The Maillard Reaction: Recent Advances in Food and Biomedical Sciences / Edition 1

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Overview

The Maillard reaction is at the crossroads of food and biomedical sciences: it contributes to the natural and normal aging of tissues, but, when accelerated, it contributes to the development of pathologic conditions in a number of age-related chronic diseases, including arthritis, atherosclerosis, diabetes, and neurodegenerative diseases.

This volume addresses these focus areas through a wide range of interdisciplinary research reports on the role of Maillard reactions in aging and disease. The role of the Maillard reaction in diabetic complications, for example, has become a major focus of recent research, leading to a better understanding of the importance of hyperglycemia, oxidative stress, and lipid peroxidation in the pathogenesis of complications, including nephropathy, retinopathy, neuropathy, and macrovascular complications.

Chemical damage to protein by glycoxidation and lipoxidation reactions are two sides of the same coin, one side representing the damage to tissue proteins by sugar, the other side by lipids. In both cases, the chemical modification of tissue proteins by oxidative chemical reactions, and underlying damage to DNA, contributes to loss of function and development of disease.

The final sections of the volume are devoted to recent research on AGE/ALE inhibitors in animal models and clinical trials and assess the current status of pharmaceutical interventions for retarding the Maillard reaction and the pathophysiology associated with aging and age-related disease.

NOTE: Annals volumes are available for sale as individual books or as a journal. For information on institutional journal subscriptions, please visit www.blackwellpublishing.com/nyas.

ACADEMY MEMBERS: Please contact the New York Academy of Sciences directly to place your order (www.nyas.org). Members of the New York Academy of Science receive full-text access to the Annals online and discounts on print volumes. Please visit http://www.nyas.org/MemberCenter/Join.aspx for more information about becoming a member

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Table of Contents

Preface: Erwin Schleicher, Veronika Somoza, and Peter Schieberle.

Part I: Keynote Papers:.

1. The Sense of Smell: Perception of Flavors: Heinz Breer.

2. Receptor for Advanced Glycation Endproducts: Fundamental Roles in the Inflammatory Response—Winding the Way to the Pathogenesis of Endothelial Dysfunction and Atherosclerosis: Ravichandran Ramasamy, Shi Fang Yan, Kevan Herold, Raphael Clynes, and Ann Marie Schmidt.

3. CNS Regulation of Energy Metabolism: Ghrelin versus Leptin: Ruben Nogueiras, Matthias H. Tschöp, and Jeffrey M. Zigman.

4. Determination of Nε-(Carboxymethyl)lysine in Foods and Related Systems: Jennifer Ames.

Part II: Plenary Lectures:.

5. Food Anoxia and the Formation of Either Flavor or Toxic Compounds by Amino Acid Degradation Initiated by Oxidized Lipids: Francisco J. Hidalgo and Rosario Zamora.

6. Post–Schiff Base Chemistry of the Maillard Reaction: Mechanism of Imine Isomerization: Fong Lam Chu and Varoujan A. Yaylayan.

7. The Usefulness of Antibodies for Evaluating the Biological Significance of AGEs: Ryoji Nagai, Yukio Fujiwara, Katsumi Mera, Keita Motomura, Yasunori Iwao, Keiichuro Tsurushima, Mime Nagai, Kazuhiro Takeo, Makiko Yoshitomi, Masaki Otagiri, and Tsuyoshi Ikeda.

8. RAGE Expression in Experimental Diabetic Retinopathy: Yumei Wang, Franziska Hagen, Frederick Pfister, Angelika Bierhaus, Yuxi Feng, and Hans-Peter Hammes.

9. AGE Homeostasis: Exogenous Oxidants and Innate Defenses: Helen Vlassara, Jaime Uribarri, Weijing Cai, and Gary Striker.

10. Formation Mechanisms of Melanoidins and Fluorescent Pyridinium Compounds as Advanced Glycation Endproducts: Fumitaka Hayase.

11. Advanced Glycation as a Basis for Understanding Retinal Aging and Noninvasive Risk Prediction: Anna M. Pawlak, John J. McGarvey, and Alan W. Stitt.

12. The Aroma Side of the Maillard Reaction: Christoph Cerny.

13. Methylglyoxal: Its Presence in Beverages and Potential Scavengers: Di Tan, Chih-Yu Lo, Shengming Sang, and Chi-Tang Ho.

