본문 바로가기
KERD
논문KCI 등재

Biological functions of histidine-dipeptides and metabolic syndrome

1

조회

0

다운로드

4

인용

0

참고문헌

키워드

초록

The rapid increase in the prevalence of metabolic syndrome, which is associated with a state of elevated systemic oxidative stress and inflammation,is expected to cause future increases in the prevalence of diabetes and cardiovascular diseases. Oxidation of polyunsaturated fatty acids and sugarsproduces reactive carbonyl species, which, due to their electrophilic nature, react with the nucleophilic sites of certain amino acids. This leads toformation of protein adducts such as advanced glycoxidation/lipoxidation end products (AGEs/ALEs), resulting in cellular dysfunction. Therefore,an effective reactive carbonyl species and AGEs/ALEs sequestering agent may be able to prevent such cellular dysfunction. There is accumulatingevidence that histidine containing dipeptides such as carnosine (β-alanyl-L-histidine) and anserine (β-alanyl-methyl-L-histidine) detoxify cytotoxicreactive carbonyls by forming unreactive adducts and are able to reverse glycated protein. In this review, 1) reaction mechanism of oxidative stressand certain chronic diseases, 2) interrelation between oxidative stress and inflammation, 3) effective reactive carbonyl species and AGEs/ALEs sequesteringactions of histidine-dipeptides and their metabolism, 4) effects of carnosinase encoding gene on the effectiveness of histidine-dipeptides, and 5)protective effects of histidine-dipeptides against progression of metabolic syndrome are discussed. Overall, this review highlights the potential beneficialeffects of histidine-dipeptides against metabolic syndrome. Randomized controlled human studies may provide essential information regarding whetherhistidine-dipeptides attenuate metabolic syndrome in humans.

Abstract

The rapid increase in the prevalence of metabolic syndrome, which is associated with a state of elevated systemic oxidative stress and inflammation,is expected to cause future increases in the prevalence of diabetes and cardiovascular diseases. Oxidation of polyunsaturated fatty acids and sugarsproduces reactive carbonyl species, which, due to their electrophilic nature, react with the nucleophilic sites of certain amino acids. This leads toformation of protein adducts such as advanced glycoxidation/lipoxidation end products (AGEs/ALEs), resulting in cellular dysfunction. Therefore,an effective reactive carbonyl species and AGEs/ALEs sequestering agent may be able to prevent such cellular dysfunction. There is accumulatingevidence that histidine containing dipeptides such as carnosine (β-alanyl-L-histidine) and anserine (β-alanyl-methyl-L-histidine) detoxify cytotoxicreactive carbonyls by forming unreactive adducts and are able to reverse glycated protein. In this review, 1) reaction mechanism of oxidative stressand certain chronic diseases, 2) interrelation between oxidative stress and inflammation, 3) effective reactive carbonyl species and AGEs/ALEs sequesteringactions of histidine-dipeptides and their metabolism, 4) effects of carnosinase encoding gene on the effectiveness of histidine-dipeptides, and 5)protective effects of histidine-dipeptides against progression of metabolic syndrome are discussed. Overall, this review highlights the potential beneficialeffects of histidine-dipeptides against metabolic syndrome. Randomized controlled human studies may provide essential information regarding whetherhistidine-dipeptides attenuate metabolic syndrome in humans.

참고문헌 (73)

