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20-September-2008 09:29:08 - K This article is about the biomolecule known as vitamin K. For the unrelated drug sometimes referred as vitamin K, see ketamine. Vitamin K1 phylloquinone. Both contain a functional naphthoquinone ring and an aliphatic side chain. Phylloquinone has a phytyl side chain. Vitamin K1 phylloquinone. Both contain a functional naphthoquinone ring and an aliphatic side chain. Phylloquinone has a phytyl side chain. Vitamin K2 menaquinone. In menaquinone the side chain is composed of a varying number of isoprenoid residues. Vitamin K2 menaquinone. In menaquinone the side chain is composed of a varying number of isoprenoid residues. Vitamin K K from Koagulations-Vitamin in German, Danish, Swedish and Norwegian1 denotes a group of lipophilic, hydrophobic vitamins that are needed for the posttranslational modification of certain proteins, mostly required for blood coagulation. Chemically they are 2-methyl-1,4-naphthoquinone derivatives. Vitamin K2 menaquinone, menatetrenone is normally produced by bacteria in the intestines, and dietary deficiency is extremely rare unless the intestines are heavily damaged or are unable to absorb the moleculecitation needed. Contents 1 Chemical structure 2 Physiology 3 Recommended amounts 4 Sources of Vitamin K 5 Role in disease 6 Use on newborn babies 7 Biochemistry 7.1 Discovery 7.2 Function in the cell 7.3 Gla-proteins 7.4 Function in Bacteria 7.5 Carcinogenicity 8 References 9 Further reading 10 External links Chemical structure All members of the vitamin K group of vitamins share a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position see figure 1. Phylloquinone also known as vitamin K1 invariably contains in its side chain four isoprenoid residues, one of which is unsaturated. Menaquinones have side chains composed of a variable number of unsaturated isoprenoid residues; generally they are designated as MK-n, where n specifies the number of isoprenoids. It is generally accepted that the naphthoquinone is the functional group, so that the mechanism of action is similar for all K-vitamins. Substantial differences may be expected, however, with respect to intestinal absorption, transport, tissue distribution, and bio-availability. These differences are caused by the different lipophilicity of the various side chains, and by the different food matrices in which they occur. Physiology Vitamin K is involved in the carboxylation of certain glutamate residues in proteins to form gamma-carboxyglutamate residues abbreviated Gla-residues. The modified residues are situated within specific protein domains called Gla domains. Gla-residues are usually involved in binding calcium. The Gla-residues are essential for the biological activity of all known Gla-proteins.2 At this time 14 human proteins with Gla domains have been discovered, and they play key roles in the regulation of three physiological processes: Blood coagulation: prothrombin factor II, factors VII, IX, X, protein C, protein S and protein Z.3 Bone metabolism: osteocalcin, also called bone Gla-protein BGP, and matrix gla protein MGP.4 Vascular biology.5 Recommended amounts The U.S. Dietary Reference Intake DRI for an Adequate Intake AI of Vitamin K for a 25-year old male is 120 micrograms/day. No Tolerable Upper Intake Level UL has been set. The human body does not store Vitamin K in large quantities, so the body requires a daily intake of Vitamin K.6 Sources of Vitamin K Vitamin K is found chiefly in leafy green vegetables, particularly the dark green ones such as spinach and kale; Brassica e.g. cabbage, cauliflower, broccoli, and brussels sprouts are also high in Vitamin K as are some fruits such as avocado and kiwifruit. By way of reference, two tablespoons of parsley contain 153% of