14. The Receptor for Advanced Glycation End Pathway: Activation and Perpetuation in the Pathogenesis of Diabetic Neuropathy: Ivan Lukic, Per Humpert, Peter P. Nawroth, and Angelika Bierhaus.

15. The Role of the Amadori Product in the Complications of Diabetes: Vincent M. Monnier, David Sell, Zhenyu Dai, Ina Nemet, Francois Collard, and Jianjye Zhang.

16. Mitigation Strategies to Reduce Acrylamide Formation in Fried Potato Products: Vincenzo Fogliano, Francisco Morales, and Edoardo Capuano.

17. Therapeutic Interruption of Advanced Glycation in Diabetic Nephropathy: Do All Roads Lead to Rome?: Karly C. Sourris, Josephine M. Forbes, and Mark E. Cooper.

18. The Other Side of the Maillard Reaction: Ram H. Nagaraj, Ashis Biswas, Antonia Miller, Tomoko Oya-Ito, and Manjunatha Bhat.

19. Dicarbonyls Stimulate Cellular Protection Systems in Primary Rat Hepatocytes and Show Anti-inflammatory Properties: Timo Buetler, Helia Latado, Alexandra Baumeyer, and Thierry Delatour.

20. N-Terminal Glycation of Proteins and Peptides in Foods and in Vivo: Evaluation by LC/MS of N-(2-furoylmethyl)valine in Acid Hydrolyzates of Human Hemoglobin: Thomas Henle.

21. The Sicarbonyl Proteome—Proteins Susceptible to Dicarbonyl Glycation at Functional Sites in Health, Aging, and Disease: Naila Rabbani and Paul J. Thornalley.

22. Peroxyl Radicals Are Essential Reagents in the Oxidation Steps of the Maillard Reaction Leading to Generation of Advanced Glycation End Products: Gerhard Spiteller.

23. Application of Mass Spectrometry for the Detection of Glycation and Oxidation Products in Milk Proteins: Jasmin Meltretter and Monika Pischetsrieder.

24. Inhibition of Advanced Glycation End Products: An Implicit Goal in Clinical Medicine for the Treatment of Diabetic Nephropathy?: Toshio Miyata and Yuko Izuhara.

25. Inflammation and the Redox-Sensitive AGE-RAGE Pathway as a Therapeutic Target in Alzheimer’s Disease: Gerald Münch, Annette Maczurek, and Kirubakaran Shanmugam.

Part III: Oral Presentations:.

26. Some Natural Compounds Enhance N -(carboxymethyl)lysine Formation: Yukio Fujiwara, Naoko Kiyota, Keita Motomura, Katsumi Mera, Motohiro Takeya, Tsuyoshi Ikeda, and Ryoji Nagai.

27. Immunological Detection of N -carboxymethylarginine by Specific Antibody: Katsumi Mera, Yukio Fujiwara, Masaki Otagiri, Noriyuki Sakata, and Ryoji Nagai.

28. Isolation and Partial Characterization of Four Fluorophores Formed by Nonenzymatic Browning of Methylglyoxal and Glutamine-derived Ammonia: Céline Niquet, Serge Pilard, David Mathiron, and Frédéric Tessier.

29. Receptor for Advanced Glycation End Product Polymorphisms and Type 2 Diabetes; The CODAM Study: Katrien Gaens, Carla Van Der Kallen, Marleen Greevenbroek, Edith Feskins, Coen Stehouwer, and Casper Schalwijk.

30. Pentosidine Effects on Human Osteoblasts in Vitro: Roberta Sanguineti, Daniela Storace, Fiammetta Monacelli, Alberto Federici, and Patrizio Odetti.

31. Strategy for the Study of Health Impact of Maillard Products in Clinical Studies: The Example of the ICARE Clinical Study on Healthy Adults: Philippe Pouillart, Héléne Mauprivez, Jean-Michel Lecerf, Amélie Cayzeele, Frédéric Tessier, and Inés Birlouez-Aragon.

32. Plasma Concentration and Urinary Excretion of N -(carboxymethyl)lysine in Breast Milk– versus Infant Formula–fed Healthy 6-month-old Infants: Katarina Sebekova, Giselle Saavedra, Cornelia Zump, Veronika Somoza, Kristina Klenovicsova, and Ines Birlouez-Aragon.

