Karmitoxin: An amine containing polyhydroxy-polyene toxin from the marine dinoflagellate Karlodinium armiger

Silas Anselm Rasmussen, Sofie Bjørnholt Binzer, Casper Hoeck, Sebastian Meier, Lívia Soman De Medeiros, Nikolaj Gedsted Andersen, Allen D Place, Kristian Fog Nielsen, Per Juel Hansen, Thomas Ostenfeld Larsen

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Abstract

Marine algae from the genus Karlodinium are known to be involved in fish-killing events worldwide. Here we report for the first time the chemistry and bioactivity of a natural product from the newly described mixotrophic dinoflagellate Karlodinium armiger. Our work describes the isolation and structural characterization of a new polyhydroxy-polyene named karmitoxin. The structure elucidation work was facilitated by use of 13C enrichment and high-field 2D NMR spectroscopy, where 1H–13C long-range correlations turned out to be very informative. Karmitoxin is structurally related to amphidinols and karlotoxins; however it differs by containing the longest carbon–carbon backbone discovered for this class of compounds, as well as a primary amino group. Karmitoxin showed potent nanomolar cytotoxic activity in an RTgill-W1 cell assay as well as rapid immobilization and eventual mortality of the copepod Acartia tonsa, a natural grazer of K. armiger.
Original languageEnglish
JournalJournal of Natural Products
Volume80
Issue number5
Pages (from-to)1287-1293
Number of pages7
ISSN0163-3864
DOIs
Publication statusPublished - 2017

Cite this

Rasmussen, S. A., Binzer, S. B., Hoeck, C., Meier, S., Soman De Medeiros, L., Andersen, N. G., Place, A. D., Nielsen, K. F., Hansen, P. J., & Larsen, T. O. (2017). Karmitoxin: An amine containing polyhydroxy-polyene toxin from the marine dinoflagellate Karlodinium armiger. Journal of Natural Products, 80(5), 1287-1293. https://doi.org/10.1021/acs.jnatprod.6b00860