From Wikipedia, the free encyclopedia
The
N,
N,
N-trimethylethanolammonium
cation, with an undefined counteranion, X
−
Choline is a water-soluble essential
nutrient.[1][2][3][4] It is
usually grouped within the Vitamin B complex. Choline generally refers
to the various quaternary
ammonium salts containing the
N,N,N-trimethylethanolammonium
cation.
These naturally-occuring ammonium salts are
found in the lipids that make up cell membranes and in the neurotransmitter acetylcholine.
Adequate intakes (AI) for this micronutrient of between 425 to 550
milligrams daily, for adults, have been established by the Food and
Nutrition Board of the Institute of Medicine of the National Academy
of Sciences.
History
Choline was discovered by Andreas Strecker in 1864 and chemically
synthesized in 1866. In 1998 choline was classified as an essential
nutrient by the Food and Nutrition Board of the Institute of Medicine (U.S.A.).
Chemistry
Choline is a quaternary saturated amine with the chemical formula (CH3)3N+CH2CH2OHX−, where
X− is a counterion such as chloride (see choline chloride), hydroxide or tartrate. Choline chloride, in mixture with urea is used as a solvent ( DES
) and the salicylate salt is used topically for pain
relief of aphthous
ulcers.
Physiology
Choline metabolism. (Choline is green box at left, second from the
bottom.)
Choline and its metabolites are needed for three main physiological purposes:
structural integrity and signaling roles for cell membranes,
cholinergic neurotransmission (acetylcholine synthesis), and as a major source
for methyl groups
via its metabolite, trimethylglycine (betaine) that
participates in the S-adenosylmethionine synthesis pathways.
When choline is metabolized by the body, it may form trimethylamine, a compound with a fishy
odor. Hence, when large amounts of choline are taken the person may
suffer from a fishy body
odor.
Choline and
Anxiety
Despite its importance in the central nervous system as a
precursor for acetylcholine and membrane phosphatidylcholine, the
role of choline in mental illness has been little studied. In a
large population-based study, choline concentrations were inversely
correlated with anxiety symptoms in subjects aged 46–49 and 70–74
years who had valid information on plasma choline concentrations
and symptoms of anxiety. [5]
Choline
as a supplement
It is well established that supplements of methyl group transfer
vitamins B6, B12, folic acid reduce the blood titer of homocysteine and so may prevent heart
disease.[6] Choline
is a necessary source of methyl groups for methyl group transfer.
Supplements of lecithin/choline were found to reduce heart
disease in laboratory studies. The reduction in heart disease with
lecithin supplements may however relate more to the cholesterol carrying
capacity of lecithin than to the methyl group transfer role of
choline.
Choline supplements are often taken as a form of 'smart drug' or
nootropic, due to the
role that the neurotransmitter acetylcholine plays in various cognition systems within
the brain. Choline is a chemical precursor or "building block"
needed to produce the neurotransmitter acetylcholine, and research
suggests that memory, intelligence and mood are mediated at least
in part by acetylcholine metabolism in the brain. In study on rats,
a correlation was shown between choline intake during pregnancy and
mental task performance of the offspring[7];
however, the same correlation has not been shown in humans[8].
However, this human study admits "Women in the current study
consumed their usual diets. They were not eating choline-enriched
diets and were not receiving choline supplementation. Therefore,
our results indicate that choline concentrations in a physiologic
range observed among women consuming a regular diet during
pregnancy are not related to IQ in their offspring. We cannot rule
out the possibility that choline supplementation could have an IQ
effect."
The compound's quaternary amine
renders it lipid insoluble which might suggest it would be unable
to cross the blood-brain barrier. However,
despite choline's lipid insolubility, a choline transporter exists
that allows transport across the blood-brain barrier. The efficacy
of these supplements in enhancing cognitive abilities is a topic of
continuing debate.
