Coenzyme Q10 moz-extension://deb01117-3b11-48dc-a28c-5112b38ae4f4/re...

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Coenzyme Q10
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Coenzyme Q10 (CoQ10 ) also known as ubiquinone, is a naturally

occurring biochemical cofactor (coenzyme) and an antioxidant produced
by the human body.[1][2][3] It can also be obtained from dietary sources,
such as meat, fish, seed oils, vegetables, and dietary supplements.[1][2]
CoQ10 is found in many organisms, including animals and bacteria.

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

Identifiers
CAS Number • 303-98-0

3D model (JSmol) • Interactive image

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ChEBI • CHEBI:46245

ChEMBL • ChEMBL454801

ChemSpider • 4445197

ECHA InfoCard 100.005.590

• C11378
KEGG

PubChem CID • 5281915

UNII • EJ27X76M46

CompTox Dashboard (EPA) • DTXSID6046054

InChI

SMILES

Properties
Chemical formula
C59H90O4

Molar mass 863.365 g·mol−1

Appearance yellow or orange solid
Melting point 48–52 °C (118–126 °F; 321–325 K)
Solubility in water
insoluble

Pharmacology
ATC code
C01EB09 (WHO)

Related compounds
1,4-Benzoquinone
Related quinones
Plastoquinone
Ubiquinol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).

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Infobox references

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.[4][5][6]

Although a ubiquitous molecule in human tissues, CoQ10 is not a dietary

nutrient and does not have a recommended intake level, and its use as a
supplement is not associated with or approved for any health or anti-
disease effect.[1][2]

Biological functions

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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]

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][5] 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.[1] 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][7]

• 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

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branched-chain amino acids oxidation (through flavin-linked

dehydrogenases) to ubiquinol–cytochrome-c reductase (complex III)
of the ETC:[1][7] 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,[1][6] inhibiting the oxidation of proteins,
DNA, and use of vitamin E.[1][9]

CoQ10 also may influence immune response by modulating the

expression of genes involved in inflammation.[10][11][12]

This article needs attention from an expert in biochemistry. See the

talk page for details. WikiProject Biochemistry may be able to help
recruit an expert. (April 2024)

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.[1][2][14] In humans, the most common form of coenzymes Q
is coenzyme Q10, also called CoQ10 () 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.[1] Ninety-five percent of the human
body's energy is generated this way.[15] Organs with the highest energy
requirements—such as the heart, liver, and kidney—have the highest
CoQ10 concentrations.[16][17][18][19]

There are three redox states of CoQ: fully oxidized (ubiquinone),

semiquinone (ubisemiquinone), and fully reduced (ubiquinol).[1] The
capacity of this molecule to act as a two-electron carrier (moving

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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.[1][14]

There are two major pathways of deficiency of CoQ10 in humans:

reduced biosynthesis, and increased use by the body.[10][20] Biosynthesis
is the major source of CoQ10. Biosynthesis requires at least 15 genes, and
mutations in any of them can cause CoQ deficiency.[20] 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).[20] Some of these,
such as mutations in COQ6, can lead to serious diseases such as steroid-
resistant nephrotic syndrome with sensorineural deafness.[21][22][23]

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.[24] Culture fibroblasts can be used
also to evaluate the rate of endogenous CoQ10 biosynthesis, by measuring
the uptake of 14C-labeled p-hydroxybenzoate.[25]

While statins may reduce CoQ10 in the blood it is unclear if they reduce
CoQ10 in muscle.[26] Evidence does not support that supplementation
improves side effects from statins.[26][27]

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.

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In its pure state, it is an orange-colored lipophile powder, and has no

taste nor odor.[14]

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.[28]

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.[24][26]

Genes involved include PDSS1, PDSS2, COQ2, and ADCK3 (COQ8, CABC1).
[29]

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.
[30]

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.[2][31]
CoQ10 is naturally produced by the body and plays a crucial role in cell
growth and protection.[6] Despite its significant role in the body, it is not

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used as a drug for the treatment of any specific disease.[1][2][3]

Nevertheless, CoQ10 is widely available as an over-the-counter dietary

supplement and is recommended by some healthcare professionals,
despite a lack of definitive scientific evidence supporting these
recommendations.[1][3]

Regulation and composition

edit

CoQ10 is not approved by the U.S. Food and Drug Administration (FDA)
for the treatment of any medical condition.[32][33][34][35] However, it is
sold as a dietary supplement not subject to the same regulations as
medicinal drugs, and is an ingredient in some cosmetics.[36] The
manufacture of CoQ10 is not regulated, and different batches and brands
may vary significantly.[34]

