Comparative radical-scavenging activity of curcumin and tetrahydrocurcumin with thiols as measured by the induction period method.
BACKGROUND
The in vivo radical-scavenging activity of curcumin (CUR) and THC (tetrahydrocurcumin, a metabolite of CUR) does not occur in isolation, but through an intricate antioxidant network together with co-antioxidants such as glutathiones (GSH). In the present investigation, the radical-scavenging activity of CUR and THC with 2-mercapto-1-methylimidazole (MMI, a thiol) was studied using the induction period method.


METHODS
The induction period (IP) and propagation rate (Rp) for mixtures of MMI with THC or CUR were determined by differential scanning calorimetry (DSC) monitoring of the polymerization of methyl methacrylate (MMA) initiated by thermal decomposition of benzoyl peroxide (BPO, a source of peroxy radical, PhCOO*) or 2,2'-azobisisobutyronitrile (AIBN, a source of alkyl radical, R*) under nearly anaerobic conditions.


RESULTS
The stoichiometric number of PhCOO* radicals that could be trapped per molecule (n) was 3.4 and 3.3 for CUR and THC, and that of the R* radical was 3.1 and 2.5, respectively. At a molar ratio of antioxidant:co-antioxidant (MMI) = 1:5, a THC/MMI mixture with PhCOO* enhanced the total radical-scavenging activity, possibly due to partial regeneration of THC, whereas a CUR/MMI mixture with PhCOO* reduced it. Similarly, CUR/MMI and THC/MMI mixtures with R*, particularly the former, reduced the total radical-scavenging activity, possibly due, in part, to destructive interference between the antioxidant and the co-antioxidant.


CONCLUSIONS
THC oxidized by peroxy radicals may be more antioxidative than the corresponding CUR in the interplay with GSH.
Kadoma
Yoshinori
Y
Division of Biofunctional Molecules, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Tokyo, Japan. y-kadoma.fm@tmd.ac.jp
Fujisawa
Seiichiro
S
D003474:Curcumin / Q000031:analogs & derivatives* / Q000737:chemistry*; D016166:Free Radical Scavengers / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
D016166:Free Radical Scavengers; D013438:Sulfhydryl Compounds; C096277:tetrahydrocurcumin; D003474:Curcumin