A new rearranged eudesmane sesquiterpene and bioactive sesquiterpenes from the twigs of Lindera glauca (Sieb. et Zucc.) Blume

Arch Pharm Res. 2016 Dec;39(12):1628-1634. doi: 10.1007/s12272-016-0838-1. Epub 2016 Sep 12.

Abstract

A new rearranged eudesmane sesquiterpene, named eudeglaucone (1), and five known sesquiterpenes including (+)-faurinone (2) and four eudesmane-type sesquiterpenes (3-6), were isolated from the twigs of Lindera glauca (Sieb. et Zucc.) Blume. The structure of 1 was elucidated by a combination of extensive spectroscopic analyses, including extensive 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY) and HR-MS. Compound 1 was a relatively rare rearranged eudesmane sesquiterpene in terpenoids. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15). Compounds 3 and 6 showed significant cytotoxicity against SK-MEL-2 and HCT-15 cell lines with IC50 values ranging from 9.98 to 12.20 μM. We also investigated the anti-neuroinflammatory activities of the isolates (1-6) in the lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cell line by measuring nitric oxide (NO) levels. All isolates significantly inhibited NO production with IC50 values of 3.67-26.48 μM without inducing cell toxicity.

Keywords: Anti-inflammation; Cytotoxicity; Lauraceae; Lindera glauca; Sesquiterpene.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Humans
  • Lindera*
  • Mice
  • Microglia / drug effects
  • Microglia / physiology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Plant Stems*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Eudesmane / chemistry*
  • Sesquiterpenes, Eudesmane / isolation & purification*
  • Sesquiterpenes, Eudesmane / pharmacology

Substances

  • Plant Extracts
  • Sesquiterpenes
  • Sesquiterpenes, Eudesmane