Analysis of the addition products of α‐tocopherol with phosphatidylcholine‐peroxyl radicals by high‐performance liquid chromatography with chemiluminescent detection

Yamauchi, Ryo; Hara, Yuji; Murase, Hironobu; Katô, Kôji

doi:10.1007/s11745-000-0658-z

Cited by 8 publications

(6 citation statements)

References 38 publications

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“…In the free radical oxidation of 1,2-dilinoleoyl PC inhibited by a hydrophilic antioxidant, Trolox, in liposomes, the ratios of 9-hydroperoxy PC (9-OOH PC) to 13-hydroperoxy PC (13-OOH PC) were constant between 0.9 and 1.3 (22). Similar symmetrical distributions of hydroperoxide isomers were obtained when α-tocopherol was added to the liposomes (23)(24)(25)(26)(27). The mechanism of this phenomenon has been explained as an easy diffusion behavior of polar peroxyl radicals from the nonpolar lipid phase to the polar interface where peroxyl radicals are trapped or terminated by a water-soluble antioxidant (24).…”

Section: Discussionsupporting

confidence: 54%

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Wang

Ushio

Ohshima

2003

Lipids

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The differences in distribution of geometric isomers of unsaturated PC hydroperoxides generated by free radical oxidation were compared, as corresponding hydroxy analogs, in heterogeneous liposomes and in a homogeneous methanol solution by using HPLC with UV detection due to the presence of conjugated dienes. Identification of fractionated peak components was carried out by GC-MS. When the oxidation of 1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine, PC(16:0/18:2), was initiated in liposomes by a hydrophilic azo radical initiator, and in a methanol solution by a hydrophobic azo radical initiator, there was no significant difference in the relative percentages of 1-palmitoyl-2-(9-hydroxy-trans-10,trans-12-octadecadienoyl)-sn-glycero-3-phosphocholine (9-t,t-OH PC) and 1-palmitoyl-2-(13-hydroxy-trans-9,trans-11-octadecadienoyl)-sn-glycero-3-phosphocholine (13-t,t-OH PC) between the PC oxidized in liposomes and in the methanol solution. For the oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine, PC(16:0/20:4), the relative percentage of 1-palmitoyl-2-(5-hydroxy-trans-6,cis-8,11,14-eicosatetraenoyl)-sn-glycero-3-phosphocholine (5-OH PC) was significantly higher (P < 0.01) than that of 1-palmitoyl-2-(15-hydroxy-cis-5,8,11,trans-13-eicosatetraenoyl)-sn-glycero-3-phosphocholine (15-OH PC) in liposomes. For the homogeneous methanol solution of PC(16:0/20:4), the relative percentage of 5-OH PC was close to that of 15-OH PC. For the PC(16:0/20:4) oxidized in bulk with added pentamethylchromanol, the individual amount of 15-OH PC, 1-palmitoyl-2-(11-hydroxy-cis-5,8,trans-12,cis-14-eicosatetraenoyl)-sn-glycero-3-phosphocholine (11-OH PC), 1-palmitoyl-2-(12-hydroxy-cis-5,8,trans-10,cis-14-eicosatetraenoyl)-sn-glycero-3-phosphocholine (12-OH PC), 1-palmitoyl-2-(8-hydroxy-cis-5,trans-9,cis-11,14-eicosatetraenoyl)-sn-glycero-3-phosphocholine (8-OH PC), 1-palmitoyl-2-(9-hydroxy-cis-5,trans-7,cis-11,14-eicosatetraenoyl)-sn-glycero-3-phosphocholine (9-OH PC), and 5-OH PC were close to each other compared to the corresponding values in liposomes and in methanol solution. The results obtained by gel permeation chromatography of the PC liposomes containing hydrophilic 2,2'-azobis-2-amidinopropane) dihydrochloride (AAPH) suggest that the AAPH added to the liposomes of PC(16:0/20:4) was partitioned into the water phase and out of the hydrophobic region of the fatty acyl moieties of the PC. These results confirm that the distance that exists in the bis-allylic carbons of the unsaturated fatty acyl moieties of PC from the interface between the hydrophilic region of PC and the water phases played an important role in influencing hydrogen abstraction to form a symmetrical distribution of hydroperoxide isomers in both the heterogeneous liposomes and the homogeneous methanol solution.

