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22-AUGUST-2008 06:13:22 - Coenzyme Q10 Redirected from Coenzyme Q Ubiquinone Ubiquinone Coenzyme Q10 also known as ubiquinone, ubidecarenone, coenzyme Q, and abbreviated at times to CoQ10, CoQ, Q10, or Q is a benzoquinone, where Q refers to the quinone chemical group, and 10 refers to the isoprenyl chemical subunits. This oil-soluble vitamin-like substance is present in most eukaryotic cells, primarily in the mitochondria. It is a component of the electron transport chain and participates in aerobic cellular respiration, generating energy in the form of ATP. Ninety-five percent of the human body's energy is generated this way.12 Therefore, those organs with the highest energy requirements - such as the heart and the liver - have the highest CoQ10 concentrations.345 Contents 1 History 2 Chemical properties 3 Biochemical role 4 Supplementation 4.1 Mitochondrial disorders 4.2 Migraine headaches 4.3 Cancer 4.4 Brain health and neurodegenerative diseases 4.5 Cardiac arrest 4.6 Blood pressure 4.7 Lifespan 5 Biosynthesis 6 Inhibition by statins and beta blockers 7 Occurrence in nature 8 References 9 See also 10 External links History Coenzyme Q was first discovered by professor Fred L. Crane and colleagues at the University of Wisconsin-Madison Enzyme Institute in 1957.67 In 1958, its chemical structure was reported by Professor Karl Folkers and coworkers at Merck.87 Chemical properties The oxidized structure of CoQ, or Q, is given here. The various kinds of Coenzyme Q can be distinguished by the number of isoprenoid side-chains they have. The most common CoQ in human mitochondria is Q10. The image to the right has three isoprenoid units and would be called Q3. If Coenzyme Q is reduced by one equivalent, the following structure results, a ubisemiquinone, and is denoted QH. Note the free-radical on one of the ring oxygens either oxygen may become a free-radical, in this case the top oxygen is shown as such. If Coenzyme Q is reduced by two equivalents, the compound becomes a ubiquinol, denoted QH2: Biochemical role Electron transport chain UQ visible in green near center. Electron transport chain UQ visible in green near center. CoQ is found in the membranes of many organelles. Since its primary function in cells is in generating energy, the highest concentration is found on the inner membrane of the mitochondrion. Some other organelles that contain CoQ10 include endoplasmic reticulum, peroxisomes, lysosomes, and vesicles. Supplementation Because of its ability to transfer electrons and therefore act as an antioxidant, Coenzyme Q is also used as a dietary supplement. When you are younger the body can synthesize Q10 from the lower-numbered ubiquinones such as Q6 or Q8.citation needed The elderly 910 and sick may not be able to make enough, thus Q10 becomes a vitamin later in life and in illness.citation needed Mitochondrial disorders Supplementation of Coenzyme Q10 is a treatment for some of the very rare and serious mitochondrial disorders and other metabolic disorders, where patients are not capable of producing enough coenzyme Q10 because of their disorder. Coenzyme Q10 is then prescribed by a physician.11 Migraine headaches Supplementation of Coenzyme Q10 has been found to have a beneficial effect on the condition of some sufferers of migraine headaches. So far, three studies have been done, of which two were small, did not have a placebo group, were not randomized, and were open-label,12 and one was a double-blind, randomized, placebo-controlled trial, which found statistically significant results despite its small sample size of 42 patients.13 Dosages were 150 to 300 mg/day. Cancer It is also being investigated as a treatment for cancer, and as relief from cancer treatment side-effects.14 Brain health and neurodegenerative diseases Recent studies have shown that the antioxidant properties of Coenzyme Q10 benefit the body and the brain in animal models.15 Some of these studies indicate that Coenzyme Q10 protects the brain from neurodegenerative disease such as Parkinson's,16 although it does not relieve the symptoms.17 Dosage was 300 mg per day. Cardiac arrest Another recent study shows a survival benefit after cardiac arrest if coenzyme Q10 is administered in addition to commencing active cooling to 32-34 degrees Celsius.18 Blood pressure There are several reports concerning the effect of CoQ10 on blood pressure in human studies.19 In a recent meta-analysis of the clinical trials of CoQ10 for hypertension, a research group led by Professor FL Rosenfeldt from the Cardiac Surgical Research