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Literature DB >> 19499908

Synthesis and antioxidant properties of an unnatural plasmalogen analogue bearing a trans O-vinyl ether linkage.

Ravi S Lankalapalli¹, Joseph T Eckelkamp, Debajit Sircar, David A Ford, Papasani V Subbaiah, Robert Bittman.

Abstract

To assess the antioxidant behavior of trans-1, we first synthesized trans-allyl ether 4 by opening an (S)-glycidol derivative with an (E)-alk-2-en-ol, and then produced the unnatural E-enol ether 1 by a stereoselective iridium(I)-catalyzed olefin isomerization. Natural cis-1 was preferentially degraded by HOCl and was more protective than trans-1 against lipid peroxidation induced by a free-radical initiator, demonstrating that the geometry of the 1'-alkenyloxy bond participates in the antioxidant defensive role of 1.

Entities: Chemical Disease Gene Species

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Year: 2009 PMID： 19499908 PMCID： PMC2741175 DOI： 10.1021/ol9009078

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

33 in total

Review 1. Plasmalogens: biosynthesis and functions.

Authors: N Nagan; R A Zoeller
Journal: Prog Lipid Res Date: 2001-05 Impact factor: 16.195

2. Reactive chlorinating species produced by myeloperoxidase target the vinyl ether bond of plasmalogens: identification of 2-chlorohexadecanal.

Authors: C J Albert; J R Crowley; F F Hsu; A K Thukkani; D A Ford
Journal: J Biol Chem Date: 2001-04-11 Impact factor: 5.157

3. Reactive chlorinating species produced during neutrophil activation target tissue plasmalogens: production of the chemoattractant, 2-chlorohexadecanal.

Authors: Arun K Thukkani; Fong-Fu Hsu; Jan R Crowley; Robert B Wysolmerski; Carolyn J Albert; David A Ford
Journal: J Biol Chem Date: 2001-11-27 Impact factor: 5.157

Review 4. A critical overview of the chemistry of copper-dependent low density lipoprotein oxidation: roles of lipid hydroperoxides, alpha-tocopherol, thiols, and ceruloplasmin.

Authors: M J Burkitt
Journal: Arch Biochem Biophys Date: 2001-10-01 Impact factor: 4.013

5. Inhibition of peroxyl radical-mediated lipid oxidation by plasmalogen phospholipids and alpha-tocopherol.

Authors: D Hahnel; K Beyer; B Engelmann
Journal: Free Radic Biol Med Date: 1999-11 Impact factor: 7.376

6. Plasmalogen degradation by oxidative stress: production and disappearance of specific fatty aldehydes and fatty alpha-hydroxyaldehydes.

Authors: S Stadelmann-Ingrand; S Favreliere; B Fauconneau; G Mauco; C Tallineau
Journal: Free Radic Biol Med Date: 2001-11-15 Impact factor: 7.376

7. Myeloperoxidase-derived reactive chlorinating species from human monocytes target plasmalogens in low density lipoprotein.

Authors: Arun K Thukkani; Carolyn J Albert; Kristin R Wildsmith; Maria C Messner; Bradley D Martinson; Fong-Fu Hsu; David A Ford
Journal: J Biol Chem Date: 2003-07-17 Impact factor: 5.157

8. Identification of alpha-chloro fatty aldehydes and unsaturated lysophosphatidylcholine molecular species in human atherosclerotic lesions.

Authors: Arun K Thukkani; Jane McHowat; Fong-Fu Hsu; Marie-Luise Brennan; Stanley L Hazen; David A Ford
Journal: Circulation Date: 2003-11-24 Impact factor: 29.690

9. Ethanolamine plasmalogens prevent the oxidation of cholesterol by reducing the oxidizability of cholesterol in phospholipid bilayers.

Authors: Ryouta Maeba; Nobuo Ueta
Journal: J Lipid Res Date: 2003-01 Impact factor: 5.922