Biological activities of semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin.

Yanagi, Toshihiko; Murata, Michio; Torigoe, Koichiro; Yasumoto, Takeshi

doi:10.1271/bbb1961.53.525

Cited by 46 publications

(23 citation statements)

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“…For 7-O-fatty acid esters of OA, the intraperitoneal toxicity in mice is reported to be lower than for OA (28), and esterification of the carboxylic group reduces the inhibitory potency of OA analogues by 3-4 orders of magnitude (29). However, esterified derivatives of OA, DTX1, and DTX2 are thought to be relatively unstable (20) and are expected to be hydrolyzed in the stomach of humans to release the parent toxin.…”

Section: Resultsmentioning

confidence: 99%

New Esters of Okadaic Acid in Seawater and Blue Mussels (Mytilus edulis)

Torgersen

Miles

Rundberget

et al. 2008

J. Agric. Food Chem.

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Marine algal toxins of the okadaic acid (OA) group can occur as diol esters and sulfated diol esters in algae and as fatty acid esters in shellfish. Several of these ester forms have been identified, but the most common procedure for detecting OA group toxin esters is by measuring the increase in parent toxin after alkaline hydrolysis. Use of this alkaline hydrolysis method led to the discovery of high levels of conjugates of OA and dinophysistoxins-2 (DTX2) in seawater and of OA, DTX1, and DTX2 in blue mussel hepatopancreas (HP) from Flødevigen, Norway, during a bloom of Dinophysis spp. In the water sample, a C 8-diol ester, a C 9-diol ester, and a previously undescribed C 8-triol ester of OA were characterized using HPLC-MS (2), -MS (3), and -MS (4) in combination with various derivatization procedures. Palmitic acid (16:0) ester derivatives of these diol/triol esters were found in mussel HP and characterized using HPLC-MS (2), -MS (3), and -MS (4). To the authors' knowledge, hybrid diol-fatty acid esters of OA have not been previously described. Mass spectral analysis showed the presence of two forms of hybrid esters: one with the fatty acid conjugated to the 7-OH of the OA moiety and the other with the fatty acid conjugated to the OH group in the "diol" moiety. In the water sample, the C 8-diol ester was the most abundant, whereas in the mussels, the 16:0-C 9-diol hybrid ester was most abundant, and only minor amounts of the 16:0-C 8-diol hybrid ester were detected, suggesting that C 8- and C 9-diol esters of OA may be metabolized differently in blue mussels. 7- O-acyl esters of OA, DTX1, and DTX2 are thought to contribute to shellfish toxicity by being hydrolyzed in the human stomach to the parent toxins, and the newly characterized hybrid esters are likely to contribute similarly.

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Section: Resultsmentioning

confidence: 99%

New Esters of Okadaic Acid in Seawater and Blue Mussels (Mytilus edulis)

Torgersen

Miles

Rundberget

et al. 2008

J. Agric. Food Chem.

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“…Information on the toxicity of fatty acid esters of phycotoxins is sparse, although for diarrhetic shellfish poisoning toxins a lower toxicity has been indicated. 37 Pinnatoxin acyl esters are worthy of investigation from a toxicological point of view as they may possess toxicities similar to the nonacylated compounds. Also, hydrolysis of the esters during digestion could potentially result in exposure to significantly higher pinnatoxin levels.…”

Section: Direct Determination Of Pinnatoxin Esters By Lc-msmentioning

confidence: 99%

Identification of Pinnatoxins and Discovery of Their Fatty Acid Ester Metabolites in Mussels (Mytilus edulis) from Eastern Canada

McCarron

Rourke

Hardstaff

et al. 2012

J. Agric. Food Chem.

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Pinnatoxins are a group of fast-acting cyclic imine toxins previously identified in shellfish from Asia, the southern Pacific, and northern Europe. In this work pinnatoxins were detected in mussels from locations across the eastern coast of Canada. Pinnatoxin G (6) was the major structural variant present, sometimes at levels >80 μg/kg, whereas much lower levels of pinnatoxin A (1) were detected in some samples. Increased concentrations were observed following base hydrolysis of extracts, leading to the discovery by LC-MS of a range of fatty acid esters of 6. Information on the structures of these acylated derivatives was provided through a series of mass spectrometric experiments, supported by partial synthesis, and it is proposed that the compounds are 28-O-acyl esters of 6. Although acyl esters of a range of other phycotoxins are known to form as metabolites in shellfish, this is the first report of their existence for this particular toxin class. The occurrence of pinnatoxins in North American shellfish further highlights the international distribution of these toxins.

