Ubiquinone-10
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Surname | Ubiquinone-10 | |||||||||||||||||||||
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Molecular formula | C 59 H 90 O 4 | |||||||||||||||||||||
Brief description |
odorless solid |
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Molar mass | 863.34 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
48-52 ° C |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Coenzyme Q10 (also UQ of Engl. Ubiquinone , or Q-10 or Coenzyme Q 10 ) is a quinone derivative having a lipophilic isoprenoid side chain, structurally related to vitamin K and vitamin E . The reduced, phenolic form is called ubihydroquinone or ubiquinol (QH 2 for short ). Ubiquinon-10 is one of the ubiquinones .
Q-10 is an electron and proton carrier between complex I or complex II and complex III of the respiratory chain .
Q-10 is offered for sale as an ingredient in cosmetic creams and as a dietary supplement .
properties
Q-10 is a yellow-orange, crystalline powder with no odor or taste. The hydrophobic isoprenoid side chain enables the molecule to be anchored in the likewise hydrophobic area of the biomembrane , which builds up the mitochondria .
Biological function
Q-10 is an endogenous substance. It is partly absorbed through food , but it is also produced in the body itself. In every human cell , the energy from food is converted into the body's own energy ( ATP ). As a coenzyme, Q-10 is involved in oxidative phosphorylation , which generates 95% of total body energy (ATP). The organs with the highest energy requirements - such as the heart , lungs and liver - therefore also have the highest Q-10 concentration.
biochemistry
The respiratory chain in the mitochondria of the cell enables the gradual transfer of electrons and protons to oxygen while at the same time obtaining ATP as a biochemical energy equivalent. This reaction takes place on localized membrane proteins, complexes I to V, and mobile components, ubiquinone and cytochrome c . The latter serve as shuttle systems between the complexes: Ubiquinone mediates between complexes I / II and III, cytochrome c between complexes III and IV.
The electrons for the reduction of ubiquinone come from the oxidation of NADH on complex I of the respiratory chain , the NADH dehydrogenase , or from the oxidation of succinate on complex II, which is identical to the succinate dehydrogenase of the citric acid cycle . An ubiquinone molecule can take up two electrons step by step. In the first step QH forms • , a fairly stable semiquinone - radical . The uptake of the second electron creates the hydroquinone ubiquinol after protonation , i.e. the reduced form. In addition to electron transport, this also enables two protons to bind - ubiquinone can thus also serve as a proton carrier. These processes are important within the respiratory chain in the Q cycle at complex III .
Prooxidant and antioxidant properties
Ubiquinone is also involved in the formation of reactive oxygen species (ROS) through the creation of superoxide by ubi semiquinone - radicals that cause oxidative damage that underlies many degenerative diseases. Paradoxically, the ubiquinone pool is also an important mitochondrial antioxidant .
defect
Permanent Q-10 deficiency is rare. It is often found in patients with myopathies . Since not all of the enzymes involved in the biosynthesis of Q-10 are known, it is quite possible that mutations in one of the affected genes have not yet been identified.
One possibility for temporary Q-10 deficiency is medication with statins , where the inhibition of HMG-CoA reductase reduces the starting materials for the biosynthesis of Q-10, which leads to a decrease in plasma levels. On the other hand, nothing is known about the availability of Q-10 in muscles, nor about the effectiveness of increased intake.
biosynthesis
The biosynthesis of Q-10 in eukaryotes starts from 4-hydroxybenzoic acid , which is obtained from the amino acid tyrosine in five steps, including hydroxyphenylsuccinic acid and 4-coumaric acid , and forms the quinone part; on the other hand, all- trans -decaprenyl phosphate is required for the side chain , which is built up from geranylgeranyl phosphate (GGP, from the mevalonate pathway ) in six steps. Both starting materials are combined to 3-decaprenyl-4-hydroxybenzoate with the help of p-hydroxybenzoate polyprenyltransferase ( EC 2.5.1.39 ). In seven further steps, ubiquinol-10 is produced , which becomes ubiquinone-10 through electron transfer.
