Active oxygen chemistry within the liposomal bilayer: Part III: Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer

Michal Afri; Benjamin Ehrenberg; Yeshayahu Talmon; Judith Schmidt; Yael Cohen; Aryeh A. Frimer

doi:10.1016/j.chemphyslip.2004.04.007

Active oxygen chemistry within the liposomal bilayer: Part III: Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer

Michal Afri, Benjamin Ehrenberg, Yeshayahu Talmon, Judith Schmidt, Yael Cohen, Aryeh A. Frimer

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87 Scopus citations

Abstract

We have previously shown that the location and orientation of compounds intercalated within the lipid bilayer can be qualitatively determined using an NMR chemical shift-polarity correlation. We describe herein the results of our application of this method to analogs of Vitamin E, ubiquinol and ubiquinone. The results indicate that tocopherol - and presumably the corresponding tocopheroxyl radical - reside adjacent to the interface, and can, therefore, abstract a hydrogen atom from ascorbic acid. On the other hand, the decaprenyl substituted ubiquinol and ubiquinone lie substantially deeper within the lipid membrane. Yet, contrary to the prevailing literature, their location is far from being the same. Ubiquinone-10 is situated above the long-chain fatty acid "slab". Ubiquinol-10 dwells well within the lipid slab, presumably out of "striking range" of Vitamin C. Nevertheless, ubiquinol can act as an antioxidant by reducing C- or O-centered lipid radicals or by recycling the lipid-resident tocopheroxyl radical.

Original language	English
Pages (from-to)	107-121
Number of pages	15
Journal	Chemistry and Physics of Lipids
Volume	131
Issue number	1
DOIs	https://doi.org/10.1016/j.chemphyslip.2004.04.007
State	Published - Aug 2004

Bibliographical note

Funding Information:
We would like to acknowledge the kind and generous support of The Israel Science Foundation (Grants Nos. 588/98 and 327/02) and The Ethel and David Resnick Chair in Active Oxygen Chemistry. This paper is based in part on the Ph.D. Thesis of Michal Afri at Bar-Ilan University ( Afri, 2001 ).

Funding

We would like to acknowledge the kind and generous support of The Israel Science Foundation (Grants Nos. 588/98 and 327/02) and The Ethel and David Resnick Chair in Active Oxygen Chemistry. This paper is based in part on the Ph.D. Thesis of Michal Afri at Bar-Ilan University ( Afri, 2001 ).

Funders	Funder number
Israel Science Foundation	327/02, 588/98

Keywords

Lipid bilayer
Liposomes
Membranes
NMR
Tocopheroxyl radical
Ubiquinol
Ubiquinone
Vitamin C
α-Tocopherol

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10.1016/j.chemphyslip.2004.04.007

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title = "Active oxygen chemistry within the liposomal bilayer: Part III: Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer",

abstract = "We have previously shown that the location and orientation of compounds intercalated within the lipid bilayer can be qualitatively determined using an NMR chemical shift-polarity correlation. We describe herein the results of our application of this method to analogs of Vitamin E, ubiquinol and ubiquinone. The results indicate that tocopherol - and presumably the corresponding tocopheroxyl radical - reside adjacent to the interface, and can, therefore, abstract a hydrogen atom from ascorbic acid. On the other hand, the decaprenyl substituted ubiquinol and ubiquinone lie substantially deeper within the lipid membrane. Yet, contrary to the prevailing literature, their location is far from being the same. Ubiquinone-10 is situated above the long-chain fatty acid {"}slab{"}. Ubiquinol-10 dwells well within the lipid slab, presumably out of {"}striking range{"} of Vitamin C. Nevertheless, ubiquinol can act as an antioxidant by reducing C- or O-centered lipid radicals or by recycling the lipid-resident tocopheroxyl radical.",

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Active oxygen chemistry within the liposomal bilayer: Part III: Locating Vitamin E, ubiquinol and ubiquinone and their derivatives in the lipid bilayer

Abstract

Bibliographical note

Funding

Keywords

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