Ion-trap tandem mass spectrometric analysis of Amadori-glycated phosphatidylethanolamine in human plasma with or without diabetes

Nakagawa, Kiyotaka; Oak, Jeong Ho; Higuchi, Ohki; Tsuzuki, Toshio; Oikawa, Shinichi; Otani, Haruhisa; Mune, Masatoshi; Cai, Hua; Miyazawa, Teruo

doi:10.1194/jlr.d500025-jlr200

Cited by 64 publications

(81 citation statements)

References 39 publications

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“…It was reported that pyridoxal 59-phosphate suppresses tumor growth (35) and that pyridoxamine prevents protein glycation (AGE formation) (28). Thus, the biological role and chemopreventive effect of vitamin B 6 have attracted considerable attention. In this study, PEpyridoxal 59-phosphate adduct was detectable in human RBCs (Figs.…”

Section: Discussionmentioning

confidence: 99%

“…This instrument is based on a triple-quadrupole ion path in which the final quadrupole can be used as a hybrid quadrupole/linear ion trap mass spectrometer (6).…”

Section: Analysis Of Pe-pyridoxal 59-phosphate Adductmentioning

confidence: 99%

“…Therefore, it is likely that PE is exposed to glycation under hyperglycemic conditions, yielding Amadori-PE in vivo. Amadori-PE causes oxidative stress (i.e., PCOOH) (5,6), leading to a disorder of cellular integrity (i.e., angiogenesis stimulation) (8). Amadori-PE and PCOOH could play a role in the development of diabetes.…”

mentioning

confidence: 99%

“…The glycated lipid was identified as an Amadori product of phosphatidylethanolamine (deoxy-D-fructosyl phosphatidylethanolamine, or Amadori-PE) ( Fig. 1) by LC online with hybrid quadrupole/linear ion-trap mass spectrometry (QTRAP LC/MS/MS) (5,6). Amadori-PE generates reactive oxygen species and thereby triggers lipid peroxidation (7).…”

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confidence: 99%

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

Higuchi

Nakagawa

Tsuzuki

et al. 2006

Journal of Lipid Research

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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 Amadoriglycated 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, atocopherol, quercetin, and rutin), and other food compounds (L-lysine, L-cysteine, pyridoxine, pyridoxal, and pyridoxal 59-phosphate) were evaluated for their antiglycative properties. Pyridoxal 59-phosphate and pyridoxal (vitamin B 6 derivatives) were the most effective antiglycative compounds. These pyridoxals could easily be condensed with PE before the glucose/ PE reaction occurred. Because PE-pyridoxal 59-phosphate adduct was detectable in human red blood cells and the increased plasma Amadori-PE concentration in streptozotocininduced diabetic rats was decreased by dietary supplementation of pyridoxal 59-phosphate, it is likely that pyridoxal 59-phosphate acts as a lipid glycation inhibitor in vivo, which possibly contributes to diabetes prevention.-Higuchi, O., K. Nakagawa, T. Tsuzuki, T. Suzuki, S. Oikawa, and T. Miyazawa. Aminophospholipid glycation and its inhibitor screening system: a new role of pyridoxal 59-phosphate as the inhibitor. Lipid peroxidation plays a role in the pathophysiology of atherogenesis, diabetes, aging, and other conditions (1). To determine lipid hydroperoxides as a primary oxidation product, we established a chemiluminescence detectionliquid chromatography (LC) method (2). Using this method, it was confirmed that plasma phosphatidylcholine hydroperoxide (PCOOH) abnormally increases in hyperlipidemic (3) and in type 2 diabetic (4) patients. Hence, we hypothesized that PCOOH-mediated cytotoxity is closely involved in the pathophysiology of these diseases.Recently, while investigating why PCOOH increases in diabetic plasma, we found that diabetic plasma contained an abnormal amount of glycated lipid. The glycated lipid was identified as an Amadori product of phosphatidylethanolamine (deoxy-D-fructosyl phosphatidylethanolamine, or Amadori-PE) (Fig. 1) by LC online with hybrid quadrupole/linear ion-trap mass spectrometry (QTRAP LC/MS/MS) (5, 6). Amadori-PE generates reactive oxygen species and thereby triggers lipid peroxidation (7). Therefore, it is likely that PE is exposed to glycation under hyperglycemic conditions, yielding Amadori-PE in vivo. Amadori-PE causes oxidative stress (i.e., PCOOH) (5, 6), leading to a disorder of cellular integrit...

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Section: Discussionmentioning

confidence: 99%

“…This instrument is based on a triple-quadrupole ion path in which the final quadrupole can be used as a hybrid quadrupole/linear ion trap mass spectrometer (6).…”

Section: Analysis Of Pe-pyridoxal 59-phosphate Adductmentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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

Higuchi

Nakagawa

Tsuzuki

et al. 2006

Journal of Lipid Research

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“…A recently developed QTRAP MS/MS offers specifi c benefi ts ( 18 ) for biomolecular analysis including lipid molecules ( 7,19,20 ). The QTRAP MS/MS allows product ion scanning, NLS, and MRM, providing useful structural information of the analytes even in the presence of background contaminants in complex biological materials.…”

Section: Discussionmentioning

confidence: 99%

LC-MS/MS analysis of carboxymethylated and carboxyethylated phosphatidylethanolamines in human erythrocytes and blood plasma

Shoji

Nakagawa

Asai

et al. 2010

Journal of Lipid Research

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Mass Spectrometry

2024

Analytical Chemistry

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Ion-trap tandem mass spectrometric analysis of Amadori-glycated phosphatidylethanolamine in human plasma with or without diabetes

Cited by 64 publications

References 39 publications

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

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

LC-MS/MS analysis of carboxymethylated and carboxyethylated phosphatidylethanolamines in human erythrocytes and blood plasma

Mass Spectrometry

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