A caryophyllane-type sesquiterpene, caryophyllenol A from Valeriana amurensis

Fitoterapia. 2014 Jul:96:18-24. doi: 10.1016/j.fitote.2014.03.025. Epub 2014 Apr 4.

Abstract

A new caryophyllane derivative, caryophyllenol A, and a new germacrane derivative, isovolvalerenal D, together with 11 known sesquiterpenoids, were isolated from a petroleum ether partition of the roots and rhizomes of Valeriana amurensis. Structure elucidation of caryophyllenol A and isovolvalerenal D was accomplished on the basis of various spectroscopic techniques including HRESIMS and 2D NMR analyses. The structure of caryophyllenol A was further confirmed by X-ray crystallography and using quantum-chemical ECD calculation adopting TDDFT method. Caryophyllenol A and other eight sesquiterpenoids were evaluated for sedative activity with the model of Drosophila melanogaster, and eight of them showed the effect of prolonging the total sleeping time (TST) of D. melanogaster, displaying significant sedative action.

Keywords: Caryophyllane; Germacrane; Sedative; Sesquiterpenoid; Valeriana amurensis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Drosophila melanogaster / drug effects*
  • Drosophila melanogaster / physiology
  • Female
  • Hypnotics and Sedatives / chemistry
  • Hypnotics and Sedatives / isolation & purification*
  • Hypnotics and Sedatives / pharmacology
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Structure
  • Plant Roots / chemistry
  • Polysaccharides / chemistry
  • Polysaccharides / isolation & purification*
  • Polysaccharides / pharmacology
  • Rhizome / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Sesquiterpenes, Germacrane / chemistry
  • Sesquiterpenes, Germacrane / isolation & purification*
  • Sesquiterpenes, Germacrane / pharmacology
  • Sesterterpenes
  • Valerian / chemistry*

Substances

  • Hypnotics and Sedatives
  • Polysaccharides
  • Sesquiterpenes
  • Sesquiterpenes, Germacrane
  • Sesterterpenes
  • caryophyllan
  • caryophyllenol A