Chemical Constituents of the Leaves of Butterbur (Petasites japonicus) and Their Anti-Inflammatory Effects

Biomolecules. 2019 Nov 29;9(12):806. doi: 10.3390/biom9120806.

Abstract

Two new aryltetralin lactone lignans, petasitesins A and B were isolated from the hot water extract of the leaves of butterbur (Petasites japonicus) along with six known compounds. The chemical structures of lignans 1 and 2 were elucidated on the basis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data, electronic circular dichroism (ECD) and vibrational circular dichroism (VCD) spectra. Petasitesin A and cimicifugic acid D showed significant inhibitory effects on the production of both prostaglandin E2 (PGE2) and NO in RAW264.7 macrophages. The expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) were inhibited by compound 1 in RAW264.7 cells. Furthermore, compounds 1 and 3 exhibited strong affinities with both iNOS and COX-2 enzymes in molecular docking studies.

Keywords: Asteraceae; COX-2; NO; PGE2; Petasites japonicus; anti-inflammation; iNOS; lignan; molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents / analysis
  • Anti-Inflammatory Agents / chemistry
  • Anti-Inflammatory Agents / pharmacology*
  • Cyclooxygenase 2 / metabolism
  • Dinoprostone / metabolism
  • Lignans / analysis
  • Lignans / chemistry
  • Lignans / pharmacology*
  • Lipopolysaccharides / pharmacology
  • Mice
  • Nitric Oxide / metabolism
  • Nitric Oxide Synthase Type II / metabolism
  • Petasites*
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Leaves / chemistry
  • RAW 264.7 Cells

Substances

  • Anti-Inflammatory Agents
  • Lignans
  • Lipopolysaccharides
  • Plant Extracts
  • Nitric Oxide
  • Nitric Oxide Synthase Type II
  • Nos2 protein, mouse
  • Ptgs2 protein, mouse
  • Cyclooxygenase 2
  • Dinoprostone