Anserine

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Anserine
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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
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3D model (JSmol)
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  • 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).

Template:Chembox Footer/trackingTemplate:Short description

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]

Anserine has biological activities similar to those of carnosine, including buffering activity, antioxidant properties, metal ion chelation, and anti-aggregation effects.[3] Both anserine and carnosine chelate copper.[4] Because of its methylation, anserine is more stable in serum and resistant to degradation than carnosine.[5] Compared with carnosine, anserine have a higher antioxidant capacity.[6]

Anserine can be found in the skeletal muscle and brain of mammals and birds.[2] Anserine is also found in human kidney.[7]

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04.[8][9]

Biosynthesis

Anserine can be synthesized through methylation of carnosine, by carnosine N-methyltransferase (CARNMT1).[3]

Anti-inflammatory effects

High concentration of anserine reduced interstitial inflammation and alleviated Kidney Fibrosis in Type-1 diabetic mice with Carnosinase-1 knock-out on high fat diet.[10] In another high-fat diet model, anserine treatment exhibited hypolipidemic and anti-obesity effects by inhibiting p-NF-κB p65 expression.[11]

Metal binding

Both anserine and carnosine bind copper and other transition metals.[12] Chelation of transition metals is one mechanism for their antioxidant activity.[4][8]

See also

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Look up anserine in Wiktionary, the free dictionary.

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Garrett CM, Grisham RH (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
  2. ^ a b Page Module:Citation/CS1/styles.css has no content.Blancquaert L, Baba SP, Kwiatkowski S, Stautemas J, Stegen S, Barbaresi S, Chung W, Boakye AA, Hoetker JD, Bhatnagar A, Delanghe J (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. ^ a b Page Module:Citation/CS1/styles.css has no content.Boldyrev AA, Aldini G, Derave W (Oct 2013). "Physiology and pathophysiology of carnosine". Physiological Reviews. 93 (4): 1803–45. doi:10.1152/physrev.00039.2012. PMID 24137022.
  4. ^ a b Page Module:Citation/CS1/styles.css has no content.Chan KM, Decker EA, Feustman C (1994). "Endogenous skeletal muscle antioxidants". Critical Reviews in Food Science and Nutrition. 34 (4): 403–426. doi:10.1080/10408399409527669. PMID 7945896.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Everaert I, Baron G, Barbaresi S, Gilardoni E, Coppa C, Carini M, Vistoli G, Bex T, Stautemas J, Blancquaert L, Derave W (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. S2CID 52945820.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Peters V, Calabrese V, Forsberg E, Volk N, Fleming T, Baelde H, Weigand T, Thiel C, et al. (Sep 2018). "Protective Actions of Anserine Under Diabetic Conditions". International Journal of Molecular Sciences. 19 (9): 2751. doi:10.3390/ijms19092751. PMC 6164239. PMID 30217069.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Peters V, Klessens CQ, Baelde HJ, Singler B, Veraar KA, Zutinic A, Drozak J, Zschocke J, et al. (2015). "Intrinsic carnosine metabolism in the human kidney". Amino Acids. 47 (12): 2541–50. doi:10.1007/s00726-015-2045-7. PMC 4633449. PMID 26206726.
  8. ^ a b Page Module:Citation/CS1/styles.css has no content.Wu G (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.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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.
  10. ^ Page Module:Citation/CS1/styles.css has no content.Pfeffer T, Wetzel C, Kirschner P, Bartosova M, Poth T, Schwab C, Poschet G, Zemva J, et al. (Jun 2023). "Carnosinase-1 Knock-Out Reduces Kidney Fibrosis in Type-1 Diabetic Mice on High Fat Diet". Antioxidants. 12 (6): 1270. doi:10.3390/antiox12061270. PMC 10295340. PMID 37372000.
  11. ^ Page Module:Citation/CS1/styles.css has no content.Luo J, Chen M, Ji H, Su W, Song W, Zhang D, Su W, Liu S (Mar 2024). "Hypolipidemic and Anti-Obesity Effect of Anserine on Mice Orally Administered with High-Fat Diet via Regulating SREBP-1, NLRP3, and UCP-1". Molecular Nutrition & Food Research. 68 (6) e2300471. doi:10.1002/mnfr.202300471. PMID 38400696.
  12. ^ Page Module:Citation/CS1/styles.css has no content.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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