Ability of Three Kind of Imidazole Dipeptides, Carnosine, Anserine, and Balenine, to Interact with Unsaturated Fatty Acid-Derived Aldehydes and Carbohydrate-Derived Aldehydes
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Imidazole dipeptides (IDPs) such as carnosine (CAR), anserine (ANS), and balenine (BAL) are widely distributed in the skeletal muscle of vertebrates. Recently, several studies have revealed that CAR plays an important role in the detoxification of cytotoxic aldehydes arising from the peroxide of unsaturated fatty acids and carbohydrate metabolite. Although intensive studies on the detoxification of aldehydes by CAR have been performed, few studies have focused on the effects of detoxification by ANS and BAL. To determine the potential of minor IDPs such as ANS and BAL to react with cytotoxic aldehydes, the present study was established to investigate the consumption of IDP after co-incubation with cytotoxic aldehydes using high-performance liquid chromatography (HPLC). In the case of unsaturated fatty acid-derived aldehydes such as 4-hydroxy-2-trans-nonenal (from n-6 fatty acid) and 4-hydroxy-2-trans-hexenal (from n-3 fatty acid), ANS and CAR decreased considerably after co-incubation, but BAL did not. In the case of 3-deoxyglucosone and methylglyoxal as carbohydrate metabolites, no IDPs decreased after co-incubation; however, the absorbance at 336 nm of the CAR and BAL mixtures increased dramatically in a time-dependent manner. In the case of glyceraldehyde, which is also a carbohydrate metabolite, all IDPs, especially BAL, decreased after co-incubation and a new peak, surmised to represent an IDP-glyceraldehyde adduct, appeared on the HPLC chromatogram. These results can help explain the unique function and behavior of ANS and BAL in specific species.
KeywordsAnserine Balenine Carnosine Aldehyde 4-Hydroxy-trans-2-nonenal Methylglyoxal
This work was supported by JSPS KAKENHI Grant Number 18K05521. The authors would like to thank Enago (www.enago.jp) for the English language review.
Compliance with Ethical Standards
Conflict of interest
Akihiro Mori, Hideo Hatate, and Ryusuke Tanaka declare that they have no conflicts of interest.
Human and Animal Rights and Informed Consent
This article does not describe any studies with human or animal subjects performed by any of the authors.
- Abe H (1995) Histidine-related dipeptides: distribution, metabolism, and physiological function. In: Hochachka P, Mommsen T (eds) Biochemistry and molecular biology of fishes, vol 4. Elsevier, Amsterdam, pp 309–333Google Scholar
- Abe H (2000) Role of histidine-related compounds as intracellular proton buffering constituents in vertebrate muscle. Biochemistry (Moscow) 65:757–765Google Scholar
- Aldini G, Granata P, Carini M (2002b) Detoxification of cytotoxic α, β-unsaturated aldehydes by carnosine: characterization of conjugated adducts by electrospray ionization tandem mass spectrometry and detection by liquid chromatography/mass spectrometry in rat skeletal muscle. J Mass Spectrom 37:1219–1228. https://doi.org/10.1002/jms.381 CrossRefPubMedGoogle Scholar
- Aldini G, Orioli M, Rossoni G, Savi F, Braidotti P, Vistoli G, Yeum K-J, Negrisoli G, Carini M (2011) The carbonyl scavenger carnosine ameliorates dyslipidaemia and renal function in Zucker obese rats. J Cell Mol Med 15:1339–1354. https://doi.org/10.1111/j.1582-4934.2010.01101.x CrossRefPubMedGoogle Scholar
- Derave W, Özdemir MS, Harris RC, Pottier A, Reyngoudt H, Koppo K, Wise JA, Achten E (2007) β-Alanine supplementation augments muscle carnosine content and attenuates fatigue during repeated isokinetic contraction bouts in trained sprinters. J Appl Physiol 103:1736–1743. https://doi.org/10.1152/japplphysiol.00397.2007 CrossRefPubMedGoogle Scholar