  1. Alberti KG, "Harmonizing the metabolic syndrome: a joint interim statement of the International Diabetes Federation Task Force on Epidemiology and Prevention; National Heart, Lung, and Blood Institute; American Heart Association; World Heart Federation; International Atherosclerosis Society; and International Association for the Study of Obesity", Circulation, 120, pp.1640~1645 (2009)
  2. Ford ES, "Increasing prevalence of the metabolic syndrome among U.S. adults", Diabetes Care, 27, pp.2444~2449 (2004)
  3. Lim S, "Increasing prevalence of metabolic syndrome in Korea: the Korean National Health and Nutrition Examination Survey for 1998-2007", Diabetes Care, 34, pp.1323~1328 (2011)
  4. Ervin RB, "Prevalence of metabolic syndrome among adults 20 years of age and over, by sex, age, race and ethnicity, and body mass index: United States, 2003-2006", Natl Health Stat Report, pp.1~7 (2009)
  5. Furukawa S, "Increased oxidative stress in obesity and its impact on metabolic syndrome", J Clin Invest, 114, pp.1752~1761 (2004)
  6. Dandona P, "The suppressive effect of dietary restriction and weight loss in the obese on the generation of reactive oxygen species by leukocytes, lipid peroxidation, and protein carbonylation", J Clin Endocrinol Metab, 86, pp.355~362 (2001)
  7. Caimi G, "Protein oxidation in a group of subjects with metabolic syndrome", Diabetes Metab Syndr, 7, pp.38~41 (2013)
  8. Festa A, "The relation of body fat mass and distribution to markers of chronic inflammation", Int J Obes Relat Metab Disord, 25, pp.1407~1415 (2001)
  9. Ford ES, "Metabolic syndrome and risk of incident diabetes: findings from the European Prospective Investigation into Cancer and Nutrition-Potsdam Study", Cardiovasc Diabetol, 7, pp.35~ (2008)
  10. Grundy SM, "A constellation of complications: the metabolic syndrome", Clin Cornerstone, 7, pp.36~45 (2005)
  11. Carini M, "Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins", Mass Spectrom Rev, 23, pp.281~305 (2004)
  12. Pedchenko VK, "Mechanism of perturbation of integrin-mediated cell-matrix interactions by reactive carbonyl compounds and its implication for pathogenesis of diabetic nephropathy", Diabetes, 54, pp.2952~2960 (2005)
  13. Uchida K, "Role of reactive aldehyde in cardiovascular diseases", Free Radic Biol Med, 28, pp.1685~1696 (2000)
  14. Poli G, "4-Hydroxynonenal in the pathomechanisms of oxidative stress", IUBMB Life, 50, pp.315~321 (2000)
  15. Dalle-Donne I, "Protein carbonylation, cellular dysfunction, and disease progression", J Cell Mol Med, 10, pp.389~406 (2006)
  16. Harcourt BE, "Targeted reduction of advanced glycation improves renal function in obesity", Kidney Int, 80, pp.190~198 (2011)
  17. Singh DK, "Oxidative stress in early diabetic nephropathy: fueling the fire", Nat Rev Endocrinol, 7, pp.176~184 (2011)
  18. Ghanem AA, "Pentosidine and N-carboxymethyl- lysine: biomarkers for type 2 diabetic retinopathy", Eur J Ophthalmol, 21, pp.48~54 (2011)
  19. Hirata K, "Relationship between blood levels of N-carboxymethyl-lysine and pentosidine and the severity of microangiopathy in type 2 diabetes", Endocr J, 51, pp.537~544 (2004)
  20. Dworacka M, "Serum N-epsilon-(carboxymethyl)lysine is elevated in nondiabetic coronary heart disease patients", J Basic Clin Physiol Pharmacol, 13, pp.201~213 (2002)
  21. Ramasamy R, "The diverse ligand repertoire of the receptor for advanced glycation endproducts and pathways to the complications of diabetes", Vascul Pharmacol, 57, pp.160~167 (2012)
  22. Bierhaus A, "Multiple levels of regulation determine the role of the receptor for AGE (RAGE) as common soil in inflammation, immune responses and diabetes mellitus and its complications", Diabetologia, 52, pp.2251~2263 (2009)
  23. Barlovic DP, "RAGE biology, atherosclerosis and diabetes", Clin Sci (Lond), 121, pp.43~55 (2011)
  24. Coughlan MT, "RAGE-induced cytosolic ROS promote mitochondrial superoxide generation in diabetes", J Am Soc Nephrol, 20, pp.742~752 (2009)
