Clerodane diterpenoids from Scutellaria formosana with inhibitory effects on NO production and interactions with iNOS protein

Phytochemistry. 2017 Dec:144:141-150. doi: 10.1016/j.phytochem.2017.09.005.

Abstract

A phytochemical study on Scutellaria formosana afforded five previously undescribed spiro-diterpenoids, scutellapenes A-E. The structures were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by the time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculations. Scutellapenes B-E possess a spiro-diterpenoid skeleton. All of the compounds showed inhibitory effects on LPS-induced nitric oxide (NO) production in murine microglial BV-2 cells. The further molecular docking studies revealed that these bioactive compounds had strong interactions with the iNOS protein.

Keywords: Labiatae; Molecular docking; NO inhibitors; Scutellaria formosana; Spiro-diterpenoids; iNOS.

MeSH terms

  • Animals
  • Cells, Cultured
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification
  • Diterpenes, Clerodane / pharmacology*
  • Dose-Response Relationship, Drug
  • Mice
  • Molecular Conformation
  • Molecular Docking Simulation
  • Nitric Oxide / antagonists & inhibitors*
  • Nitric Oxide / biosynthesis
  • Nitric Oxide Synthase Type II / chemistry
  • Nitric Oxide Synthase Type II / metabolism*
  • Scutellaria / chemistry*
  • Structure-Activity Relationship

Substances

  • Diterpenes, Clerodane
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse