Anserine

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For the subfamily of waterfowl, see Anserinae.
Anserine
Anserine.svg
Names
Preferred IUPAC name
(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
Other names
beta-Alanyl-3-methyl-L-histidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.679 Edit this at Wikidata
KEGG
UNII
  • 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  (what is checkY☒N ?)
Infobox references

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-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]

Absorption and clearance[]

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]

Clinical significance[]

Neuroprotective effects[]

An animal model study of Alzheimer's disease using mice found 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 carnosine supplements for one year showed increased blood flow in the prefrontal cortex on MRI.[6]

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 Arc protein is used to produce dendrite protein for connecting nerve cells.[2]

Pes Anserine Bursitis[]

Bursitis is inflammation of the small, enclose jelly-like sacs known as bursae. The bursae are located near the shoulder, hip, heel, knees, and elbows acting as soft cushions to reduce friction. Having bursitis may limit motion but is generally a condition that is temporary and usually won't cause any deformities. Pes Anserine Bursitis is inflammation of the bursae between the tibia and three tendons of the hamstring muscle inside the knee. This will occur when the bursa produces too much fluid causing it to be irritated, and swell up putting pressure on the knees.

See also[]

References[]

  1. ^ a b Garrett CM, Grisham RH (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
  2. ^ a b Ding Q, Tanigawa K, Kaneko J, Totsuka M, Katakura Y, Imabayashi E, et al. (June 2018). "Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4". Aging and Disease. 9 (3): 334–345. doi:10.14336/ad.2017.0809. PMID 29896423.
  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): 1781–1785. doi:10.1021/jf8030875. PMID 19256552.
  5. ^ 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. doi:10.1038/s41598-017-12785-7. PMID 28974740.
  6. ^ Ding Q, Tanigawa K, Kaneko J, Totsuka M, Katakura Y, Imabayashi E, et al. (June 2018). "Anserine/Carnosine Supplementation Preserves Blood Flow in the Prefrontal Brain of Elderly People Carrying APOE e4". Aging and Disease. 9 (3): 334–345. doi:10.14336/ad.2017.0809. PMID 29896423.
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