ANNALS OF THE NEW YORK ACADEMY OF SCIENCES Valume 1126

The Maillard Reaction Recent Advances in Food and Biom.edical Sciences

Edited by ERWIN SCHLEICHER, VERONIKA SOMOZA,

AND

PET ER SCHIEBERLE

Published by Blackwell Publishing on behalf of the Neu' lork Acaden~v Boston, Massachusetts 2008

of Seienefs

ANNALS OF THE NEW YORK ACADEMY OF SCIENCES

Volume 1126 April 2008

The Maillard Reaction Recent Advances in Food and Biorn.edical Sciences Editors ERWIN SCHLEICHER, VERONIKA SOMOZA, AND PETER SCHIEBERLE

This volume is the result of the 9th International SYDlposhuIl on the Maillard Reaction, held September 1-5, 2007 in Munieh, Germany.

CONTENTS Preface. By Erwin Schleicher, Veronika Somoza, and Peter Schieb erle

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Part I. Keynote Papers

The Sense ofSmell: Reception ofFlavors. ßy H. Breer ... " .................. . Receptor far Advanced Glycation End Products: Fundamental Roles in thc Inflammatory Response: Winding the Way to the Pathogenesis of Endothelial Dysfunction and Atherosclerosis. By Ravichandran Ramasamy, Shi Fang Yan, Kevan Herold, Raphael Clynes, and Ann Marie Schmidt ................. Central Nervous System Regulation ofEnergy Metabolism: Ghrelin versus Leptin. By Ruben Nogueiras, Matthias H. Tschöp, andJeffrey M. Zigman .. Determination of .N'-(Carboxymethyl)lysine in Foods and Related Systems. By Jennifer M. Ames . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

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Part 11. Plenary Lectures

Food Anoxia and the Formation of Either Flavar ar Toxic Compounds by Amino Acid Degradation Initiated by Oxidized Lipids. ßy FranciscoJ. Hidalgo and Rosario Zamora ........... , ......... " ....................... " . .. . . . . Post-Schiff Base Chemistry ofthe Maillard Reaction: Mechanism ofImine Isomerization. By Fong Lam Chu and Varoujan A. Yaylayan .............. vii

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Annals of the New York Academy of Sciences

