F 2-Dihomo-isoprostanes arise from free radical attack on adrenic acid

Journal of Lipid Research

Volumn 49, Issue 5, 2008, Pages 995-1005

  Vanrollins, Mike ^a   Woltjer, Randall L ^a   Yin, Huiyong ^b   Morrow, Jason D ^b   Montine, Thomas J ^a  

^a UNIVERSITY OF WASHINGTON   (United States)

^b VANDERBILT UNIVERSITY   (United States)

Author keywords

Alzheimer's disease brain lipids; Damage; Myelin

Indexed keywords

ADRENIC ACID; ARACHIDONIC ACID; BIOLOGICAL MARKER; F2 DIHOMO ISOPROSTANE; F4 NEURO ISOPROSTANE; FREE RADICAL; ISOPROSTANE DERIVATIVE; MYELIN; PHOSPHOLIPID; UNCLASSIFIED DRUG; ALDEHYDE; ERUCIC ACID; PROSTAGLANDIN; UNSATURATED FATTY ACID;

ADULT; AGED; ALZHEIMER DISEASE; BRAIN; CONFERENCE PAPER; CONTROLLED STUDY; FEMALE; GRAY MATTER; HUMAN; HUMAN TISSUE; IN VIVO STUDY; MALE; OXIDATION; PRIMATE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; ARTICLE; BRAIN LEVEL; CHEMISTRY; KINETICS; METABOLISM; MYELIN SHEATH;

ALDEHYDES; BRAIN; BRAIN CHEMISTRY; CEREBRUM; ERUCIC ACIDS; FATTY ACIDS, UNSATURATED; FREE RADICALS; HUMANS; ISOPROSTANES; KINETICS; MYELIN SHEATH; PHOSPHOLIPIDS; PROSTAGLANDINS;

EID: 50049106295     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M700503-JLR200     Document Type: Conference Paper

References (37)

