Isolation, Structure Elucidation, Relative LC-MS Response, and in Vitro Toxicity of Azaspiracids from the Dinoflagellate Azadinium spinosum

Abstract

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Mediterranean Azadinium dexteroporum (Dinophyceae) produces six novel azaspiracids and azaspiracid-35: a structural study by a multi-platform mass spectrometry approach

“…Compared to other Amphidomataceae species, for which only a few azaspiracids have been reported, the diversity of AZAs in the Mediterranean A. dexteroporum strain seems to be exceptional. However, a high diversity of AZAs is now also known from A. spinosum [17,29] and future studies using the multi-platform approach or computational approaches such as molecular networking [31] might show this for other species/strains as well. The presence of so many AZAs is even more surprising if compared to the complete absence of AZAs in the Arctic strain of the same species [27], although cases of intraspecific differences in toxin profiles are widespread [14,32].…”

“…Recent studies on the toxicity of some purified AZA analogues relative to AZA-1 showed that all analyzed AZAs were toxic and that AZA-2, AZA-3, and AZA-6 were more toxic than AZA-1 by 8.3, 4.5, and 7 times, respectively [10], 37-epi-AZA-1 was 5 times more toxic [11], AZA-33 and AZA-34 were 5 times less toxic and 5 times more toxic, respectively [17], and AZA-36 and AZA-37 were 6 and 3 times less toxic, respectively [15]. As major differences in toxicity can be related to slightly different structures of AZAs, the actual toxicity of the different compounds produced by the Mediterranean A. dexteroporum is worthy of consideration in future toxicological studies.…”

“…Over the last years, several analogues of AZA-1 have been discovered either in shellfish [7][8][9][10][11] or in dinoflagellates [6,[12][13][14][15][16][17] and structurally characterized by tandem mass spectrometry (MS/MS) and partly also by nuclear magnetic resonance (NMR) spectroscopy. Some AZAs (AZA-1 and AZA-2, among others) are actually produced by the dinoflagellates, whereas others (e.g., AZA-3 to AZA-19) seem to derive from biotransformation occurring in shellfish [9].…”

Structure Elucidation, Relative LC–MS Response and In Vitro Toxicity of Azaspiracids 7–10 Isolated from Mussels (Mytilus edulis)

“…6-9 AZA1, 1, (Figure 1) is a K + channel blocker, 10 and is highly cytotoxic to multiple cell types which undergo atypical apoptosis after exposure. 11 AZAs were first identified in the late 1990s and since then more than 30 analogues have been observed in shellfish, 12 phytoplankton, [13][14][15] crabs 16 and a marine sponge. 17 Only 1, AZA2, 2, and AZA3, 3, (Figure 1) are currently regulated in raw shellfish.…”

Relative molar response of lipophilic marine algal toxins in liquid chromatography/electrospray ionization mass spectrometry

“…This practice is acceptable if relative molar responses (RMRs) between analogs have been assessed. Studies evaluating response factors for toxins have been limited, but a recent study highlighted that RMRs for AZAs were dependent both on chromatographic and MS acquisition parameters . There is lack of knowledge concerning response factors for other regulated toxins including OA/DTXs, the PTXs, the YTXs and the cyclic imines.…”