Abietane Diterpenoids with Antioxidative Damage Activity from Rosmarinus officinalis

J Agric Food Chem. 2020 May 20;68(20):5631-5640. doi: 10.1021/acs.jafc.0c01347. Epub 2020 May 7.

Abstract

Nine new and nineteen known compounds were isolated and identified from Rosmarinus officinalis under the guidance of bioassay and LCMS. They all belonged to abietane diterpenoids which enriched the types of compounds in R. officinalis, especially the discovery of a series of 20-norabietane diterpenoids (4, 6-9, and 26-27). The antioxidative damage activity of the compounds was tested on H2O2 damaged SH-SY5Y cells. Compounds 5, 6, and 7 presented moderate ability for promoting the growth of damaged cells. Compounds 10, 11, 13-20, 27, and 28 displayed a high antioxidative damage effect whose cell viability rates were more than 80%. The antioxidative damage effect of 11, 16, 18, and 20 were higher than that of EGCG (positive control) in which 11, 18, and 20 were the acetylated derivatives of carnosic acid (10), 7α-methoxy-isocarnosol (16), and carnosol (19), respectively. It suggested that 10-carboxyl/formyl of abietane diterpenoids was essential for maintaining the antioxidative damage activity and the adjacent hydroxyl groups on the benzene ring was less important for holding the bioactivity. These acetylated derivatives with high bioactivity and stability could be regarded as new sources of antioxidants or antioxidative damage agents being used in the food and medical industry.

Keywords: LCMS; Rosmarinus officinalis; abietane diterpenoids; antioxidative damage activity.

MeSH terms

  • Abietanes / chemistry*
  • Abietanes / pharmacology
  • Antioxidants / chemistry*
  • Antioxidants / pharmacology
  • Cell Line
  • Cell Survival / drug effects
  • Humans
  • Hydrogen Peroxide / toxicity
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • Rosmarinus / chemistry*

Substances

  • Abietanes
  • Antioxidants
  • Plant Extracts
  • Hydrogen Peroxide