the recommended daily amount of vitamin K.7. Some vegetable oils, notably soybean, contain vitamin K, but at levels that would require relatively large caloric consumption to meet the USDA recommended levels.8 Phylloquinone vitamin K1 is the major dietary form of vitamin K. Menaquinone-4 and Menaquinone-7 vitamin K2 are found in meat, eggs, dairy 9 and natto10. MK-4 is synthesized by animal tissues, the rest mainly MK-7 are synthesized by bacteria during fermentation. In natto 0% of Vitamin K is from MK-4 and in cheese 2-7%.11 Role in disease Vitamin K-deficiency may occur by disturbed intestinal uptake such as would occur in a bile duct obstruction, by therapeutic or accidental intake of vitamin K-antagonists or, very rarely, by nutritional vitamin K-deficiency. As a result, Gla-residues are inadequately formed and the Gla-proteins are insufficiently active. Lack of control of the three processes mentioned above may lead to the following: risk of massive, uncontrolled bleeding, cartilage calcification and severe malformation of developing bone, or deposition of insoluble calcium salts in the walls of arteries. The deposition of calcium in soft tissues, including arterial walls, is quite common, especially in those suffering from atherosclerosis, suggesting that Vitamin K deficiency is more common than previously thought.5 Menaquinone, but not phylloquinone, intake is associated with reduced risk of CHD mortality, all-cause mortality and severe aortic calcification.121314 In a cohort study in Germany 11319 men, mean follow-up time 8.6y, Menaquinone intake was associated with decreased incidence of advanced prostate cancer.15 Postmenopausal and elderly women in Thailand have high risk of Vitamin K2 deficiency, comparing to the normal value of young, reproductive females.16 Current dosage recommendations for Vitamin K may be too low.17 Use on newborn babies In some countries, injections of Vitamin K are routinely given to newborn babies. Vitamin K is used as prophylactic measure to prevent late-onset haemorrhagic disease HDN. Since HDN is a relatively rare problem, many parents now choose for their babies not to have such an injection; most pediatricians, however, highly recommend the prophylactic dose for adequate protection. Biochemistry Discovery In 1929, Danish scientist Henrik Dam investigated the role of cholesterol by feeding chickens a cholesterol-depleted diet.18 After several weeks, the animals developed hemorrhages and started bleeding. These defects could not be restored by adding purified cholesterol to the diet. It appeared that - together with the cholesterol - a second compound had been extracted from the food, and this compound was called the coagulation vitamin. The new vitamin received the letter K because the initial discoveries were reported in a German journal, in which it was designated as Koagulationsvitamin. Edward Adelbert Doisy of Saint Louis University did much of the research that led to the discovery of the structure and chemical nature of Vitamin K.19 Dam and Doisy shared the 1943 Nobel Prize for medicine for their work on Vitamin K. Several laboratories synthesized the compound in 1939.20 For several decades the vitamin K-deficient chick model was the only method of quantitating vitamin K in various foods: the chicks were made vitamin K-deficient and subsequently fed with known amounts of vitamin K-containing food. The extent to which blood coagulation was restored by the diet was taken as a measure for its vitamin K content. The first published report of successful treatment with vitamin K of life-threatening hemorrhage in a jaundiced patient with prothrombin deficiency was made in 1938 at the University of Iowa Department of Pathology by Drs. Harry Pratt Smith, Emory Warner, Kenneth Brinkhous, and Walter Seegers.21 