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“…Later, OA and DTX-2 acyl esters were found in Irish mussels (Marr et al 1992). As they have not yet been detected in the Dinophysis cells and are less toxic than their parent molecules (Yanagi et al 1989), it has been assumed that these acyl esters are the products of metabolic activity in bivalve digestive glands (Suzuki et al 1999(Suzuki et al , 2005. The toxins from the OA family are often referred to as "dinophysistoxins" or "DTXs" in the literature, even though historically the term DTXs refers only to DTX-1, DTX-2 and their acylate analogues.…”

Section: Introductionmentioning

confidence: 99%

Effect of food supply on the detoxification in the blue mussel,Mytilus edulis, contaminated by diarrhetic shellfish toxins

Marcaillou

Haure

Mondeguer

et al. 2010

Aquat. Living Resour.

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-The objective of this study was to identify a possible effect of food on the acceleration of decontamination in blue mussels, Mytilus edulis, containing diarrhetic toxins belonging to the okadaic acid (OA) structural group. An experimental protocol was designed to describe and compare the decontamination kinetics and detoxification rates of naturally OA-contaminated mussels that had either received or not received food for three weeks. The protocol was applied in two trials (in June 2006 and June 2007, called Ker06 and Ker07), conducted one year apart on samples of mussels collected in the same area, at the same season. Okadaic acid (OA), the main lipophilic toxin produced by the toxic alga Dinophysis acuminata, was analysed over the course of the decontamination, in hydrolysed (total OA) and non hydrolysed (free OA) digestive gland extracts, in order to estimate acyl-esters (7-O-acyl-ester derivatives of OA) concentrations. OA analyses were also made for toxin presence in biodeposits and in the aqueous phase. Bivalve physiological status was evaluated by biomass measurements (dry weight of flesh) and two biochemical compounds (total lipid and glycogen concentrations). Measured physiological parameters showed that mussels did not suffer under experimental conditions. Both trials showed that the food accelerated the elimination of free and total OA. This effect cannot be attributed to a dilution of the toxin in the tissue, as results expressed in toxin burden led to the same conclusion. The kinetic models of decontamination differed between the two experiments: the model was linear for Ker06, provided that the values corresponding to the first two days were discarded, whereas data fitted a decreasing exponential curve better in Ker07. Detoxification rates increased as the food supply increased. After three weeks of experimentation, the detoxification rates for total OA in Ker06 and Ker07 were 52 and 61%, respectively, in unfed mussels and 90 and 89% in fed mussels (with the highest level in Ker07). Comparisons between the free OA and esters showed that detoxification rate was higher for free OA than for esters, whatever the level of food supply. The results of this study suggest that food increase probably accelerates elimination of OA and OA-esters but the latter are eliminated at a lower speed. Key words:Mussel / Feeding / Digestive gland / Depuration / Okadaic acid / Acyl esters / Marine lipophilic biotoxins / Mass spectrometry Résumé -L'objectif de cette étude est de mettre en évidence un effet éventuel de la nourriture sur la vitesse de décontamination de moules, Mytilus edulis, contenant des toxines diarrhéiques de la famille de l'acide okadaïque (OA). Un protocole expérimental est conçu pour décrire les cinétiques durant 3 semaines d'expérience et comparer les taux de détoxication d'une part chez des moules nourries et d'autre part chez des moules maintenues à jeun. Ce protocole est appliqué sur des moules prélevées au même endroit, à la même saison, en 2006et 2007. L'acide okadaïque, principale ...

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Biological activities of semisynthetic analogs of dinophysistoxin-3, the major diarrhetic shellfish toxin.

Cited by 46 publications

References 0 publications

New Esters of Okadaic Acid in Seawater and Blue Mussels (Mytilus edulis)

New Esters of Okadaic Acid in Seawater and Blue Mussels (Mytilus edulis)

Identification of Pinnatoxins and Discovery of Their Fatty Acid Ester Metabolites in Mussels (Mytilus edulis) from Eastern Canada

Effect of food supply on the detoxification in the blue mussel,Mytilus edulis, contaminated by diarrhetic shellfish toxins

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