A New Monoterpene from the Leaves of a Radiation Mutant Cultivar of Perilla frutescens var. crispa with Inhibitory Activity on LPS-Induced NO Production

Molecules. 2017 Sep 4;22(9):1471. doi: 10.3390/molecules22091471.

Abstract

The leaves of Perilla frutescens var. crispa (Lamiaceae)-known as 'Jureum-soyeop' or 'Cha-jo-ki' in Korean, 'ZI SU YE' in Chinese, and 'Shiso' in Japan-has been used as a medicinal herb. Recent gamma irradiated mutation breeding on P. frutescens var. crispa in our research group resulted in the development of a new perilla cultivar, P. frutescens var. crispa (cv. Antisperill; PFCA), which has a higher content of isoegomaketone. The leaves of PFCA were extracted by supercritical carbon dioxide (SC-CO₂) extraction, and phytochemical investigation on this extract led to the isolation and identification of a new compound, 9-hydroxy-isoegomaketone [(2E)-1-(3-furanyl)-4-hydroxy-4-methyl-2-penten-1-one; 1]. Compound 1 exhibited inhibitory activity on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW264.7 cells with an IC50 value of 14.4 μM. The compounds in the SC-CO₂ extracts of the radiation mutant cultivar and the original plant were quantified by high-performance liquid chromatography with diode array detection.

Keywords: 9-Hydroxy-isoegomaketone; Perilla frutescens var. crispa; anti-inflammation; radiation mutant cultivar.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Furans / chemistry
  • Furans / pharmacology
  • Gamma Rays
  • Ketones / chemistry
  • Ketones / pharmacology
  • Lipopolysaccharides / pharmacology
  • Mice
  • Monoterpenes / chemistry*
  • Monoterpenes / pharmacology
  • Mutation
  • Nitric Oxide / biosynthesis*
  • Perilla frutescens / chemistry*
  • Perilla frutescens / genetics
  • Perilla frutescens / radiation effects
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Plant Leaves / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Furans
  • Ketones
  • Lipopolysaccharides
  • Monoterpenes
  • Plant Extracts
  • Nitric Oxide