Function in the cell The precise function of vitamin K was not discovered until 1974, when three laboratories Stenflo et al.22, Nelsestuen et al.23, and Magnusson et al.24 isolated the vitamin K-dependent coagulation factor prothrombin Factor II from cows that received a high dose of a vitamin K antagonist, warfarin. It was shown that while warfarin-treated cows had a form of prothrombin that contained 10 glutamate amino acid residues near the amino terminus of this protein, the normal untreated cows contained 10 unusual residues which were chemically identified as gamma-carboxyglutamate, or Gla. The extra carboxyl group in Gla made clear that vitamin K plays a role in a carboxylation reaction during which Glu is converted into Gla. The biochemistry of how Vitamin K is used to convert Glu to Gla has been elucidated over the past thirty years in academic laboratories throughout the world. Within the cell, Vitamin K undergoes electron reduction to a reduced form of Vitamin K called Vitamin K hydroquinone by the enzyme Vitamin K epoxide reductase or VKOR.25 Another enzyme then oxidizes Vitamin K hydroquinone to allow carboxylation of Glu to Gla; this enzyme is called the gamma-glutamyl carboxylase2627 or the Vitamin K-dependent carboxylase. The carboxylation reaction will only proceed if the carboxylase enzyme is able to oxidize Vitamin K hydroquinone to vitamin K epoxide at the same time; the carboxylation and epoxidation reactions are said to be coupled reactions. Vitamin K epoxide is then re-converted to Vitamin K by the Vitamin K epoxide reductase. These two enzymes comprise the so-called Vitamin K cycle.28 One of the reasons why Vitamin K is rarely deficient in a human diet is because Vitamin K is continually recycled in our cells. Warfarin and other coumadin drugs block the action of the Vitamin K epoxide reductase.29 This results in decreased concentrations of Vitamin K and Vitamin K hydroquinone in the tissues, such that the carboxylation reaction catalyzed by the glutamyl carboxylase is inefficient. This results in the production of clotting factors with inadequate Gla. Without Gla on the amino termini of these factors, they no longer bind stably to the blood vessel endothelium and cannot activate clotting to allow formation of a clot during tissue injury. As it is impossible to predict what dose of Warfarin will give the desired degree of suppression of the clotting, Warfarin treatment must be carefully monitored to avoid over-dosing. See Warfarin. Gla-proteins At present, the following human Gla-containing proteins have been characterized to the level of primary structure: the blood coagulation factors II prothrombin, VII, IX, and X, the anticoagulant proteins C and S, and the Factor X-targeting protein Z. The bone Gla-protein osteocalcin, the calcification inhibiting matrix gla protein MGP, the cell growth regulating growth arrest specific gene 6 protein Gas6, and the four transmembrane Gla proteins TMGPs the function of which is at present unknown. Gas6 can function as a growth factor that activates the Axl receptor tyrosine kinase and stimulates cell proliferation or prevents apoptosis in some cells. In all cases in which their function was known, the presence of the Gla-residues in these proteins turned out to be essential for functional activity. Gla-proteins are known to occur in a wide variety of vertebrates: mammals, birds, reptiles, and fish. The venom of a number of Australian snakes acts by activating the human blood clotting system. Remarkably, in some cases activation is accomplished by snake Gla-containing enzymes that bind to the endothelium of human blood vessels and catalyze the conversion of procoagulant clotting factors into activated ones, leading to unwanted and potentially deadly clotting. Another interesting class of invertebrate Gla-containing proteins is synthesized by the fish-hunting snail Conus geographus.30 These snails produce a venom containing hundreds of neuro-active peptides, or conotoxins, which is sufficiently toxic to kill an adult human. Several of the conotoxins contain 2-5 Gla residues.31 Function in Bacteria Many bacteria, such as Escherichia coli found in the large intestine, can synthesize Vitamin K2 menaquinone,32 but not Vitamin K1 phylloquinone. In these bacteria, menaquinone will transfer two electrons between two different small molecules, in a process called anaerobic respiration.33 For example, a small molecule with an excess of electrons also called an electron donor such as lactate, formate, or NADH, with the help of an enzyme, will pass two electrons to a menaquinone. The menaquinone, with the help of another enzyme, will in turn transfer these 2 electrons to a suitable oxidant, such fumarate or nitrate also called an electron acceptor. Adding two electrons to fumarate or nitrate will convert the molecule to succinate or nitrite + water, respectively. Some of these reactions generate a cellular energy source, ATP, in a manner similar to eukaryotic cell aerobic respiration, except that the final electron acceptor is not molecular oxygen, but say fumarate or nitrate In aerobic respiration, the final oxidant is molecular oxygen O2 , which accepts four electrons from an electron donor such as NADH to be converted to water. Escherichia coli can carry out aerobic respiration and menaquninone-mediated anaerobic respiration. Carcinogenicity Vitamin K substances are IARC Group 3 carcinogens. One study conducted in the United Kingdom in 1970 found a nearly two-fold increase of leukaemia in children administered synthetic Vitamin K1 phytomenadione intramuscularly34, but later studies have failed to find whether Vitamin K is carcinogenic or not.35363738 References ^ Dam, Henrik 1935, http://www.biochemj.org/bj/029/1273/0291273.pdf The Antihaemorrhagic Vitamin Of The Chick, Biochemical Journal XXIX82: 1273-1285, http://www.biochemj.org/bj/029/1273/0291273.pdf ^ Furie B, Bouchard BA, Furie BC 1999. Vitamin K-dependent biosynthesis of gamma-carboxyglutamic acid. Blood 93 6: 1798-808. PMID 10068650. ^ Mann KG 1999. Biochemistry and physiology of blood coagulation. Thromb. Haemost. 82 2: 165-74. PMID 10605701. ^ Price PA 1988. Role of vitamin-K-dependent proteins in bone metabolism. Annu. Rev. Nutr. 8: 565-83. doi:10.1146/annurev.nu.08.070188.003025. PMID 3060178. ^ a b Berkner KL, Runge KW 2004. The physiology of vitamin K nutriture and vitamin K-dependent protein function in atherosclerosis. J. Thromb. Haemost. 2 12: 2118-32. doi:10.1111/j.1538-7836.2004.00968.x. PMID 15613016. ^ Higdon February 2008. Vitamin K. Linus Pauling Institute, Oregon State University. Retrieved on 2008-04-12. ^ Nutrition Facts and Information for Parsley, raw ^ Nutrition facts, calories in food, labels, nutritional information and analysis - NutritionData.com ^ Elder SJ, Haytowitz DB, Howe J, Peterson JW, Booth SL January 2006. Vitamin k contents of meat, dairy, and fast food in the u.s. Diet. J. Agric. Food Chem. 54 2: 463-7. doi:10.1021/jf052400h. PMID 16417305. ^ Tsukamoto Y, Ichise H, Kakuda H, Yamaguchi M 2000. Intake of fermented soybean natto increases circulating vitamin K2 menaquinone-7 and gamma-carboxylated osteocalcin concentration in normal individuals. J. Bone Miner. Metab. 18 4: 216-22. PMID 10874601. ^ On the Trail of the Elusive X-Factor: Vitamin K2 Revealed. ^ Geleijnse JM, Vermeer C, Grobbee DE, et al 2004. Dietary intake of menaquinone is associated with a reduced risk of coronary heart disease: the Rotterdam Study. J. Nutr. 134 11: 3100-5. PMID 15514282. ^ Erkkilä AT, Booth SL 2008. Vitamin K intake and atherosclerosis. Curr. Opin. Lipidol. 