Teotihuacanin, a Diterpene with an Unusual Spiro-10/6 System from Salvia amarissima with Potent Modulatory Activity of Multidrug Resistance in Cancer Cells

Org Lett. 2015 Jul 2;17(13):3280-2. doi: 10.1021/acs.orglett.5b01320. Epub 2015 Jun 18.

Abstract

Teotihuacanin (1), an unusual rearranged clerodane diterpene with a new carbon skeleton containing a spiro-10/6 bicyclic system, was isolated from the leaves and flowers of Salvia amarissima. Its structure was determined through spectroscopic analyses. Its absolute configuration was established by single-crystal X-ray diffraction. Compound 1 showed potent modulatory activity of multidrug resistance in vinblastine-resistant MCF-7 cancer cell line (reversal fold, RFMCF-7/Vin+ > 10703) at 25 μg/mL.

MeSH terms

  • Crystallography, X-Ray
  • Diterpenes, Clerodane / chemistry
  • Diterpenes, Clerodane / isolation & purification*
  • Diterpenes, Clerodane / pharmacology*
  • Drug Resistance, Neoplasm / drug effects
  • Drug Screening Assays, Antitumor
  • Female
  • HCT116 Cells
  • HeLa Cells
  • Humans
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Salvia / chemistry*
  • Vinblastine / pharmacology

Substances

  • Diterpenes, Clerodane
  • teotihuacanin
  • Vinblastine