Obscurumines H-P, new Lycopodium alkaloids from the club moss Lycopodium obscurum

Fitoterapia. 2016 Mar:109:155-61. doi: 10.1016/j.fitote.2015.12.017. Epub 2015 Dec 29.

Abstract

Seven new fawcettimine-type (1-7) and two new lycopodine-type (8 and 9) Lycopodium alkaloids, as well as 10 known compounds, were isolated from the club moss, Lycopodium obscurum L. The structures of obscurumines H-P (1-9) were determined based on high-resolution MS and 1D and 2D NMR data. Compounds 1 and 2 include a new skeleton that is formed via the linkage of C-9-N-2', which is rarely present in Lycopodium alkaloids. The in vitro acetylcholinesterase (AChE) inhibitory activity assay showed that 5 exhibited weak anti-AChE activity with an IC50 value of 81.0 μM. Compound 8 exhibited inhibition of the secretion of IL-2 in phytohemagglutinin (PHA) and phorbol myristate acetate (PMA) stimulated Jurkat cells, and the IC50 value was 17.2 μM.

Keywords: Anti-AChE activity; Immunosuppressive activity; Lycopodium alkaloids; Lycopodium obscurum L.; Obscurumines H-P.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylcholinesterase / metabolism
  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Cholinesterase Inhibitors / chemistry*
  • Cholinesterase Inhibitors / isolation & purification
  • Humans
  • Immunosuppressive Agents / chemistry*
  • Immunosuppressive Agents / isolation & purification
  • Jurkat Cells
  • Lycopodium / chemistry*
  • Molecular Structure
  • Quinolizines / chemistry
  • Quinolizines / isolation & purification

Substances

  • Alkaloids
  • Cholinesterase Inhibitors
  • Immunosuppressive Agents
  • Quinolizines
  • obscurumine L
  • obscurumine O
  • Acetylcholinesterase