Tocotrienamines and tocopheramines: Reactions with radicals and metal ions

Add time:07/30/2019    Source:sciencedirect.com

The antioxidant activity of vitamin E (VE) homologs α, γ and δ-tocotrienamines (4b–6b), never studied before, and α, γ and δ-tocopheramines (4a–7a) was investigated by means of different total antioxidant capacity (TAC) tests. In all the test model systems, compounds 4a–7a and 4b–6b showed similar or higher TAC values than the parental vitamin E forms and their physiological metabolites. α-Homologs of VE amines showed markedly higher activity than the VE congeners in the TEAC test, which is tailored for liposoluble antioxidants, while γ-homologs of the amine analogs showed higher activity in the FRAP tests. Kinetics analysis of the reaction with DPPH showed higher second order rate k for 4a than for α-tocopherol (1a). α-Tocopherolquinone 1f was the common main oxidation product for both 1a and α-tocopheramine (4a) exposed to ferric ions or DPPH, and the implied oxidative deamination of 4a was accompanied by a nitration reaction of phenolic substrates that were added to the reaction medium. Possible mechanisms of these reactions were studied.

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