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Blooms of the microalga Prymnesium parvum cause devastating fish kills worldwide, which are suspected to be caused by the supersized ladder-frame polyether toxins prymnesin-1 and -2. These toxins have, however, only been detected from P. parvum in rare cases since they were originally described two decades ago. Here, we report the isolation and characterization of a novel B-type prymnesin, based on extensive analysis of 2D- and 3D-NMR data of natural as well as 90% (13)C enriched material. B-type prymnesins lack a complete 1,6-dioxadecalin core unit, which is replaced by a short acyclic C2 linkage compared to the structure of the original prymnesins. Comparison of the bioactivity of prymnesin-2 with prymnesin-B1 in an RTgill-W1 cell line assay identified both compounds as toxic in the low nanomolar range. Chemical investigations by liquid chromatography high-resolution mass spectrometry (LC-HRMS) of 10 strains of P. parvum collected worldwide showed that only one strain produced the original prymnesin-1 and -2, whereas four strains produced the novel B-type prymnesin. In total 13 further prymnesin analogues differing in their core backbone and chlorination and glycosylation patterns could be tentatively detected by LC-MS/HRMS, including a likely C-type prymnesin in five strains. Altogether, our work indicates that evolution of prymnesins has yielded a diverse family of fish-killing toxins that occurs around the globe and has significant ecological and economic impact.
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http://dx.doi.org/10.1021/acs.jnatprod.6b00345 | DOI Listing |
Harmful Algae
December 2024
College of Environmental Science and Engineering, Ocean University of China, Qingdao, 266100, China; Key Laboratory of Marine Environment and Ecology, Ocean University of China, Ministry of Education, Qingdao, 266100, China. Electronic address:
Environ Sci Process Impacts
November 2024
Department of Environmental Science, Stockholm University, Sweden.
Hydrophobic organic contaminants (HOCs) affect phytoplankton at cellular to population levels, ultimately impacting communities and ecosystems. Baseline toxicants, such as some HOCs, predominantly partition to biological membranes and storage lipids. Predicting their toxic effects on phytoplankton populations therefore requires consideration beyond cell uptake and diffusion.
View Article and Find Full Text PDFSci Total Environ
December 2024
U.S. Geological Survey and Texas Cooperative Fish and Wildlife Research Unit, Texas Tech University, Lubbock, TX, USA. Electronic address:
Growth of the toxic alga Prymnesium parvum is hormetically stimulated with environmentally relevant concentrations of glyphosate. The mechanisms of glyphosate hormesis in this species, however, are unknown. We evaluated the transcriptomic response of P.
View Article and Find Full Text PDFMar Pollut Bull
November 2024
Physical Oceanography Laboratory/IAOS and Frontiers Science Center for Deep Ocean Multispheres and Earth System/Sanya Oceanographic Institution, Ocean University of China, Qingdao/Sanya, China.
Tin-free self-polishing antifouling coatings have the highest market share since organotin self-polishing antifouling coatings have been banned. However, its high dependence on cuprous oxide was found to have caused potential harm to the environment, making it necessary to improve the functionality of the resin. In this paper, a zinc acrylate resin with side chain hanging indole derivative structure was prepared by using N-(1H-5-bromoindole-3-methylene) (BIAM) with good biological activity as functional monomer.
View Article and Find Full Text PDFAquat Toxicol
November 2024
Department of Food Chemistry and Toxicology, Faculty of Chemistry, University of Vienna, Währinger Str. 38-40, 1090 Vienna, Austria; Unit Food Hygiene and Technology, Centre for Food Science and Veterinary Public Health, Clinical Department for Farm Animals and Food System Science, University of Veterinary Medicine, Vienna, Veterinärplatz 1, 1210 Vienna, Austria. Electronic address:
Prymnesins, produced by the haptophyte Prymnesium parvum, are considered responsible for fish kills when this species blooms. Although their toxic mechanism is not fully understood, membrane disruptive properties have been ascribed to A-type prymnesins. Currently it is suggested that pore-formation is the underlying cause of cell disruption.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!