A new acetophenone derivative from flowers of Helichrysum italicum (Roth) Don ssp. italicum

Fitoterapia. 2014 Dec:99:198-203. doi: 10.1016/j.fitote.2014.09.019. Epub 2014 Oct 5.

Abstract

A new acetophenone derivative named gnaphaliol 9-O-propanoate (1) was isolated from the chloroform fraction of EtOH extract of Helichrysum italicum ssp. italicum flowers along with the five known acetophenones 12-acetoxytremetone (2), 13-(2-methylpropanoyloxy)toxol (3), [2,3-dihydro-2-[1-(hydroxymethyl)ethenyl]-5-benzofuranyl]-ethanone (4), 1-[2-[1-[(acetyloxy)methyl]ethenyl]-2,3-dihydro-3-hydroxy-5-benzofuranyl]-ethanone (5) and gnaphaliol (6). The structures of compounds 1-6 were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR (DQF-COSY, HSQC, HMBC, TOCSY and ROESY) experiments as well as ESIMS analysis. The isolated compounds were investigated for their cytotoxicity, anti-inflammatory and antioxidant properties. Biological assays on human colonic epithelial cells showed that compound 2 possessed antioxidant effects reducing reactive oxygen species (ROS) production.

Keywords: Acetophenones; Antioxidant; Asteraceae; Helichrysum italicum; Inflammation; Reactive oxygen species.

MeSH terms

  • Acetophenones / chemistry*
  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Antioxidants / chemistry
  • Cell Line
  • Epithelial Cells / drug effects*
  • Flowers / chemistry*
  • Helichrysum / chemistry*
  • Humans
  • Macrophages / drug effects
  • Mice
  • Oxidative Stress
  • Reactive Oxygen Species / metabolism

Substances

  • Acetophenones
  • Anti-Inflammatory Agents
  • Antioxidants
  • Reactive Oxygen Species
  • acetophenone