Anserine: Difference between revisions
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'''Anserine''' (β-alanyl-''N''-methylhistidine) is a [[dipeptide]] containing [[beta-Alanine|β-alanine]] and [[1-methylhistidine]],<ref name = "Garrett_2012">{{cite book | first1 = Reginald H. | last1 = Garrett | first2 = Charles M. | last2 = Grisham | title = Biochemistry | edition = 5th | date = 2012 | publisher = Cengage Learning | isbn = 978-1-133-10629-6 | page = 46 }}</ref> and is a derivative of [[carnosine]], which had been methylated.<ref name=":1">{{Cite journal|last=Ding|first=Qiong|last2=Tanigawa|first2=Kitora|last3=Kaneko|first3=Jun|last4=Totsuka|first4=Mamoru|last5=Katakura|first5=Yoshinori|last6=Imabayashi|first6=Etsuko|last7=Matsuda|first7=Hiroshi|last8=Hisatsune|first8=Tatsuhiro|date=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|doi=10.14336/ad.2017.0809|issn=2152-5250|doi-access=free}}</ref> Anserine can be found in the [[skeletal muscle]] and [[brain]] of [[mammal]]s<ref>{{cite journal | vauthors = Zapp Jr JA | title = Quantitative studies of carnosine and anserine in mammalian muscle. II. The distribution of carnosine and anserine in various muscles of different species. | journal = J. Biol. Chem. | date = 1938 | volume = 126 | pages = 19–27 | url = http://www.jbc.org/cgi/reprint/126/1/19 }}</ref> and birds. |
'''Anserine''' (β-alanyl-''N''-methylhistidine) is a [[dipeptide]] containing [[beta-Alanine|β-alanine]] and [[1-methylhistidine]],<ref name = "Garrett_2012">{{cite book | first1 = Reginald H. | last1 = Garrett | first2 = Charles M. | last2 = Grisham | title = Biochemistry | edition = 5th | date = 2012 | publisher = Cengage Learning | isbn = 978-1-133-10629-6 | page = 46 }}</ref> and is a derivative of [[carnosine]], which had been methylated.<ref name=":1">{{Cite journal|last=Ding|first=Qiong|last2=Tanigawa|first2=Kitora|last3=Kaneko|first3=Jun|last4=Totsuka|first4=Mamoru|last5=Katakura|first5=Yoshinori|last6=Imabayashi|first6=Etsuko|last7=Matsuda|first7=Hiroshi|last8=Hisatsune|first8=Tatsuhiro|date=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|doi=10.14336/ad.2017.0809|issn=2152-5250|doi-access=free}}</ref> Anserine can be found in the [[skeletal muscle]] and [[brain]] of [[mammal]]s<ref>{{cite journal | vauthors = Zapp Jr JA | title = Quantitative studies of carnosine and anserine in mammalian muscle. II. The distribution of carnosine and anserine in various muscles of different species. | journal = J. Biol. Chem. | date = 1938 | volume = 126 | pages = 19–27 | url = http://www.jbc.org/cgi/reprint/126/1/19 }}</ref> and birds. |
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| ⚫ | Due to its presence in lean muscles, like fish and poultry, there have been |
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== Research == |
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In addition, anserine can also be beneficial for patients with [[Alzheimer's disease]]. In a recent study including an Alzheimer's model mice, the use of anserine reduced the inflammation of [[Astrocyte|astrocytes]], showing that treatment with anserine can reduce memory loss.<ref name=":2">{{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 | pmc = 5626714 | doi = 10.1038/s41598-017-12785-7 | bibcode = 2017NatSR...712571K }}</ref> Similarly, to arrive at this conclusion, scientists stained [[Pericyte|pericytes]] from mice and found that anserine treated mice had greater surface area of cells than those that were not treated with anserine. The greater area of pericyte is commensurate with improved memory because pericyte warp around brain capillary to control blood flow and gate cells from neurotoxin, blocking inflammation.<ref name=":0">{{Cite journal|last=Kaneko|first=Jun|last2=Enya|first2=Akiko|last3=Enomoto|first3=Kota|last4=Ding|first4=Qiong|last5=Hisatsune|first5=Tatsuhiro|date=2017-10-03|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|doi=10.1038/s41598-017-12785-7|issn=2045-2322|doi-access=free}}</ref> Furthermore, scientists performed [[Morris water navigation task|Morris Water Maze]] tests on mice and found that anserine treated mice had overall better spatial memory. <ref name=":0" /> |
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=== Absorption and clearance of dietary anserine === |
