Effects of different ester chains on the antioxidant activity of caffeic acid

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review

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Author(s)

  • Yan-Zhen Zheng
  • Geng Deng
  • Rui Guo
  • Zhong-Min Fu
  • Da-Fu Chen

Related Research Unit(s)

Detail(s)

Original languageEnglish
Article number104341
Journal / PublicationBioorganic Chemistry
Volume105
Online published7 Oct 2020
Publication statusPublished - Dec 2020

Abstract

Caffeic acid ester derivatives have been widely found in propolis extract and plants. In this work, the effect of ester groups with different aromatic and alkyl chains on the antioxidant activity of caffeic acid was performed on the double H+/e process using DFT calculations. We found that 1) O3–H3⋯O4 intramolecular hydrogen-bonds exist in the catechol moiety of the investigated compounds, which have the same strength and are closed shell interactions, weak-strength and electrostatic in nature, making the 4–OH more favourable than 3–OH to trap free radicals. 2) In weak polarity phases, caffeic acid and its derivatives prefer to perform the double H+/e processes via the dHAT mechanism. In the polar phases, the SdPLdET mechanism is more favoured. The first step of these mechanisms is more possible in 4–OH groups. 3) The ester group with different aromatic and alkyl chains would enhance the antioxidant capacities of caffeic acid.

Research Area(s)

  • Caffeic acid, Density functional theory, Ester derivatives, Solvent effect, Structure–antioxidant activity relationship

Citation Format(s)

Effects of different ester chains on the antioxidant activity of caffeic acid. / Zheng, Yan-Zhen; Deng, Geng; Guo, Rui et al.
In: Bioorganic Chemistry, Vol. 105, 104341, 12.2020.

Research output: Journal Publications and ReviewsRGC 21 - Publication in refereed journalpeer-review