Anserine: Difference between revisions

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{{about||the subfamily of waterfowl|Anserinae|pes anserine bursitis|Bursitis}}

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| ImageFile = Anserine.svg

| ImageSize = 220px

| SystematicName = (''Z'')-''N''-(3-Amino-1-hydroxypropylidene)-3-methyl-<small>L</small>-histidine

| OtherNames = ''beta''-Alanyl-3-methyl-<small>L</small>-histidine

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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

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| UNII = HDQ4N37UGV

| PubChem=112072

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| ChEBI = 18323

| Section2 = {{Chembox Properties

| Formula = C₁₀H₁₆N₄O₃

| MolarMass = 240.25904 g/mol

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'''Anserine''' (β-alanyl-''3''-methylhistidine) is a [[dipeptide]] containing [[Beta-Alanine|β-alanine]] and [[3-methylhistidine]].<ref name="Garrett_2012">{{cite book |title=Biochemistry |vauthors=Garrett CM, Grisham RH |date=2012 |publisher=Cengage Learning |isbn=978-1-133-10629-6 |edition=5th |page=46}}</ref> Anserine is a derivative of [[carnosine]], which has been methylated.<ref name="Blancquaert 4849–4863">{{cite journal |last1=Blancquaert |first1=Laura |last2=Baba |first2=Shahid P. |last3=Kwiatkowski |first3=Sebastian |last4=Stautemas |first4=Jan |last5=Stegen |first5=Sanne |last6=Barbaresi |first6=Silvia |last7=Chung |first7=Weiliang |last8=Boakye |first8=Adjoa A. |last9=Hoetker |first9=J. David |last10=Bhatnagar |first10=Aruni |last11=Delanghe |first11=Joris |date=2016-09-01 |title=Carnosine and anserine homeostasis in skeletal muscle and heart is controlled by β-alanine transamination |journal=The Journal of Physiology |volume=594 |issue=17 |pages=4849–4863 |doi=10.1113/JP272050 |issn=1469-7793 |pmc=5009790 |pmid=27062388}}</ref>

Both anserine and carnosine chelate copper.<ref name=":3" /> Due to its [[methylation]], anserine is more stable in serum and resistant to degradation than carnosine.<ref>{{cite journal |last1=Everaert |first1=Inge |last2=Baron |first2=Giovanna |last3=Barbaresi |first3=Silvia |last4=Gilardoni |first4=Ettore |last5=Coppa |first5=Crescenzo |last6=Carini |first6=Marina |last7=Vistoli |first7=Giulio |last8=Bex |first8=Tine |last9=Stautemas |first9=Jan |last10=Blancquaert |first10=Laura |last11=Derave |first11=Wim |date=January 2019 |title=Development and validation of a sensitive LC-MS/MS assay for the quantification of anserine in human plasma and urine and its application to pharmacokinetic study |url=https://pubmed.ncbi.nlm.nih.gov/30302566/ |journal=Amino Acids |volume=51 |issue=1 |pages=103–114 |doi=10.1007/s00726-018-2663-y |issn=1438-2199 |pmid=30302566|hdl=2434/599742 |s2cid=52945820 |hdl-access=free }}</ref> Anserine can be found in the [[skeletal muscle]] and [[brain]] of [[mammal]]s and birds.<ref name="Blancquaert 4849–4863"/>

The [[Acid dissociation constant|pKa]] of the [[imidazole]] ring of [[histidine]], when contained in anserine, is 7.04.<ref>{{cite journal |last=Wu |first=Guoyao |date=March 2020 |title=Important roles of dietary taurine, creatine, carnosine, anserine and 4-hydroxyproline in human nutrition and health |journal=Amino Acids |volume=52 |issue=3 |pages=329–360 |doi=10.1007/s00726-020-02823-6 |issn=1438-2199 |pmc=7088015 |pmid=32072297}}</ref><ref name=":0" />

