Di-nor- and 17-nor-pimaranes from Icacina trichantha

J Nat Prod. 2016 Jul 22;79(7):1815-21. doi: 10.1021/acs.jnatprod.6b00289. Epub 2016 Jun 24.

Abstract

Six new pimarane derivatives, including two di-nor-pimaranes (1, 2), two 17-nor-pimaranes (3, 4), and two 17-nor-(9β-H)-pimaranes (5, 6), were isolated from the tuber of Icacina trichantha. Their structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 1 and 5 were determined by single-crystal X-ray diffraction, and that of 2 was established by electronic circular dichroism data analysis. Compound 3 possesses a unique C-20 acetal moiety. This is the first report of the isolation of di-nor-(9β-H)-pimarane derivatives from Icacina plants. Compounds 5 and 6 showed moderate cytotoxicity against MDA-MB-435, MDA-MB-231, and OVCAR3 cell lines, with IC50 values of 2.91-7.60 and 1.48-3.23 μM, respectively.

MeSH terms

  • Abietanes / chemistry
  • Abietanes / isolation & purification*
  • Abietanes / pharmacology
  • Crystallography, X-Ray
  • Drug Screening Assays, Antitumor
  • Magnoliopsida / chemistry*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Tubers / chemistry

Substances

  • Abietanes
  • pimarane