Terpene

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Coenzyme Q10
Names
Preferred IUPAC name
2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Other names
  • In general: Ubiquinone, coenzyme Q, CoQ, vitamin Q
  • This form: ubidecarenone,

Q10, CoQ10 /ˌkoʊˌkjuːˈtɛn/

Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.590 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ checkY
    Key: ACTIUHUUMQJHFO-UPTCCGCDSA-N checkY
  • InChI=1/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+
    Key: ACTIUHUUMQJHFO-UPTCCGCDBK
  • O=C1/C(=C(\C(=O)C(\OC)=C1\OC)C)C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C
Properties
C59H90O4
Molar mass 863.365 g·mol−1
Appearance yellow or orange solid
Melting point 48–52 °C (118–126 °F; 321–325 K)
insoluble
Pharmacology
C01EB09 (WHO)
Related compounds
Related quinones
 1,4-Benzoquinone
Plastoquinone
Ubiquinol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Coenzyme Q10 (CoQ10 /ˌkoʊkjuːˈtɛn/) also known as ubiquinone, is a naturally occurring biochemical cofactor (coenzyme) and an antioxidant produced by the human body.[1][2] It can also be obtained from dietary sources, such as meat, fish, seed oils, vegetables, and dietary supplements.[1] CoQ10 is found in many organisms, including animals and bacteria.

CoQ10 plays a role in mitochondrial oxidative phosphorylation, aiding in the production of adenosine triphosphate (ATP), which is involved in energy transfer within cells.[1] The structure of CoQ10 consists of a benzoquinone moiety and an isoprenoid side chain, with the "10" referring to the number of isoprenyl chemical subunits in its tail.[3][4][5]

Although a ubiquitous molecule in human tissues, CoQ10 is not a dietary nutrient, does not have a recommended intake level, and its use as a supplement is not associated with any health or anti-disease effect.[1][2]

Biological functions[edit]

See also: Q cycle

CoQ10 is a component of the mitochondrial electron transport chain (ETC), where it plays a role in oxidative phosphorylation, a process required for the biosynthesis of adenosine triphosphate, the primary energy source of cells.[1][6][7][5]

CoQ10 is a lipophilic molecule that is located in all biological membranes of human body and serves as a component for the synthesis of ATP and is a life-sustaining cofactor for the three complexes (complex I, complex II, and complex III) of the ETC in the mitochondria.[1][4] CoQ10 has a role in the transport of protons across lysosomal membranes to regulate pH in lysosome functions.[1]

The mitochondrial oxidative phosphorylation process takes place in the inner mitochondrial membrane of eukaryotic cells. This membrane is highly folded into structures called cristae, which increase the surface area available for oxidative phosphorylation. CoQ10 plays a role in this process as an essential cofactor of the ETC located in the inner mitochondrial membrane and serves the following functions:[1][6]

  • electron transport in the mitochondrial ETC, by shuttling electrons from mitochondrial complexes like nicotinamide adenine dinucleotide (NADH), ubiquinone reductase (complex I), and succinate ubiquinone reductase (complex II), the fatty acids and branched-chain amino acids oxidation (through flavin-linked dehydrogenases) to ubiquinol–cytochrome-c reductase (complex III) of the ETC:[1][6] CoQ10 participates in fatty acid and glucose metabolism by transferring electrons generated from the reduction of fatty acids and glucose to electron acceptors;[8]
  • antioxidant activity as a lipid-soluble antioxidant together with vitamin E, scavenging reactive oxygen species and protecting cells against oxidative stress,[6][5] inhibiting the oxidation of proteins and DNA.[9]

CoQ10 also may influence immune response by modulating the expression of genes involved in inflammation.[10][11][12]

Biochemistry[edit]

Coenzymes Q is a coenzyme family that is ubiquitous in animals and many Pseudomonadota,[13] a group of gram-negative bacteria. The fact that the coenzyme is ubiquitous gives the origin of its other name, ubiquinone.[14] In humans, the most common form of coenzymes Q is coenzyme Q10, also called CoQ10 (/ˌkoʊkjuːˈtɛn/) or ubiquinone-10.[1]

Coenzyme Q10 is a 1,4-benzoquinone, in which "Q" refers to the quinone chemical group and "10" refers to the number of isoprenyl chemical subunits (shown enclosed in brackets in the diagram) in its tail.[1] In natural ubiquinones, there are from six to ten subunits in the tail, with humans having a tail of 10 isoprene units (50 carbon atoms) connected to its benzoquinone "head".[1]

This family of fat-soluble substances is present in all respiring eukaryotic cells, primarily in the mitochondria.[15] Ninety-five percent of the human body's energy is generated this way.[16] Organs with the highest energy requirements—such as the heart, liver, and kidney—have the highest CoQ10 concentrations.[17][18][19][20]

