Synthesis of short‐chain‐fatty‐acid resveratrol esters and their antioxidant properties

You Lin Tain, Sam K.C. Chang, Jin Xian Liao, Yu Wei Chen, Hung Tse Huang, Yu Lun Li, Chih Yao Hou*

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

26 Scopus citations

Abstract

To expand the applications and enhance the stability and bioactivity of resveratrol (RE), and to simultaneously include the potential health benefits of short chain fatty acids (SCFA) esters of RE were prepared by Steglich reactions with acetic, propionic, and butyric acids, respectively. RE and the esterified RE‐SCFA products (including RAE, RPE, and RBE) were analyzed using nuclear magnetic resonance (NMR), Fourier‐transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), differential thermal analysis (DTA), and liquid chromatography–mass spectrome-try (LC–MS). The FTIR and13C NMR spectra of the esterified products included ester‐characteristic peaks at 1751 cm−1 and 171 ppm, respectively. Moreover, the peaks in the range of 1700 to 1600 cm−1 in the FTIR spectra of the esterified products indicated that the esterification of RE‐SCFA was suc-cessful. The TGA results revealed that the RE‐SCFA esters decomposed at lower temperatures than RE. The peaks in the LC–MS profiles of the esterified products indicated the formation of mono-and diesters, and the calculated monoester synthesis rates ranged between 45.81 and 49.64%. The RE esters inhibited the Cu2+‐induced low‐density lipoprotein oxidation reaction, exhibited antioxi-dant activity in bulk oil, and effectively inhibited the hydroxyl radical‐induced DNA scission. More-over, the RE‐SCFA esters had better hydrogen peroxide scavenging activity than RE. Our results are the first in the literature to successfully including short chain fatty acids in the esters of resvera-trol, and the products could be used as a functional food ingredient in processed foods or can be used as dietary supplements to promote health.

Original languageEnglish
Article number420
Pages (from-to)1-14
Number of pages14
JournalAntioxidants
Volume10
Issue number3
DOIs
StatePublished - 03 2021

Bibliographical note

Publisher Copyright:
© 2021 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

  • Antioxida-tion
  • Resveratrol
  • Resveratrol esters
  • Short‐chain fatty acids
  • Steglich esterification

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