Naslov
Contribution of C-ring Hydrogens to Free Radical Scavenging by Equol

Autori
Amić, Ana ; Milenković, Dejan ; Dimitrić Marković, Jasmina ; Marković, Zoran

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Math/Chem/Comp 2021 - 32nd MC2 Conference Book of Abstracts / Vančik, Hrvoj ; Cioslowski, Jerzy ; Namjesnik, Danijel - Zagreb : Hrvatsko kemijsko društvo, 2021, 32-32

ISBN
978-953-8334-02-3

Skup
32nd International Course and Conference on the Interfaces among Mathematics, Chemistry and Computer Sciences: Mathematics, Chemistry, Computing (Math/Chem/Comp, MC2-32)

Mjesto i datum
Dubrovnik, Hrvatska, 07.06.2021. - 11.06.2021

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
equol ; BDE ; kinetics ; tunneling ; scavenging potency

Sažetak
Epidemiological studies have shown that diets rich in soy isoflavones are beneficial to human health [1]. However, these benefits aren’t ascribed to parental molecules of ingested isoflavones but to their intestinal metabolites [2]. Among these metabolites, equol has been extensively studied because of its bioactivity [3, 4], which may help to reduce the incidence of age-related disorders [1]. In this work, free radical scavenging potency of equol was investigated by using M06-2X/6-311++G(d, p) level of theory, accompanied with the TST and Eckart tunneling corrections for the estimation of rate constants. The influence of solvents was calculated with an implicit continuum solvation model, SMD [5]. Spin unrestricted calculations were used for openshell systems. Local minima and transition states (TSs) were identified by the number of imaginary frequencies (0 and 1, respectively). Intrinsic reaction coordinate calculation was performed on both sides of the TS to confirm that it properly connects with the corresponding reactants and products. All computations were performed in gas-phase, pentyl ethanoate and water at 298.15 K. BDE related to H-atom donation was calculated as described elsewhere [6]. Performed electronic structure and kinetic calculations indicate phenolic hydrogens of equol as much more abstractable than C-ring hydrogens. Thus, the C-ring hydrogens are poor HOO• scavengers with negligible contribution to equol antioxidant potency. This is in line with the known facts related to phenolic O−H vs C−H reactivity and structural requirements needed for antioxidant activity of flavonoids, but opposite to recently published predictions.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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