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

Kotora P, Šeršeň F, Filo J, Loos D, Gregáň J, Gregáň F - Molecules (2016)

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, 842 15 Bratislava, Slovakia. kotora@fns.uniba.sk.

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.

No MeSH data available.


Preparation of iminophenol analogs of resveratrol.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4759939&req=5

Figure 4: Preparation of iminophenol analogs of resveratrol.

Mentions: The starting compounds for preparation of (hydroxyphenyliminomethyl)phenols were mono aminophenols (APs) and mono-, di- and trihydroxybenzaldehydes (HBAs). Twenty-one (hydroxyphenyliminomethyl)phenols (compounds 1-21, for full names see Section 3.2. Synthesis) were prepared by condensation reactions where the first step was addition of amino group on carbonyl group followed by elimination of water according to protocols of Tanaka and Shiraishi [16] and Lu et al. [29] (Scheme 1). Briefly, equimolar amounts of appropriate AP and HBA were stirred in a small amount of distilled water at room temperature (25 °C) for 2 h. Obtained products were filtered, washed several times with distilled water and dried at 45 °C in vacuum. Yields of (hydroxyphenyliminomethyl)phenols ranged between 26% and 95%. The compounds were characterized by melting point, elemental analysis, 1H- and 13C-NMR, IR and MS spectra.


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

Kotora P, Šeršeň F, Filo J, Loos D, Gregáň J, Gregáň F - Molecules (2016)

Preparation of iminophenol analogs of resveratrol.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4759939&req=5

Figure 4: Preparation of iminophenol analogs of resveratrol.
Mentions: The starting compounds for preparation of (hydroxyphenyliminomethyl)phenols were mono aminophenols (APs) and mono-, di- and trihydroxybenzaldehydes (HBAs). Twenty-one (hydroxyphenyliminomethyl)phenols (compounds 1-21, for full names see Section 3.2. Synthesis) were prepared by condensation reactions where the first step was addition of amino group on carbonyl group followed by elimination of water according to protocols of Tanaka and Shiraishi [16] and Lu et al. [29] (Scheme 1). Briefly, equimolar amounts of appropriate AP and HBA were stirred in a small amount of distilled water at room temperature (25 °C) for 2 h. Obtained products were filtered, washed several times with distilled water and dried at 45 °C in vacuum. Yields of (hydroxyphenyliminomethyl)phenols ranged between 26% and 95%. The compounds were characterized by melting point, elemental analysis, 1H- and 13C-NMR, IR and MS spectra.

Bottom Line: 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.

View Article: PubMed Central - PubMed

Affiliation: Institute of Chemistry, Faculty of Natural Sciences, Comenius University in Bratislava, Mlynská dolina, 842 15 Bratislava, Slovakia. kotora@fns.uniba.sk.

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.

No MeSH data available.