The Food and
Drug Administration (FDA) requires that infant formula
not made from cow's milk be
supplemented with choline.[9]
Due to its role in lipid metabolism, choline has also
found its way into nutritional supplements which claim to reduce body fat; but
there is little or no evidence to prove that it has any
effect on reducing excess body fat or that taking high amounts of
choline will increase the rate at which fat is metabolised.
Pharmaceutical Uses
In addition to its role as a nutritional supplement, Choline is
also used in the treatment of liver disorders,
[10] [11] Alzheimer's disease, [12]and bipolar depression. [13]
Some studies show that as a supplement, choline is also used in
treating hepatitis, glaucoma, [14], atherosclerosis, and, possible,
neurological disorders. [15].
Choline has also been proved to have a positive effect on those
suffering from alcoholism. [16] [17]
Fish odor
syndrome
Choline is a precursor to trimethylamine, which some persons are
not able to break down due to a genetic disorder. Persons suffering
from this disorder, called trimethylaminuria, may suffer from a
strong fishy or otherwise unpleasant body odor due to the body's
release of odorous trimethylamine. A body odor will occur even on a
normal diet - i.e., one that is not particularly high in
choline. Persons with trimethylaminuria are advised to restrict the
intake of foods high in choline; this may help to reduce the
sufferer's body odor.
Choline
hydroxide
Choline hydroxide is one of the class of phase transfer catalysts which are used to
carry the hydroxide ion
into organic systems, and because of this it is considered a strong
base. It is the least costly phase transfer catalyst, and is used
as a cheap method of stripping photoresists in circuit boards.
Choline hydroxide is not completely stable and it slowly breaks
down into trimethylamine.
Sources
The foods richest in phosphatidylcholine — the major
delivery form of choline — are egg yolks, soy, wheat germ and cooked beef, chicken, veal
and turkey livers. In 2004,
the USDA released
its first database of the choline content in common foods.[18]
The most often available choline dietary supplement is lecithin, derived from soy or
egg yolks, often used as a food additive. Phosphatidylcholine is
also available as a supplement, in pill or powder form.
Supplementary choline is also available as choline chloride, which
comes as a liquid due to its hydrophilic properties. Choline
chloride is sometimes preferred as a supplement because
phosphatidylcholine can have gastrointestinal side effects.
The human body can make some choline, but it is generally
recognized that it is important to get dietary choline as well.
Although most foods have at least a little choline, some people may
have to pay close attention to get enough in their diets,
particularly if they do not eat many whole eggs.[19]
Additional
images
See also
References
- ^
Jane Higdon, "Choline", Micronutrient
Information Center, Linus Pauling
Institute
- ^
"Choline,
PDRHealth
- ^
"Choline" (An interview
with Steven Zeisel, Editor-in-Chief of the Journal of Nutritional
Biochemistry), Radio National Health Report with Norman
Swan, Monday 17 April 2000
- ^
"[1]" Dietary
Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6,
Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline (1998),
Institute of Medicine.
- ^
Bjelland I, Tell GS, Vollset SE, Konstantinova S, Ueland PM, "Choline in anxiety and
depression: the Hordaland Health Study.", The American
Journal of Clinical Nutrition.
- ^
Verhoef, Petra; Stampfer, Meir J;
Buring, Julie F; Gaziano, J. Michael; Allen, Robert H; Stabler,
Sally P; Reynolds, Robert D; Kok, Frans J; Hennekens, Charles H;
Willett, Walter C (1996). "Homocysteine Metabolism and Risk of
Myocardial Infarction: Relation with Vitamins B6, B12, and Folate".
American Journal of Epidemiology 143 (9):
845–859.
- ^
Robert J. Sternberg, "Handbook of intelligence", Cambridge
University Press, 2000, ISBN 0521596483, 9780521596480, page
77.
- ^
Caroline Signore, Per Magne Ueland, James Troendle and James L
Mills, "Choline concentrations in human maternal and cord blood and
intelligence at 5 y of age", American Journal of Clinical
Nutrition, Vol. 87, No. 4, 896-902, April 2008 (abstract).