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Section: Discussionsupporting

confidence: 54%

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Wang

Ushio

Ohshima

2003

Lipids

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“…Furthermore, Miyashita et al (31) have demonstrated that oxygenation of methyl linoleate hydroperoxides yields dimers composed of octadecadienoate and octadecenoate moieties crosslinked through either ether or peroxy linkages across the 9-or 13-positions. Yamauchi et al (49) have shown the formation of α-tocopherol adducts with phosphatidylcholine peroxy radicals.…”

Section: Discussionmentioning

confidence: 99%

Formation of triacylglycerol core aldehydes during rapid oxidation of corn and sunflower oils with tert‐butyl hydroperoxide/Fe²⁺

Sjövall

Kuksis

Kallio

2002

Lipids

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The lipid ester core aldehydes formed during a rapid oxidation (7.8 M tert-butyl hydroperoxide, 90 min at 37 degrees C) of the triacylglycerols of purified corn and sunflower oils were isolated as dinitrophenylhydrazones by preparative thin-layer chromatography and identified by reversed-phase high-performance liquid chromatography with on-line electrospray ionization mass spectrometry and by reference to standards. A total of 113 species of triacylglycerol core aldehydes were specifically identified, accounting for 32-53% of the 2,4-dinitrophenylhydrazine (DNPH)-reactive material of high molecular weight representing 25-33% of the total oxidation products. The major core aldehyde species (50-60% of total triacylglycerol core aldehydes) were the mono(9-oxo)nonanoyl- and mono(12-oxo)-9,10-epoxy dodecenoyl- or (12-oxo)-9-hydroxy-10,11-dodecenoyl-diacylglycerols. A significant proportion of the total (9-oxo)nonanoyl and epoxidized (12-oxo)-9,10-dodecenoyl core aldehydes was found in complex combinations with hydroperoxy or hydroxy fatty acyl groups (6-10% of total triacylglycerol core aldehydes). Identified were also di(9-oxo)nonanoylmonoacylglycerols (0.5% of total) and tri(9-oxo)nonanoylglycerols (trace). The identification of the oxoacylglycerols was consistent with the products anticipated from tert-butyl hydroperoxide oxidation of the major species of corn and sunflower oil triacylglycerols (mainly linoleoyl esters). However, the anticipated (13-oxo)-9,11-tridecadienoyl aldehyde-containing acylglycerols were absent because of further oxidation of the dienoic core aldehyde. A significant proportion of the unsaturated triacylglycerol core aldehydes contained tert-butyl groups linked to the unsaturated fatty chains via peroxide bridges (2-9%). The study demonstrates that rapid peroxidation with tert-butyl hydroperoxide constitutes an effective method for enriching natural oils and fats in triacylglycerol core aldehydes for biochemical and metabolic testing.

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“…An HPLC-CL method was developed for the assay of α-tocopherol with phosphatidylcholine-peroxyl radicals (TOO-PC) using 2-methyl-6-phenyl-3,7-dihydroimidazo [1,2-a]pyrazin-3-one, a Cypridina luciferin analog, as the sensitive amplifier of CL produced by the iron-induced decomposition of TOO-PC under acidic conditions [109].…”

Section: Miscellaneousmentioning

confidence: 99%

Chemiluminescence detection with separation techniques for bioanalytical applications

Tsunoda

2009

Bioanal Rev

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Chemiluminescence detection is known to be a sensitive, selective, and versatile method that can be used in combination with separation techniques such as highperformance liquid chromatography, capillary electrophoresis, and chip electrophoresis. This article reviews the bioanalytical applications of a combination of chemiluminescence detection and separation techniques published in the literature between 1999 and 2008. Luminol chemiluminescene, peroxyoxalate chemiluminescence, and electrochemiluminescence have been mainly used for bioanalytical application. In this paper, only the applications of the method for the analysis of biosamples, serum, plasma, urine, and tissue samples are discussed.

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Analysis of the addition products of α‐tocopherol with phosphatidylcholine‐peroxyl radicals by high‐performance liquid chromatography with chemiluminescent detection

Cited by 8 publications

References 38 publications

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Formation of triacylglycerol core aldehydes during rapid oxidation of corn and sunflower oils with tert‐butyl hydroperoxide/Fe²⁺

Chemiluminescence detection with separation techniques for bioanalytical applications

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Analysis of the addition products of α‐tocopherol with phosphatidylcholine‐peroxyl radicals by high‐performance liquid chromatography with chemiluminescent detection

Cited by 8 publications

References 38 publications

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Distributions of hydroperoxide positional isomers generated by oxidation of 1‐palmitoyl‐2‐arachidonoyl‐sn‐glycero‐3‐phosphocholine in liposomes and in methanol solution

Formation of triacylglycerol core aldehydes during rapid oxidation of corn and sunflower oils with tert‐butyl hydroperoxide/Fe2+

Chemiluminescence detection with separation techniques for bioanalytical applications

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Product

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Formation of triacylglycerol core aldehydes during rapid oxidation of corn and sunflower oils with tert‐butyl hydroperoxide/Fe²⁺