Probing structural properties and antioxidant activity mechanisms for eleocarpanthraquinone
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ORIGINAL PAPER
Probing structural properties and antioxidant activity mechanisms for eleocarpanthraquinone ´ ˜ C. da Silva1 · Virg´ınia C. P. Silva1 · Gabriel L. C. de Souza1,2 Jose´ L. F. Santos1 · Angelica C. Kauffmann1 · Sebastiao Received: 14 March 2020 / Accepted: 8 July 2020 © Springer-Verlag GmbH Germany, part of Springer Nature 2020
Abstract In this work, we present a computational investigation on the structure and energetics of eleocarpanthraquinone, a newly isolated polyphenolic anthrone-antraquinone. Properties such as bond lengths, angles, atomic charges, bond dissociation enthalpies (BDEs), and ionization potential (IP) were determined through the use of density functional theory (DFT). The B3LYP and M06-2X exchange-correlation functionals were employed along with the 6-31+G(d,p), 6-31++G(d,p), and 6-311+G(d,p) basis sets for performing computations in the gas-phase, water, methanol, and ethanol. The conformation presenting all the hydroxyl groups undergoing hydrogen-bond interactions with neighboring oxygen atoms (conformation 5) was assigned as the most stable structure while its counterpart presenting no hydrogen-bond interaction was found to be 36.45 kcal/mol less stable than conformation 5 in the potential energy surface probed at the B3LYP/6-311+G(d,p) level of theory in the gas-phase, for instance. More importantly, the lowest O–H bond dissociation enthalpy was determined to be 93.80 kcal/mol at the B3LYP/6-311+G(d,p) level of theory in water against the 146.58 kcal/mol regarding the IP computed at the same approach, suggesting the hydrogen atom transfer mechanism as being preferred over the single electron transfer mechanism in regards to the antioxidant potential for the case of eleocarpanthraquinone; the same conclusion was drawn from the outcomes of all the other approaches used. Keywords Antioxidant potential · Eleocarpanthraquinone · BDEs · IPs · Density Functional Theory (DFT)
Introduction From a general perspective, natural products (NPs) (i.e., any chemical substance produced by a living source [1]) are among the most researched entities in countries owning biologically diverse ecosystems, such as Brazil. In terms of chemistry, NPs can be defined as purified organic compounds isolated from natural sources that are produced
Electronic supplementary material The online version of this article (https://doi.org/10.1007/s00894-020-04469-3) contains supplementary material, which is available to authorized users. This paper belongs to Topical Collection XX - Brazilian Symposium of Theoretical Chemistry (SBQT2019) Gabriel L. C. de Souza
[email protected] 1
Departamento de Qu´ımica, Universidade Federal de Mato Grosso, Cuiab´a, Mato Grosso 78060-900, Brazil
2
Department of Chemistry, Washington State University, Pullman, WA 99164, USA
by the pathways of primary or secondary metabolism [2]. The scientific interest about these species is based (mainly) on the fact that several naturally occurring molecules present quite desirable features, including anticancer, antiviral, and anti-i
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