Effect of arylthiolated 2,3-dimethoxy-1,4-benzoquinones on respiratory activity and lipid peroxidation in bovine heart mitochondria.
A series of arylthiolated 2,3-dimethoxy-1,4-benzoquinones was synthesized and tested for the effect on the respiratory system and the lipid peroxidation in bovine heart mitochondria (BHM). These quinones showed intense inhibitory activities on the respiratory system in BHM. Their inhibitory activity in the succinate oxidase system was greater than that in the NADH oxidase system. No difference between the difference spectra, with and without these quinones, of the reduced minus oxidized forms of cytochromes (cyt.) suggested that these quinones inhibit at the site after cyt. a+a3 in the respiratory chain. Moreover, these quinones were as efficient as exogenous ubiquinone-10 (UQ-10) for the inhibition of lipid peroxidation. 5- And 5,6-di-arylthio groups on the quinone ring were found to be favorable for inhibition of the respiratory system and lipid peroxidation. Our results suggest that arylthiolated 2,3-dimethoxy-1,4-benzoquinones act as antioxidants by increasing the amount of endogenous reduced UQ-10 in BHM.
Mori
K
K
Faculty of Pharmaceutical Sciences, Kobe-Gakuin University, Kobe, Japan.
Ushio
T
T
Okamoto
T
T
Kishi
T
T
Sayo
H
H
D000818:Animals; D016227:Benzoquinones / Q000494:pharmacology*; D002417:Cattle; D004579:Electron Transport / Q000187:drug effects; D015227:Lipid Peroxidation / Q000187:drug effects*; D008929:Mitochondria, Heart / Q000187:drug effects* / Q000201:enzymology / Q000378:metabolism; D009097:Multienzyme Complexes / Q000378:metabolism; D009247:NADH, NADPH Oxidoreductases / Q000378:metabolism; D010088:Oxidoreductases / Q000378:metabolism; D014451:Ubiquinone / Q000494:pharmacology
D016227:Benzoquinones; D009097:Multienzyme Complexes; D014451:Ubiquinone; C004532:quinone; D010088:Oxidoreductases; C022691:succinate oxidase; C023107:NADH oxidase; D009247:NADH, NADPH Oxidoreductases; C025204:Ubiquinone Q2