J. Lipid Res.
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Originally published In Press as doi:10.1194/jlr.M500348-JLR200 on February 9, 2006

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Journal of Lipid Research, Vol. 47, 964-974, May 2006
Copyright © 2006 by American Society for Biochemistry and Molecular Biology

Aminophospholipid glycation and its inhibitor screening system: a new role of pyridoxal 5'-phosphate as the inhibitor

Ohki Higuchi*, Kiyotaka Nakagawa*, Tsuyoshi Tsuzuki*, Toshihide Suzuki{dagger}, Shinichi Oikawa§ and Teruo Miyazawa1,*

* Food and Biodynamic Chemistry Laboratory, Graduate School of Agricultural Science, Tohoku University, Sendai 981-8555, Japan
{dagger} Laboratory of Toxicology, Faculty of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa 199-0195, Japan
§ Department of Medicine, Nippon Medical School, Tokyo 113-8603, Japan

Published, JLR Papers in Press, February 9, 2006.

1 To whom correspondence should be addressed. e-mail: miyazawa{at}biochem.tohoku.ac.jp

Peroxidized phospholipid-mediated cytotoxity is involved in the pathophysiology of a number of diseases [i.e., the abnormal increase of phosphatidylcholine hydroperoxide (PCOOH) found in the plasma of type 2 diabetic patients]. The PCOOH accumulation may relate to Amadori-glycated phosphatidylethanolamine (deoxy-D-fructosyl PE, or Amadori-PE), because Amadori-PE causes oxidative stress. However, lipid glycation inhibitor has not been discovered yet because of the lack of a lipid glycation model useful for inhibitor screening. We optimized and developed a lipid glycation model considering various reaction conditions (glucose concentration, temperature, buffer type, and pH) between PE and glucose. Using the developed model, various protein glycation inhibitors (aminoguanidine, pyridoxamine, and carnosine), antioxidants (ascorbic acid, {alpha}-tocopherol, quercetin, and rutin), and other food compounds (L-lysine, L-cysteine, pyridoxine, pyridoxal, and pyridoxal 5'-phosphate) were evaluated for their antiglycative properties. Pyridoxal 5'-phosphate and pyridoxal (vitamin B6 derivatives) were the most effective antiglycative compounds. These pyridoxals could easily be condensed with PE before the glucose/PE reaction occurred. Because PE-pyridoxal 5'-phosphate adduct was detectable in human red blood cells and the increased plasma Amadori-PE concentration in streptozotocin-induced diabetic rats was decreased by dietary supplementation of pyridoxal 5'-phosphate, it is likely that pyridoxal 5'-phosphate acts as a lipid glycation inhibitor in vivo, which possibly contributes to diabetes prevention.

Supplementary key words lipid glycation inhibitor • phosphatidylethanolamine • diabetes

Abbreviations: AGE, advanced glycation end product; dioleoyl-PE, 1,2-di(cis-9-octadecenoyl)-sn-glycero-3-phosphoethanolamine; ELSD, evaporative light-scattering detection; LC, liquid chromatography; MRM, multiple reaction monitoring; MS, mass spectrometry; PCOOH, phosphatidylcholine hydroperoxide; PE, phosphatidylethanolamine; QTRAP LC/MS/MS, quadrupole/linear ion-trap liquid chromatography tandem mass spectrometry; RBC, red blood cell; STZ; streptozotocin


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