Anthoteibinenes A–E from the Irish Deep-Sea Coral <i>Anthothela grandiflora</i>: An Amination Puzzle
Chemical investigation of extracts from the Irish deep-sea soft coral <i>Anthothela grandiflora</i> 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 (<b>2</b>) exhibited 49% inhibition of respiratory syncytial virus (RSV) at 3.1 μM with no cytotoxicity.
Authors
- Kim C. Tran (ORCID: https://orcid.org/0000-0003-1121-6029)
- Sam Afoullouss (ORCID: https://orcid.org/0000-0003-0479-8032)
- Michael N. Teng (ORCID: https://orcid.org/0000-0002-0722-3659)
- Mark P. Johnson (ORCID: https://orcid.org/0000-0002-5078-1410)
- Bill J. Baker (ORCID: https://orcid.org/0000-0003-3033-5779)
- Ryan Young (ORCID: https://orcid.org/0000-0002-1219-9665)
- A. Louise Allcock (ORCID: https://orcid.org/0000-0002-4806-0040)
- Stine S. H. Olsen
Institutions
- Ollscoil na Gaillimhe – University of Galway (IE)
- University of South Florida (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-09-03
- DOI
- https://doi.org/10.1021/acs.orglett.4c02549
- Citations
- 6
- Primary Topic
- Marine Sponges and Natural Products
- Type
- article
- Field-Weighted Citation Impact
- 2.32
Funders
- Science Foundation Ireland
- National Institutes of Health
- European Regional Development Fund
- National Center for Complementary and Integrative Health