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. 2016 Jan 21;21(1):E127.
doi: 10.3390/molecules21010127.

The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol

Peter Kotora  1 , František Šeršeň  2 , Juraj Filo  3 , Dušan Loos  4 , Juraj Gregáň  5   6 , Fridrich Gregáň  7
Affiliations

The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol

Peter Kotora et al. Molecules. .

Abstract

Resveratrol (3,5,4'-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) and 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS) radicals. The antioxidant activity efficiency correlated with the number and position of hydroxyl groups. The most effective antioxidants were resveratrol analogs containing three hydroxyl groups in the benzylidene part of their molecules. These results provide new insights into the relationship between the chemical structure and biological activity of resveratrol analogs.

Keywords: antioxidant activity; iminophenols; resveratrol analogs.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Structure of resveratrol and studied Hydroxyphenyliminomethyl)phenols.
Scheme 1
Scheme 1
Preparation of iminophenol analogs of resveratrol.
Figure 2
Figure 2
Dependence of SC50 of DPPH, GOR and ABTS scavenging by studied (Hydroxyphenyliminomethyl)phenols on PA + ETE entalpies. Dashed lines denote the SC50 values of resveratrol.
Figure 3
Figure 3
Fluorescence excitation spectra of studied (Hydroxyphenyliminomethyl)phenols: 5 (A); 14 (B) and 15 (C) in methanol at concentration of 0.9 mg/dm3. The excitation and emission slits were 2 resp. 10 nm.
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