Karmitoxin: an amine containing polyhydroxy-polyene toxin from the marine dinoflagellate Karlodinium armiger
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Karmitoxin : an amine containing polyhydroxy-polyene toxin from the marine dinoflagellate Karlodinium armiger. / Rasmussen, Silas Anselm; Binzer, Sofie Bjørnholt; Hoeck, Casper; Meier, Sebastian; Soman de Medeiros, Lívia; Andersen, Nikolaj Gedsted; Place, Allen; Nielsen, Kristian Fog; Hansen, Per Juel; Larsen, Thomas Ostenfeld.
I: Journal of Natural Products, Bind 80, Nr. 5, 05.04.2017, s. 1287−1293.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Karmitoxin
T2 - an amine containing polyhydroxy-polyene toxin from the marine dinoflagellate Karlodinium armiger
AU - Rasmussen, Silas Anselm
AU - Binzer, Sofie Bjørnholt
AU - Hoeck, Casper
AU - Meier, Sebastian
AU - Soman de Medeiros, Lívia
AU - Andersen, Nikolaj Gedsted
AU - Place, Allen
AU - Nielsen, Kristian Fog
AU - Hansen, Per Juel
AU - Larsen, Thomas Ostenfeld
PY - 2017/4/5
Y1 - 2017/4/5
N2 - 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 mixotrophicdinoflagellate Karlodinium armiger. Our work describes the isolation and structural characterization of a new polyhydroxypolyene 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 eventualmortality of the copepod Acartia tonsa, a natural grazer of K. armiger.
AB - 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 mixotrophicdinoflagellate Karlodinium armiger. Our work describes the isolation and structural characterization of a new polyhydroxypolyene 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 eventualmortality of the copepod Acartia tonsa, a natural grazer of K. armiger.
U2 - 10.1021/acs.jnatprod.6b00860
DO - 10.1021/acs.jnatprod.6b00860
M3 - Journal article
C2 - 28379705
VL - 80
SP - 1287−1293
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 5
ER -
ID: 174459466