Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
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

PubMed Disclaimer

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

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Halliwell BG. Free Radicals in Biology and Medicine. 3rd. Oxford University Press; New York: 1999.
    1. Yin H, Porter NA. Antioxid Redox Signal. 2005;7:170. - PubMed
    1. Morrow JD, Awad JA, Boss HJ, Blair IA, Roberts LJ. Proc Natl Acad Sci USA. 1992;89:10721. - PMC - PubMed
    1. Morrow JD, Hill E, Burk RF, Nammour TM, Badr KF, Roberts LJ., Jr Proc Natl Acad Sci USA. 1990;87:9383. - PMC - PubMed
    1. Kadiiska MB, Gladen BC, Baird DD, Germolec D, Graham LB, Parker CE, Nyska A, Wachsman JT, Ames BN, Basu S, Brot N, FitzGerald GA, Floyd RA, George M, Heinecke JW, Hatch GE, Hensley K, Lawson JA, Marnett LJ, Morrow JD, Murray DM, Plastaras J, R LJ, II, Rokach J, Shigenaga MK, Sohal RS, Sun J, Tice RR, Thiel DHV, Wellner D, Walter PB, Tome KB, Mason RP, Barrett JC. Free Radic Biol Med. 2005;38:698. - PubMed

Publication types