Coscinoderines A-J: Trisubstituted Pyridinium-Containing Norterpenoids Isolated from Coscinoderma bakusi, a Tropical Marine Sponge

J Nat Prod. 2023 Sep 22;86(9):2145-2150. doi: 10.1021/acs.jnatprod.3c00358. Epub 2023 Aug 23.

Abstract

Ten new norterpene alkaloids, coscinoderines A-J (1-10), were isolated from the marine sponge Coscinoderma bakusi. Each coscinoderine contains a 1,2,5-trisubstituted pyridinium moiety bearing a terpene unit at the C-2 position. Their structures were elucidated by analysis of NMR and HRMS data, and the absolute stereochemistry of 4 with a 2-methylbutyl group attached to the nitrogen was determined from a comparison of the calculated and measured ECD spectra. The isolation of coscinoderines expands the repertoire of pyridinium alkaloids isolated from marine sponges.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Animals
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Porifera* / chemistry
  • Terpenes

Substances

  • Alkaloids
  • Terpenes