19 1: 39-42. doi:10.1097/MOL.0b013e3282f1c57f inactive 2008-06-25. PMID 18196985. ^ Wallin R, Schurgers L, Wajih N 2008. Effects of the blood coagulation vitamin K as an inhibitor of arterial calcification. Thromb. Res. 122: 411. doi:10.1016/j.thromres.2007.12.005. PMID 18234293. ^ Nimptsch K, Rohrmann S, Linseisen J April 2008. Dietary intake of vitamin K and risk of prostate cancer in the Heidelberg cohort of the European Prospective Investigation into Cancer and Nutrition EPIC-Heidelberg. Am. J. Clin. Nutr. 87 4: 985-92. PMID 18400723. ^ Bunyaratavej N 2007. Experience of vitamin K2 in Thailand in Japanese. Clin Calcium 17 11: 1752-60. doi:CliCa071117521760 inactive 2008-06-25. PMID 17982197. ^ Adams J, Pepping J 2005. Vitamin K in the treatment and prevention of osteoporosis and arterial calcification. Am J Health Syst Pharm 62 15: 1574-81. doi:10.2146/ajhp040357. PMID 16030366. ^ Dam H. The antihemorrhagic vitamin of the chick. Occurrence and chemical nature, Nature, 1935;135:652 ^ MacCorquodale, DW, Binkley, SB, Thayer, SA, Doisy, EA, On the constitution of Vitamin K1, Journal of the American Chemical Society, 1939, 61:1928-1929 ^ Fieser, LF, Synthesis of Vitamin K1, Journal of the American Chemical Society,1939, 61:3467-3475 ^ Warner, ED, Brinkhous, KM, Smith, HP, Proceedings of the Society of Experimental Biology and Medicine, 1938, 37:628 ^ Stenflo J, Fernlund P, Egan W, Roepstorff P., Vitamin K-dependent modifications of glutamic acid residues in prothrombin, Proceedings of the National Academy of Sciences, USA, 1974, 71:2730-3. PMID 4528109 ^ Nelsestuen GL, Zytkovicz TH, Howard JB., The mode of action of vitamin K. Identification of gamma-carboxyglutamic acid as a component of prothrombin, Journal of Biological Chemistry, 1974, 24919:6347-50. PMID 4214105 ^ Magnusson S, Sottrup-Jensen L, Petersen TE, Morris HR, Dell A, Primary structure of the vitamin K-dependent part of prothrombin. FEBS Letters, 1974, 442:189-93. PMID 4472513 ^ Oldenburg J, Bevans CG, Muller CR, Watzka M, Vitamin K epoxide reductase complex subunit 1 VKORC1: the key protein of the vitamin K cycle, Antioxidants and Redox Signaling, 2006, 83-4:347-53. Review. PMID 16677080 ^ Suttie JW, Vitamin K-dependent carboxylase, Annual Review of Biochemistry,1985, 54:459-77. Review. PMID 3896125 ^ Presnell SR, Stafford DW, The vitamin K-dependent carboxylase, Thrombosis and Haemostasis, 2002, 876:937-46. Review. PMID 12083499 ^ Stafford DW, The vitamin K cycle, Journal of Thrombosis Haemostasis, 2005, 8:1873-8. Review. PMID 16102054 ^ Whitlon DS, Sadowski JA, Suttie JW, Mechanisms of coumarin action: significance of vitamin K epoxide reductase inhibition, Biochemistry, 1978, 17:1371-7. PMID 646989 ^ Terlau H, Olivera BM. Conus venoms: a rich source of novel ion channel-targeted peptides, Physiological Reviews, 2004, 841:41-68. Review. PMID 14715910 ^ Buczek O, Bulaj G, Olivera BM, Conotoxins and the posttranslational modification of secreted gene products, Cell and Molecular Life Sciences, 2005, 6224:3067-79. Review. PMID:16314929 ^ Bentley, R, Meganathan, R., Biosynthesis of Vitamin K menaquinone in Bacteria, Bacteriological Reviews, 1982, 463:241-280. Review. ^ Haddock, BA, Jones, CW, Bacterial Respiration, Bacteriological Reviews, 1977, 411:74-99. Review. ^ Vitamin K: controversy? what controversy? ^ Controversies concerning vitamin K and the newborn. American Academy of Pediatrics Committee on Fetus and Newborn 2003. Pediatrics 112 1 Pt 1: 191-2. PMID 12837888. ^ Fear NT, Roman E, Ansell P, Simpson J, Day N, Eden OB 2003. Vitamin K and childhood cancer: a report from the United Kingdom Childhood Cancer Study. Br. J. Cancer 89 7: 1228-31. doi:10.1038/sj.bjc.6601278. PMID 14520451. ^ von Kries R 1999. Oral versus intramuscular phytomenadione: safety and efficacy compared. Drug Saf 