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.
Highlights
The structure ofphenols (Figure 1) is similar to the structure of resveratrol (3,5,41 -trihydroxystilbene), which exhibits various biological activities
Resveratrol has gained widespread attention due to its ability to extend the lifespan of various organisms, to protect against age-related diseases such as cancer and a broad range of biological activities including antiviral and antioxidant properties [1,2,3,4]. It is not clear whether the health benefits associated with wine drinking (“French paradox”, the observation of reduced incidence of cardiovascular disease in regions of France where red wine and fats are consumed in large quantities) are due to resveratrol [5]
The starting compounds for preparation ofphenols were mono were mono aminophenols (APs) and mono, diand trihydroxybenzaldehydes (HBAs)
Summary
The structure of (hydroxyphenyliminomethyl)phenols (Figure 1) is similar to the structure of resveratrol (3,5,41 -trihydroxystilbene), which exhibits various biological activities. Resveratrol has gained widespread attention due to its ability to extend the lifespan of various organisms, to protect against age-related diseases such as cancer and a broad range of biological activities including antiviral and antioxidant properties [1,2,3,4]. It is not clear whether the health benefits associated with wine drinking (“French paradox”, the observation of reduced incidence of cardiovascular disease in regions of France where red wine and fats are consumed in large quantities) are due to resveratrol [5]
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