Absolute configuration of labdane diterpenoids from Physalis nicandroides

J Nat Prod. 2015 Feb 27;78(2):202-7. doi: 10.1021/np500688c. Epub 2015 Jan 29.

Abstract

A mixture of the new epimeric labdenetriols 1 and 2 was isolated from the aerial parts of Physalis nicandroides. The structures of 1 and 2, including their absolute configurations, were established by analyses of their spectroscopic data, together with the X-ray diffraction analysis of acetonide 3 and chemical correlation with (-)-(13E)-labd-13-ene-8α,15-diol (6), whose absolute configuration was also confirmed by X-ray analysis of its dibromo derivative 7. The epimeric labdenediols 8 and 9, the known labdanes 6 and 11, and the acylsucroses 12 and 13 were also isolated. Labdanes 6 and 11 showed moderate anti-inflammatory activities in the induced ear edema model.

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / isolation & purification*
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Crystallography, X-Ray
  • Disease Models, Animal
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification*
  • Diterpenes / pharmacology
  • Ear / pathology
  • Edema / chemically induced
  • Male
  • Mexico
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Physalis / chemistry*
  • Plant Components, Aerial / chemistry
  • Stereoisomerism

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Diterpenes