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Karmitoxin: An Amine-Containing Polyhydroxy-Polyene Toxin from the Marine Dinoflagellate Karlodinium armiger.


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.

SUBMITTER: Rasmussen SA 

PROVIDER: S-EPMC6446557 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Karmitoxin: An Amine-Containing Polyhydroxy-Polyene Toxin from the Marine Dinoflagellate Karlodinium armiger.

Rasmussen Silas Anselm SA   Binzer Sofie Bjørnholt SB   Hoeck Casper C   Meier Sebastian S   de Medeiros Livia Soman LS   Andersen Nikolaj Gedsted NG   Place Allen A   Nielsen Kristian Fog KF   Hansen Per Juel PJ   Larsen Thomas Ostenfeld TO  

Journal of natural products 20170405 5


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 <sup>13</sup>C enrichment and high-field 2D NMR spectroscopy, where <sup>1  ...[more]

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