  25. Aldini G, "Molecular strategies to prevent, inhibit, and degrade advanced glycoxidation and advanced lipoxidation end products", Free Radic Res, 47(Suppl 1), pp.93~137 (2013)
  26. Quinn PJ, "Carnosine: its properties, functions and potential therapeutic applications", Mol Aspects Med, 13, pp.379~444 (1992)
  27. Park YJ, "Quantitation of carnosine in humans plasma after dietary consumption of beef", J Agric Food Chem, 53, pp.4736~4739 (2005)
  28. Chan KM, "Endogenous skeletal muscle antioxidants", Crit Rev Food Sci Nutr, 34, pp.403~426 (1994)
  29. Gil-Agustí M, "Anserine and carnosine determination in meat samples by pure micellar liquid chromatography", J Chromatogr A, 118(9), pp.444~450 (2008)
  30. Horinishi H, "Purification and characterization of carnosine synthetase from mouse olfactory bulbs", J Neurochem, 31, pp.909~919 (1978)
  31. Teufel M, "Sequence identification and characterization of human carnosinase and a closely related non-specific dipeptidase", J Biol Chem, 278, pp.6521~6531 (2003)
  32. Yeum KJ, "Profiling histidine dipeptides in plasma and urine after ingesting beef, chicken or chicken broth in humans", Amino Acids, 38, pp.847~858 (2010)
  33. Kohen R, "Antioxidant activity of carnosine, homocarnosine, and anserine present in muscle and brain", Proc Natl Acad Sci U S A, 85, pp.3175~3179 (1988)
  34. Jung Hoon Kang, "Carnosine and Related Dipeptides Protect Human Ceruloplasmin against Peroxyl Radical-mediated Modification", Molecules and Cells, 13(3), pp.498~502 (2002), 한국분자세포생물학회
  35. Egorov SYu, "Quenching of singlet molecular oxygen by carnosine and related antioxidants. Monitoring 1270-nm phosphorescence in aqueous media", Biochem Mol Biol Int, 41, pp.687~694 (1997)
  36. Brownson C, "Carnosine reacts with a glycated protein", Free Radic Biol Med, 28, pp.1564~1570 (2000)
  37. Carini M, "Acroleinsequestering ability of endogenous dipeptides: characterization of carnosine and homocarnosine", acrolein adducts by electrospray ionization tandem mass spectrometry, 2003, pp.38, 996~1006
  38. Aldini G, "Carnosine is a quencher of 4-hydroxy-nonenal: through what mechanism of reaction?", Biochem Biophys Res Commun, 298, pp.699~706 (2002)
  39. Miller ER 3rd, "Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality", Ann Intern Med, 142, pp.37~46 (2005)
  40. Lawson KA, "Multivitamin use and risk of prostate cancer in the National Institutes of Health-AARP Diet and Health Study", J Natl Cancer Inst, 99, pp.754~764 (2007)
  41. Bjelakovic G, "Antioxidant supplements for prevention of mortality in healthy participants and patients with various diseases", Cochrane Database Syst Rev, 3, pp.CD007176~ (2012)
  42. Rietjens IM, "The pro-oxidant chemistry of the natural antioxidants vitamin C, vitamin E, carotenoids and flavonoids", Environ Toxicol Pharmacol, 11, pp.321~333 (2002)
  43. Veeramachaneni S, "High dose lycopene supplementation increases hepatic cytochrome P4502E1 protein and inflammation in alcohol-fed rats", J Nutr, 138, pp.1329~1335 (2008)
  44. van Helden YG, "Beta-carotene metabolites enhance inflammation-induced oxidative DNA damage in lung epithelial cells", Free Radic Biol Med, 46, pp.299~304 (2009)
  45. Hipkiss AR, "Non-enzymatic glycosylation of the dipeptide L-carnosine, a potential anti-protein-cross-linking agent", FEBS Lett, 371, pp.81~85 (1995)
  46. Sato M, "Safety evaluation of chicken breast extract containing carnosine and anserine", Food Chem Toxicol, 46, pp.480~489 (2008)
  47. Gardner ML, "Intestinal absorption of the intact peptide carnosine in man, and comparison with intestinal permeability to lactulose", J Physiol, 439, pp.411~422 (1991)
  48. Son DO, "Characterization of carnosine uptake and its physiological function in human intestinal epithelial Caco-2 cells", Biofactors, 21, pp.395~398 (2004)
  49. Cahill LE, "Functional genetic variants of glutathione S-transferase protect against serum ascorbic acid deficiency", Am J Clin Nutr, 90, pp.1411~1417 (2009)
