Anserine

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine.[1] Anserine is a derivative of carnosine, which has been methylated.[2] Both anserine and carnosine are capable of chelating copper.[3] Due to its methylation, anserine is more stable in serum and resistant to degradation than carnosine.[4] Anserine can be found in the skeletal muscle and brain of mammals and birds.[2] It can also be found in high levels in the human kidneys.[5] The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04, making it an effective buffer at physiologic pH.[6][7]

For the subfamily of waterfowl, see Anserinae. For pes anserine bursitis, see Bursitis.
Anserine
Names
Systematic IUPAC name
(2S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Other names
beta-Alanyl-3-methyl-L-histidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.679
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).
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Infobox references

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.[8] These results were based on L-histidine concentrations at different time intervals.[8] 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.[8] 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.[8]

Clinical significance

Neuroprotective effects

An animal model study of Alzheimer's disease using mice found that treatment with anserine reduced memory loss.[9] Anserine reduced glial inflammatory activity (particularly of astrocyte).[7] The study also found that anserine-treated mice had greater pericyte surface area.[7] 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).[7] The anserine-treated mice overall performed better on a spatial memory test (Morris Water Maze).[7]

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.[9]

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.[10]

Both Anserine and Carnosine are chelating agents for copper and other transition metals.[11] 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.[3]

See also
Look up anserine in Wiktionary, the free dictionary.

References
  1. Garrett CM, Grisham RH (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
  2. Blancquaert, Laura; Baba, Shahid P.; Kwiatkowski, Sebastian; Stautemas, Jan; Stegen, Sanne; Barbaresi, Silvia; Chung, Weiliang; Boakye, Adjoa A.; Hoetker, J. David; Bhatnagar, Aruni; Delanghe, Joris (2016-09-01). "Carnosine and anserine homeostasis in skeletal muscle and heart is controlled by β-alanine transamination". The Journal of Physiology. 594 (17): 4849–4863. doi:10.1113/JP272050. ISSN 1469-7793. PMC 5009790. PMID 27062388.
  3. Kohen, Ron; Yamamoto, Yorihiro; Cundy, Kenneth C.; Ames, Bruce N. (1988). "Antioxidant Activity of Carnosine, Homocarnosine, and Anserine Present in Muscle and Brain". Proceedings of the National Academy of Sciences of the United States of America. 85 (9): 3175–3179. ISSN 0027-8424.
  4. Everaert, Inge; Baron, Giovanna; Barbaresi, Silvia; Gilardoni, Ettore; Coppa, Crescenzo; Carini, Marina; Vistoli, Giulio; Bex, Tine; Stautemas, Jan; Blancquaert, Laura; Derave, Wim (January 2019). "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". Amino Acids. 51 (1): 103–114. doi:10.1007/s00726-018-2663-y. hdl:2434/599742. ISSN 1438-2199. PMID 30302566.
  5. Peters, Verena; Calabrese, Vittorio; Forsberg, Elisabete; Volk, Nadine; Fleming, Thomas; Baelde, Hans; Weigand, Tim; Thiel, Christian; Trovato, Angela; Scuto, Maria; Modafferi, Sergio (2018-09-13). "Protective Actions of Anserine Under Diabetic Conditions". International Journal of Molecular Sciences. 19 (9): E2751. doi:10.3390/ijms19092751. ISSN 1422-0067. PMC 6164239. PMID 30217069.
  6. Wu, Guoyao (March 2020). "Important roles of dietary taurine, creatine, carnosine, anserine and 4-hydroxyproline in human nutrition and health". Amino Acids. 52 (3): 329–360. doi:10.1007/s00726-020-02823-6. ISSN 1438-2199. PMC 7088015. PMID 32072297.
  7. 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.
  8. 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.
  9. 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.
  10. 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.
  11. Kohen, R.; Misgav, R.; Ginsburg, I. (1991). "The SOD like activity of copper:carnosine, copper:anserine and copper:homocarnosine complexes". Free Radical Research Communications. 12-13 Pt 1: 179–185. doi:10.3109/10715769109145784. ISSN 8755-0199. PMID 1649087.
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