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| ⚫ | Due to its presence in lean muscles, like fish and poultry, there have been studies showing that inclusion of anserine in the diet may be beneficial for blood clearance and food absorption. These results were based on [[Histidine|L-histidine]] concentrations at different time intervals. A study observing the effect of anserine diet on blood clearance and food absorption concluded that the data showed an ephemeral anserine level peak in blood after consumption of anserine, followed by a prolonged, high level of methylhistidine. This indicates rapid absorption and clearing of anserine because anserine is catabolized into methylhistidine and alanine by a circulating enzyme. {{clarify|date=February 2021 |reason= Convoluted, needs to be re-written in clear language.|text= A succeeding experiment was performed to test the difference between the first group of people consuming extracted anserine and the latter consuming natural anserine as found in food. In these two groups, while the concentrations of L-histidine-related compound varied depending on the amount of anserine consumed, the absorption level patterns in blood were congruous, proving that anserine taken in food equally helps rapid absorption of food compared to when extracted anserine is taken alone.}}<ref>{{cite journal|vauthors=Kubomura D, Matahira Y, Masui A, Matsuda H|date=March 2009|title=Intestinal absorption and blood clearance of L-histidine-related compounds after ingestion of anserine in humans and comparison to anserine-containing diets|journal=Journal of Agricultural and Food Chemistry|volume=57|issue=5|pages=1781–5|doi=10.1021/jf8030875|pmid=19256552}}</ref> |
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=== Neuroprotective effects === |
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An animal model study of Alzheimer's disease using mice foud that treatment with anserine reduced memory loss. Anserine reduced glial inflammatory activity (particularly of [[astrocyte]]). The study also found that anserine-treated mice had greater [[pericyte]] surface area. The greater area of pericytes was commensurate with improved memory (pericytes warp around brain capillary to control blood flow and gate cells from neurotoxin, blocking inflammation). The anserine-treated mice overall performed better on a spatial memory test ([[Morris water navigation task|Morris Water Maze]]).<ref name=":0">{{Cite journal|last=Kaneko|first=Jun|last2=Enya|first2=Akiko|last3=Enomoto|first3=Kota|last4=Ding|first4=Qiong|last5=Hisatsune|first5=Tatsuhiro|date=2017-10-03|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|doi=10.1038/s41598-017-12785-7|issn=2045-2322|doi-access=free}}</ref> |
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| ⚫ | A human study on 84 elderly subjects showed that subjects who took anserine and carnonsine supplements for one year showed increased blood flow in the prefrontal cortex on MRI.<ref name=":12">{{Cite journal|last=Ding|first=Qiong|last2=Tanigawa|first2=Kitora|last3=Kaneko|first3=Jun|last4=Totsuka|first4=Mamoru|last5=Katakura|first5=Yoshinori|last6=Imabayashi|first6=Etsuko|last7=Matsuda|first7=Hiroshi|last8=Hisatsune|first8=Tatsuhiro|date=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|doi=10.14336/ad.2017.0809|issn=2152-5250|doi-access=free}}</ref> |
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A study demonstrated that 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" /> |
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== See also == |
== See also == |
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Revision as of 02:10, 1 March 2021
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| Names | |
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| IUPAC name
(2S)-2-[(3-Amino-1-oxopropyl)amino]-3-(3-methyl-4-imidazolyl)propanoic acid
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| Other names
beta-Alanyl-N(pi)-methyl-L-histidine
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.008.679 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C10H16N4O3 | |
| Molar mass | 240.25904 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Anserine (β-alanyl-N-methylhistidine) is a dipeptide containing β-alanine and 1-methylhistidine,[1] and is a derivative of carnosine, which had been methylated.[2] Anserine can be found in the skeletal muscle and brain of mammals[3] and birds.
