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Encyclopedia > Ubiquinol
Ubiquinone

Coenzyme Q10 (also known as ubiquinone, ubidecarenone, or CoQ10) is a benzoquinone, where the "Q" and the "10" in the name refer to the quinone chemical group and the 10 isoprenyl chemical subunits, respectively. Quinone is generally defined as an aromatic beneze molecule containing a double ketone functional group. ... A quinone (or benzoquinone) is either one of the two isomers of cyclohexadienedione or a derivative thereof. ...


This vitamin-like substance is, by nature, present in all human cells and responsible for the production of the body’s own energy. In each human cell food energy is converted into energy for our body in the mitochondria with the aid of CoQ10. 95% of all our body’s energy requirements (ATP) is converted with the aid of CoQ10[1][2]. Therefore it is obvious that those organs with the highest energy requirements – such as the heart, the lungs and the liver – have been shown to have the highest CoQ10 concentrations[3][4][5]. Retinol (Vitamin A) For the record label, see Vitamin Records Vitamins are nutrients required in tiny amounts for essential metabolic reactions in the body. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ...

Contents

History

Coenzyme Q was first discovered by professor Fred L. Crane and colleagues at the University of Wisconsin-Madison Enzyme Institute in 1957.[6][7] In 1958, its chemical structure was reported by Professor Karl Folkers and coworkers at Merck.[8][7] For his discovery of the significant part played by CoQ10 in energy production, the British scientist Peter D. Mitchell was awarded the Nobel Prize for chemistry in 1978. The University of Wisconsin–Madison (also known as UW–Madison, Madison, Wisconsin, University of Wisconsin, or UW) is a highly selective public research university located in Madison, Wisconsin. ... 1957 (MCMLVII) was a common year starting on Tuesday of the Gregorian calendar. ... Year 1958 (MCMLVIII) was a common year starting on Wednesday of the Gregorian calendar. ... It has been suggested that Rosetta Biosoftware be merged into this article or section. ... Peter D. Mitchell (September 29, 1920- April 10, 1992) was a British biochemist who was awarded the 1978 Nobel Prize for Chemistry for formulation of the chemiosmotic theory of mitochondrial function. ... List of Nobel Prize laureates in Chemistry from 1901 to the present day. ...


Chemical properties

Description Image
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:

Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... The term Side chain can have different meanings depending on the context: In chemistry and biochemistry a side chain is a part of a molecule attached to a core structure. ... In cell biology, a mitochondrion is an organelle found in the cells of most eukaryotes. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... structure of ubiquinone 3. ... In chemistry free radicals are uncharged atomic or molecular species with unpaired electrons or an otherwise open shell configuration. ... structure of ubisemiquinone 3. ... structure of ubiquinol 3. ...

Biochemical role

Electron transport chain ("UQ" visible in green near center.)

CoQ is found in the membranes of endoplasmic reticulum, peroxisomes, lysosomes, vesicles and notably the inner membrane of the mitochondrion where it is an important part of the electron transport chain; there it passes reducing equivalents to acceptors such as Coenzyme Q : cytochrome c - oxidoreductase: Image File history File links ETC.png‎ A diagram of an ETC gun. ... Image File history File links ETC.png‎ A diagram of an ETC gun. ... The Electron Transport Chain. ... A biological membrane or biomembrane is an enclosing or separating tissue which acts as a barrier within or around a cell. ... The endoplasmic reticulum or ER is an organelle found in all eukaryotic cells that is an interconnected network of tubules, vesicles and cisternae that is responsible for several specialized functions: Protein translation, folding, and transport of proteins to be used in the cell membrane (e. ... Basic structure of a peroxisome Electron micrograph of a section of a liver cell showing glycogen deposits as accumulations of electron dense particles (arrows). ... Organelles. ... This article or section is in need of attention from an expert on the subject. ... Electron micrograph of a mitochondrion showing its mitochondrial matrix and membranes In cell biology, a mitochondrion (plural mitochondria) (from Greek μιτος or mitos, thread + κουδριον or khondrion, granule) is a membrane-enclosed organelle, found in most eukaryotic cells. ... The Electron Transport Chain. ... CoQ Cytochrome c reductase The Coenzyme Q - cytochrome c reductase complex, sometimes called the cytochrome bc1 complex, and at other times Complex III, is the third complex in the electron transfer chain (PDB 1KYO, EC 1. ...

CoQH2+ 2 FeIII-cytochrome c → CoQ + 2 FeII-cytochrome c

CoQ is also essential in the formation of the apoptosome along with other adapter proteins. The loss of trophic factors activates pro-apoptotic enzymes, causing the breakdown of mitochondria. The apoptosome is a big multi-protein structure formed in the process of apoptosis. ... A cell undergoing apoptosis. ...


