Ubichromanol: A prodrug to support mitochondrial ubiquinone functions?

Lars Gille, Werner Stamberg, Wolfgang Gregor, Walter Jäger, Gottfried Reznicek, Thomas Netscher, Thomas Rosenau, Hans Nohl

Veröffentlichungen: Beitrag in FachzeitschriftArtikelPeer Reviewed

Abstract

Ubichromanol-9 (UCa9, with a side chain consisting of nine isoprene units) is a reductive cyclization product of ubiquinone-10 (UQ 10). It acts as a radical scavenging antioxidant and is about half as effective as α-tocopherol. Already decades ago its one-electron oxidation product, the ubichromanoxyl radical had been identified. However, nothing was known so far about the two-electron oxidation product of this antioxidant and its bioactivity. This study proves that ubichromanol can be oxidized to a ubiquinone-like compound with a hydroxyl-substituted side chain (UQ 10OH), a metabolite that is naturally present in bovine liver mitochondria. The bioactivity of this ubiquinone derivative in its reduced form as substrate for mitochondrial complex III (cytochrome bc1 complex) was slightly below that of native ubiquinol, but significantly higher than that of reduced α-tocopheryl quinone. Since ubiquinone-like molecules (UQ 10OH, UQ10) were identified as oxidation products of UCa9 during lipid peroxidation, this ubiquinone derivative could provide a possibility to combine antioxidant properties of chromanols and bioenergetic benefits of UQ10.

OriginalspracheEnglisch
Seiten (von - bis)83-90
Seitenumfang8
FachzeitschriftBioFactors
Jahrgang32
Ausgabenummer1-4
DOIs
PublikationsstatusVeröffentlicht - 1 Jan. 2008

ÖFOS 2012

  • 301207 Pharmazeutische Chemie

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