F₂-Isoprostanes in HDL are bound to neutral lipids and phospholipids

References

• Gordon T, Castelli WP, Hjortland MC, Kannel WB, Dawber TR. High density lipoprotein as a protective factor against coronary heart disease. The Framingham Study. Am J Med 1977;62:707–714.
   PubMed Web of Science ®Google Scholar
• Miller M, Seidler A, Kwiterovich PO, Pearson TA. Long-term predictors of subsequent cardiovascular events with coronary artery disease and 'desirable' levels of plasma total cholesterol. Circulation 1992;86:1165–1170.
   PubMed Web of Science ®Google Scholar
• Barter P, Gotto AM, LaRosa JC, Maroni J, Szarek M, Grundy SM, et al. HDL cholesterol, very low levels of LDL cholesterol, and cardiovascular events. N Engl J Med 2007;357:1301–1310.
   PubMed Web of Science ®Google Scholar
• Barter PJ, Caulfield M, Eriksson M, Grundy SM, Kastelein JJ, Komajda M, et al. Effects of torcetrapib in patients at high risk for coronary events. N Engl J Med 2007;357:2109–2122.
   PubMed Web of Science ®Google Scholar
• Boden WE, Probstfield JL, Anderson T, Chaitman BR, Desvignes-Nickens P, Koprowicz K, et al. Niacin in patients with low HDL cholesterol levels receiving intensive statin therapy. N Engl J Med 2011;365:2255–2267.
   PubMed Web of Science ®Google Scholar
• Schwartz GG, Olsson AG, Abt M, Ballantyne CM, Barter PJ, Brumm J, et al. Effects of dalcetrapib in patients with a recent acute coronary syndrome. N Engl J Med 2012;367:2089–2099.
   PubMed Web of Science ®Google Scholar
• Rached FH, Chapman MJ, Kontush A. HDL particle subpopulations: focus on biological function. Biofactors 2015;41:67–77.
   PubMed Web of Science ®Google Scholar
• Duffy D, Rader DJ. Emerging therapies targeting high-density lipoprotein metabolism and reverse cholesterol transport. Circulation 2006;113:1140–1150.
   PubMed Web of Science ®Google Scholar
• Navab M, Hama SY, Anantharamaiah GM, Hassan K, Hough GP, Watson AD, et al. Normal high density lipoprotein inhibits three steps in the formation of mildly oxidized low density lipoprotein: steps 2 and 3. J Lipid Res 2000;41:1495–1508.
   PubMed Web of Science ®Google Scholar
• Barter PJ, Nicholls S, Rye KA, Anantharamaiah GM, Navab M, Fogelman AM. Antiinflammatory properties of HDL. Circ Res 2004;95:764–772.
   PubMed Web of Science ®Google Scholar
• Camont L, Lhomme M, Rached F, Le Goff W, Nègre-Salvayre A, Salvayre R, et al. Small, dense high-density lipoprotein-3 particles are enriched in negatively charged phospholipids: relevance to cellular cholesterol efflux, antioxidative, antithrombotic, anti-inflammatory, and antiapoptotic functionalities. Arterioscler Thromb Vasc Biol 2013;33:2715–2723.
   PubMed Web of Science ®Google Scholar
• Du X, Kim MJ, Hou L, Le Goff W, Chapman MJ, van Eck M, et al. HDL particle size is a critical determinant of ABCA1-mediated macrophage cellular cholesterol export. Circ Res 2015;116:1133–1142.
   PubMed Web of Science ®Google Scholar
• Proudfoot JM, Barden AE, Loke WM, Croft KD, Puddey IB, Mori TA. HDL is the major lipoprotein carrier of plasma F2-isoprostanes. J Lipid Res 2009;50:716–722.
   PubMed Web of Science ®Google Scholar
• Morrow JD, Hill KD, Burk RF, Nammour TM, Badr KF, Roberts LJ. 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 1990;87:9383–9387.
   PubMed Web of Science ®Google Scholar
• Morrow JD, Awad JA, Boss HJ, Blair IA, Roberts LJ. Non-cyclooxygenase-derived prostanoids (F2-isoprostanes) are formed in situ on phospholipids. Proc Natl Acad Sci USA 1992;89:10721–10725.
   PubMed Web of Science ®Google Scholar
• Ahmed Z, Ravandi A, Maguire GF, Emili A, Draganov D, La Du BN, et al. Apolipoprotein A-I promotes the formation of phosphatidylcholine core aldehydes that are hydrolyzed by paraoxonase (PON-1) during high density lipoprotein oxidation with a peroxynitrite donor. J Biol Chem 2001;276:24473–24481.
