Comparison of Formation of D2/E2-Isoprostanes and F2-Isoprostanesin Vitroandin Vivo— Effects of Oxygen Tension and Glutathione

Morrow, Jason D.; Roberts, L. Jackson; Daniel, Vincent C.; Awad, Joseph; Mirochnitchenko, Oleg; Swift, Larry L.; Burk, Raymond F.

doi:10.1006/abbi.1998.0645

Cited by 76 publications

(56 citation statements)

References 35 publications

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“…The presented structure of the ion with m/z = 189 is also consistent with published data ( 39 ). In addition, PGE 2 standards labeled with deuterium at 17,17,18,18,19,19,20,20,20 (PGE 2 d 9 ) or at 3, 3, 4, 4 (PGE 2 d 4 ) positions were used to confi rm the pathway for an ion with m/z 189 generation from PGE 2 . Upon PGE 2 d 9 collision, the ion with m/z = 189.5 was predominant over the 198.5 ion, whereas PGE 2 d 4 produced mainly 193.5 rather than 189.5 product ions, thereby confi rming the loss of side chain from PGE 2 -end (data not shown).…”

Section: Selection Of Ms/ms Mass Transitionsupporting

confidence: 81%

“…As indicated in Fig. 6 , entPGE 2 and PGE 2 were generated in equal quantities (48.4 ± 3.5% and 51.7 ± 3.7%, respectively, n = 3), which is consistent with the presence of esterifi ed isoPG onto PL ( 13,19,20 ). However, in brains subjected to ischemia followed by microwave irradiation, PGE 2 mass was signifi cantly higher as compared with ent-PGE 2 ( Fig.…”

Section: Pge 2 and Entpge 2 Determination In Brain Tissuesupporting

confidence: 78%

“…Because PGE 2 and entPGE 2 are produced in equal quantities through free radical oxidation of 20:4n-6 ( 13,19,20 ), but only PGE 2 is the major product of COX1/2 dependent pathway, the determination of PGE 2 /entPGE 2 ratio might be important in determining PGE 2 origin in biological samples. However, the LC/MS/ MS methods used to date do not allow for separation of PGE 2 and entPGE 2 without derivatization and multiple HPLC separations ( 13,19,20 ). PGE 2 and entPGE 2 were not resolved on nonchiral HPLC even when the best conditions for the other isoPGE 2 separation were used (Luna C18(2) column eluted with acetonitrile/water/0.1% formic acid gradient).…”

Section: Chiral Chromatography For Pge 2 and Entpge 2 Separationmentioning

confidence: 99%

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LC/MS/MS method for analysis of E2 series prostaglandins and isoprostanes

Brose

Thuen

Golovko

2011

Journal of Lipid Research

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Section: Selection Of Ms/ms Mass Transitionsupporting

confidence: 81%

Section: Pge 2 and Entpge 2 Determination In Brain Tissuesupporting

confidence: 78%

Section: Chiral Chromatography For Pge 2 and Entpge 2 Separationmentioning

confidence: 99%

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LC/MS/MS method for analysis of E2 series prostaglandins and isoprostanes

Brose

Thuen

Golovko

2011

Journal of Lipid Research

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“…In addition, these findings support the notion that quantification of A 4 /J 4 -NPs may be a more sensitive indicator of DHA oxidation and neural tissue oxidative stress than other classes of NPs. Factors that may influence the formation of A/J-ring NPs over other NPs are not known, although we have shown previously (26) that agents such as GSH and other thiols reduce IsoP endoperoxide intermediates resulting in generation of F 2 -IsoPs over E 2 /D 2 -IsoPs. It might thus be predicted that the presence of reducing substances would analogously decrease cyclopentenone eicosanoid formation, although this issue has not been explored.…”

Section: Discussionmentioning

confidence: 97%

“…3). Esterified A 4 /J 4 -NPs in phospholipids were hydrolyzed using chemical saponification with potassium hydroxide (26), following treatment with methoxyamine HCl in chloroform/methanol 2:1 for 1 h at room temperature. Purification was performed as for free A 4 /J 4 -NPs, and levels of A 4 /J 4 -NPs were then quantified by GC/MS.…”

