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 Jun 24;16(7):5333-48.
doi: 10.3390/molecules16075333.

Generation and detection of levuglandins and isolevuglandins in vitro and in vivo

Ming Zhang  1 , Wei Li, Tao Li
Affiliations
Review

Generation and detection of levuglandins and isolevuglandins in vitro and in vivo

Ming Zhang et al. Molecules. .

Abstract

Levuglandins (LGs) and isolevuglandins (isoLGs), formed by rearrangement of endoperoxide intermediates generated through the cyclooxygenase and free radical induced oxidation of polyunsaturated fatty acids (PUFAs), are extraordinarily reactive, forming covalent adducts incorporating protein lysyl ε-amino groups. Because they accumulate, these adducts provide a dosimeter of oxidative injury. This review provides an updated and comprehensive overview of the generation of LG/isoLG in vitro and in vivo and the detection methods for the adducts of LG/isoLG and biological molecules in vivo.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Decomposition of PGH2: Generation of levuglandins, anhydrolevuglandins and Δ9-levuglandins.
Scheme 2
Scheme 2
Generation of isolevuglandins and isolevuglandin-protein adducts during free radical oxidation of AA and AA-esters.
Scheme 3
Scheme 3
F4-C22-isoprostane and C22-isolevuglandin (11-isoLGE4) generation from nonenzymatic peroxidation of docosahexaenoic acid (DHA).
Scheme 4
Scheme 4
MS/MS fragmentation of isolevuglandin-derived lysyl lactams.
See this image and copyright information in PMC

References

    1. Ames B.N. Dietary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science. 1983;221:1256–1264. doi: 10.1126/science.6351251. - DOI - PubMed
    1. Montine T.J., Neely M.D., Quinn J.F., Beal M.F., Markesbery W.R., Roberts L.J., Morrow J.D. Lipid peroxidation in aging brain and Alzheimer’s disease. Free Radic. Biol. Med. 2002;33:620–626. doi: 10.1016/S0891-5849(02)00807-9. - DOI - PubMed
    1. Smith M.A., Perry G., Richey P.L., Sayre L.M., Anderson V.E., Beal M.F., Kowall N. Oxidative damage in Alzheimer’s. Nature. 1996;382:120–121. doi: 10.1038/382120b0. - DOI - PubMed
    1. Davies S.S., Amarnath V., Montine K.S., Bernoud-Hubac N., Boutaud O., Montine T.J., Roberts L.J., 2nd Effects of reactive gamma-ketoaldehydes formed by the isoprostane pathway (isoketals) and cyclooxygenase pathway (levuglandins) on proteasome function. FASEB J. 2002;16:715–717. doi: 10.1096/fj.01-0696fje. - DOI - PubMed
    1. Amarnath V., Valentine W.M., Amarnath K., Eng M.A., Graham D.G. The mechanism of nucleophilic substitution of alkylpyrroles in the presence of oxygen. Chem. Res. Toxicol. 1994;7:56–61. doi: 10.1021/tx00037a008. - DOI - PubMed

LinkOut - more resources