Anti-inflammatory neo-Clerodane Diterpenoids from Ajuga pantantha

J Nat Prod. 2020 Apr 24;83(4):894-904. doi: 10.1021/acs.jnatprod.9b00629. Epub 2020 Mar 27.

Abstract

Eight new neo-clerodane diterpenoids (1-8) were acquired from the aerial parts of Ajuga pantantha. Spectroscopic data analysis permitted the definition of their structures, and experimental and calculated electronic circular dichroism data were used to define their absolute configurations. Compounds 2 and 4-8 were found to have NO inhibitory effects with IC50 values of 20.2, 45.5, 34.0, 27.0, 45.0, and 25.8 μM, respectively. The more potent compounds 2, 6, and 8 were analyzed to establish their anti-inflammatory mechanism, including regulation of the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) proteins as well as their binding interactions with the two proteins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ajuga / chemistry*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology*
  • Cyclooxygenase 2 Inhibitors / chemistry
  • Cyclooxygenase 2 Inhibitors / pharmacology
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology*
  • Diterpenes, Clerodane / chemistry*
  • Diterpenes, Clerodane / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Docking Simulation
  • Molecular Structure
  • Nitric Oxide / antagonists & inhibitors
  • Nitric Oxide Synthase Type II / antagonists & inhibitors
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Protein Binding / drug effects

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Cyclooxygenase 2 Inhibitors
  • Diterpenes
  • Diterpenes, Clerodane
  • Plant Extracts
  • Nitric Oxide
  • Nitric Oxide Synthase Type II