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Review
. 2011 Oct 12;111(10):5973-96.
doi: 10.1021/cr200160h. Epub 2011 Aug 18.

Isoprostane generation and function

Ginger L Milne  1 , Huiyong Yin, Klarissa D Hardy, Sean S Davies, L Jackson Roberts 2nd
Affiliations
Review

Isoprostane generation and function

Ginger L Milne et al. Chem Rev. .
No abstract available

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Figures

Figure 1
Figure 1
Structures of polyunsaturated fatty acids that have been shown to generate isoprostane-like compounds.
Figure 2
Figure 2
Oxidation of arachidonic acid via free radical-catalyzed peroxidation can yield a number of isoprostanes with varying ring structures.
Figure 3
Figure 3
Mechanism of formation of F2-isoprostanes from the free radical-initiated peroxidation of arachidonic acid.
Figure 4
Figure 4
Dioxolane-isoprostanes are generated from 8-series and 12-series isoprostanes but not from 5-series and 15-series isoprostanes.
Figure 5
Figure 5
Structures of isotopically-labeled internal standards typically used to quantify F2-isoprostanes.
Figure 6
Figure 6
Urinary metabolites of 15-F2t-IsoP. Note: Glucuronide could conjugate with any of the three hydroxyl groups on 15-F2t-IsoP. Additionally, it is possible that multiple glucuronides could conjugate with 15-F2t-IsoP. As the exact glucuronide species generated have not been characterized, the current structure is shown for simplicity.
Figure 7
Figure 7
The major urinary metabolite of 15-A2t-IsoP identified in the rat.
Figure 8
Figure 8
15-deoxy-Δ,-PGJ2 can be formed from cyclooxygenase-derived PGD2 as well as from the non-enzymatic free radical-catalyzed peroxidation of arachidonic acid.
Figure 9
Figure 9
Multiple 15-d-PGJ2 regioisomers can be generated during free radical-catalyzed peroxidation of arachidonic acid.
Figure 10
Figure 10
Four different regioisomers of E2/D2-isoketals are be generated from isoprostane bicycloendoperoxides.
Figure 11
Figure 11
Reaction of γ-ketoaldehydes with primary amines yields formation of stable adducts.
Figure 12
Figure 12
Structures of γ-ketoaldehyde scavengers.
Figure 13
Figure 13
Mechanism of formation of isofurans compared to the mechanism of formation of F2-isoprostanes.
Figure 14
Figure 14
Formation of epoxy-isoprostanes esterified in phosphatidylcholine.
Figure 15
Figure 15
Chemical strategies to characterize epoxy-isoprostane-PC.
Figure 16
Figure 16
F-ring isoprostanes from arachidonic acid, docosahexaenoic acid, adrenic acid, and eicosapentaenoic acid.
See this image and copyright information in PMC

References

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