   PubMed Web of Science ®Google Scholar
• Ahmed Z, Ravandi A, Maguire GF, Emili A, Draganov D, La Du BN, et al. Multiple substrates for paraoxonase-1 during oxidation of phosphatidylcholine by peroxynitrite. Biochem Biophys Res Commun 2002;290:391–396.
   PubMed Web of Science ®Google Scholar
• Mori TA, Croft KD, Puddey IB, Beilin LJ. An improved method for the measurement of urinary and plasma F2-isoprostanes using gas chromatography-mass spectrometry. Anal Biochem 1999;268:117–125.
   PubMed Web of Science ®Google Scholar
• Oger C, Brinkmann Y, Bouazzaoui S, Durand T, Galano JM. Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework. Org Lett 2008;10:5087–5090.
   PubMed Web of Science ®Google Scholar
• Kaburagi Y, Kishi Y. Operationally simple and efficient workup procedure for TBAF-mediated desilylation: application to halichondrin synthesis. Org Lett 2007;9:723–726.
   PubMed Web of Science ®Google Scholar
• Longmire AW, Swift LL, Roberts LJ, Awad JA, Burk RF, Morrow JD. Effect of oxygen tension on the generation of F2-isoprostanes and malondialdehyde in peroxidizing rat liver microsomes. Biochem Pharmacol 1994;47:1173–1177.
   PubMed Web of Science ®Google Scholar
• Folch J, Lees M, Sloane Stanley GH. A simple method for the isolation and purification of total lipides from animal tissues. J Biol Chem 1957;226:497–509.
   PubMed Web of Science ®Google Scholar
• Agren JJ, Julkunen A, Penttila I. Rapid separation of serum lipids for fatty acid analysis by a single aminopropyl column. J Lipid Res 1992;33:1871–1876.
   PubMed Web of Science ®Google Scholar
• Kontush A, Lindahl M, Lhomme M, Calabresi L, Chapman MJ, Davidson WS. Structure of HDL: particle subclasses and molecular components. Handb Exp Pharmacol 2015;224:3–51.
   PubMedGoogle Scholar
• Amigó N, Mallol R, Heras M, Martínez-Hervás S, Blanco-Vaca F, Escolà-Gil JC, et al. Lipoprotein hydrophobic core lipids are partially extruded to surface in smaller HDL: ’Herniated’ HDL, a common feature in diabetes. Sci Rep 2016;6:19249.
   PubMed Web of Science ®Google Scholar
• Vieu C, Jaspard B, Barbaras R, Manent J, Chap H, Perret B, Collet X. Identification and quantification of diacylglycerols in HDL and accessibility to lipase. J Lipid Res 1996;37:1153–1161.
   PubMed Web of Science ®Google Scholar
• Wiesner P, Leidl K, Boettcher A, Schmitz G, Liebisch G. Lipid profiling of FPLC-separated lipoprotein fractions by electrospray ionization tandem mass spectrometry. J Lipid Res 2009;50:574–585.
   PubMed Web of Science ®Google Scholar
• Ståhlman M, Fagerberg B, Adiels M, Ekroos K, Chapman JM, Kontush A, Borén J. Dyslipidemia, but not hyperglycemia and insulin resistance, is associated with marked alterations in the HDL lipidome in type 2 diabetic subjects in the DIWA cohort: impact on small HDL particles. Biochim Biophys Acta 2013;1831:1609–1617.
   PubMed Web of Science ®Google Scholar
• Barden AE, Mas E, Croft KD, Phillips M, Mori TA. Minimizing artifactual elevation of lipid peroxidation products (F2-isoprostanes) in plasma during collection and storage. Anal Biochem 2014;449:129–131.
   PubMed Web of Science ®Google Scholar
• Rasmiena AA, Barlow CK, Ng TW, Tull D, Meikle PJ. High density lipoprotein efficiently accepts surface but not internal oxidised lipids from oxidised low density lipoprotein. Biochim Biophys Acta 2016;1861:69–77.
   PubMed Web of Science ®Google Scholar
• Christison JK, Rye KA, Stocker R. Exchange of oxidized cholesteryl linoleate between LDL and HDL mediated by cholesteryl ester transfer protein. J Lipid Res 1995;36:2017–2026.
   PubMed Web of Science ®Google Scholar
• Zerrad-Saadi A, Therond P, Chantepie S, Couturier M, Rye KA, Chapman MJ, Kontush A. HDL3-mediated inactivation of LDL-associated phospholipid hydroperoxides is determined by the redox status of apolipoprotein A-I and HDL particle surface lipid rigidity: relevance to inflammation and atherogenesis. Arterioscler Thromb Vasc Biol 2009;29:2169–2175.
   PubMed Web of Science ®Google Scholar