Unit, Alfred Hospital, Melbourne, Australia reviewed all published trials of Coenzyme Q10 for hypertension, and assessed overall efficacy, consistency of therapeutic action, and side-effect incidence. Meta-analysis was performed in 12 clinical trials 362 patients comprising three randomized controlled trials, one crossover study, and eight open-label studies. The research group concluded that coenzyme Q10 has the potential in hypertensive patients to lower systolic blood pressure by up to 17 mm Hg and diastolic blood pressure by up to 10 mm Hg without significant side-effects.20 Lifespan Studies have shown that low dosages of Coenzyme Q10 reduce oxidation and DNA double-strand breaks, and a combination of a diet rich in polyunsaturated fatty acids and Coenzyme Q10 supplementation leads to a longer lifespan in rats21 Biosynthesis The benzoquinone portion of Coenzyme Q10 is synthesized from tyrosine, whereas the isoprene sidechain is synthesized from acetyl-CoA through the mevalonate pathway. The mevalonate pathway is also used for the first steps of cholesterol biosynthesis. Inhibition by statins and beta blockers Coenzyme Q10 shares a common biosynthetic pathway with cholesterol. The synthesis of an intermediary precursor of Coenzyme Q10, mevalonate, is inhibited by some beta blockers, blood pressure-lowering medication,22 and statins, a class of cholesterol-lowering drugs.23 Statins can reduce serum levels of coenzyme Q10 by up to 40%.24 Some research suggests the logical option of supplementation with coenzyme Q10 as a routine adjunct to any treatment that may reduce endogenous production of coenzyme Q10, based on a balance of likely benefit against very small risk.2526 Occurrence in nature This article or section may require restructuring to meet 's quality standards. Please discuss this issue on the talk page. July 2008 CoQ10 occurs in mackerel and herring fresh heart tissue in concentrations of 105-148 μg/g. In fresh mackerel red and white tissue, CoQ10 concentrations of 67 and 15 μg/g, respectively, have been reported. In fresh herring tissue, an amount of 15-24 μg/g of CoQ10 has been reported.27 CoQ10 Content of various foods:28 Food CoQ10 μg/g Portion of Food g CoQ10 Amount in Portion mg Pork heart 203 120 24 Soybean Oil29 100 9.2 Canola Oil29 100 7.3 Peanut Oil29 100 5.2 Chicken leg 17 120 2.0 Beef heart 41 120 4.8 Sesame seeds Oil29 100 3.2 Cooking by frying reduces Q10 content from 14-32%.30 References ^ Ernster L, Dallner G: Biochemical, physiological and medical aspects of ubiquinone function. Biochim Biophys Acta 1271: 195-204, 1995 ^ Dutton PL, Ohnishi T, Darrouzet E, Leonard, MA, Sharp RE, Cibney BR, Daldal F and Moser CC. 4 Coenzyme Q oxidation reduction reactions in mitochondrial electron transport pp 65-82 in Coenzyme Q: Molecular mechanisms in health and disease ed by Kagan VE and Quinn PJ, CRC Press 2000, Boca Raton ^ Okamoto, T.et al 1989 Interna.J.Vit.Nutr.Res.,59,288-292 ^ Aberg,F.et al 1992Archives of Biochemistry and Biophysics, 295, 230-234 ^ Shindo, Y., Witt, E., Han, D., Epstein, W., and Packer, L., Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin, Invest. Dermatol., 102 1994 122-124. ^ Crane F, Hatefi Y, Lester R, Widmer C 1957. Isolation of a quinone from beef heart mitochondria. Biochim Biophys Acta 25 1: 220-1. doi:10.1016/0006-30025790457-2. PMID 13445756. ^ a b Peter H. Langsjoen, Introduction of Coezyme Q10 ^ Wolf DE, Hoffman CH, Trenner NR, Arison BH, Shunk CH, Linn BD, McPherson JF, and Folkers K. Structure studies on the coenzyme Q group. J Am Chem Soc 1958: 80:4752. ^ 14. Kalen, A. Age related changes in the lipid compositions of rat and human tissues. Lipids 1989 247: 579-84. ^ Rosenfeldt FLY Pepe S, Ou R, Mariani JA, Rowland MA, Nagley P, Linnane AW. Coenzyme Q10 improves the tolerance of the senescent myocardium to aerobic and ischemic stress: studies in rats and in human atrial tissue. Biofactors 1999;92-4:29 1-9 ^ Berbel-Garcia, A.; et al. July 2004. Coenzyme Q 10 improves lactic acidosis, strokelike episodes, and epilepsy in a patient with MELAS. Clinical Neuropharmacology 27: 187-191. doi:10.1097/01.wnf.0000137862.67131.bf. PMID 15319706. Retrieved on 2006-12-01. ^ Rozen T, Oshinsky M, Gebeline C, Bradley K, Young W, Shechter A, Silberstein S 2002. Open label trial of coenzyme Q10 as a migraine preventive. Cephalalgia 22 2: 137-41. doi:10.1046/j.1468-2982.2002.00335.x. PMID 11972582. ^ Sándor PS, et al. 2005. Efficacy of coenzyme Q10 in migraine prophylaxis: A randomized controlled trial. Neurology 64: 713-715. doi:10.1212/01.WNL.0000151975.03598.ED inactive 2008-06-26. PMID 15728298. ^ Katsuhisa Sakano, Mami Takahashi, Mitsuaki Kitano, Takashi Sugimura, Keiji Wakabayashi: Suppression of Azoxymethane-induced Colonic Premalignant Lesion Formation by Coenzyme Q10 in Rats. Asian Pacific J Cancer Prev, 7, 599-603, 2006 ^ Matthews, R. T.; et al. July 1998. Coenzyme Q10 administration increases brain mitochondrial concentrations and exerts neuroprotective effects. PNAS 95: 8892-8897. doi:10.1073/pnas.95.15.8892. PMID 9671775. Retrieved on 2006-12-01. ^ Biol Signals Recept. 