There are three redox states of CoQ: fully oxidized (ubiquinone), semiquinone (ubisemiquinone), and fully reduced (ubiquinol). The capacity of this molecule to act as a two-electron carrier (moving between the quinone and quinol form) and a one-electron carrier (moving between the semiquinone and one of these other forms) is central to its role in the electron transport chain due to the iron–sulfur clusters that can only accept one electron at a time, and as a free radical–scavenging antioxidant.[14][15]

Deficiency[edit]

There are two major pathways of deficiency of CoQ10 in humans: reduced biosynthesis, and increased use by the body.[10][21] Biosynthesis is the major source of CoQ10. Biosynthesis requires at least 15 genes, and mutations in any of them can cause CoQ deficiency.[21] CoQ10 levels also may be affected by other genetic defects (such as mutations of mitochondrial DNA, ETFDH, APTX, FXN, and BRAF, genes that are not directly related to the CoQ10 biosynthetic process).[21] Some of these, such as mutations in COQ6, can lead to serious diseases such as steroid-resistant nephrotic syndrome with sensorineural deafness.[22][23][24]

Some adverse effects, largely gastrointestinal, are reported with very high intakes. The observed safe level (OSL) risk assessment method indicated that the evidence of safety is strong at intakes up to 1200 mg/day, and this level is identified as the OSL.[25]

Assessment[edit]

Although CoQ10 may be measured in blood plasma, these measurements reflect dietary intake rather than tissue status. Currently, most clinical centers measure CoQ10 levels in cultured skin fibroblasts, muscle biopsies, and blood mononuclear cells.[26] Culture fibroblasts can be used also to evaluate the rate of endogenous CoQ10 biosynthesis, by measuring the uptake of 14C-labeled p-hydroxybenzoate.[27]

Statins[edit]

While statins may reduce CoQ10 in the blood it is unclear if they reduce CoQ10 in muscle.[28] Evidence does not support that supplementation improves side effects from statins.[28] However, a more recent metanalysis conducted in China, one of the world's largest producers of this supplement, concluded that, "CoQ10 supplementation ameliorated SAMSs [statin‐associated muscle symptoms], implying that CoQ10 supplementation might be a complementary approach to ameliorate statin‐induced myopathy."[29]

Chemical properties[edit]

The oxidized structure of CoQ10 is shown below. The various kinds of coenzyme Q may be distinguished by the number of isoprenoid subunits in their side-chains. The most common coenzyme Q in human mitochondria is CoQ10.[1] Q refers to the quinone head and "10" refers to the number of isoprene repeats in the tail. The molecule below has three isoprenoid units and would be called Q3.

Coenzyme Q3

In its pure state, it is an orange-colored lipophile powder, and has no taste nor odor.[14]

Biosynthesis[edit]

Biosynthesis occurs in most human tissue. There are three major steps:

  1. Creation of the benzoquinone structure (using phenylalanine or tyrosine, via 4-hydroxybenzoate)
  2. Creation of the isoprene side chain (using acetyl-CoA)
  3. The joining or condensation of the above two structures

The initial two reactions occur in mitochondria, the endoplasmic reticulum, and peroxisomes, indicating multiple sites of synthesis in animal cells.[30]

An important enzyme in this pathway is HMG-CoA reductase, usually a target for intervention in cardiovascular complications. The "statin" family of cholesterol-reducing medications inhibits HMG-CoA reductase. One possible side effect of statins is decreased production of CoQ10, which may be connected to the development of myopathy and rhabdomyolysis. However, the role statins play in CoQ deficiency is controversial. Although statins reduce blood levels of CoQ, studies on the effects of muscle levels of CoQ are yet to come. CoQ supplementation also does not reduce side effects of statin medications.[26][28]

Genes involved include PDSS1, PDSS2, COQ2, and ADCK3 (COQ8, CABC1).[31]

Organisms other than humans produce the benzoquinone and isoprene structures from somewhat different source chemicals. For example, the bacteria E. coli produces the former from chorismate and the latter from a non-mevalonate source. The common yeast S. cerevisiae, however, derives the former from either chorismate or tyrosine and the latter from mevalonate. Most organisms share the common 4-hydroxybenzoate intermediate, yet again uses different steps to arrive at the "Q" structure.[32]

Uses and research[edit]

Dietary supplement[edit]

Although neither a prescription drug nor an essential nutrient, CoQ10 is commonly used as a dietary supplement with the intent to prevent or improve disease conditions, such as cardiovascular disorders.[14][15][33] CoQ10 is naturally produced by the body and plays a crucial role in cell growth and protection.[5] Despite its significant role in the body, it is not used as a drug for the treatment of any specific disease.[1][2][15]

Nevertheless, CoQ10 is widely available as an over-the-counter dietary supplement and is recommended by some healthcare professionals. Nevertheless, definitive scientific evidence supporting these claims is absent.[1][2][15] Despite the lack of FDA approval, CoQ10 continues to be used in various forms, including in some cosmetics, in spite of the lack of proven benefits.[15]

