TY - JOUR
T1 - Ubichromanol
T2 - A prodrug to support mitochondrial ubiquinone functions?
AU - Gille, Lars
AU - Stamberg, Werner
AU - Gregor, Wolfgang
AU - Jäger, Walter
AU - Reznicek, Gottfried
AU - Netscher, Thomas
AU - Rosenau, Thomas
AU - Nohl, Hans
PY - 2008/1/1
Y1 - 2008/1/1
N2 - 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.
AB - 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.
KW - Antioxidant
KW - Cytochrome bc complex
KW - Mitochondria
KW - Ubichromanol
KW - Ubichromenol
KW - Ubiquinone metabolites
UR - http://www.scopus.com/inward/record.url?scp=58149377635&partnerID=8YFLogxK
U2 - 10.1002/biof.5520320110
DO - 10.1002/biof.5520320110
M3 - Article
C2 - 19096103
AN - SCOPUS:58149377635
SN - 0951-6433
VL - 32
SP - 83
EP - 90
JO - BioFactors
JF - BioFactors
IS - 1-4
ER -