The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04, making it an effective buffer at physiologic pH.[1]
Research
Absorption and clearance of dietary anserine
Due to its presence in lean muscles, like fish and poultry, there have been studies showing that inclusion of anserine in the diet may be beneficial for blood clearance and food absorption. These results were based on L-histidine concentrations at different time intervals. A study observing the effect of anserine diet on blood clearance and food absorption concluded that the data showed an ephemeral anserine level peak in blood after consumption of anserine, followed by a prolonged, high level of methylhistidine. This indicates rapid absorption and clearing of anserine because anserine is catabolized into methylhistidine and alanine by a circulating enzyme. A succeeding experiment was performed to test the difference between the first group of people consuming extracted anserine and the latter consuming natural anserine as found in food. In these two groups, while the concentrations of L-histidine-related compound varied depending on the amount of anserine consumed, the absorption level patterns in blood were congruous, proving that anserine taken in food equally helps rapid absorption of food compared to when extracted anserine is taken alone.[clarification needed][4]
Neuroprotective effects
An animal model study of Alzheimer's disease using mice foud that treatment with anserine reduced memory loss. Anserine reduced glial inflammatory activity (particularly of astrocyte). The study also found that anserine-treated mice had greater pericyte surface area. The greater area of pericytes was commensurate with improved memory (pericytes warp around brain capillary to control blood flow and gate cells from neurotoxin, blocking inflammation). The anserine-treated mice overall performed better on a spatial memory test (Morris Water Maze).[5]
A human study on 84 elderly subjects showed that subjects who took anserine and carnonsine supplements for one year showed increased blood flow in the prefrontal cortex on MRI.[6]
A study demonstrated that free N-terminal of histidine on anserine and carnosine protect against zinc-caused neurotoxicity and regulate the Arc pathway in which Arc protein is used to produce dendrite protein for connecting nerve cells.[2]
See also
References
- ^ a b Garrett, Reginald H.; Grisham, Charles M. (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
- ^ a b Ding, Qiong; Tanigawa, Kitora; Kaneko, Jun; Totsuka, Mamoru; Katakura, Yoshinori; Imabayashi, Etsuko; Matsuda, Hiroshi; Hisatsune, Tatsuhiro (2018). "Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4". Aging and Disease. 9 (3): 334. doi:10.14336/ad.2017.0809. ISSN 2152-5250.
- ^ Zapp Jr JA (1938). "Quantitative studies of carnosine and anserine in mammalian muscle. II. The distribution of carnosine and anserine in various muscles of different species". J. Biol. Chem. 126: 19–27.
- ^ Kubomura D, Matahira Y, Masui A, Matsuda H (March 2009). "Intestinal absorption and blood clearance of L-histidine-related compounds after ingestion of anserine in humans and comparison to anserine-containing diets". Journal of Agricultural and Food Chemistry. 57 (5): 1781–5. doi:10.1021/jf8030875. PMID 19256552.
- ^ Kaneko, Jun; Enya, Akiko; Enomoto, Kota; Ding, Qiong; Hisatsune, Tatsuhiro (2017-10-03). "Anserine (beta-alanyl-3-methyl-L-histidine) improves neurovascular-unit dysfunction and spatial memory in aged AβPPswe/PSEN1dE9 Alzheimer's-model mice". Scientific Reports. 7 (1). doi:10.1038/s41598-017-12785-7. ISSN 2045-2322.
- ^ Ding, Qiong; Tanigawa, Kitora; Kaneko, Jun; Totsuka, Mamoru; Katakura, Yoshinori; Imabayashi, Etsuko; Matsuda, Hiroshi; Hisatsune, Tatsuhiro (2018). "Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4". Aging and Disease. 9 (3): 334. doi:10.14336/ad.2017.0809. ISSN 2152-5250.
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