Nutritional supplement
A person ingests around three to five milligrams of the coenzyme daily through food, which is not absolutely necessary. In rare cases of increased Q-10 requirement, nutritional supplements can help avoid or compensate for a deficiency. For an adult, the dosage of Q-10 recommended by most scientists in such a case is 30–200 mg per day as a dietary supplement. The Federal Office for Consumer Protection and Food Safety has decreed that in Germany food supplements in capsule form with Q-10 may only be placed on the market if "the daily consumption of 100 mg coenzyme Q10 is not exceeded with a recommended consumption of one capsule per day" and the Labeling warns against consumption by pregnant and breastfeeding women, children and adolescents under 18 years of age.
Cosmetics
Q-10 is also a promoted active ingredient in skin creams that are widely available . They are supposed to compensate for the supposedly increasing lack of Q-10 with old age. B. ensure the breakdown of harmful radicals.
Occurrence
Q-10 is found abundantly in the meat of organs ( liver ), oily fish ( sardines , mackerel , etc.), nuts (e.g. pistachios), legumes , sesame seeds, sunflower seeds, vegetable oils , cabbage, onions, potatoes, spinach, Brussels sprouts and broccoli. Cooking can destroy the coenzyme, however.
Manufacturing
Three processes are used to manufacture Q-10: fermentation of yeast , fermentation of bacteria, and chemical synthesis.
During the yeast fermentation process, Q-10 is created in the so-called trans configuration, which means that it is identical to the naturally occurring CoQ 10 , as found in meat, fish or other foods.
The safety of yeast fermentation has been confirmed by several safety studies carried out by one of the world's leading testing laboratories ( Covance Laboratories Inc. ). In addition, a double-blind, randomized, placebo-controlled study has shown that CoQ 10 from yeast fermentation in doses of up to 900 milligrams per day is absolutely safe and well tolerated.
Q-10, produced by chemical synthesis, contains the cis isomer (a molecular structure that does not exist in naturally occurring Q-10), the safety of which has not yet been investigated intensively.
history
Ubiquinone-10 was discovered in 1957 and was first isolated from bovine hearts by Fred L. Crane . The chemical structure was clarified in 1958 by Karl August Folkers . The British scientist Peter D. Mitchell received the 1978 Nobel Prize in Chemistry for his findings on the role of Q-10 in the Q cycle of complex III of the respiratory chain .
swell
- ↑ a b c d e f Data sheet Coenzyme Q-10, 98 +% at AlfaAesar, accessed on June 17, 2019 ( PDF )(JavaScript required) .
- ↑ a b Federal Office for Consumer Protection and Food Safety : Announcement of a general decree in accordance with Section 54 of the Food and Feed Code (LFGB) for bringing into the Federal Republic of Germany and placing a food supplement with the addition of coenzyme Q10 (BVL 14/01/002) dated 12 February 2014 (Federal Gazette of March 4, 2014).
- ↑ L. Ernster, G. Dallner: Biochemical, physiological and medical aspects of ubiquinone function . Biochim. Biophys. Acta . Volume 1271, 1995, pp. 195-204. PMID 7599208
- ↑ PL Dutton et al: Coenzyme Q oxidation reduction reactions in mitochondrial electron transport. In: VE Kagan, PJ Quinn (ed.): Coenzyme Q: Molecular mechanisms in health and disease. CRC Press, 2000, pp. 65-82.
- ^ Y. Shindo, E. Witt, D. Han, W. Epstein, L. Packer: Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. In: Invest. Dermatol. 102, 1994, pp. 122-124.
- ↑ AM James et al.: Antioxidant and prooxidant properties of mitochondrial coenzymes Q. In: Arch. Biochem. Biophys. Volume 423, 2004, pp. 47-56. PMID 14989264
- ↑ M. Mancuso, D. Orsucci, L. Volpi, V. Calsolaro, G. Siciliano: Coenzyme Q10 in neuromuscular and neurodegenerative disorders . In: Curr Drug Targets . tape 11 , no. 1 , January 2010, p. 111-121 , PMID 20017723 .
