United States Pharmacopeia (USP) Reference Standard
Synonym: 1-β-D-Ribofuranosyluracil,
Uracil-1-β-D-ribofuranoside
·
Empirical Formula (Hill Notation) C9H12N2O6
·
Molecular Weight 244.20
·
Beilstein Registry Number 754902
Properties
Related Categories
|
|
InChI Key
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DRTQHJPVMGBUCF-XVFCMESISA-N
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mp
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163-167 °C(lit.)
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solubility
|
H2O:
soluble
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Uridine is a
glycosylated pyrimidine-analog
containing uracil attached to a ribose ring (or more specifically, a ribofuranose) via a β-N1-glycosidic bond.
Detailed description
It is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter
codes U, A, T, C and G respectively. However, thymidine is more commonly
written as 'dT' ('d' represents 'deoxy') as it contains a 2'-deoxyribofuranose
moiety rather than the ribofuranose ring found in uridine. This is because
thymidine is found in deoxyribonucleic acid (DNA) and not ribonucleic acid (RNA). Conversely, uridine is found in RNA and
not DNA. The remaining three nucleosides may be found in both RNA and DNA. In
RNA, they would be represented as A, C and G whereas in DNA they would be represented
as dA, dC and dG.
Dietary sources of uridine
Some foods that contain uridine in the form of RNA
are listed below. Although claimed that virtually none of the uridine in this
form is bioavailable "since - as shown by Handschumacher's Laboratory at Yale School of Medicine in 1981[1] - it is destroyed in
the liver and gastrointestinal tract, and no food, when consumed, has ever been
reliably shown to elevate blood uridine levels', this is contradicted by
Yamamoto et al.,[2] plasma uridine
levels rose 1.8 fold 30 minutes after beer ingestion, suggesting, at the very
least, conflicting data. On the other hand, ethanol on its own (which is
present in beer) increases uridine levels, which may explain the raise of uridine
levels in the study by Yamamoto et al.[3] In infants consuming
mother's milk or commercial infant formulas, uridine is present as its
monophosphate, UMP,[4] and this source of
uridine is indeed bioavailable[5] and enters the
blood.
·
Tomatoes (0.5 to 1.0 g
uridine per kilogram dry weight
Consumption of RNA-rich foods may lead to high
levels of purines (adenine and
guanosine) in blood. High levels of purines are known to increase uric acid production and may
aggravate or lead to conditions such as gout. Moderate consumption of yeast, about 5 grams per day,
should provide adequate uridine for improved health with minimal side effects.
Note: It has been suggested that the RNA content of
yeast products should be chemically reduced if these products are to be
consumed in high amounts (50 grams or more per day) as a source of
protein. However, such processing is expensive and, as of 2008, commonly
available brewer's yeast products were not RNA-reduced.
Harvard researchers report that omega-3 fatty acids
and uridine, two substances in foods such as fish, walnuts, molasses, and sugar
beets, prevented depression in rats as effectively as antidepressant drugs.
“Giving rats a combination of uridine and omega-3 fatty acids produced
immediate effects that were indistinguishable from those caused by giving the
rats standard antidepressant medications,” said lead author of the study
William Carlezon, director of McLean’s Behavioral Genetics Laboratory.
In the glycolysis pathway
Uridine plays a role in the glycolysis pathway of galactose.[13] There is no catabolic process to
metabolize galactose. Therefore, galactose is converted to glucose and metabolized in
the common glucose pathway. Once the incoming galactose has been converted into galactose 1-phosphate (Gal-1-P), it is
involved in a reaction with UDP-glucose, a glucose molecule
bonded to uridine diphosphate (UDP). This process
is catalyzed by the enzyme galactose-1-phosphate
uridyl transferase and transfers the
UDP to the galactose molecule. The end result is UDP-galactose and
glucose-1-phosphate. This process is continued to allow the proper glycolysis
of galactose.
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