Regulation and composition[edit]

CoQ10 is not approved by the U.S. Food and Drug Administration (FDA) for the treatment of any medical condition.[34][35][36][37] However, it is sold as a dietary supplement in the name of UbiQ 300 & UbiQ 100, not subject to the same regulations as medicinal drugs, and is an ingredient in some cosmetics.[38][39] The manufacture of CoQ10 is not regulated, and different batches and brands may vary significantly:[36] a 2004 laboratory analysis by ConsumerLab.com of CoQ10 supplements on sale in the US found that some did not contain the quantity identified on the product label. Amounts ranged from "no detectable CoQ10", through 75% of stated dose, up to a 75% excess.[40][41]

Generally, CoQ10 is well tolerated. The most common side effects are gastrointestinal symptoms (nausea, vomiting, appetite suppression, and abdominal pain), rashes, and headaches.[42]

Heart disease[edit]

A 2014 Cochrane review found insufficient evidence to make a conclusion about its use for the prevention of heart disease.[43] A 2016 Cochrane review concluded that CoQ10 had no effect on blood pressure.[44] A 2021 Cochrane review found "no convincing evidence to support or refute" the use of CoQ10 for the treatment of heart failure.[45]

A 2017 meta-analysis of people with heart failure 30–100 mg/d of CoQ10 found a 31% lower mortality and increased exercise capacity, with no significant difference in the endpoints of left heart ejection fraction.[46]

In a 2023 meta-analysis of older people ubiquinone was compared with ubiquinol. The results demonstrate a beneficial cardiovascular effect of ubiquinone. This could not be confirmed for ubiquinol.[47]

Migraine headaches[edit]

The Canadian Headache Society guideline for migraine prophylaxis recommends, based on low-quality evidence, that 300 mg of CoQ10 be offered as a choice for prophylaxis.[48]

Statin myopathy[edit]

Although CoQ10 has been used to treat purported muscle-related side effects of statin medications, a 2015 meta-analysis found that CoQ10 had no effect on statin myopathy.[49] A 2018 meta-analysis concluded that there was preliminary evidence for oral CoQ10 reducing statin-associated muscle symptoms, including muscle pain, muscle weakness, muscle cramps and muscle tiredness.[29]

Cancer[edit]

As of 2014 no large clinical trials of CoQ10 in cancer treatment had been conducted.[36] The US's National Cancer Institute identified issues with the few, small studies that had been carried out, stating, "the way the studies were done and the amount of information reported made it unclear if benefits were caused by the CoQ10 or by something else".[36] The American Cancer Society concluded, "CoQ10 may reduce the effectiveness of chemo and radiation therapy, so most oncologists would recommend avoiding it during cancer treatment."[50]

Dental disease[edit]

A 1995 review study found that there is no clinical benefit to the use of CoQ10 in the treatment of periodontal disease.[51]

Pharmacology[edit]

Absorption[edit]

CoQ10 in the pure form is a crystalline powder insoluble in water. Absorption as a pharmacological substance follows the same process as that of lipids; the uptake mechanism appears to be similar to that of vitamin E, another lipid-soluble nutrient.[20] This process in the human body involves secretion into the small intestine of pancreatic enzymes and bile, which facilitates emulsification and micelle formation required for absorption of lipophilic substances.[52] Food intake (and the presence of lipids) stimulates bodily biliary excretion of bile acids and greatly enhances absorption of CoQ10. Exogenous CoQ10 is absorbed from the small intestine and is best absorbed if taken with a meal. Serum concentration of CoQ10 in fed condition is higher than in fasting conditions.[53][54]

Metabolism[edit]

Data on the metabolism of CoQ10 taken as a pharmacological substance in animals and humans are limited.[20] A study with 14C-labeled CoQ10 in rats showed most of the radioactivity in the liver two hours after oral administration when the peak plasma radioactivity was observed.[55] It appears that CoQ10 is metabolized in all tissues, while a major route for its elimination is biliary and fecal excretion; after the withdrawal of CoQ10 supplementation, the levels return to normal within a few days, irrespective of the type of formulation used.[56]

Pharmacokinetics[edit]

Some reports have been published on the pharmacokinetics of CoQ10. The plasma peak can be observed 2–6 hours after oral administration when taken as a pharmacological substance; still, this data is inconclusive, because the differences in the duration of onset of plasma peak levels depended on the design of the study. In some studies, a second plasma peak also was observed at approximately 24 hours after administration, probably due to both enterohepatic recycling and redistribution from the liver to circulation.[52] Deuterium-labeled crystalline CoQ10 was used to investigate pharmacokinetics in humans to determine an elimination half-time of 33 hours.[57]