Usefulness of Antibodics for E\'alliating thc Biological Significancc oL\(; Es, l!r Ryoji Nagai, Yukio Fuji\\'ara, Kat~lImi ~1~Ta, ~eita. ~l.()t(}ml.lra: . Yasunori Iwao, Keiichiro TsUrllShlllla, ~ IlllH' :\ agal, KaZlIlllJ'O Ltkco. Makiko Yoshitomi, ~Iasaki Otagiri, allel 'lSlIyoshi Ikcela ., . , , , .. , ....... , , . Receptor for Advanceel Glycation End Proeluct E~pressi()n in Experimental Diabetic Retinopathy. ß.r Vumei "'ang, Franziska \U!11 HagcIL Frederick Pfister, Angelika Bicrhaus, Vuxi Feng, Rcinholel Gans, ami Hans-Peter Hammes .................................................. . Advanced Glvcation End Product Homcostasis: Exogenous Oxielants ancl Innate Defenses: By Helen Vlassara, jaime Cribarri, \\'cijing Cai, ami Gar) Strikcr Formation 1Iechanisms of11elanoidins and Fluoresccnt P\Tielinilim Compollnds as Aelvanced Glycation End Products. ß.)' Fumitaka H~l)asc, Tcrll)lIki Csui, Yoriyuki Ono, Yoshinobu Shirahashi, Tomomi '\lachida, Takashi lto, Nozomu Nishitani, Kazuhito Shimohira, and Hirohito "'atanahc , ........ . Advanced Glycation as a Basis for ünelcrstanding Retinal Aging anel :'\()nill\'as~\'(' Risk Preeliction. By Anna 11. Pawlak, joscphine V GlcllJl, Jalllcs R. Ikattw, johnJ McGarvey, and Alan W. Stitt .................................... . The Aroma Siele of the Maillard Reaction. l!Ji Christoph (:(TJlY ............... . Methylglyoxal: Its Presence in Bcvcrages anel Potcnt ial SCa\·cJlgcrs. 1!J' Di TlIl, Yu Wang, Chih-Yu Lo, Shengmin Sang, ami Chi-Tang Ho ............... . The RAGE Pathway: Activation and PcrpctuatioJl ill thc Pat!Jogcllcsis of Dialwtic Neuropathy. By Ivan K. Lukic, Per ~L Humpert, Peter l~ Nawroth, ami Angelika Bierhaus .................................................... . The Role of the Amadori Product in the Complications of Diabetes. ß.r Vincent M. Monnier, David R. SeIl, Zhenyu Dai, Ina Nemet, Francois Collard, andJianye Zhang .................................... . Mitigation Strategies to Reduce Acrylamide Formation in Fried Potato Products. By Francisco Morales, Edoardo Capuano, and Vincenzo Fogliano ......... . Therapeutic Interruption of Advanced Glycation in Diabetic Nephropathy: Do All Roads Lead to Rome? By Karly C. Sourris,josephine M. Forbes, and Mark E. Cooper ...................................................... . The Other Side ofthe Maillard Reaction. By Ram H. Nagaraj, Ashis Bis\vas, Antonia Miller, Tomoko Oya-Ito, and Manjunatha Bhat ................. . Dicarbonyls Stimulate Cellular Protection Systems in Primary Rat Hepatocytes and Show Anti-inftammatory Properties. By Timo M. Buetlcr, HeIia Latado, Alexandra Baumeyer, and Thierry Delatour ............................ . N-terminal Glycation of Proteins and Peptides in Foods and in Vivo: Evaluation of N-(2-Furoylmethyl)Valine in Acid Hydrolyzates ofHuman Hemoglobin. By Ilka Penndorf, Changhao Li, Uwe Schwarzenbolz, and Thomas Henle ..... The Dicar?onyl ~rot~ome: Proteins Susceptible to Dicarbonyl Glycation at FunctlOnal Sltes 111 Health, Aging, and Disease. By Naila Rabbani and Paul]. Thornalley .................................................... . Peroxyl R~dicals A~e Essential Reagents in the Oxidation Steps of the Maillard ReactlOn Lead111g to Generation of Advanced Glycation End Products. By Gerhard Spiteller ..................................................... . Applica~ion. of Mass Spectrometry for the Detection of Glycation and OXldatlOn Products in Milk Proteins. By Jasmin Meltretter and Monika Pischetsrieder ................................................. .

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Contents

Inhibition of Advanced Glycation End Products: An Implicit Goal in Clinical Medicine for the Treatment ofDiabctic Nephropathy? By Toshio Miyata and Yuko Izuhara . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Inflammation and thc Rcdox-sensitive AGE-RAGE Pathway as a Therapeutic Target in Alzheimer's Disease. By Annette Maczurek, Kirubakaran Shanmugam, and Gerald Münch . . . . . . . . . . . . . . . . . . . . . . . . . . .