2001 May-Aug;103-4:224-53 ^ Alexander Storch, MD; Wolfgang H. Jost, MD; Peter Vieregge, MD; Jörg Spiegel, MD; Wolfgang Greulich, MD; Joachim Durner, MD; Thomas Müller, MD; Andreas Kupsch, MD; Henning Henningsen, MD; Wolfgang H. Oertel, MD; Gerd Fuchs, MD; Wilfried Kuhn, MD; Petra Niklowitz, MD; Rainer Koch, PhD; Birgit Herting, MD; Heinz Reichmann, MD; for the German Coenzyme Q10 Study Group 2007-05-14. Randomized, Double-blind, Placebo-Controlled Trial on Symptomatic Effects of Coenzyme Q10 in Parkinson Disease. Archives of Neurologu. ^ Damian, M. S.; et al. July 2004. Coenzyme Q10 Combined With Mild Hypothermia After Cardiac Arrest. Circulation, American Heart Foundation 110: 3011-3016. doi:10.1161/01.CIR.0000146894.45533.C2. PMID 15520321. Retrieved on 2006-12-01. ^ Cupp MJ and Tracy TS. Chapter 4: Coenzyme Q10 Ubiquinone, Ubidecarenone, pp 53-85 in Dietary Supplements ed by Cupp MJ and Tracy TS Humana press, Totowa, New Jersey 2003 ^ Rosenfeldt FL, Haas SJ, Krum H, Hadj A, Ng K, Leong J-Y, Watts GF. Coenzyme Q10 in the treatment of hypertension: a meta-analysis of the clinical trials. J Human Hypertension 21: 297-306, 2007 ^ Quiles JL, Ochoa JJ, Huertas JR, Mataix J 2004. Coenzyme Q supplementation protects from age-related DNA double-strand breaks and increases lifespan in rats fed on a PUFA-rich diet.. Exp Gerontol. 39 2: 189-94. doi:10.1016/j.exger.2003.10.002. PMID 15036411. ^ Kishi T, Watanabe T, Folkers K 1977. Bioenergetics in clinical medicine XV. Inhibition of coenzyme Q10-enzymes by clinically used adrenergic blockers of beta-receptors. Res Commun Chem Pathol Pharmacol 17 1: 157-64. PMID 17892. ^ The Synthesis of Cholesterol ^ Ghirlanda G, Oradei A, Manto A, Lippa S, Uccioli L, Caputo S, Greco A, Littarru G 1993. Evidence of plasma CoQ10-lowering effect by HMG-CoA reductase inhibitors: a double-blind, placebo-controlled study. J Clin Pharmacol 33 3: 226-9. PMID 8463436. ^ Sarter B 2002. Coenzyme Q10 and cardiovascular disease: a review. J Cardiovasc Nurs 16 4: 9-20. doi:10.1002/cncr.11242hra inactive 2008-06-26. PMID 12597259. ^ Thibault A, Samid D, Tompkins A, Figg W, Cooper M, Hohl R, Trepel J, Liang B, Patronas N, Venzon D, Reed E, Myers C 1996. Phase I study of lovastatin, an inhibitor of the mevalonate pathway, in patients with cancer. Clin Cancer Res 2 3: 483-91. PMID 9816194. ^ Nathalie Soucheta and Serge Laplante, Seasonal variation of Co-enzyme Q10 content in pelagic fish tissues from Eastern Quebec ^ www.thefactsaboutfitness.com ^ a b c d Phytochemicals in Nutrition and Health: Their Role in Nutrition and Health p.148 ISBN:1587160838 ^ The coenzyme Q10 content of the average Danish die...Int J Vitam Nutr Res. 1997 - PubMed Result See also Idebenone - synthetic analog with reduced oxidant generating properties External links An Introduction to Coenzyme Q10 at University of Washington Possible Health Benefits of Coenzyme Q10 at Oregon State University Study Suggests Coenzyme Q10 Slows Functional Decline in Parkinson's Disease at National Institute of Neurological Disorders and Stroke v d e Mitochondrial electron transport chain/oxidative phosphorylation Primary Complex I/NADH dehydrogenase - Complex II/Succinate dehydrogenase - Coenzyme Q - Complex III/Coenzyme Q - cytochrome c reductase - Cytochrome c - Complex IV/Cytochrome c oxidase Other Alternative oxidase - Electron-transferring-flavoprotein dehydrogenase 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 Retrieved from http://en..org/wiki/Coenzyme_Q10 Categories: Cellular respiration | Glycolysis | Antioxidants | Dietary antioxidants | Coenzymes | QuinonesHidden categories: Pages with DOIs broken since 2008 | All articles with statements | Articles with statements since February 2007 | Articles with statements since April 2007 | Cleanup from July 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 БългарÑ?ки ÄŒesky Deutsch Español Français Italiano Nederlands 日本語 Occitan Polski Português SlovenÅ¡Ä?ina Suomi УкраїнÑ?ька This page was last modified on 17 August 2008, at 02:36. of the GNU Free Documentation License. ® , Inc., a U.S.
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