Antioxidant role of CoQ10 in the body

Apart from being a cofactor in the mitochondrial electron transport chain, CoQ10 in its reduced form (ubiquinol or CoQ10 H2) serves as an important antioxidant in both mitochondria and lipid membranes, where it protects our cells in their battle against the destructive effects of free radicals. In human LDL it affords protection against the oxidative modifications of LDL themselves, thus lowering their atherogenic potency [9]. CoQ10 is essential in vitamin E regeneration. Ubiquinol, inhibits protein and lipid oxidation in cell membranes, and helps to minimize oxidative injury to DNA[10]. CoQ10 is an integral part of the respiratory chain and thereby located exactly where the free radicals are generated, in the mitochondria. These endogeneously produced free radicals are considered as an import factor of the aging process [11]. Low-density lipoprotein (LDL) refers to a class and range of lipoprotein particles, varying somewhat in their size and contents, which carry cholesterol in the blood and around the body, for use by various cells. ...


Supplementation

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 to produce enough coenzyme Q10 because of their disorder. Coenzyme Q10 is then prescribed by a medical doctor. [12] Mitochondrial diseases are a group of disorders relating to the mitochondria, the organelles that are the powerhouses of the eukaryotic cells that comprise higher-order lifeforms (including humans). ... A metabolic disorder is a medical disorder which affects the production of energy within individual human (or animal) cells. ...


Because of its ability to transfer electrons and therefore act as an antioxidant, Coenzyme Q is also used as a dietary supplement. Young people are able to make Q10 from the lower numbered ubiquinones such as Q6 or Q8.[citation needed] The sick and elderly may not be able to make enough, thus Q10 becomes a vitamin later in life and in illness.[citation needed] Space-filling model of the antioxidant metabolite glutathione. ... A dietary supplement is intended to supply nutrients, (vitamins, minerals, fatty acids or amino acids) that are missing or not consumed in sufficient quantity in a persons diet. ... Retinol (Vitamin A) For the record label, see Vitamin Records Vitamins are nutrients required in tiny amounts for essential metabolic reactions in the body. ...


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 (migraine patients knew they were taking coenzyme Q10), and one was a double-blind, randomized, placebo-controlled trial in a very small group of 42 patients. [13].


It is also being investigated as a treatment for cancer, and as relief from cancer treatment side effects.[14] Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ...


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 Parkinsons[16], although it does not relieve the symptoms[17]. 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] In animals the brain, or encephalon (Greek for in the head), is the control center of the central nervous system, responsible for thought. ... Parkinsons disease (PD; paralysis agitans) is a neurodegenerative disease of the substantia nigra (an area in the basal ganglia of the brain). ...


There are several reports concerning the effect of CoQ10 on blood pressure in human studies (for review: [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, assessed overall efficacy and 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]


Biosynthesis

The benzoquinone portion of Coenzyme Q10 is synthesized from amino acids, while the isoprene sidechain is synthesized from acetyl-CoA through the mevalonate pathway. The mevalonate pathway is used for the first steps of cholesterol biosynthesis. 1,4-Benzoquinone, also cyclohexa-2,5-diene-1,4-dione, is a ketone, with formula C6H4O2. ... Phenylalanine is one of the standard amino acids. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ... Categories: Biochemistry stubs | Thiols ... The mevalonate pathway or HMG-CoA reductase pathway or mevalonate-dependent (MAD) route, is an important cellular metabolic pathway present in all higher eukaryotes and many bacteria. ...


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,[21] and statins, a class of cholesterol lowering drugs.[22] Statins can reduce serum levels of coenzyme Q10 by up to 40%.[23] Some research suggests the logical option of supplementation with coenzyme Q10 as a routine adjunct to any treatment which may reduce endogenous production of coenzyme Q10, based on a balance of likely benefit against very small risk.[24][25] Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ... Mevalonic acid is a key organic compound in biochemistry. ... Beta blockers or beta-adrenergic blocking agents are a class of drugs used to treat a variety of cardiovascular conditions and some other diseases. ... Lovastatin, the first statin to be marketed The statins form a class of hypolipidemic agents. ...


