Antiprotozoal Isoprenoids from Salvia hydrangea

  • J Nat Prod. 2018 Dec 28;81(12):2682-2691. doi: 10.1021/acs.jnatprod.8b00498.
Marzieh Tabefam  1  2 ,  Mahdi Moridi Farimani  1 ,  Ombeline Danton  2 ,  Justine Ramseyer  2 ,  Samad Nejad Ebrahimi  1 ,  Markus Neuburger  3 ,  Marcel Kaiser  4  5 ,  Peyman Salehi  1 ,  Olivier Potterat  2 ,  Matthias Hamburger  2
Affiliations
  • 1. Department of Phytochemistry, Medicinal Plants and Drugs Research Institute , Shahid Beheshti University , G. C., Evin , Tehran , Iran.
  • 2. Department of Pharmaceutical Biology , University of Basel , Klingelbergstrasse 50 , 4056 Basel , Switzerland.
  • 3. Inorganic Chemistry, Department of Chemistry , University of Basel , Mattenstrasse 24a , 4058 Basel , Switzerland.
  • 4. Swiss Tropical and Public Health Institute , Socinstrasse 57 , 4002 Basel , Switzerland.
  • 5. University of Basel , 4001 Basel , Switzerland.
PMID: 30565934 DOI: 10.1021/acs.jnatprod.8b00498
Abstract

Fractionation of the n-hexane extract of Salvia hydrangea afforded seven isoprenoids including six new compounds (1-6) and salvadione A (7). Their structures were established by comprehensive spectroscopic and spectrometric data analysis (1D and 2D NMR, HRMS). The absolute configuration of salvadione A (7) was established by single-crystal X-ray diffraction analysis with Cu/Kα radiation. In addition, the absolute configuration of all compounds was determined by electronic circular dichroism spectroscopy. A biosynthetic pathway for the formation of the scaffold of 1 is proposed. The antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense, Trypanosoma cruzi, Leishmania donovani, and Plasmodium falciparum was determined, and cytotoxicity was assessed in rat myoblast L6 cells. Perovskone C (2) exhibited good activity against P. falciparum (IC50 0.6 μM) and a selectivity index of 62.2.