== Neuroprotective effects ==

An animal model study of Alzheimer's disease using mice found that treatment with anserine reduced memory loss.<ref name=":12" /> Anserine reduced glial inflammatory activity (particularly of [[astrocyte]]).<ref name=":0" /> The study also found that anserine-treated mice had greater [[pericyte]] surface area.<ref name=":0" /> The greater area of pericytes was commensurate with improved memory (pericytes wrap around brain capillary to control blood flow and gate cells from neurotoxin, blocking inflammation).<ref name=":0" /> The anserine-treated mice overall performed better on a spatial memory test ([[Morris water navigation task|Morris Water Maze]]).<ref name=":0">{{cite journal | vauthors = Kaneko J, Enya A, Enomoto K, Ding Q, Hisatsune T | title = Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AβPPswe/PSEN1dE9 Alzheimer's-model mice | journal = Scientific Reports | volume = 7 | issue = 1 | pages = 12571 | date = October 2017 | pmid = 28974740 | doi = 10.1038/s41598-017-12785-7 | doi-access = free | pmc = 5626714 | bibcode = 2017NatSR...712571K }}</ref>

A human study on 84 elderly subjects showed that subjects who took anserine and carnosine supplements for one year showed increased blood flow in the prefrontal cortex on MRI.<ref name=":12">{{cite journal | vauthors = Ding Q, Tanigawa K, Kaneko J, Totsuka M, Katakura Y, Imabayashi E, Matsuda H, Hisatsune T | display-authors = 6 | title = Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4 | journal = Aging and Disease | volume = 9 | issue = 3 | pages = 334–345 | date = June 2018 | pmid = 29896423 | doi = 10.14336/ad.2017.0809 | doi-access = free | pmc = 5988590 }}</ref>

A study demonstrated that the free N-terminal of histidine on anserine and carnosine protect against zinc-caused neurotoxicity and regulate the Arc pathway in which [[Activity-regulated cytoskeleton-associated protein|Arc protein]] is used to produce dendrite protein for connecting nerve cells.<ref name=":1">{{cite journal |display-authors=6 |vauthors=Ding Q, Tanigawa K, Kaneko J, Totsuka M, Katakura Y, Imabayashi E, Matsuda H, Hisatsune T |date=June 2018 |title=Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4 |journal=Aging and Disease |volume=9 |issue=3 |pages=334–345 |doi=10.14336/ad.2017.0809 |pmid=29896423 |doi-access=free|pmc=5988590 }}</ref>

Both Anserine and Carnosine are chelating agents for copper and other transition metals.<ref>{{cite journal |last1=Kohen |first1=R. |last2=Misgav |first2=R. |last3=Ginsburg |first3=I. |date=1991 |title=The SOD like activity of copper:carnosine, copper:anserine and copper:homocarnosine complexes |url=https://pubmed.ncbi.nlm.nih.gov/1649087/ |journal=Free Radical Research Communications |volume=12-13 Pt 1 |pages=179–185 |doi=10.3109/10715769109145784 |issn=8755-0199 |pmid=1649087}}</ref> Chelation of transition metals is one method used by antioxidants to protect their targets from oxidative stress as it prevents them from undergoing Fenton reactions with peroxides. In the olfactory bulbs, the concentration of both of these molecules was found to be in the millimolar range, whereas the concentration of copper was approximately 50μM. these found concentrations indicate the chelation of copper by Anserine and Carnosine.<ref name=":3">{{cite journal |last1=Kohen |first1=Ron |last2=Yamamoto |first2=Yorihiro |last3=Cundy |first3=Kenneth C. |last4=Ames |first4=Bruce N. |date=1988 |title=Antioxidant Activity of Carnosine, Homocarnosine, and Anserine Present in Muscle and Brain |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=85 |issue=9 |pages=3175–3179 |doi=10.1073/pnas.85.9.3175 |doi-access=free |jstor=31967 |pmid=3362866 |pmc=280166 |bibcode=1988PNAS...85.3175K |issn=0027-8424}}</ref>

== See also ==

{{Wiktionary|anserine}}

* [[Carnosine]]

== References ==

{{reflist}}

[[Category:Dipeptides]]