Correlation between the potency of flavonoids for cytochrome c reduction and inhibition of cardiolipin-induced peroxidase activity.
There are large differences between flavonoids to protect against apoptosis, a process in which cytochrome c (Cyt c) plays a key role. In this work, we show that 7 of 13 flavonoids studied have a capacity to reduce Cyt c similar or higher than ascorbate, the flavonols quercetin, kaempferol and myricetin, flavanol epigallocatechin-gallate, anthocyanidins cyanidin and malvidin, and the flavone luteolin. In contrast, the kaempferol 3(O)- and 3,4'(O)-methylated forms, the flavanone naringenin, and also apigenin and chrysin, had a negligible reducing capacity. Equilibrium dialysis and quenching of 1,6-diphenyl-1,3,5-hexatriene fluorescence experiments showed that flavonoids did not interfere with Cyt c binding to cardiolipin (CL)/phosphatidylcholine (PC) vesicles. However, the CL-induced loss of Cyt c Soret band intensity was largely attenuated by flavonoids, pointing out a stabilizing action against Cyt c unfolding in the complex. Moreover, flavonoids that behave as Cyt c reductants also inhibited the pro-apoptotic CL-induced peroxidase activity of Cyt c, indicating that modulation of Cyt c signaling are probable mechanisms behind the protective biological activities of flavonoids. © 2016 BioFactors, 43(3):451-468, 2017.
ESTG, Polytechnic Institute of Leiria, Morro do Lena, Alto do Vieiro, Leiria, 2411-901, Portugal.|Department of Biochemistry and Molecular Biology, Faculty of Sciences, University of Extremadura, Avenida de Elvas s/n, Badajoz, 06006, Spain.
Ricardo
http://orcid.org/0000-0003-2375-6612
R
Lagoa
Department of Biochemistry and Molecular Biology, Faculty of Sciences, University of Extremadura, Avenida de Elvas s/n, Badajoz, 06006, Spain.
Alejandro K
AK
Samhan-Arias
Department of Biochemistry and Molecular Biology, Faculty of Sciences, University of Extremadura, Avenida de Elvas s/n, Badajoz, 06006, Spain.
Carlos
C
Gutierrez-Merino
D000818:Animals; D000872:Anthocyanins / Q000737:chemistry; D001205:Ascorbic Acid / Q000737:chemistry; D002308:Cardiolipins / Q000737:chemistry*; D002392:Catechin / Q000031:analogs & derivatives / Q000737:chemistry; D045304:Cytochromes c / Q000737:chemistry*; D004161:Diphenylhexatriene; D005419:Flavonoids / Q000737:chemistry*; D005456:Fluorescent Dyes; D006736:Horses; D044949:Kaempferols / Q000737:chemistry; D047311:Luteolin / Q000737:chemistry; D010084:Oxidation-Reduction; D010544:Peroxidases / Q000037:antagonists & inhibitors / Q000737:chemistry*; D010713:Phosphatidylcholines / Q000737:chemistry; D011485:Protein Binding; D011487:Protein Conformation; D011794:Quercetin / Q000737:chemistry; D019163:Reducing Agents / Q000737:chemistry*; D013050:Spectrometry, Fluorescence; D055672:Static Electricity; D053835:Unilamellar Liposomes / Q000737:chemistry*
D000872:Anthocyanins; D002308:Cardiolipins; D005419:Flavonoids; D005456:Fluorescent Dyes; D044949:Kaempferols; D010713:Phosphatidylcholines; D019163:Reducing Agents; D053835:Unilamellar Liposomes; C065861:malvidin; D004161:Diphenylhexatriene; C006552:kaempferol; C040015:myricetin; C017154:cyanidin; D002392:Catechin; D045304:Cytochromes c; D011794:Quercetin; C045651:epigallocatechin gallate; D010544:Peroxidases; D047311:Luteolin; D001205:Ascorbic Acid
antioxidants; flavonoids; metalloproteins; mitochondria; oxidative stress