Section: Methodsmentioning

confidence: 99%

Formation of Highly Reactive A-ring and J-ring Isoprostane-like Compounds (A4/J4-neuroprostanes) in Vivo from Docosahexaenoic Acid

Fam

Murphey

Terry

et al. 2002

Journal of Biological Chemistry

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Free radical-initiated oxidant injury and lipid peroxidation have been implicated in a number of neural disorders. Docosahexaenoic acid is the most abundant unsaturated fatty acid in the central nervous system. We have shown previously that this 22-carbon fatty acid can yield, upon oxidation, isoprostane-like compounds termed neuroprostanes, with E/D-type prostane rings (E 4 /D 4 -neuroprostanes). Eicosanoids with E/D-type prostane rings are unstable and dehydrate to cyclopentenone-containing compounds possessing A-type and J-type prostane rings, respectively. We thus explored whether cyclopentenone neuroprostanes (A 4 /J 4 -neuroprostanes) are formed from the dehydration of E 4 /D 4 -neuroprostanes. Indeed, oxidation of docosahexaenoic acid in vitro increased levels of putative A 4 /J 4 -neuroprostanes 64-fold from 88 ؎ 43 to 5463 ؎ 2579 ng/mg docosahexaenoic acid. Chemical approaches and liquid chromatography/electrospray ionization tandem mass spectrometry definitively identified them as A 4 /J 4 -neuroprostanes. We subsequently showed these compounds are formed in significant amounts from a biological source, rat brain synaptosomes. A 4 /J 4 -neuroprostanes increased 13-fold, from a basal level of 89 ؎ 72 ng/mg protein to 1187 ؎ 217 ng/mg (n ‫؍‬ 4), upon oxidation. We also detected these compounds in very large amounts in fresh brain tissue from rats at levels of 97 ؎ 25 ng/g brain tissue (n ‫؍‬ 3) and from humans at levels of 98 ؎ 26 ng/g brain tissue (n ‫؍‬ 5), quantities that are nearly an order of magnitude higher than other classes of neuroprostanes. Because of the fact that A 4 /J 4 -neuroprostanes contain highly reactive cyclopentenone ring structures, it would be predicted that they readily undergo Michael addition with glutathione and adduct covalently to proteins. Indeed, incubation of A 4 /J 4 -neuroprostanes in vitro with excess glutathione resulted in the formation of large amounts of adducts. Thus, these studies have identified novel, highly reactive A/J-ring isoprostanelike compounds that are derived from docosahexaenoic acid in vivo.

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Measurement of Isoprostanes as Markers of Oxidative Stress in Neuronal Tissue

Milatović

Aschner

2009

CP Toxicology

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Oxidative stress is implicated in the pathogenesis of a variety of human diseases, including neurodegenerative disease, atherosclerosis and cancer, as well as progressive and even normal aging processes. Increased generation of free radicals derived primarily from molecular oxygen has also been associated with neuronal damage induced by a variety of environmental agents. However, measuring oxidative stress in biological systems is complex and requires accurate quantification of either free radicals or damaged biomolecules. One method to quantify oxidative injury is to measure lipid peroxidation. Lipids are readily attacked by free radicals, resulting in the formation of a number of peroxidation products. F 2 -isoprostanes (F 2 -IsoPs) are one group of these compounds, which are derived by the free radical peroxidation of arachidonic acid (AA). The F 2 -IsoPs, prostaglandine F 2 -like compounds, have been shown as the most accurate measure of oxidative damage in vivo. This review summarizes current methodology used to quantify F 2 -IsoPs and discusses the utility of these and other prostaglandine (PG)-like compounds as in vivo biomarkers of oxidative stress in neuronal tissues.

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Comparison of Formation of D2/E2-Isoprostanes and F2-Isoprostanesin Vitroandin Vivo— Effects of Oxygen Tension and Glutathione

Cited by 76 publications

References 35 publications

LC/MS/MS method for analysis of E2 series prostaglandins and isoprostanes

LC/MS/MS method for analysis of E2 series prostaglandins and isoprostanes

Formation of Highly Reactive A-ring and J-ring Isoprostane-like Compounds (A4/J4-neuroprostanes) in Vivo from Docosahexaenoic Acid

Measurement of Isoprostanes as Markers of Oxidative Stress in Neuronal Tissue

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