References

  1. ^ Ernster L, Dallner G: Biochemical, physiological and medical aspects of ubiquinone function. Biochim Biophys Acta 1271: 195-204, 1995
  2. ^ 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 edited by Kagan VE and Quinn PJ, CRC Press (2000), Boca Raton
  3. ^ Okamoto, T.et al (1989) Interna.J.Vit.Nutr.Res.,59,288-292
  4. ^ Aberg,F.et al (1992)Archives of Biochemistry and Biophysics, 295, 230-234
  5. ^ 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.
  6. ^ Crane F, Hatefi Y, Lester R, Widmer C (1957). "Isolation of a quinone from beef heart mitochondria". Biochim Biophys Acta 25 (1): 220-1. PMID 13445756. 
  7. ^ a b http://faculty.washington.edu/~ely/coenzq10.html
  8. ^ 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.
  9. ^ Alleva R, Tomasetti M, Battino M, Curatola G, Littarru GP, Folkers K: The roles of coenzyme Q10 and vitamin E on peroxidation of human low density subfractions. Proc Nat Acad Sci. USA, 92: 9388-9391, 1995
  10. ^ Tomasetti M., Littarru G.P., Stocker R., Alleva R.: Coenzyme Q10 enrichment decreases oxidative DNA damage in human lymphocytes. Free Radic Biol Med. 27: 1027-1032, 1999
  11. ^ Lenaz G, Bovina C, D'Aurelio M, Fato R, Formiggini G, Genova ML, Giuliano G, Pich MM, Paolucci U, Castelli GP, Ventura B: Role of mitochondria in oxidative stress and aging. Ann N Y Acad Sci 959:199-213, 2002
  12. ^ 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. PMID 15319706. Retrieved on 2006-12-01. 
  13. ^ 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. PMID 11972582. 
  14. ^ 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
  15. ^ Matthews, R. T.; et al. (July 1998). "Coenzyme Q10 administration increases brain mitochondrial concentrations and exerts neuroprotective effects". PNAS 95: 8892-8897. Retrieved on 2006-12-01. 
  16. ^ Biol Signals Recept. 2001 May-Aug;10(3-4):224-53
  17. ^ 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 (May 14, 2007). Randomized, Double-blind, Placebo-Controlled Trial on Symptomatic Effects of Coenzyme Q10 in Parkinson Disease. Archives of Neurologu.
  18. ^ Damian, M. S.; et al. (July 2004). "Coenzyme Q10 Combined With Mild Hypothermia After Cardiac Arrest". Circulation, American Heart Foundation 110: 3011-3016. Retrieved on 2006-12-01. 
  19. ^ Cupp MJ and Tracy TS. Chapter 4: Coenzyme Q10 (Ubiquinone, Ubidecarenone), pp 53-85 in Dietary Supplements edited by Cupp MJ and Tracy TS Humana press, Totowa, New Jersey (2003)
  20. ^ 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
  21. ^ 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. 
  22. ^ http://www.cholesterol-and-health.com/Synthesis-Of-Cholesterol.html
  23. ^ 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. 
  24. ^ Sarter B (2002). "Coenzyme Q10 and cardiovascular disease: a review". J Cardiovasc Nurs 16 (4): 9-20. PMID 12597259. 
  25. ^ 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. 

For the Manfred Mann album, see 2006 (album). ... December 1 is the 335th (in leap years the 336th) day of the year in the Gregorian calendar. ... For the Manfred Mann album, see 2006 (album). ... December 1 is the 335th (in leap years the 336th) day of the year in the Gregorian calendar. ... For the Manfred Mann album, see 2006 (album). ... December 1 is the 335th (in leap years the 336th) day of the year in the Gregorian calendar. ...

External links

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Mitochondrial electron transport chain/oxidative phosphorylation

Complex I - Complex II - Coenzyme Q - Complex III - Cytochrome C - Complex IV - Alternative oxidase The University of Washington, founded in 1861, is a public research university in Seattle, Washington. ... Oregon State University (OSU) is a four-year research and degree-granting public university, located in Corvallis, Oregon in the United States. ... The National Institute of Neurological Disorders and Stroke is a part of the U.S. National Institutes of Health. ... The Electron Transport Chain. ... The Electron Transport Chain. ... NADH dehydrogenase NADH dehydrogenase (EC 1. ... Succinate—coenzyme Q reductase (EC 1. ... Coenzyme Q (CoQ), also known as ubiquinone or ubiquinol, is a biologically active quinone with an isoprenoid side chain, related in structure to vitamin K and vitamin E. // History Coenzyme Q was first discovered in 1957 by professor F. L. Crane and colleagues at the University of Wisconsin Enzyme Institute. ... CoQ Cytochrome c reductase The Coenzyme Q - cytochrome c reductase complex, sometimes called the cytochrome bc1 complex, and at other times Complex III, is the third complex in the electron transfer chain (PDB 1KYO, EC 1. ... Cytochrome c with heme c. ... Cytochrome c oxidase The enzyme cytochrome c oxidase (PDB 2OCC, EC 1. ...



 

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