Neo-debromoaplysiatoxin C, with new structural rearrangement, derived from debromoaplysiatoxin

Nat Prod Res. 2020 Aug;34(15):2151-2156. doi: 10.1080/14786419.2019.1577840. Epub 2019 Mar 5.

Abstract

Neo-debromoaplysiatoxin C (1), a new member of the aplysiatoxin family, was isolated from the marine cyanobacterium Lyngbya sp. The structure of 1 was elucidated based on spectroscopic data, and its stereochemistry was determined from NOESY spectrum and biosynthetic considerations. This new compound presents an intriguing 10-membered lactone ring skeleton derived from debromoaplysiatoxin by structural rearrangement, which is the first example in the aplysiatoxin family. Its biological properties were evaluated for cytotoxicity, PKCδ activation and inhibitory effects on potassium channel.

Keywords: Lyngbya sp; Neo-debromoaplysiatoxin C; debromoaplysiatoxin; newly discovered structural frame.

MeSH terms

  • Cyanobacteria / chemistry*
  • Cytotoxins / pharmacology
  • Lactones / chemistry
  • Lactones / pharmacology
  • Lyngbya Toxins / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Potassium Channel Blockers / pharmacology
  • Protein Kinase C-delta / drug effects
  • Seaweed / chemistry

Substances

  • Cytotoxins
  • Lactones
  • Lyngbya Toxins
  • Potassium Channel Blockers
  • debromoaplysiatoxin
  • aplysiatoxin
  • Protein Kinase C-delta