21 1: 1-6. PMID 10433349. ^ IARC Monograph volume 76. Retrieved on 2008-03-07. Further reading Dam, H., Researches in Vitamin K, In: Pespectives in Biological Chemistry RE Olson, ed., Marcel Dekker, 1970. The Nobel Prize winner recounts the history of the discovery of Vitamin K. Suttie, J.W., Vitamin K, In: Handbook of Lipid research: The fat-soluble vitamins HF DeLuca, ed., Plenum Press, 1978. Outstanding review of Vitamin K research from 1930-1978 by one of the leaders in the field. David A. Bender, Nutritional biochemistry of the vitamins, Cambridge University Press, 2003 G. F. M. Ball, Vitamins: their role in the human body, Blackwell Science, 2004 Gerald F. Combs, The vitamins: fundamental aspects in nutrition and health, Academic Press, 1998 External links Jane Higdon, Vitamin K, Micronutrient Information Center, Linus Pauling Institute Vitamin K: Another Reason to Eat Your Greens Vitamin K: Signs of Deficiency Vitamin K Deficiency - from the Merck Manual An Alternative Perspective on Vitamin K Prophylaxis Vitamin K Content - USDA National Nutrient Database for Standard Reference, Release 19 v d e Vitamins A11 Fat soluble A: Retinol - Beta-carotene - Tretinoin - Alpha-carotene D3: 7-Dehydrocholesterol → Previtamin D3 → Cholecalciferol D3 → Calcidiol → Calcitriol active form → Calcitroic acid D2: Ergosterol → Ergocalciferol D2 D analogues: Dihydrotachysterol - Calcipotriol - Tacalcitol E: Tocopherol - Tocotrienol K: Naphthoquinone - Phylloquinone/K1 - Menatetrenone/K2 Water soluble: B vitamins B1 Thiamine - B2 Riboflavin - B3 Niacin, Nicotinamide - B5 Pantothenic acid, Dexpanthenol, Pantethine - B6 Pyridoxine, Pyridoxal phosphate, Pyridoxamine - B7 Biotin - B9 Folic acid, Folinic acid - B12 Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide Water soluble: other C Ascorbic acid - Choline see also enzyme cofactors v d e Enzyme cofactors Coenzymes vitamins: NAD+ B3 | NADP+ B3 | Coenzyme A B5 | THF / H4F B9, DHF, MTHF | Ascorbic acid C | Menaquinone K | Coenzyme F420 non-vitamins: ATP | CTP | SAM | PAPS | GSH | Coenzyme B | Coenzyme M | Coenzyme Q | Methanofuran | BH4 | H4MPT Organic prosthetic groups vitamins: TPP / ThDP B1 | FMN, FAD B2 | PLP / P5P B6 | Biotin B7 | Methylcobalamin, Cobamamide B12 non-vitamins: Haem / Heme | Lipoic acid | Molybdopterin | PQQ Metal prosthetic groups Ca2+ | Cu2+ | Fe2+, Fe3+ | Mg2+ | Mn2+ | Mo | Ni2+ | Se | Zn2+ Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles v d e Antihemorrhagics B02 Coagulation Vitamin K Phytomenadione - Menadione Fibrinogen Fibrinogen Coagulation factors IX/Nonacog alfa - II - VII/Eptacog alfa - X - VIII - Thrombin Antifibrinolytics amino acids Aminocaproic acid, Tranexamic acid, Aminomethylbenzoic acid serpins Aprotinin, Alfa1 antitrypsin, C1-inhibitor, Camostat Local hemostatics Absorbable gelatin sponge - Oxidized cellulose - Tetragalacturonic acid hydroxymethylester - Adrenalone - Thrombin - Collagen - Calcium alginate - Epinephrine Other systemic hemostatics Etamsylate - Carbazochrome - Batroxobin - Romiplostim Retrieved from http://en..org/wiki/Vitamin_K Categories: Quinones | Polycyclic aromatic compounds | Terpenes and terpenoids | Vitamins | AntihemorrhagicsHidden categories: Pages with DOIs broken since 2008 | All articles with statements | Articles with statements since December 2007 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 العربية Bân-lâm-gú Bosanski Català Česky Dansk Deutsch Español Euskara Français í•œêµì–´ Hrvatski Bahasa Indonesia Ã?slenska Italiano עברית Lietuvių മലയാളം Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português РуÑ?Ñ?кий Simple English SlovenÄ?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Suomi Svenska Türkçe ä¸æ–‡ This page was last modified on 1 August 2008, at 17:47
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