Inhibition of amyloid fibrillation of lysozyme by phenolic compounds involves quinoprotein formation.
Numerous phenolic compounds have been reported to have an inhibitory role on amyloid formation of proteins. The present study, utilizing lysozyme as a model system, examined the anti-amyloidogenic effects of phenol and three diphenol epimers. The results indicated that catechol and hydroquinone dose-dependently inhibited lysozyme fibrillation and covalently bound to the peptide chains to form quinoproteins, showing a similar effect to benzoquinone. In contrast, phenol and resorcinol did not modify the peptide with a quinone moiety, showing no effect on lysozyme fibrillation. We suggest that quinone intermediates are the active form for a phenolic compound to inhibit lysozyme fibrillation. The modification of lysozyme with quinone moieties alters the interacting forces between peptide chains and consequently interrupts the process of lysozyme fibrillation.
Key Laboratory of Analytical Chemistry for Life Science of Shaanxi Province, College of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062, China.
Shuang
S
Feng
Xiu-Huan
XH
Song
Cheng-Ming
CM
Zeng
D000682:Amyloid / Q000037:antagonists & inhibitors / Q000378:metabolism* / Q000648:ultrastructure; D016227:Benzoquinones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002396:Catechols / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004591:Electrophoresis, Polyacrylamide Gel; D006873:Hydroquinones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D007700:Kinetics; D046529:Microscopy, Electron, Transmission; D015394:Molecular Structure; D009113:Muramidase / Q000037:antagonists & inhibitors / Q000378:metabolism* / Q000648:ultrastructure; D010636:Phenols / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D011485:Protein Binding; D012118:Resorcinols / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology
D000682:Amyloid; D016227:Benzoquinones; D002396:Catechols; D006873:Hydroquinones; D010636:Phenols; D012118:Resorcinols; C004532:quinone; C421864:hen egg lysozyme; D009113:Muramidase; C034221:catechol; C031927:hydroquinone; C031389:resorcinol