- ↑ SR Lalani, DG Vladutiu, K. Plunkett, TE Lotze, AM Adesina, F. Scaglia: Isolated mitochondrial myopathy associated with muscle coenzyme Q10 deficiency . In: Arch. Neurol. tape 62 , no. 2 , February 2005, p. 317-320 , doi : 10.1001 / archneur.62.2.317 , PMID 15710863 .
- ↑ S. Sacconi, E. Trevisson, L. Salviati include: Coenzyme Q10 is frequently reduced in muscle of patients with mitochondrial myopathy . In: Neuromuscul. Disord. tape 20 , no. 1 , January 2010, p. 44-48 , doi : 10.1016 / j.nmd.2009.10.014 , PMID 19945282 .
- ^ L. Marcoff, PD Thompson: The role of coenzyme Q10 in statin-associated myopathy: a systematic review . In: J. Am. Coll. Cardiol. tape 49 , no. June 23 , 2007, pp. 2231-2237 , doi : 10.1016 / j.jacc.2007.02.049 , PMID 17560286 ( onlinejacc.org ).
- ↑ MetaCyc: ubiquinone-10 biosynthesis (eukaryotic)
- ^ C. Weber: Dietary intake and absorption of coenzyme Q. In: VE Kagan, PJ Quinn (Ed.): Coenzyme Q: Molecular mechanisms in health and disease. CRC Press, 2000, pp. 209-215.
- ↑ A. Kalén, EL Appelkvist, G. Dallner: Age-related changes in the lipid Compositions of rat and human tissues . In: Lipids . tape 24 , no. 7 , July 1989, p. 579-584 , PMID 2779364 .
- ↑ FL Crane: Biochemical functions of coenzyme Q10. In: Journal of the American College of Nutrition. Volume 20, Number 6, December 2001, pp. 591-598. PMID 11771674 (Review).
- ↑ Q10 - We apply cream to ourselves young .
- ↑ KD Williams, JD Maneka, M. Abdel-Hameed, RL Hall, TE Palmer, M. Kitano, T. Hidaka: 52-Week oral gavage chronic toxicity study with ubiquinone in rats with a 4-week recovery. In: J Agric Food Chem . 47, 1999, pp. 3756-3763.
- ↑ H. Ikematsu, K. Nakamura, S. Harashima, K. Fujii, N. Fukutomi: Safety assessment of Coenzyme Q10 (Kaneka Q10) in healthy subjects: A double-blind, randomized, placebo-controlled trial. In: Regul Toxicol Pharmacol . 44, 2006, pp. 212-218.
- ↑ FL Crane et al.: Isolation of a quinone from beef heart mitochondria. In: Biochim. Biophys. Acta. Volume 25, 1957, pp. 220-221. PMID 13445756 .
- ^ Obituary: Karl Folkers
literature
- FL Crane: Biochemical functions of coenzyme Q10. In: Journal of the American College of Nutrition. Volume 20, Number 6, December 2001, pp. 591-598. PMID 11771674 (Review).
- JTA Ely, CA Krone: A brief update on ubiquinone (coenzyme Q10) . In: J. Orthomolecular. Med. Vol. 15, 2000, pp. 63-68.
- L. Ernster, G. Dallner: Biochemical, physiological and medical aspects of ubiquinone function. In: Biochim. Biophys. Acta. Volume 1271, 1995, pp. 195-204. PMID 7599208 .
See also
Web links
- Federal Institute for Risk Assessment : Nutritional medical assessment of advertising statements on Coenzyme Q 10. Opinion of April 20, 2001. (PDF; 51 kB)
- drug telegram: Coenzyme Q10 interferes with oral anticoagulation
- Possible Health Benefits of Coenzyme Q10 (English)
- Introduction to Coenzymne Q10 (English; PDF; 52 kB)
- IUPAC nomenclature of the quinones (English)