- ^
Isadora B. Stehlin, Infant Formula: Second Best
but Good Enough, U.S. Food and Drug Administration.
- ^
Tolvanen T, Yli-Kerttula T, Ujula T,
Autio A, Lehikoinen P, Minn H, Roivainen A. (January 2010).
"Biodistribution and radiation dosimetry of [(11)C]choline: a
comparison between rat and human data.". Eur J Nucl Med Mol
Imaging. PMID 20069295.
- ^
Behari J, Yeh TH, Krauland L, Otruba
W, Cieply B, Hauth B, Apte U, Wu T, Evans R, Monga SP. (December
2009). "Liver-Specific {beta}-Catenin Knockout Mice Exhibit
Defective Bile Acid and Cholesterol Homeostasis and Increased
Susceptibility to Diet-Induced Steatohepatitis.". Am J
Pathol.. PMID 20019186.
- ^
Schroeder MA, Atherton HJ, Ball DR,
Cole MA, Heather LC, Griffin JL, Clarke K, Radda GK, Tyler DJ.
(Janurary 2010). "The cerebrovascular role of the cholinergic
neural system in Alzheimer's disease.". Van Beek AH, Claassen
JA.. PMID 20060023.
- ^
Ongür D, Prescot AP, Jensen JE,
Rouse ED, Cohen BM, Renshaw PF, Olson DP. (January 2010). "T2
relaxation time abnormalities in bipolar disorder and
schizophrenia.". Magn Reson Med. 63 (1):
1-8. PMID 19918902.
- ^
Chan KC, So KF, Wu EX. (January
2009). "Proton magnetic resonance spectroscopy revealed choline
reduction in the visual cortex in an experimental model of chronic
glaucoma.". Exp Eye Res. 88 (1): 65-70.
PMID 18992243.
- ^
Zeisel SH, da Costa KA. (November
2009). "Choline: an essential nutrient for public health.".
Nutr Rev. 67 (11): 615-623. PMID 19906248.
- ^
Gerald Klatskin M.D. and Willard A.
Krehl Ph.D. (1954). "THE EFFECT OF ALCOHOL ON THE
CHOLINE REQUIREMENT : II. INCIDENCE OF RENALNECROSIS iN
WEANLING RATS FOLLOWING SHORT TERM INGESTION OF ALCOHOL".
The Journal of Experimental Medicine 100:
615-627. http://jem.rupress.org/cgi/content/abstract/100/6/615.
- ^
Nery FG, Stanley JA, Chen HH, Hatch
JP, Nicoletti MA, Serap Monkul E, Lafer B, Soares JC. (October
2009). "Bipolar disorder comorbid with alcoholism: A (1)H magnetic
resonance spectroscopy study.". J Psychiatr Res.. PMID 19818454.
- ^
"USDA Database for the Choline
Content of Common Foods - 2004", USDA Nutrient Data
Laboratory
- ^
Hasler C.M. The Changing Face of Functional Foods. J. Am. Coll.
