High resolution mass spectrometry investigation of an extract of the toxic cyanobacterium Sphaerospermopsis torques-reginae ITEP-024 led to the discovery of four new spumigin congeners. The structures for these peptides were postulated on the basis of accurate mass data and isotopic pattern information of both full scan and product ion spectra. This is the first reported evidence of spumigins on Sphaerospermopsis species.
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http://dx.doi.org/10.1016/j.toxicon.2015.09.019 | DOI Listing |
ACS Catal
July 2023
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States.
Cyclic arginine noncanonical amino acids (ncAAs) are found in several actinobacterial peptide natural products with therapeutically useful antibacterial properties. The preparation of ncAAs like enduracididine and capreomycidine currently takes multiple biosynthetic or chemosynthetic steps, thus limiting the commercial availability and applicability of these cyclic guanidine-containing amino acids. We recently discovered and characterized the biosynthetic pathway of guanitoxin, a potent freshwater cyanobacterial neurotoxin, that contains an arginine-derived cyclic guanidine phosphate within its highly polar structure.
View Article and Find Full Text PDFChemosphere
August 2023
Laboratory of Environmental Biogeochemistry, Center for Nuclear Energy in Agriculture, University of São Paulo, Piracicaba, Brazil; Laboratory of Toxins and Natural Algae Products, School of Pharmaceutical Sciences, University of São Paulo, São Paulo, Brazil; Food Research Center (FoRC - CEPID), University of São Paulo, São Paulo, Brazil. Electronic address:
Anthropogenic activity has dramatically deteriorated aquatic ecosystems in recent years. Such environmental alterations could change the primary producers' composition, exacerbating the proliferation of harmful microorganisms such as cyanobacteria. Cyanobacteria can produce several secondary metabolites, including guanitoxin, a potent neurotoxin and the only naturally occurring anticholinesterase organophosphate ever reported in the literature.
View Article and Find Full Text PDFbioRxiv
March 2023
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, United States.
Cyclic arginine noncanonical amino acids (ncAAs) are found in several actinobacterial peptide natural products with therapeutically useful antibacterial properties. The preparation of ncAAs like enduracididine and capreomycidine currently takes multiple biosynthetic or chemosynthetic steps, thus limiting the commercial availability and applicability of these cyclic guanidine-containing amino acids. We recently discovered and characterized the biosynthetic pathway of guanitoxin, a potent freshwater cya-nobacterial neurotoxin, that contains an arginine-derived cyclic guanidine phosphate within its highly polar structure.
View Article and Find Full Text PDFJ Am Chem Soc
June 2022
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, La Jolla, California 92093, United States.
Harmful cyanobacterial blooms (cyanoHABs) cause recurrent toxic events in global watersheds. Although public health agencies monitor the causal toxins of most cyanoHABs and scientists in the field continue developing precise detection and prediction tools, the potent anticholinesterase neurotoxin, guanitoxin, is not presently environmentally monitored. This is largely due to its incompatibility with widely employed analytical methods and instability in the environment, despite guanitoxin being among the most lethal cyanotoxins.
View Article and Find Full Text PDFSci Total Environ
August 2022
Laboratory of Toxins and Natural Algae Products, School of Pharmaceutical Sciences, University of São Paulo, Av. Professor Lineu Prestes, 05508-000 São Paulo, Brazil; Tropical Ecosystems Operation Division, Nuclear Energy in Agriculture Center, University of São Paulo, Av. Centenário, 13416-000 Piracicaba, Brazil; Food Research Center (FoRC-CEPID), University of São Paulo, Rua do Lago, 05508-080 São Paulo, Brazil.
Changes in environmental conditions in aquatic ecosystems caused by anthropic actions can modify the composition of primary producers, promoting the excessive proliferation of cyanobacteria. These organisms can form cyanobacterial blooms, which directly affect aquatic life. The present study investigated the mutagenicity of the cyanobacterium Sphaerospermopsis torques-reginae (strain ITEP-024), guanitoxin-producing (natural organophosphate), and sublethal effects on fish in relevant environment concentrations.
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