The Missing Piece in Biosynthesis of Amphidinols: First Evidence of Glycolate as a Starter Unit in New Polyketides from Amphidinium carterae

Cutignano, Adele; Sardo, Angela; Fontana, Angelo

doi:10.3390/md15060157

Cited by 28 publications

(32 citation statements)

References 35 publications

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“…The preliminary SRM scan also revealed some other known AM, which have been identified by mass spectrometry by Nuzzo et al (2014) [ 7 ] and Cutignano et al (2017) [ 23 ] before. Their CID spectra differ significantly from the AM detected above.…”

Section: Resultsmentioning

confidence: 76%

LC-MS/MS Method Development for the Discovery and Identification of Amphidinols Produced by Amphidinium

et al. 2020

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Amphidinols are polyketides produced by dinoflagellates suspected of causing fish kills. Here, we demonstrate a liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the identification and quantification of amphidinols (AM). Novel AM were detected by neutral loss (NL) scan and then quantified together with known AM by selection reaction monitoring (SRM). With the new method, AM were detected in four of eight analyzed strains with a maximum of 3680 fg toxin content per cell. In total, sixteen novel AM were detected by NL scan and characterized via their fragmentation patterns. Of these, two substances are glycosylated forms. This is the first detection of glycosylated AM.

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Section: Resultsmentioning

confidence: 76%

LC-MS/MS Method Development for the Discovery and Identification of Amphidinols Produced by Amphidinium

et al. 2020

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“…326 An Italian strain of A. carterae was the source of two further amphidinols 840, 841 and investigations into the biosynthesis of 840 utilising 13 C labelled acetate and glycolate proved that glycolate is the starter unit for polyketide chain assembly in amphidinols. 327 A further strain of Amphidinium yielded 842, 843, 15-and 19-membered macrolides respectively. 328 Karmitoxin 844, isolated from a culture of Karlodinium armiger, is a polyhydroxy-polyene that is structurally related to both amphidinols and karlotoxins but contains a primary amino group.…”

Section: Dinoagellatesmentioning

confidence: 99%

Marine natural products

et al. 2019

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“…Recent studies including competition-binding assays, electrophysiological techniques and in silico simulations have been performed with prorocentrolide-A to determine potency and biological activity (Amar et al, 2018). Such cyclic imines have been reported to be antagonists of muscle and neuronal (Kobayashi and Kubota, 2007;Cutignano et al, 2017). Reprinted with permission from Kobayashi and Kubota (2007).…”

Section: Determination Of Toxin Composition Occurrence and Associatementioning

confidence: 99%

A Review on the Biodiversity and Biogeography of Toxigenic Benthic Marine Dinoflagellates of the Coasts of Latin America

2019

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Many benthic dinoflagellates are known or suspected producers of lipophilic polyether phycotoxins, particularly in tropical and subtropical coastal zones. These toxins are responsible for diverse intoxication events of marine fauna and human consumers of seafood, but most notably in humans, they cause toxin syndromes known as diarrhetic shellfish poisoning (DSP) and ciguatera fish poisoning (CFP). This has led to enhanced, but still insufficient, efforts to describe benthic dinoflagellate taxa using morphological and molecular approaches. For example, recently published information on epibenthic dinoflagellates from Mexican coastal waters includes about 45 species from 15 genera, but many have only been tentatively identified to the species level, with fewer still confirmed by molecular criteria. This review on the biodiversity and biogeography of known or putatively toxigenic benthic species in Latin America, restricts the geographical scope to the neritic zones of the North and South American continents, including adjacent islands and coral reefs. The focus is on species from subtropical and tropical waters, primarily within the genera Prorocentrum, Gambierdiscus/Fukuyoa, Coolia, Ostreopsis and Amphidinium. The state of knowledge on reported taxa in these waters is inadequate and time-series data are generally lacking for the prediction of regime shift and global change effects. Details of their respective toxigenicity and toxin composition have only recently been explored in a few locations. Nevertheless, by describing the specific ecosystem habitats for toxigenic benthic dinoflagellates, and by comparing those among the three key regions-the Gulf of Mexico, Caribbean Sea and the subtropical and tropical Pacific coast, insights for further risk assessment of the global spreading of toxic benthic species is generated for the management of their effects in Latin America.

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The Missing Piece in Biosynthesis of Amphidinols: First Evidence of Glycolate as a Starter Unit in New Polyketides from Amphidinium carterae

Cited by 28 publications

References 35 publications

LC-MS/MS Method Development for the Discovery and Identification of Amphidinols Produced by Amphidinium

LC-MS/MS Method Development for the Discovery and Identification of Amphidinols Produced by Amphidinium

Marine natural products

A Review on the Biodiversity and Biogeography of Toxigenic Benthic Marine Dinoflagellates of the Coasts of Latin America

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