- Hipkiss AR (2009) Carnosine and its possible roles in nutrition and health. In: Steve LT (ed) Advances in food and nutrition research, vol 57. Academic Press, Cambridge, pp 87–154Google Scholar
- Kish SJ, Perry TL, Hansen S (1979) Regional distribution of homocarnosine, homocarnosine-carnosine synthetase and homocarnosinase in human brain. J Neurochem 32:1629–1636. https://doi.org/10.1111/j.1471-4159.1979.tb02272.x CrossRefPubMedGoogle Scholar
- Mori A, Hikihara R, Ishimaru M, Hatate H, Tanaka R (2018) Evaluation of histidine-containing dipeptides in twelve marine organisms and four land animal meats by hydrophilic interaction liquid chromatography with ultraviolet detection. J Liq Chromatogr Relat Technol 41:849–854. https://doi.org/10.1080/10826076.2018.1526803 CrossRefGoogle Scholar
- Negre-Salvayre A, Coatrieux C, Ingueneau C, Salvayre R (2008) Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors. Br J Pharmacol 153:6–20. https://doi.org/10.1038/sj.bjp.0707395 CrossRefPubMedGoogle Scholar
- Pietkiewicz J, Bronowicka-Szydełko A, Dzierzba K, Danielewicz R, Gamian A (2011) Glycation of the muscle-specific enolase by reactive carbonyls: effect of temperature and the protection role of carnosine, pirydoxamine and phosphatidylserine. Protein J 30:149–158. https://doi.org/10.1007/s10930-011-9307-3 CrossRefPubMedGoogle Scholar
- Pocchiari F, Tentori L, Vivaldi G (1962) The presence of the dipeptide β-alanyl-3-methylhistidine in whale meat extract. Sci Rept Ist Super Sanita 2:188Google Scholar
- Sabeena Farvin KH, Andersen LL, Otte J, Nielsen HH, Jessen F, Jacobsen C (2016) Antioxidant activity of cod (Gadus morhua) protein hydrolysates: fractionation and characterisation of peptide fractions. Food Chem 204:409–419. https://doi.org/10.1016/j.foodchem.2016.02.145 CrossRefPubMedGoogle Scholar
- Saunders B, Artioli GG, Sale C, Gualano B (2015) β-Alanine, muscle carnosine and exercise. In: Preedy V (ed) Food and nutritional components in focus, vol 8. Royal Society of Chemistry, London, pp 277–294Google Scholar
- Seidler NW, Shokry SS, Nauth J (2001) Properties of a glycation product derived from carnosine. J Biochem Mol Biol Biophys 5:153–162Google Scholar
- Sugino T, Yasunaga G, Fukuda M (2013) Effect of whale meat extract on fatigue induced by physical load and by daily activities in humans. Jpn Pharmacol Ther 41:879–893Google Scholar
- Tanaka R, Sugiura Y, Matsushita T (2013) Simultaneous identification of 4-hydroxy-2-hexenal and 4-hydroxy-2-nonenal in foods by pre-column fluorigenic labeling with 1,3-cyclohexanedione and reversed-phase high-performance liquid chromatography with fluorescence detection. J Liq Chromatogr Relat Technol 36:881–896. https://doi.org/10.1080/10826076.2012.678454 CrossRefGoogle Scholar
- Wada N, Yamanaka S, Shibato J, Rakwal R, Hirako S, Iizuka Y, Kim H, Matsumoto A, Kimura A, Takenoya F, Yasunaga G, Shioda S (2016) Behavioral and omics analyses study on potential involvement of dipeptide balenine through supplementation in diet of senescence-accelerated mouse prone 8. Genom Data 10:38–50. https://doi.org/10.1016/j.gdata.2016.09.004 CrossRefPubMedPubMedCentralGoogle Scholar
- Weigand T, Singler B, Fleming T, Nawroth P, Klika KD, Thiel C, Baelde H, Garbade SF, Wagner AH, Hecker M, Yard BA, Amberger A, Zschocke J, Schmitt CP, Peters V (2018) Carnosine catalyzes the formation of the oligo/polymeric products of methylglyoxal. Cell Physiol Biochem 46:713–726. https://doi.org/10.1159/000488727 CrossRefPubMedGoogle Scholar
- Wolff WA, Wilson DW (1935) Carnosine and anserine in mammalian skeletal muscle. J Biol Chem 109:565–571Google Scholar
- Zhao Y, Xu S, Lu H, Zhang D, Liu F, Lin J, Zhou C, Mu W (2017) Effects of the plant volatile trans‑2-hexenal on the dispersal ability, nutrient metabolism and enzymatic activities of Bursaphelenchus xylophilus. Pestic Biochem Physiol 143:147–153. https://doi.org/10.1016/j.pestbp.2017.08.004 CrossRefPubMedGoogle Scholar