  50. Milman U, "Vitamin E supplementation reduces cardiovascular events in a subgroup of middleaged individuals with both type 2 diabetes mellitus and the haptoglobin 2-2 genotype: a prospective double-blinded clinical trial", Arterioscler Thromb Vasc Biol, 28, pp.341~347 (2008)
  51. Janssen B, "Carnosine as a protective factor in diabetic nephropathy: association with a leucine repeat of the carnosinase gene CNDP1", Diabetes, 54, pp.2320~2327 (2005)
  52. Freedman BI, "A leucine repeat in the carnosinase gene CNDP1 is associated with diabetic end-stage renal disease in European Americans", Nephrol Dial Transplant, 22, pp.1131~1135 (2007)
  53. Stadtman ER, "Metal ion-catalyzed oxidation of proteins: biochemical mechanism and biological consequences", Free Radic Biol Med, 9, pp.315~325 (1990)
  54. McGrath LT, "Increased oxidative stress in Alzheimer's disease as assessed with 4-hydroxynonenal but not malondialdehyde", QJM, 94, pp.485~490 (2001)
  55. Neuhouser ML, "Multivitamin use and risk of cancer and cardiovascular disease in the Women's Health Initiative cohorts", Arch Intern Med, 169, pp.294~304 (2009)
  56. Aldini G, "Detoxification of 4-hydroxynonenal (HNE) in keratinocytes: characterization of conjugated metabolites by liquid chromatography", electrospray ionization tandem mass spectrometry, 2003, pp.38, 1160~1168
  57. Seidler NW, "Carnosine disaggregates glycated alpha-crystallin: an in vitro study", Arch Biochem Biophys, 427, pp.110~115 (2004)
  58. Seidler NW, "Carnosine prevents the glycation-induced changes in electrophoretic mobility of aspartate aminotransferase", J Biochem Mol Toxicol, 14, pp.215~220 (2000)
  59. Aldini G, "The carbonyl scavenger carnosine ameliorates dyslipidaemia and renal function in Zucker obese rats", J Cell Mol Med, 15, pp.1339~1354 (2011)
  60. Aldini G, "A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: a new tool for studying vascular carbonylation", J Mass Spectrom, 43, pp.1470~1481 (2008)
  61. Aldini G, "Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species?", Chem Res Toxicol, 21, pp.824~835 (2008)
  62. Okada K, "4-Hydroxy-2-nonenal-mediated impairment of intracellular proteolysis during oxidative stress. Identification of proteasomes as target molecules", J Biol Chem, 274, pp.23787~23793 (1999)
  63. Mistry N, "Antiserum detection of reactive carbonyl species-modified DNA in human colonocytes", Free Radic Res, 42, pp.344~353 (2008)
  64. Roberts MJ, "DNA damage by carbonyl stress in human skin cells", Mutat Res, 522, pp.45~56 (2003)
  65. Gallant S, "Carnosine as a potential anti-senescence drug", Biochemistry (Mosc), 65, pp.866~868 (2000)
  66. Hipkiss AR, "Glycation, ageing and carnosine: are carnivorous diets beneficial?", Mech Ageing Dev, 126, pp.1034~1039 (2005)
  67. Lee YT, "Histidine and carnosine delay diabetic deterioration in mice and protect human low density lipoprotein against oxidation and glycation", Eur J Pharmacol, 513, pp.145~150 (2005)
  68. Kurata H, "Renoprotective effects of l-carnosine on ischemia", reperfusion-induced renal injury in rats, 2006, pp.319, 640~647
  69. Nagai K, "Possible role of L-carnosine in the regulation of blood glucose through controlling autonomic nerves", Exp Biol Med (Maywood), 228, pp.1138~1145 (2003)
  70. Gualano B, "Reduced muscle carnosine content in type 2, but not in type 1 diabetic patients", Amino Acids, 43, pp.21~24 (2012)
  71. Sauerhöfer S, "L-carnosine, a substrate of carnosinase-1, influences glucose metabolism", Diabetes, 56, pp.2425~2432 (2007)
  72. Tsoi B, "Carnosine ameliorates stress-induced glucose metabolism disorder in restrained mice", J Pharmacol Sci, 117, pp.223~229 (2011)
  73. Chez MG, "Double-blind, placebo-controlled study of L-carnosine supplementation in children with autistic spectrum disorders", J Child Neurol, 17, pp.833~837 (2002)

관련 논문AI추천

이 간행물의 다른 논문 (14건)