Lycopodium Alkaloids from Huperzia goebelii

Chem Biodivers. 2024 Apr;21(4):e202400209. doi: 10.1002/cbdv.202400209. Epub 2024 Mar 15.

Abstract

One new fawcettimine-type Lycopodium alkaloid, hupertimine F (1), together with five known (2-6) Lycopodium alkaloids were isolated from Huperzia goebelii. The structure of 1 was elucidated by 1D and 2D NMR spectra, HRESIMS, and X-ray diffraction. Structurally, 1 represents the fourth example of Lycopodium alkaloids characterized by a 5/5/5/5/6 pentacyclic ring system with a 1-aza-7-oxabicyclo[2.2.1]heptane moiety. These known compounds 2, 3, 5, and 6 were isolated from H. goebelii for the first time. Compounds 1-6 were evaluated for acetylcholinesterase, butyrylcholinesterase and monoamine oxidase B inhibitory activities in vitro.

Keywords: Hupertimine F; Huperzia goebelii; Huperzine A; Lycopodium alkaloid.

MeSH terms

  • Acetylcholinesterase / chemistry
  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Butyrylcholinesterase
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Huperzia* / chemistry
  • Lycopodium* / chemistry
  • Molecular Structure

Substances

  • Butyrylcholinesterase
  • Acetylcholinesterase
  • Cholinesterase Inhibitors
  • Alkaloids