A 2014 Cochrane review found insufficient evidence to make a

conclusion about its use for the prevention of heart disease.[37] A 2016
Cochrane review concluded that CoQ10 had no effect on blood pressure.
[38] A 2021 Cochrane review found "no convincing evidence to support or
refute" the use of CoQ10 for the treatment of heart failure.[39]

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.[40] A
2021 meta-analysis found that coenzyme Q10 was associated with a 31%
lower all-cause mortality in HF patients.[41] In a 2023 meta-analysis of
older people, ubiquinone had evidence of a cardiovascular effect, but
ubiquinol did not.[42]

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.[43] 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.[44]

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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.[19] 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.[45] 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.[46][47]

CoQ10 is metabolized in all tissues, with the metabolites being

phosphorylated in cells.[2] CoQ10 is reduced to ubiquinol during or after
absorption in the small intestine.[2] It is absorbed by chylomicrons, and
redistributed in the blood within lipoproteins.[2] Its elimination occurs
via biliary and fecal excretion.[2]

Some reports have been published on the pharmacokinetics of CoQ10.

The plasma peak can be observed 6–8 hours after oral administration
when taken as a pharmacological substance.[2] 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.[45]

Deuterium-labeled crystalline CoQ10 was used to investigate

pharmacokinetics in humans to determine an elimination half-time of 33
hours.[48]

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.[49][50]
Bioavailability of CoQ10 supplements may be reduced due to the
lipophilic nature of its molecule and large molecular weight.[49]

Reduction of particle size

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Nanoparticles have been explored as a delivery system for various drugs,

such as improving the oral bioavailability of drugs with poor absorption
characteristics.[51] However, this has not proved successful with CoQ10,
although reports have differed widely.[52][53] The use of aqueous
suspension of finely powdered CoQ10 in pure water also reveals only a
minor effect.[54]

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.[19] Examples of such approaches are use of the aqueous
dispersion of solid CoQ10 with the polymer tyloxapol,[55] formulations
based on various solubilising agents, such as hydrogenated lecithin,[56]
and complexation with cyclodextrins; among the latter, the complex with
β-cyclodextrin has been found to have highly increased
bioavailability[57][58] and also is used in pharmaceutical and food
industries for CoQ10-fortification.[19]

Adverse effects and precautions

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Generally, oral CoQ10 supplementation is well tolerated.[1] The most

common side effects are gastrointestinal symptoms (nausea, vomiting,
appetite suppression, and abdominal pain), rashes, and headaches.[59]
Some adverse effects, largely gastrointestinal, are reported with intakes.
[2] Doses of 100–300 mg per day may induce insomnia or elevate liver
enzymes.[2] The observed safe level risk assessment method indicated
that the evidence of safety is acceptable at intakes up to 1200 mg per day.
[60]

Use of CoQ10 supplementation is not recommended in people with liver

or kidney disease, during pregnancy or breastfeeding, or in the elderly.[2]

Potential drug interactions

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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.[61] 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.[59]

Dietary concentrations

edit

Detailed reviews on occurrence of CoQ10 and dietary intake were

published in 2010.[62] 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[62]

Food CoQ10 concentration (mg/kg)
soybean oil 54–280
olive oil 40–160
Vegetable oils grapeseed oil 64–73
sunflower oil 4–15
canola oil 64–73
heart 113
Beef liver 39–50
muscle 26–40
heart 12–128
Pork liver 23–54
muscle 14–45
breast 8–17
Chicken thigh 24–25
wing 11
sardine 5–64
Fish mackerel – red flesh 43–67
mackerel – white flesh 11–16

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salmon 4–8
tuna 5
peanut 27
walnut 19
sesame seed 18–23
Nuts
pistachio 20
hazelnut 17
almond 5–14
parsley 8–26
broccoli 6–9
Vegetables cauliflower 2–7
spinach up to 10
Chinese cabbage 2–5
avocado 10
blackcurrant 3
grape 6–7
strawberry 1
Fruit
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.[62]

In the developed world, the estimated daily intake of CoQ10 has been
determined at 3–6 mg per day, derived primarily from meat.[62]

South Koreans have an estimated average daily CoQ (Q9 + Q10) intake of
11.6 mg/d, derived primarily from kimchi.[63]

Effect of heat and processing

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Cooking by frying reduces CoQ10 content by 14–32%.[64]

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.[65] 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.[65][66] The Q-275/substance SA was later renamed
ubiquinone as it was a ubiquitous quinone found in all animal tissues.[65]
In 1958, its full chemical structure was reported.[65][67] Ubiquinone was
later called either mitoquinone or coenzyme Q due to its participation to
the mitochondrial electron transport chain.[65] In 1966, a study reported
that reduced CoQ6 was an effective antioxidant in cells.[68]

• Idebenone – synthetic analog with reduced oxidant generating

properties
• Mitoquinone mesylate – synthetic analog with improved
mitochondrial permeability

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