33. Maillard Reaction Products in the Escherichia coli–derived Therapeutic Protein Interferon Alfacon-1: Roumyana Mironova, Angelina Sredovska, Ivan Ivanov, and Toshimitsu Niwa.

34. Acrolein Induces Inflammatory Response Underlying Endothelial Dysfunction: a Risk Factor for Atherosclerosis: Yong Seek Park and Naoyuki Taniguchi.

35. Oxidative Stress and Advanced Glycation in Diabetic Nephropathy: Linda T. Coughlan, Amy L. Mibus, Karly C. Sourris, Felicia Yt Yap, Adeline Tan, Sally A. Penfold, Anna Gasser, Brooke Harcourt, Sofianos Andrikopoulos, Mark E. Cooper, and Josephine M. Forbes.

36. Vitamin C–Mediated Maillard Reaction in the Lens probed in a Transgenic Mouse Model: Xingjun Fan.

37. Ne(Carboxymethyl)lysine Is Increased in Plasma, Urine, and the Kidney of Spontaneous Hypertensive Rats during the Early Development of Hypertension and Is Independent of Renal Function or Oxydative Stress: Marcus Baumann, Casper Schalkwijk, Jean Scheijen, Uwe Heemann, Harry Struijker Boudier, and Coen Stehouwer.

38. Aging, Diabetes, and Renal Failure Catalyze the Oxidation of Lysyl Residues to 2-aminoadipic Acid in Human Skin Collagen: Evidence for Metal-catalyzed Oxidation Mediated by α-dicarbonyls: David R. Sell, Christopher M. Strauch, Wei Shen, and Vincent M. Monnier.

39. a-Dicarbonyl Compounds—Key Intermediates for the Formation of Carbohydrate-based Melanoidins: Lothar W. Kroh.

40. Approaches to Wine Aroma: C1 Transfer during the Reaction between Diacetyl and Cysteine: John Almy and Gilles De Revel.

41. Antioxidant Activity and Chemical Properties of Crude and Fractionated Maillard Reaction Products Derived from Four Sugar–Amino Acid Maillard Reaction Model Systems: Xiu-Min Chen and David Kitts.

42. Advanced Glycation Endproducts in Chronic Heart Failure: Andries Smit, Jasper Hartog, Adriaan A. Voors, and Dirk Jan Van Veldhuisen.

43. Methylglyoxal and Methylglyoxal-arginine Adducts Do Not Directly Inhibit Endothelial Nitric Oxide Synthase: Olaf Brouwers, Tom Teerlink, Jan Van Bezu, Rob Barto, Coen Stehouwer, and Casper Schalkwijk.

44. Kinetic Study of the Reaction between Glycolaldehyde and Two Glycation Target Models: N-Ac-Phe-Lys and N-Ac-Cys: M. Adrover, B. Vilanova, J. Frau, J. Ortega, A. Salvà, F. Muñoz, and J. Donoso.

45. Origin and Yields of Acetic Acid in Pentose-based Maillard Reaction Systems: Tomas Davidek, Elizabeth Gouezec, Stephanie Devaud, and Imre Blank.

46. Peptide-catalyzed Maillard Reaction: Characterization of 13C reductones: Leif-Alexander Garbe, Alexander Würtz, Christian T. Piechotta, and Roland Tressl.

47. Model Studies on Protein Glycation: Influence of Cysteine on the Reactivity of Arginine and Lysine Residues toward Glyoxal: Uwe Schwarzenbolz, Susann Mende, and Thomas Henle.

48. Analysis of Amadori Peptides Enriched by Boronic Acid Affinity Chromatography: Andrej Frolov, David Singer, and Ralf Hoffmann.

49. Induction of Heat-shock Proteins and the Proteasome System by Casein-Ne-Carboxymethyllysine and Ne-Carboxymethyllysine in CACO-2 Cells: Veronika Somoza, Karoline Schmid, Sebastian Foth, and Martin Haslbeck.

50. Reversal of Hyperglycemia-Induced Angiogenesis Deficit of Human Endothelial Cells by Overexpression of Glyoxalase I in Vitro: Usman Ahmed, Darin Dobler, Sarah Carpenter, Naila Rabbani, and Paul Thornalley.

51. Pathophysiological Role of the Glyoxalase System in Renal Hypoxic Injury: Takanori Kumagai, Masaomi Nangaku, Hideki Kato, Ichiro Kojima, Takahisa Kawakami, Daisuke Son, Julie R. Ingelfinger, Toshio Miyata, Toshiro Fujita, and Reiko Inagi.

