Mechanism of the OH radical scavenging activity of nordihydroguaiaretic acid: a combined theoretical and experimental study.
The antioxidant nordihydroguaiaretic acid (NDGA) is a plant phenolic lignan originally isolated from the creosote bush (Larrea tridentata). It has been shown that NDGA scavenges efficiently hydroxyl radicals ((*)OH). In the present paper the mechanism by which NDGA scavenges (*)OH is addressed performing a combined experimental and theoretical investigation. We found that NDGA protects, in a concentration-dependent way, bovine serum albumin and DNA from the damage induced by (*)OH generated by the Fenton reaction. In addition, the NDGA + (*)OH reaction is predicted to be diffusion-controlled. The first step of this reaction is proposed to occur mainly by a sequential electron proton transfer from NDGA to (*)OH generating a neutral radical of NDGA, which after a second oxidation step gives a diradical that after a cascade sequential complex reaction produces a cyclic compound. This cyclic product is predicted to have a UV-vis spectrum very similar to that of NDGA, making its identification by this technique very difficult. The electrochemical studies performed in water support the formation of a cyclic compound (C2) as the main product of the reaction. It is concluded that NDGA can scavenge at least two (*)OH.
Galano
Annia
A
Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, 09340 City, México. agalano@prodigy.net.mx
Macías-Ruvalcaba
Norma A
NA
Medina Campos
Omar Noel
ON
Pedraza-Chaverri
José
J
D000818:Animals; D002417:Cattle; D004247:DNA / Q000737:chemistry; D055664:Electrochemical Techniques; D016166:Free Radical Scavengers / Q000737:chemistry*; D017665:Hydroxyl Radical / Q000737:chemistry*; D007700:Kinetics; D032442:Larrea / Q000737:chemistry; D009637:Masoprocol / Q000737:chemistry*; D012710:Serum Albumin, Bovine / Q000737:chemistry; D013816:Thermodynamics
D016166:Free Radical Scavengers; D012710:Serum Albumin, Bovine; D017665:Hydroxyl Radical; D009637:Masoprocol; D004247:DNA