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Part IH. Oral Presentations

Some Natural Compounds Enhance .JVE-(Carboxymethyl)lysine Formation. By Yukio Fujiwara, Naoko Kiyota, Keita Motomura, Katsumi .Mera, Motohiro Takeya, Tsuyoshi Ikeda, and Ryoji Nagai .......... '" . . . .. .. . . . Immunological Detection of NW-(Carboxymethyl)arginine by a Spccific Antibody. By ~atsum~ Mera, Yukio Fujiwara, Masaki Otagiri, Noriyuki Sakata, and RYOJI Nagal ........................................................... Isolation and Partial Characterization of Four Fluorophores Formed by Nonenzymatic Browning ofMethylglyoxal and Glutamine-derivcd Ammonia. By Celine Niquet, Serge Pilard, David Mathiron, and FredericJ. Tcssicr Receptor for Advanced Glycation End Product Polymorphisms and Type 2 Diabetes: The CODAM Study. By Katrien HJ. Gacns, CarlaJ.H. van der Kallen, Marleen MJ. van Greevenbroek, EdithJ. Feskens, Coen D.A. Stehouwcr, and Casper G. Schalkwijk . . . . . . . . . . . . . . . . . . . . . . . . . Pentosidine Effects on Human Osteoblasts in Vitra. By Roberta Sanguineti, Daniela Storace, Fiammetta Monacelli, Alberto Federici, and Patrizio Odetti . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Strategy for the Study ofthe Hcalth Impact ofDietary ~1aillard Products in Clinical Studies: The Example of the ICARE Clinical Study on Healthy Adults. By Philippe Pouillart, Helene Mauprivez, Lamia Ait-Ameur, Amelie Cayzeelc,Jean-Michel Lecerf, FredcricJ. Tessier, and 1. Birloucz-Aragon . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Plasma Conccntration and Urinary Excretion of.JVE-(Carboxymt'thyl)lysine in Breast Milk-- and Formula-fC:d Infants. By Katarina Sebekova, GiscHc Saavedra, Cornelia Zumpe, Veronika Somoza, Kristina KlenovicsO\'a, and Ines Birlouez-Aragon .............................................. Maillard Rcaction Products in the Escherichia coli-derived Therapeutic Protein Interferon Alfacon-l. By Roumyana ~1ironova, Angelina Sredovska, Ivan Ivanov, and Toshimitsu Niwa ...................................... Acrolein Induccs Inflammatory Response Underlying Endothelial Dysfunction: A Risk Faetor for Atherosclerosis. By Yong Seek Park and Naoyuki Taniguchi .................................................... Oxidative Stress and Advanced Glycation in Diabetic Nephropathy. 1!J1 Melinda T. Coughlan, Amy L. Mibus, andJosephine M. Forbes . . . . . . . . . . . . Vitamin C-mediatcd Maillard Reaction in the Lens Probed in a Transgenic-mouse Model. By Xingjun -Fan and Vincent M. Monnic'}' . . . . . . . .JVE-(Carboxymethyl)lysine during the Early Development ofHypcrtension. ~)I Marcus Baumann, Coen Stehouwcr,Jcan Scheijen, Uwe Hccmann, Harry Struijker Boudier, and Casper Schalkwijk . . . . . . . . . . . . . . . . . . . . . . . . . .

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Annals of the New York Academy of Sciences

Aging, Diabetes, and Renal Failurc Catalyzc thl' Oxicl,~tioll of Ly~yl Rcsiclucs to 2-Aminoadipic Acid in Human Skin (:ol!agen: Enc\cllcc for :"\letal-catalyzcd Oxidation Mediated bv a-Dicarbonds. 1$)' Dm'id R. SclL Christophcr :"\1. Strauch, Wei Shen, and Vincent :"\1.\10,lnicr ............................ a-Dicarbonyl Compounds--Key Intermediates for the Formation of . Carbohvdrate-based ~lelanoidins. B), Lothar \\'. Kroh, Thorsten Frecller. and Janine Wagner ................... ~ . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . Approaches to Wine Aroma: Cl Transfer du ring the Reaction bet\\een Diacetyl and Cysteine. By John Almy and Gilles dl' Revel . . . . . . . . . . . . . . . . . . . . . . . . .. Antioxidant Activity and Chemical Properties of Crude and Fractionated Maillard Reaction Products Derived from Four Sugar-Amino Acid :"\laillard Reaction Model Systems. By Xiu-~Iin Chen and Da\'id D. Kitts ........... Advanced Glycation Endproducts in Chronic Hcart Failure. l~)' Andries.J. Smit, Jasper W L. Hartog, Adriaan A. Voors, and Dirk.J. van Vclclhuiscn ........ Methylglyoxal and Methylglyoxal-argininc Adducts Do l'\O( Dircctly Inhibit Endothelial Nitric Oxide Synthase. I~y Olaf Brouwcrs, Tom Tccrlink, Jan van Bezu, Rob Barto, Coen D.A. StchOUWlT, ,md Caspcr G Schalkwijk ............................................................ Kinetic Study ofthe Reaction ofGlycolalckhyck with Two (;I~Ta(ion 'Lu'ge( Models. By Miquel Adrover, Bartolomt'· Vilanov