Bioavailability[edit]

In contrast to intake of CoQ10 as a constituent of food, such as nuts or meat, from which CoQ10 is normally absorbed, there is a concern about CoQ10 bioavailability when it is taken as a dietary supplement.[58][59] Bioavailability of supplements may be reduced due to the lipophilic nature and large molecular weight of CoQ10.[58]

Reduction of particle size[edit]

Nanoparticles have been explored as a delivery system for various drugs, such as improving the oral bioavailability of drugs with poor absorption characteristics.[60] However, this has not proved successful with CoQ10, although reports have differed widely.[61][62] The use of aqueous suspension of finely powdered CoQ10 in pure water also reveals only a minor effect.[56]

Water-solubility[edit]

Facilitating drug absorption by increasing its solubility in water is a common pharmaceutical strategy and also has been shown to be successful for CoQ10. Various approaches have been developed to achieve this goal, with many of them producing significantly better results over oil-based softgel capsules in spite of the many attempts to optimize their composition.[20] Examples of such approaches are use of the aqueous dispersion of solid CoQ10 with the polymer tyloxapol,[63] formulations based on various solubilising agents, such as hydrogenated lecithin,[64] and complexation with cyclodextrins; among the latter, the complex with β-cyclodextrin has been found to have highly increased bioavailability[65][66] and also is used in pharmaceutical and food industries for CoQ10-fortification.[20]

Potential drug interactions[edit]

CoQ10 taken as a pharmacological substance has potential to inhibit the effects of theophylline as well as the anticoagulant warfarin; CoQ10 may interfere with warfarin's actions by interacting with cytochrome p450 enzymes thereby reducing the INR, a measure of blood clotting.[67] The structure of CoQ10 is similar to that of vitamin K, which competes with and counteracts warfarin's anticoagulation effects. CoQ10 is not recommended in people taking warfarin due to the increased risk of clotting.[42]

Dietary concentrations[edit]

Detailed reviews on occurrence of CoQ10 and dietary intake were published in 2010.[68] Besides the endogenous synthesis within organisms, CoQ10 also is supplied by various foods.[1] CoQ10 concentrations in various foods are:[1]

CoQ10 levels in selected foods[68]
Food CoQ10 concentration (mg/kg)
Vegetable oils soybean oil 54–280
olive oil 40–160
grapeseed oil 64–73
sunflower oil 4–15
canola oil 64–73
Beef heart 113
liver 39–50
muscle 26–40
Pork heart 12–128
liver 23–54
muscle 14–45
Chicken breast 8–17
thigh 24–25
wing 11
Fish sardine 5–64
mackerel – red flesh 43–67
mackerel – white flesh 11–16
salmon 4–8
tuna 5
Nuts peanut 27
walnut 19
sesame seed 18–23
pistachio 20
hazelnut 17
almond 5–14
Vegetables parsley 8–26
broccoli 6–9
cauliflower 2–7
spinach up to 10
Chinese cabbage 2–5
Fruit avocado 10
blackcurrant 3
grape 6–7
strawberry 1
orange 1–2
grapefruit 1
apple 1
banana 1

Vegetable oils, meat and fish are quite rich in CoQ10 levels.[1] Dairy products are much poorer sources of CoQ10 than animal tissues. Among vegetables, broccoli and cauliflower are good sources of CoQ10.[1] Most fruit and berries are poor sources of CoQ10, with the exception of avocados, which have a relatively high oil and CoQ10 content.[68]

Intake[edit]

In the developed world, the estimated daily intake of CoQ10 has been determined at 3–6 mg per day, derived primarily from meat.[68][68]

South Koreans have an estimated average daily CoQ (Q9 + Q10) intake of 11.6 mg/d, derived primarily from kimchi.[69]

Effect of heat and processing[edit]

Cooking by frying reduces CoQ10 content by 14–32%.[70]

History[edit]

In 1950, a small amount of CoQ10 was isolated from the lining of a horse's gut, a compound initially called substance SA, but later deemed to be quinone found in many animal tissues.[71] In 1957, the same compound was isolated from mitochondrial membranes of beef heart, with research showing that it transported electrons within mitochondria. It was called Q-275 as a quinone.[71][72] The Q-275/substance SA was later renamed ubiquinone as it was a ubiquitous quinone found in all animal tissues.[71] In 1958, its full chemical structure was reported.[71][73] Ubiquinone was later called either mitoquinone or coenzyme Q due to its participation to the mitochondrial electron transport chain.[71] In 1966, a study reported that reduced CoQ6 was an effective antioxidant in cells.[74]

See also[edit]

  • Idebenone – synthetic analog with reduced oxidant generating properties
  • Mitoquinone mesylate – synthetic analog with improved mitochondrial permeability

References[edit]

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External links[edit]

source: https://en.wikipedia.org/wiki/Coenzyme_Q10

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