Two new sesquiterpenoid glycosides from Nicotiana tabacum

J Asian Nat Prod Res. 2014;16(6):611-6. doi: 10.1080/10286020.2014.922553. Epub 2014 Jun 9.

Abstract

Two new sesquiterpenoid glycosides, nicotabalactonecoside (1) and nicotabadiolcoside (2), along with four known terpenoids (3-6) were isolated from the leaves of Nicotiana tabacum. The structures of compounds 1 and 2 were determined as dihydrodeacetylphytuberin-2-one 11-O-β-D-glucopyranoside and 1,2-dehydro-4-epieremophil-9-ene-11,12-diol 12-O-β-D-glucopyranoside by extensive spectroscopic analyses (HR-ESI-MS, UV, IR, 1D, and 2D NMR) and chemical method. Compound 1 is an unusual phytuberin-type sesquiterpenoid with a 6/5/5 tricyclic system.

Keywords: nicotabadiolcoside; nicotabalactonecoside; sesquiterpenoids; Nicotiana tabacum.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Molecular Structure
  • Nicotiana / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*

Substances

  • Drugs, Chinese Herbal
  • Glycosides
  • Sesquiterpenes
  • nicotabadiolcoside
  • nicotabalactonecoside
  • phytuberin