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Anserine

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For the subfamily of waterfowl, see Anserinae.
Anserine
Names
IUPAC name
(2S)-2-[(3-Amino-1-oxopropyl)amino]-3-(3-methyl-4-imidazolyl)propanoic acid
Other names
beta-Alanyl-N(pi)-methyl-L-histidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.679 Edit this at Wikidata
KEGG
  • InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1 checkY
    Key: MYYIAHXIVFADCU-QMMMGPOBSA-N checkY
  • InChI=1/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
    Key: MYYIAHXIVFADCU-QMMMGPOBBJ
  • O=C(O)[C@@H](NC(=O)CCN)Cc1cncn1C
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).
checkY verify (what is checkY☒N ?)

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.

Due to its presence in lean muscles, like fish and poultry, there have been recent studies showing that anserine's inclusion to our diets can be beneficial for blood clearance and food absorption. These results were based on L-histidine concentrations at different time intervals.[4] 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 enzyme found in blood. Then, a succeeding experiment was laid out to test the difference between the first group of people consuming extracted anserine and the latter consuming 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.[5]

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 astrocytes, showing that treatment with anserine can improve memory loss.[6] To arrive at this conclusion, scientists stained pericytes from mouse and found that anserine treated mouse 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.[7] Furthermore, they performed Morris Water Maze tests on mouse and found that anserine treated mouse had overall better spatial memory. [7] The effects of anserine and carnosine were also observed in humans; One study done with 84 elders in Tokyo found that elders who took 500mg of anserine and carnonsine for one year showed more blood flow in the prefrontal cortex through the MRI. [8] There has also been study revealing that free N-terminal of histidine on anserine and carnosine protect against zinc-caused neurotoxicity and regulate Arc pathway in which Arc proteinis used to produce dendrite protein for connecting nerve cells.[9]

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04, making it an effective buffer at physiologic pH.[1]

See also

References

  1. ^ a b Garrett, Reginald H.; Grisham, Charles M. (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ Kubomura, Daiki; Matahira, Yoshiharu; Masui, Ayano; Matsuda, Hideki (2009-03-11). "Intestinal Absorption and Blood Clearance ofl-Histidine-Related Compounds after Ingestion of Anserine in Humans and Comparison to Anserine-Containing Diets". Journal of Agricultural and Food Chemistry. 57 (5): 1781–1785. doi:10.1021/jf8030875. ISSN 0021-8561.
  6. ^ Kaneko J, Enya A, Enomoto K, Ding Q, Hisatsune T (October 2017). "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): 12571. Bibcode:2017NatSR...712571K. doi:10.1038/s41598-017-12785-7. PMC 5626714. PMID 28974740.
  7. ^ a b 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.
  8. ^ 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.
  9. ^ Mizuno, Dai; Konoha-Mizuno, Keiko; Mori, Miwako; Sadakane, Yutaka; Koyama, Hironari; Ohkawara, Susumu; Kawahara, Masahiro (2015). "Protective activity of carnosine and anserine against zinc-induced neurotoxicity: a possible treatment for vascular dementia". Metallomics. 7 (8): 1233–1239. doi:10.1039/c5mt00049a. ISSN 1756-5901.
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