1. Sastry, P. S. 1985. Lipids of nervous tissue: composition and metabolism. Prog. Lipid Res. 24: 69-176.
2. Montine, T. J., M. D. Neely, J. F. Quinn, M. F. Beal, W. R. Markesbery, L. J. Roberts, and J. D. Morrow. 2002. Lipid peroxidation in aging brain and Alzheimer's disease. Free Radio. Biol. Med. 33: 620-626.
3. Montine, T.J., K. S. Montine, W. McMahan, W. R. Markesbery, J. F. Quinn, and J. D. Morrow. 2005. F2-isoprostanes in Alzheimer and other neurodegenerative diseases. Antioxid. Redox Signal. 7: 269-275.
4. Pratico, D. 2002. Alzheimer's disease and oxygen radicals: new insights. Biochem. Pharmacol. 63: 563-567.
5. Roberts, L. J., 2nd, T. J. Montine, W. R. Markesbery, A. R. Tapper, P. Hardy, S. Chemtob, W. D. Dettbarn, and J. D. Morrow. 1998. Formation of isoprostane-like compounds (neuroprostanes) in vivo from docosahexaenoic acid. J. Biol. Chem. 273: 13605-13612.
6. Back, S. A., N. L. Luo, R. A. Mallinson, J. P. O'Malley, L. D. Wallen, B. Frei, J. D. Morrow, C. K. Petito, C. T. Roberts, Jr., G. H. Murdoch, et al. 2005. Selective vulnerability of preterm white matter to oxidative damage defined by F2-isoprostanes. Ann. Neurol. 58: 108-120.
7. Bartzokis, G. 2004. Age-related myelin breakdown: a developmental model ofcognitive decline and Alzheimer's disease. Neurobiol. Aging. 25: 5-18.
8. Skinner, E. R., C. Watt, J. A. Besson, and P. V. Best. 1993. Differences in the fatty acid composition of the grey and white matter of different regions of the brains of patients with Alzheimer's disease and control subjects. Brain. 116: 717-725.
9. Han, X., D. M. Holtzman, and D. W. McKeel,Jr. 2001. Plasmalogen deficiency in early Alzheimer's disease subjects and in animal models: molecular characterization using electrospray ionization mass spectrometry. J. Neurochem. 77: 1168-1180.
10. Nourooz-Zadeh, J., B. Halliwell, and E. E. Anggard. 1997. Evidence for the formation of F3-isoprostanes during peroxidation of eicosapentaenoic acid. Biochem. Biophys. Res. Commun. 236: 467-472.
11. Milatovic, D., M. VanRollins, K. Li, K. S. Montine, and T. J. Montine. 2005. Suppression of murine cerebral F2-isoprostanes and F4-neuroprostanes from excitotoxicity and innate immune response in vivo by alpha- or gamma-tocopherol. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 827: 88-93.
12. Musiek, E. S., J. K. Cha, H. Yin, W. E. Zackert, E. S. Terry, N. A. Porter, T. J. Montine, and J. D. Morrow. 2004. Quantification of F-ring isoprostane-like compounds (F4-neuroprostanes) derived from docosahexaenoic acid in vivo in humans by a stable isotope dilution mass spectrometric assay. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 799: 95-102.
13. Pace-Asciak, C., and L. S. Wolfe. 1971. N-Butylboronate derivatives of the F prostaglandins. Resolution of prostaglandins of the E and F series by gas-liquid chromatography. J. Chromatogr. 56: 129-133.
14. Nourooz-Zadeh, J., E. H. Liu, B. Yhlen, E. E. Anggard, and B. Halliwell. 1999. F4-isoprostanes as specific markers of docosahexaenoic acid peroxidation in Alzheimer's disease. J. Neurochem. 72: 734-740.
15. Norton, W. T. 1974. Isolation of myelin from nerve tissue. Methods Enzymol. 31: 435-444.
16. The National Institute on Aging and Reagan Institute Working Group on Diagnostic Criteria for the Neuropathological Assessment of Alzheimer's Disease. 1997 Consensus recommendations for the postmortem diagnosis of Alzheimer's disease. Neurobiol. Aging. 18 (Suppl.): S1-2.
17. Laemmli, U. K. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227: 680-685.
18. Wang, Q., R. L. Woltjer, P. J. Cimino, C. Pan, K. S. Montine, J. Zhang, and T. J. Montine. 2005. Proteomic analysis of neurofibril-lary tangles in Alzheimer disease identifies GAPDH as a detergent-insoluble paired helical filament tau binding protein. FASEB J. 19: 869-871.
19. Moriguchi, T., S. Y. Lim, R. Greiner, W. Lefkowitz, J. Loewke, J. Hoshiba, and N. Salem, Jr. 2004. Effects of an n-3-deficient diet on brain, retina, and liver fatty acyl composition in artificially reared rats. J. Lipid Res. 45: 1437-1445.
20. Lepage, G., and C. C. Roy. 1984. Improved recovery of fatty acid through direct transesterification without prior extraction or purification. J. Lipid Res. 25: 1391-1396.
21. Masood, A., K. D. Stark, and N. Salem, Jr. 2005. A simplified and efficient method for the analysis of fatty acid methyl esters suitable for large clinical studies. J. Lipid Res. 46: 2299-2305.
22. Ways, P., and D. J. Hanahan. 1964. Characterization and quantification of red cell lipids in normal man. J. Lipid Res. 5: 318-328.
23. rd edition. Oily Press, Bridgewater, England.
24. Rouser, G., G. Kritchevsky, and A. Yamamoto. 1967. Column chromatographic and associated procedures for separation and determination of phosphatides and glycolipids. In Lipid Chroma-tographic Analysis. G. V. Marinetti, editor. M. Dekker, New York. 99-162.
25. Nourooz-Zadeh, J., E. H. Liu, E. Anggard, and B. Halliwell. 1998. F4-isoprostanes: a novel class of prostanoids formed during peroxidation of docosahexaenoic acid (DHA). Biochem. Biophys. Res. Commun. 242: 338-344.
26. Morrow, J. D., K. E. Hill, R. F. Burk, T. M. Nammour, K. F. Badr, and L. J. Roberts, 2nd. 1990. A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism. Proc. Natl. Acad. Sci. USA. 87: 9383-9387.
27. Yin, H., and N. A. Porter. 2005. New insights regarding the autoxidation of polyunsaturated fatty acids. Antioxid. Redox Signal. 7: 170-184.
28. Yin, H., N. A. Porter, and J. D. Morrow. 2005. Separation and identification of F2-isoprostane regioisomers and diastereomers by novel liquid chromatographic/mass spectrometric methods. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 827: 157-164.
29. Yin, H., J. D. Morrow, and N. A. Porter. 2004. Identification of a novel class of endoperoxides from arachidonate autoxidation. J. Biol. Chem. 279: 3766-3776.
30. Morell, P., and R. H. Quarles. 1999. Myelin formation, structure and biochemistry. In Basic Neurochemistry. G. J. Siegel, editor. Lippincott, Williams & Wilkins, Philadelphia, PA. 69-94.
31. Lepage, G., and C. C. Roy. 1986. Direct transesterification of all classes of lipids in a one-step reaction. J. Lipid Res. 27: 114-120.
32. Svennerholm, L. 1968. Distribution and fatty acid composition of phosphoglycerides in normal human brain. J. Lipid Res. 9: 570-579.
33. Yanagihara, T., and J. N. Cumings. 1969. Alterations of phospho-lipids, particularly plasmalogens, in the demyelination of multiple sclerosis as compared with that ofcerebral oedema. Brain. 92: 59-70.
34. Horrocks, L. A. 1972. Content, composition, and metabolism of mammalian and avian lipid that contain ether groups. In Ether Lipids. F. Snyder, editor. Academic Press, New York. 177-272.
35. Stahl, R., O. Dietrich, S. J. Teipel, H. Hampel, M. F. Reiser, and S. O. Schoenberg. 2007. White matter damage in Alzheimer disease and mild cognitive impairment: assessment with diffusion-tensor MR imaging and parallel imaging techniques. Radiology. 243: 483-492.
36. Sprecher, H., M. VanRollins, F. Sun, A. Wyche, and P. Needleman. 1982. Dihomo-prostaglandins and -thromboxane. A prostaglandin family from adrenic acid that may be preferentially synthesized inthe kidney. J. Biol. Chem. 257: 3912-3918.
37. VanRollins, M., L. Horrocks, and H. Sprecher. 1985. Metabolism of 7,10,13,16-docosatetraenoic acid to dihomo-thromboxane, 14-hydroxy-7,10,12- nonadecatrienoic acid and hydroxy fatty acids by human platelets. Biochim. Biophys. Acta. 833: 272-280.