Anthoteibinenes A-E from the Irish Deep-Sea Coral Anthothela grandiflora: An Amination Puzzle

Org Lett. 2024 Nov 8;26(44):9419-9424. doi: 10.1021/acs.orglett.4c02549. Epub 2024 Sep 3.

Abstract

Chemical investigation of extracts from the Irish deep-sea soft coral Anthothela grandiflora revealed cadinene-like sesquiterpenes, anthoteibinenes A-E, bearing unusual dimethylamine substitution. Structure elucidation was accomplished using 1D/2D NMR spectroscopy and high-resolution mass spectrometry, while NOESY NMR experiments, gauge invariant atomic orbital (GIAO) NMR calculations coupled with DP4+ probabilities measures, and ECD comparisons were incorporated to propose their relative and absolute configurations. Anthoteibinene B (2) exhibited 49% inhibition of respiratory syncytial virus (RSV) at 3.1 μM with no cytotoxicity.

MeSH terms

  • Animals
  • Anthozoa* / chemistry
  • Antiviral Agents / chemistry
  • Antiviral Agents / isolation & purification
  • Antiviral Agents / pharmacology
  • Molecular Structure
  • Respiratory Syncytial Viruses / drug effects
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology

Substances

  • Sesquiterpenes
  • Antiviral Agents