Nine sesquiterpenes from Solanum torvum

Nat Prod Res. 2016 Aug;30(15):1682-9. doi: 10.1080/14786419.2015.1135142. Epub 2016 Jan 29.

Abstract

Three new sesquiterpenes, namely 3β,11-dihydroxy-4,14-oxideenantioeudesmane (1), 1β,10β,12,14-tetrahydroxy-allo-aromadendrane (2) and 1β,10β,13,14-tetrahydroxy-allo-aromadendrane (3), along with six known sesquiterpenes (4-9), were isolated from the roots of Solanum torvum. Compound 4 and 5 are epimers, their main difference lies in the C-11 configulation. Normally, epimers do not make a huge difference in C NMR spectra, but in this kind of structure of A, B, C rings, and C ring is sterically strained structure, stericall effects influence strongly the (13)C NMR chemical shifts, when C-11 configulation changed, it makes a huge difference in the three ring of structure, such as C-6, C-7, C-11. New compound 2 and 3 are epimers and similar to compound 4 and 5, their just increase a hydroxy in C-1 and have a same regular pattern in C NMR spectra, otherwise, compound 5 was firstly confirmed by single-crystal X-ray diffraction.

Keywords: 13C NMR; Solanum torvum; epimers; sesquiterpenes.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Plant Roots / chemistry
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Solanum / chemistry*
  • X-Ray Diffraction

Substances

  • Sesquiterpenes