Three new tyrosol derivatives from Huangjing wine

J Asian Nat Prod Res. 2022 Nov;24(11):1018-1024. doi: 10.1080/10286020.2021.2008371. Epub 2021 Nov 29.

Abstract

Phytochemical investigation on the concentrate of Huangjing wine, resulted in the isolation of three new tyrosol derivatives 4'''-hydroxyphenethyl 2-(R)-hydroxy-3-phenylpropionate (1), 4'''-hydroxyphenethyl(4'-hydroxy-3'-methoxyphenyl)propionate (2) and 4''-hydroxyphenethyl ethyl succinate (3), together with 5 known compounds, ferulic acid (4), L-phenyllactic acid (5), hydroxytyrosol (6), dihydroferulic acid (7), cyclo(L-Pro-D-Tyr) (8). Their structures were elucidated using spectroscopic analysis and by comparison with the literature data. All compounds displayed antioxidant effect in the DPPH (2,2-diphenyl-1-picrylhydrazyl) radical. Among them, the new compound 2 exhibited obvious antioxidant effect, and new compounds 1 and 3 exhibited medium antioxidant effect.

Keywords: Huangjing wine; anti-oxidation; extraction and isolation; structural identification; tyrosol derivative.

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Molecular Structure
  • Wine* / analysis

Substances

  • 4-hydroxyphenylethanol
  • Antioxidants