Rapid formation of 4-hydroxy-2-nonenal, malondialdehyde, and phosphatidylcholine aldehyde from phospholipid hydroperoxide by hemoproteins

Hayashi, Takaaki; Uchida, Koji; Takebe, Gen; Takahashi, Kazuhiko

doi:10.1016/j.freeradbiomed.2004.01.006

Cited by 18 publications

(17 citation statements)

References 28 publications

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“…The reaction of one of the phospholipid hydroperoxides, PLPC-OOH, with hemoprotein has demonstrated the rapid formation of HNE (18). Reaction of ferric ion with PLPC-OOH is very slow and no HNE formation has been observed (18).…”

Section: Discussionmentioning

confidence: 99%

“…Human Aβ and Aβ were purchased from Peptide Institute Inc. (Osaka, Japan); Aβ 1-28 , 1-palmitoyl-2-(13-hydroperoxy-cis-9, trans-11-octadecadienoyl) phosphatidylcholine (PLPC-OOH) was prepared from PLPC as described previously (18,32,33). Other chemicals were of the highest quality commercially available.…”

Section: Methodsmentioning

confidence: 99%

“…The HPLC conditions for the determination of HNE were described previously (18). An ODS column (5μm, 4.6 × 250mm, TSK ODS-80Ts, Tosoh Co., Tokyo, Japan) was used.…”

Section: Determination Of Phospholipid Hydroperoxides and Hnementioning

confidence: 99%

“…The UV peaks were monitored at 222 nm, the absorption maximum of HNE. The chemiluminescence detection-high performance liquid chromatography (CL-HPLC) conditions for the determination of PLPC-OOH were described previously (18). An ODS column (5μm, 4.6 × 250mm, TSK ODS-80Ts, Tosoh Co., Tokyo, Japan) was used.…”

Section: Determination Of Phospholipid Hydroperoxides and Hnementioning

confidence: 99%

“…The formation of HNE has been demonstrated by the reaction of one of the phospholipid hydroperoxides, 1-palmitoyl-2-(13-hydroperoxy-cis-9, trans-11-octadecadienoyl) phosphatidylcholine (PLPC-OOH), with hemoprotein (18). Lipid hydroperoxides are generally known to be degraded by transition metal ions and is known that Aβ shows a strong affinity for transition metal ions, especially Cu 2+ such that Aβ is assumed to bind with Cu 2+ physiologically (19)(20)(21)(22)(23).…”

Section: Introductionmentioning

confidence: 99%

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Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-β peptide

Hayashi

Takahashi‐Shishido

Nakayama

et al. 2007

Free Radical Biology and Medicine

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Abstract-The lipid peroxidation product 4-hydroxy-2-nonenal (HNE) is proposed to be a toxic factor in the pathogenesis of Alzheimer's disease. The primary products of lipid peroxidation are phospholipid hydroperoxides and degraded reactive aldehydes, such as HNE, as secondary peroxidation products. In this study, we investigated the role of amyloid-β peptide (Aβ) in the formation of phospholipid hydroperoxides and HNE by copper ion bound to Aβ. The Aβ 1-42 -Cu 2+ (1:1 molar ratio) complex showed an activity to form phospholipid hydroperoxides from phospholipid, 1-palmitoyl-2-linoleoyl phosphatidylcholine (PLPC), through Cu 2+ reduction in the presence of ascorbic acid. The phospholipid hydroperoxides were considered to be racemic mixture of 9-hydroperoxide and 13-hydroperoxide of linoleoyl residue. When Cu 2+ was bound to two molar equivalents of Aβ 1-42 (2 Aβ 1-42 -Cu 2+ ), lipid peroxidation was inhibited.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The HPLC conditions for the determination of HNE were described previously (18). An ODS column (5μm, 4.6 × 250mm, TSK ODS-80Ts, Tosoh Co., Tokyo, Japan) was used.…”

Section: Determination Of Phospholipid Hydroperoxides and Hnementioning

confidence: 99%

Section: Determination Of Phospholipid Hydroperoxides and Hnementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-β peptide

Hayashi

Takahashi‐Shishido

Nakayama

et al. 2007

Free Radical Biology and Medicine

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Dietary advanced lipid oxidation endproducts are risk factors to human health

Kanner¹

2007

Molecular Nutrition Food Res

334

252

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Lipid oxidation in foods is one of the major degradative processes responsible for losses in food quality. The oxidation of unsaturated fatty acids results in significant generation of dietary advanced lipid oxidation endproducts (ALEs) which are in part cytotoxic and genotoxic compounds. The gastrointestinal tract is constantly exposed to dietary oxidized food compounds, after digestion a part of them are absorbed into the lymph or directly into the blood stream. After ingestion of oxidized fats animals and human have been shown to excrete in urine increase amounts of malondialdehyde but also lipophilic carbonyl compounds. Oxidized cholesterol in the diet was found to be a source of oxidized lipoproteins in human serum. Some of the dietary ALEs, which are absorbed from the gut to the circulatory system, seems to act as injurious chemicals that activate an inflammatory response which affects not only circulatory system but also organs such as liver, kidney, lung, and the gut itself. We believe that repeated consumption of oxidized fat in the diet poses a chronic threat to human health. High concentration of dietary antioxidants could prevent lipid oxidation and ALEs generation not only in foods but also in stomach condition and thereby potentially decrease absorption of ALEs from the gut. This could explains the health benefit of diets containing large amounts of dietary antioxidants such those present in fruits and vegetables, or products such as red-wine or tea consuming during the meal.

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Effect of Oxidized Phosphatidylcholine on Biomarkers of Oxidative Stress in Rats

Al-Orf

2011

Ind J Clin Biochem

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In this study it was planned to investigate the effect of oxidized phosphatidylcholine (derived from egg) feeding on lipid peroxidation of different tissues in rats. Male Wistar albino rats were fed oxidized and unoxidized phosphatidylcholine for 2 and 4 weeks, respectively. During the period of study food intake and body weights of animals increased gradually. Animals fed oxidized phosphatidylcholine for 2 and 4 weeks showed 33 and 15% spontaneous hemolysis of red blood cells in vitro. Under identical experimental conditions animals given unoxidized phosphatidylcholine showed 14.5 and 13.4% hemolysis for 2 and 4 week's period, respectively. Thiobarbituric acid reactive substances (TBARS) level in thymus, spleen, kidney, heart, liver and lung significantly increased in rats given oxidized phosphatidylcholine as compared to unoxidized group. Furthermore, in oxidized phosphatidylcholine group TBARS values in kidney, liver and lungs continued to rise for 4 weeks of treatment while TBARS level in heart, spleen and thymus was found to be decreased at the end of 4 weeks of oxidized phosphatidylcholine feeding. Plasma triacylglycerol and cholesterol was found to increase in rats who had received oxidized phosphatidylcholine for 2 weeks. These findings suggest that excess and persistent intake of oxidized phosphatidylcholine can cause significant damage to organs.

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Rapid formation of 4-hydroxy-2-nonenal, malondialdehyde, and phosphatidylcholine aldehyde from phospholipid hydroperoxide by hemoproteins

Cited by 18 publications

References 28 publications

Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-β peptide

Lipid peroxidation and 4-hydroxy-2-nonenal formation by copper ion bound to amyloid-β peptide

Dietary advanced lipid oxidation endproducts are risk factors to human health

Effect of Oxidized Phosphatidylcholine on Biomarkers of Oxidative Stress in Rats

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