center Molecule of the Month at University of Bristol v d e Dietary supplements Types Amino acids Bodybuilding supplement Energy drink Energy bar Fatty acids Herbal Supplements Minerals Prebiotics Probiotics Lactobacillus, Bifidobacterium Vitamins Whole food supplements, effervescent Vitamins and minerals Retinol Vitamin A B vitamins: Thiamine B1 Riboflavin B2 Niacin B3 Pantothenic acid B5 Pyridoxine B6 Biotin B7 Folic acid B9 Cyanocobalamin B12 Ascorbic acid Vitamin C Ergocalciferol and Cholecalciferol Vitamin D Tocopherol Vitamin E Naphthoquinone Vitamin K Calcium Choline Chlorine Chromium Cobalt Copper Fluorine Iodine Iron Magnesium Manganese Molybdenum Phosphorus Potassium Selenium Sodium Sulfur Zinc Other common ingredients Carnitine Chondroitin sulfate Cod liver oil Copper gluconate Creatine/Creatine supplements Dietary fiber Elemental calcium Ephedra Fish oil Folic acid Ginseng Glucosamine Glutamine Iron supplements Japanese Honeysuckle Krill oil Lingzhi Linseed oil Melatonin Red yeast rice Royal jelly Saw palmetto Spirulina Taurine Wheatgrass Wolfberry Yohimbine Zinc gluconate Related articles Codex Alimentarius Enzyte Metabolife Hadacol Nutraceutical Multivitamin Nutrition v d e Other alimentary tract and metabolism products A16 Amino acids and derivatives Levocarnitine - Ademetionine - Levoglutamide - Mercaptamine - Carglumic acid - Betaine Enzymes Alglucerase - Imiglucerase - Agalsidase alfa - Agalsidase beta - Laronidase - Sacrosidase - Alglucosidase alfa - Galsulfase - Idursulfase Various alimentary tract and metabolism products Tioctic acid - Anethole trithione - Sodium phenylbutyrate - Nitisinone - Zinc acetate - Miglustat Retrieved from http://en..org/wiki/Carnitine Categories: Hydroxy acids | Quaternary ammonium compounds | Dietary supplements | Amino acidsHidden categories: All articles with statements | Articles with statements since May 2008 | Articles with statements since April 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages ÄŒesky Deutsch Español Esperanto Ù?ارسی Bahasa Indonesia Italiano Lietuvių Nederlands 日本語 Polski Português РуÑ?Ñ?кий SlovenÄ?ina СрпÑ?ки / Srpski Svenska Türkçe ä¸æ–‡ This page was last modified on 11 September 2008, at 20:35
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