Bioactive eudesmane and germacrane derivatives from Inula wissmanniana Hand.-Mazz

Phytochemistry. 2013 Dec:96:214-22. doi: 10.1016/j.phytochem.2013.10.006. Epub 2013 Nov 1.

Abstract

Phytochemical investigation of Inula wissmanniana Hand.-Mazz. afforded 21 eudesmane and germacrane derivatives, including rare 4,5-secoeudesman-12,5-olide, eudesman-12,5-olide, 3,4-secoeudesman-12-oic acid, and germacra-4-en-12,6-olides. Their structures were elucidated by combinative analyses of MS, NMR, electronic circular dichroism, and X-ray crystallography data. Moreover, most of the isolates exhibited inhibition against lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages and cytotoxicity in HepG2, PC-3, and MGC-803 tumor cells.

Keywords: Asteraceae; Cytotoxicity; Eudesmane; Germacrane; Inula wissmanniana Hand.-Mazz.; NO production.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Algorithms
  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Hep G2 Cells
  • Humans
  • Inula / chemistry*
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Sesquiterpenes, Eudesmane / chemistry
  • Sesquiterpenes, Eudesmane / isolation & purification*
  • Sesquiterpenes, Eudesmane / pharmacology*
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / isolation & purification*
  • Sesquiterpenes, Germacrane / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Lipopolysaccharides
  • Sesquiterpenes, Eudesmane
  • Sesquiterpenes, Germacrane
  • Nitric Oxide