52. A419C (E111A) Polymorphism of the Glyoxalase I Gene Is Associated with Vascular Complications in Chronic Hemodialysis Patients: Marta Kalousová, Alexandra Germanová, Marie Jáchymová, Oto Mestek, Vladimír Tesař, and Tomáš Zima.

53. Succination of Proteins by Fumarate: Mechanism of Inactivation of Glyceraldehyde-3-Phosphate Dehydrogenase in Diabetes: Matthew Blatnik, Suzanne Thorpe, and John Baynes.

54. Dietary Advanced Glycation End Products and Oxidative Stress: in Vivo Effects on Endothelial Function and Adipokines: Alin Stirban, Monica Negrean, Christian Götting, Thomas Gawlowski, Bernd Stratmann, Knut Kleesiek, and Diethelm Tschöpe.

55. Preparation of Nucleotide Advanced Glycation Endproducts: Imidazopurinone Adducts Formed by Glycation of Deoxyguanosine with Glyoxal and Methylglyoxal: Thomas Fleming, Naila Rabbani, and Paul J.Thornalley.

56. Maillard Products as Biomarkers in Cancer: Beatrice nachmeier, Andreas Nerlich, Helmut Rohrbach, Erwin Schleicher, and Ulrich Friess.

57. Glycation of Plasma Lipoprotein Lipid Membrane: Kiyotaka Nakagawa, Daigo Ibusuki, and Teruo Miyazawa.

58. Analysis of Amadori-PE in Healthy and Diabetic Plasma by LC-MS/MS: Teruo Miyazawa, Kiyotaka Nakagawa, Daigo Ibusuki, and Shin-Ichi Oikawa.

59. Nonenzymatically Glycated Lipoprotein Apo-AI in Plasma of Diabetic and Nephropathic Patients: Annunziata Lapolla, Maura Brioschi, Elena Trimoli, Chiara Cosma, Luciana Bonfante, Simone Cristoni, Roberta Seraglia, and Pietro Traldi.

60. Evaluating the Extent of Protein Damage in Dairy Products: Simultaneous Determination of Early and Advanced Glycation-induced Lysine Modifications: Thierry Delatour, René Krause, Anke Foerster, Véronique Parisod, Janique Richoz, Sarah Maurer, Jörg Hegele, Thomas Henle, and Timo Buetler.

61. A Novel Yellow Pigment, Furpipate, Derived from Lysine and Furfural: Masatsune Murata, Hana Totsuka, and Hiroshi Ono.

62. Time-dependent Component-specific Regulation of Gastric Acid Secretion-related Proteins by Roasted Coffee Constituents: Malte Rubach, Roman Lang, Thomas Hofmann, and Veronika Somoza.

63. Molecular Heterogeneity in the Maillard Reaction versus Other Nonenzymatic Reactions in Neurodegenerative Processes: Reinald Pamplona, Ekaterina Ilieva, Victoria Ayala, M. Josep Bellmunt Daniel Cacabelos, Esther Dalfo, Isidro Ferrer, and Manuel Portero-Otin.

64. Suppression of Renal a-Dicarbonyl Compounds Generated following Ureternal Obstruction by Kidney-Specific a-dicarbonyl/l-xylulose Reductase: Hiroko Odani, Jun Asami, Aiko Ishii, Kayoko Oide, Takako Sudo, Atsushi Nakamura, Noriyuki Miyata, Noboru Otsuka, Kenji Maeda, and Junichi Nakagawa.

65. Comparison of Pharmacokinetics between Highly and Mildly Modified AGE Proteins in Mice: Mime Nagai, Katsumi Mera, Yukio Fujiwara, and Ryoji Nagai.

66. Modification of Vimentin: A General Mechanism of Nonenzymatic Glycation in Human Skin: Thomas Kueper, Tilman Grune, Stefanie Prahl, Holger Lenz, Vivienne Welge, Tanja Biernoth, Yvonne Vogt, Gesa-Meike Muhr, Astrid Gaemlich, Tobias Jung, Gerrit Boemke, Hans-Peter Elsässer, Klaus-Peter Wittern, Horst Wenck, Franz Stäb, and Thomas Blatt.

Errata.

Index of Contributors

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