Inhibitory Effect of Phenolic Compounds on Amyloid Fibrillation of Insulin†

doi:10.7503/cjcu20150087

Abstract

Abstract:

More than 20 human diseases are considered to be associated with amyloid fibrillation in polypeptides. Polyphenolic compounds have been demonstrated to disrupt amyloid structures and attenuate cytotoxicity of amyloid fibrils. In the present study, the inhibitory effects of four phenolic compounds on amyloid formation were investigated using bovine insulin as a model peptide. The results indicated that catechol and hydroquinone inhibited insulin fibrillation and bonded to the peptide chains with quinone moieties, showing a similar effect to benzoquinone. In contrast, phenol and resorcinol did not modify insulin with a quinone moiety, showing no effect on amyloid fibrillation. Furthermore, catechol and hydroquinone were less effective as an inhibitor of insulin fibrillation under anaerobic conditions, suggested that the formation of quinone intermediates via oxidation and subsequently transform insulin into quinopeptide were prerequisites for a phenolic compound to inhibit amyloid fibrillation. The results show that quinone intermediates are the active form for phenolic compounds to inhibit insulin amyloid fibrillation.

Key words: Phenolic compound, Insulin, Amyloid fibrillation, Quinone, Quinopeptide

CLC Number:

O625
Q949.64

TrendMD:

ZHANG Yujie, CAO Na, ZENG Chengming. Inhibitory Effect of Phenolic Compounds on Amyloid Fibrillation of Insulin^†[J]. Chem. J. Chinese Universities, 2015, 36(7): 1310.

Figures/Tables 4

Fig.1 ThT fluorescence of insulin amyloid fibrillation(A) Effects of phenols on insulin fibrillation. Bovine insulin(100 μmol/L) was incubated in the absence and presence of 200 μmol/L phenols and benzoquinone. Dose-dependent inhibition of insulin fibrillation by hydroquinone(B) and benzoquinone(C). (A) a. Insulin only; b. phenol; c. resorcinol; d. catechol; e. hydroquinone; f. benzoquinone. (B) c(hydroquinone)/(μmol·L-1): a. 0; b. 20; c. 50; d. 100; e. 200. (C) c(benzoquinone)/(μmol·L-1): a. 0; b. 20; c. 50; d. 100; e. 200.

Fig.2 TEM images of insulin amyloid fibrilsInsulin was incubated in the absence(A) and presence of 200 μmol/L phenol(B), resorcinol(C), catechol(D), hydroquinone(E) and 100 μmol/L benzoquinone(F), respectively.

Fig.3 Results of SDS-PAGE(A) and NBT assay(B)(A) SDS-PAGE of insulin amyloid fibrils prepared in the absence and presence of 200 μmol/L phenols and benzoquinone; (B) NBT-staining results of insulin assemblies. a and lane 1: native insulin; b and lane 2: insulin fibrils; c and lane 3: +phenol; d and lane 4: + catechol; e and lane 5: +resorcinol; f and lane 6: +hydroquinone; g and lane 7: benzoquinone.

Fig.4 Inhibition of insulin fibrillation by phenolic compounds under anaerobic condition(A) ThT assay. Insulin was incubated with a phenol(200 μmol/L) for 5 d. Asterisks represent P< 0.01 vs. the corresponding aerobic values. a. Insulin only; b. phenol; c. resorcinol; d. catechol; e. hydroquinone. TEM images of insulin fibrils prepared in the presence of catechol(B) and hydroquinone(C) under anaerobic condition.

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