Nutr. 19, 2000; 499S-506
| Vitamins (A11) |
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| Fat soluble |
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D2 (Ergosterol, Ergocalciferol) ·
D3 (7-Dehydrocholesterol, Previtamin D3, Cholecalciferol, 25-hydroxycholecalciferol, Calcitriol (1,25-dihydroxycholecalciferol),
Calcitroic
acid)
D4 ( Dihydroergocalciferol) · D5 · D
analogues ( Dihydrotachysterol, Calcipotriol, Tacalcitol, Paricalcitol)
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| Water soluble |
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B1 (Thiamine) ·
B2 (Riboflavin) ·
B3 (Niacin, Nicotinamide) ·
B5 (Pantothenic acid, Dexpanthenol, Pantethine) · B6
(Pyridoxine, Pyridoxal
phosphate, Pyridoxamine)
B7 ( Biotin) ·
B9 ( Folic acid, Dihydrofolic acid, Folinic acid) · B12
( Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide) · Choline
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| Cholinergics |
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Receptor
Ligands |
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Agonists:
77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30 • AF150(S) • AF267B
• AFDX-384 • Alvameline • AQRA-741 • Arecoline • Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097 •
CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane •
Ethoxysebacylcholine • LY-593,039 • L-689,660 • LY-2,033,298 •
McNA343 • Methacholine • Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine •
PD-151,832 • Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine
• Suberylcholine • Talsaclidine • Thiopilocarpine • Vedaclidine •
VU-0029767 • VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 •
WAY-132,983 • Xanomeline • YM-796
Antagonists: 3-Quinuclidinyl Benzilate •
4-DAMP • Atropine •
Atropine Methonitrate • Benactyzine • Benzatropine (Benztropine) • Benzydamine • BIBN 99 •
Biperiden • Bornaprine • CAR-226,086 • CAR-301,060 • CAR-302,196 •
CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 •
Cyclobenzaprine • Cyclopentolate •
Darifenacin •
DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine
(Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin • Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-031,120 • Ipratropium • J-104,129
• Hyoscyamine • Mamba Toxin 3 • Mamba Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-Ethyl-3-Piperidyl
Benzilate • N-Methyl-3-Piperidyl
Benzilate • Orphenadrine • Otenzepad • Oxybutynin • PBID •
PD-102,807 • Phenglutarimide • Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-47,213
• SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) • Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl
• Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Zamifenacin;
Others: 1st
Generation Antihistamines ( Brompheniramine • Chlorpheniramine, Cyclizine, Cyproheptadine, Dimenhydrinate,
Diphenhydramine, Doxylamine, Hydroxyzine, Meclizine, Mepyramine/ Pyrilamine, Phenindamine, Pheniramine, Tripelennamine,
Triprolidine, etc)
• Tricyclic Antidepressants ( Amitriptyline, Doxepin, Trimipramine, etc) •
Tetracyclic Antidepressants
( Amoxapine, Maprotiline, etc) • Typical
Antipsychotics ( Chlorpromazine, Thioridazine, etc) • Atypical Antipsychotics ( Clozapine, Olanzapine, Quetiapine, etc)
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Agonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 • ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • AR-R17779 • Butyrylcholine •
Carbachol • Cotinine • Cytisine • Decamethonium • Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium •
Epibatidine • Epiboxidine •
Ethoxysebacylcholine • EVP-4473 • EVP-6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487) • Nicotine • NS-1738 • PHA-543,613 •
PHA-709,829 • PNU-120,596 • PNU-282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y
• SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 •
TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 • Varenicline • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin • Alcuronium • Anatruxonium • Atracurium • Bupropion (Amfebutamone) •
Chandonium • Chlorisondamine • Cisatracurium •
Coclaurine • Coronaridine • Dacuronium • Decamethonium • Dextromethorphan • Dextropropoxyphene • Dextrorphan • Diadonium
• DHβE • Dimethyltubocurarine (Metocurine) •
Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador • Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium (Benzohexonium) • Ibogaine • Ketamine • Kynurenic Acid •
Levacetylmethadol • Malouetine • Mecamylamine • Memantine • Methadone • Methorphan
(Racemethorphan) • Methyllycaconitine • Metocurine • Mivacurium • Morphanol (Racemorphanol) •
Neramexane • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine • Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin • Suxamethonium
(Succinylcholine) • Toxiferine • Trimethaphan •
Tropeinium • Tubocurarine • Vecuronium
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Reuptake
Inhibitors |
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Enzyme
Inhibitors |
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1-(-Benzoylethyl)pyridinium •
2-(α-Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole •
4-(1-Naphthylvinyl)pyridine • Acetylseco Hemicholinium-3 •
Acryloylcholine • AF64A • B115 • BETA • CM-54,903 •
N,N-Dimethylaminoethylacrylate •
N,N-Dimethylaminoethylchloroacetate
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Many of the
acetylcholinesterase inhibitors listed above act as
butyrylcholinesterase inhibitors.
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Others |
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External
Links