Synthesis and biological evaluation of ( - )-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool

Nat Prod Res. 2015 Feb;29(3):207-12. doi: 10.1080/14786419.2014.942299. Epub 2014 Jul 30.

Abstract

13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6-C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.

Keywords: abietane; cytotoxicity; leishmanicidal; podocarpane; trypanocidal.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiprotozoal Agents / pharmacology*
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Diterpenes / pharmacology
  • Fibroblasts / drug effects
  • Humans
  • Inhibitory Concentration 50
  • Leishmania mexicana / drug effects
  • MCF-7 Cells
  • Molecular Structure
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma cruzi / drug effects

Substances

  • 13,14-dihydroxy-8,11,13-podocarpatrien-7-one
  • Antiprotozoal Agents
  • Diterpenes
  • Trypanocidal Agents
  • manool