Palhicerines A-F, Lycopodium alkaloids from the club moss Palhinhaea cernua

Phytochemistry. 2016 Nov:131:130-139. doi: 10.1016/j.phytochem.2016.08.010. Epub 2016 Aug 27.

Abstract

Four fawcettimine-type (palhicerines A-D, resp.) and two lycopodine-type (palhicerines E and F) Lycopodium alkaloids together with twenty known ones were isolated from the whole plant of Palhinhaea cernua. The structures and absolute configurations of the palhicerines A-F were determined by extensive spectroscopic methods, single-crystal X-ray diffraction analyses, chemical transformation, and electronic circular dichroism (ECD) calculations or induced electronic circular dichroism (IECD) spectra. Among the isolates, the new C/D-ring of the palhicerines A-C (trans-fused fawcettimine-type alkaloids) are rare, and each possesses a β-oriented C-16 methyl group and a distinctive tertiary methoxy group at C-13. Chemotaxonomy for differentiating species in the genus Palhinhaea is briefly discussed.

Keywords: Lycopodiaceae; Lycopodium alkaloids; Palhicerines; Palhinhaea cernua.

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Crystallography, X-Ray
  • Lycopodiaceae / chemistry*
  • Lycopodiaceae / genetics
  • Molecular Conformation
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Quinolizines / chemistry

Substances

  • Alkaloids
  • Quinolizines
  • fawcettimine
  • palhicerine A
  • palhicerine E
  • lycopodine