Reducing power of simple polyphenols by electron-transfer reactions using a new stable radical of the PTM series, tris(2,3,5,6-tetrachloro-4-nitrophenyl)methyl radical.
The synthesis and characterization of a new radical and its use for testing the antioxidant activity of polyphenols by electron transfer are reported. This new and stable species of magnetic nature, tris(2,3,5,6-tetrachloro-4-nitrophenyl)methyl (TNPTM) radical, has been characterized by electron paramagnetic resonance and its molecular structure determined by X-ray analysis. This new radical of the PTM (perchlorotriphenylmethyl) series, unlike 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, is stable in conditions of hydrogen abstraction reactions. TNPTM radical is able to discriminate between the antioxidant activities of catechol and pyrogallol in hydroxylated solvent mixtures such as chloroform/methanol (2:1). These features determine the antioxidant/pro-oxidant character and the biological activities of natural and synthetic flavonoids.
Torres
Josep Lluís
JL
Institut d'Investigacions Químiques i Ambientals-CSIC, Jordi Girona 18-26, 08034 Barcelona, Spain.
Carreras
Anna
A
Jiménez
Aurora
A
Brillas
Enric
E
Torrelles
Xavier
X
Rius
Jordi
J
Juliá
Luis
L
D002396:Catechols / Q000737:chemistry; D002713:Chlorine / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004583:Electrons; D005419:Flavonoids / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D059808:Polyphenols; D011748:Pyrogallol / Q000737:chemistry
C520705:(2,3,5,6-tetrachloro-4-nitrophenyl)methyl radical; D002396:Catechols; D005419:Flavonoids; D005609:Free Radicals; D009574:Nitro Compounds; D010636:Phenols; D059808:Polyphenols; D011748:Pyrogallol; C051224:methyl radical; D002713:Chlorine; C034221:catechol; D008697:Methane