Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E

Baj, Aneta; Cedrowski, Jakub; Olchowik-Grabarek, Ewa; Ratkiewicz, Artur; Witkowski, Stanislaw

doi:10.3390/antiox8120589

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Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E

Aneta Baj

Jakub Cedrowski

Ewa Olchowik-Grabarek

³,

Artur Ratkiewicz

and

Stanislaw Witkowski

^1,*

Faculty of Chemistry, University of Bialystok, Ciolkowskiego 1K, 15-245 Bialystok, Poland

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland

Faculty of Biology, University of Bialystok, Ciolkowskiego 1J, 15-245 Bialystok, Poland

Author to whom correspondence should be addressed.

Antioxidants 2019, 8(12), 589; https://doi.org/10.3390/antiox8120589

Received: 17 October 2019 / Revised: 14 November 2019 / Accepted: 20 November 2019 / Published: 26 November 2019

(This article belongs to the Special Issue The Chemistry of Antioxidant Activity)

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Abstract

Vitamin E is the most active natural lipophilic antioxidant with a broad spectrum of biological activity. α-Tocopherol (α-T), the main representative of the vitamin E family, is a strong inhibitor of lipid peroxidation as a chain-breaking antioxidant. Antioxidant and antiradical properties of vitamin E result from the presence of a phenolic hydroxyl group at the C-6 position. Due to stereoelectronic effects in the dihydropyranyl ring, the dissociation enthalpy for phenolic O–H bond (BDE_OH) is reduced. The high chain-breaking reactivity of α-T is mainly attributed to orbital overlapping of the 2p-type lone pair on the oxygen atom (O1) in para position to the phenolic group, and the aromatic π-electron system. The influence of the O1 atom on the antioxidant activity of vitamin E was estimated quantitatively. The all-rac-1-carba-α-tocopherol was synthesized for the first time. Along with model compounds, 1-carba-analog of Trolox and its methyl ester were screened for their in vitro antioxidant activity by inhibition of styrene oxidation, and for the radical-reducing properties by means of 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH) scavenging assay. To study the antioxidant activity, density functional theory (DFT) was also applied. Reaction enthalpies related to HAT (hydrogen atom transfer), SET–PT (sequential electron transfer—proton transfer), and SPLET (sequential proton loss—electron transfer) mechanisms were calculated. View Full-Text

Keywords: vitamin E; Trolox; carba-analogs; antioxidant activity

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Baj, A.; Cedrowski, J.; Olchowik-Grabarek, E.; Ratkiewicz, A.; Witkowski, S. Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E. Antioxidants 2019, 8, 589. https://doi.org/10.3390/antiox8120589

AMA Style

Baj A, Cedrowski J, Olchowik-Grabarek E, Ratkiewicz A, Witkowski S. Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E. Antioxidants. 2019; 8(12):589. https://doi.org/10.3390/antiox8120589

Chicago/Turabian Style

Baj, Aneta, Jakub Cedrowski, Ewa Olchowik-Grabarek, Artur Ratkiewicz, and Stanislaw Witkowski. 2019. "Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E" Antioxidants 8, no. 12: 589. https://doi.org/10.3390/antiox8120589

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Synthesis, DFT Calculations, and In Vitro Antioxidant Study on Novel Carba-Analogs of Vitamin E

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