Lycoplanine A, a C16N Lycopodium Alkaloid with a 6/9/5 Tricyclic Skeleton from Lycopodium complanatum

Org Lett. 2017 Sep 1;19(17):4668-4671. doi: 10.1021/acs.orglett.7b02293. Epub 2017 Aug 22.

Abstract

Lycoplanine A (1), a Lycopodium alkaloid with a 6/9/5 tricyclic ring skeleton fused with the γ-lactone ring and featuring an unusual 1-oxa-6-azaspiro[4.4]nonane moiety and an unprecedented 3-azabicyclo[6.3.1]dodecane unit, was isolated from the club moss Lycopodium complanatum. The structure and absolute configuration of 1 were identified by a combination of NMR spectroscopic analysis and single-crystal X-ray diffraction. Biological studies showed that 1 is a potent Cav3.1 T-type calcium channel (TTCC) inhibitor with an IC50 value of 6.06 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids
  • Crystallography, X-Ray
  • Lycopodium*
  • Molecular Structure

Substances

  • Alkaloids