Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning

Murata, Michio; Kumagai, Masanori; Lee, Jong Soo; Yasumoto, Takeshi

doi:10.1016/s0040-4039(01)81076-5

Cited by 360 publications

(148 citation statements)

References 10 publications

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“…A main event gaining attention was when Protoceratium recticulatum was identified as a producer of yessotoxins (YTX), first confirmed in cultures of P. reticulatum from New Zealand (Satake et al, 1997). Yessotoxins, a group of disulfated polyether toxins, were first isolated from Japanese scallops by Murata et al (1987). Effects of YTX tested in mice seem to be more serious when YTX are supplied by intraperitoneal injection than oral administration.…”

Section: Introductionmentioning

confidence: 99%

Growth and bioactive secondary metabolites of arctic Protoceratium reticulatum (Dinophyceae)

et al. 2016

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Section: Introductionmentioning

confidence: 99%

Growth and bioactive secondary metabolites of arctic Protoceratium reticulatum (Dinophyceae)

et al. 2016

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“…These natural compounds are included among algal toxins because i.p. injection of yessotoxin into mice leads to death at doses as low as 80 mg kg À1 (Murata et al, 1987;Ciminiello et al, 1997;Ogino et al, 1997). As YTXs can be accumulated in edible molluscs, such as scallops and mussels (Murata et al, 1987;Ciminiello et al, 1997), by filter feeding, the current European legislation sets the limits of YTX contamination in material destined to human consumption (European Communities, 2002).…”

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Selective disruption of the E-cadherin–catenin system by an algal toxin

et al. 2004

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Yessotoxins (YTXs) are algal toxins that can be accumulated in edible molluscs. YTX treatment of MCF-7 breast cancer cells causes the accumulation of a 100 kDa fragment of E-cadherin, which we have named ECRA 100 . A relative decrease in the concentrations of intact E-cadherin did not accompany the accumulation of ECRA 100 in cytosoluble extracts of MCF-7 cells on the first day of YTX treatment, but a collapse of the E-cadherin system was detected after 2 -5 days of treatment with the toxin. An analysis of the general structure of ECRA 100 revealed that it consists of an E-cadherin fragment lacking the intracellular domain of the protein.ECRA 100 was not released into culture media of YTX-treated cells. Accumulation of ECRA 100 was observed in other epithelial cells, such as human intestine Caco-2 and MDCK cells after treatment with YTX. In turn, YTX could not induce accumulation of fragments of other members of the cadherin family, such as N-cadherin in the PC12 cell line and K-cadherin in sensitive cells (MCF-7, Caco-2, MDCK). The accumulation of a 100 kDa fragment of E-cadherin devoid of its intracellular domain induced by YTX was accompanied by reduced levels of b-and g-catenins bound to E-cadherin, without a concomitant decrease in the total cytosoluble pools of b-and g-catenins. Taken together, the results we obtained show that YTX causes the selective disruption of the E-cadherin -catenin system in epithelial cells, and raise some concern about the potential that an algal toxin found in seafood might disrupt the tumour suppressive functions of E-cadherin.

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“…YTX and its analogs were first isolated from Patinopecten yessoensis in Japan (8) and were long classified as one of the categories of diarrheic shellfish poisoning (DSP) toxins (9). However, as these toxins cannot induce diarrhea, nor inhibit protein phosphatase 2A, like other DSP toxins, they were classified as an independent group by the European Union Commission in 2002 (10).…”

Section: Introductionmentioning

confidence: 99%

Effect of yessotoxin on cytosolic calcium levels in human hepatocellular carcinoma cells in vitro

et al. 2013

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Abstract. Yessotoxin (YTX) and its analogs are a type of marine toxins found in marine environments in numerous coastal countries. These toxins tend to accumulate in filter-feeding molluscs and may threaten the shellfish industry and public health. Several previous studies indicated that YTX IntroductionYessotoxin (YTX) and its analogs are a group of lipophilic marine toxins mainly produced by the dinoflagellates Protoceratium reticulatum, Gonyaulax spinifera and Lingulodinium polyedrum. These toxins tend to accumulate in filter-feeding molluscs, have been found in numerous countries worldwide (1-6) and were first detected in shellfish samples collected from Chinese coastal areas in 2009 (7).YTX and its analogs were first isolated from Patinopecten yessoensis in Japan (8) and were long classified as one of the categories of diarrheic shellfish poisoning (DSP) toxins (9). However, as these toxins cannot induce diarrhea, nor inhibit protein phosphatase 2A, like other DSP toxins, they were classified as an independent group by the European Union Commission in 2002 (10).Apoptosis is a programmed form of cell suicide. The process of apoptosis is controlled by genes and is crucial in disease outbreaks, including cancer. Once the signaling pathway of apoptosis is activated, the process cannot be easily undergone, even by tumor cells. Thus, there is an increasing number of studies on tumor cell apoptosis, with the aim to design an effective cancer treatment (11-13). Several studies indicated that YTX may induce apoptosis in different types of cell lines (14-21). However, the exact underlying mechanisms have not been elucidated.As the chemical structure of YTX is similar to that of brevetoxins and ciguatoxins, which were shown to interfere with voltage-gated sodium channels, the effects of YTX on transmembrane ion channels were previously investigated (22,23). The present study mainly investigated the YTX-induced alterations in intracellular Ca 2+ levels in Bel7402 human hepatocellular carcinoma cells and the possible underlying mechanisms. Materials and methodsReagents. Pure YTX was purchased from the National Research Council (NRC; Ottawa, ON, Canada). Fluo-3 acetoxymethyl ester (AM) solution (5 mM) was purchased from Beyotime Institute of Biotechnology (Shanghai, China). Nifedipine was purchased from Sigma (St. Louis, MO, USA) and was dissolved in dimethyl sulfoxide (Merck KGaA, Darmstadt, Germany). All other chemicals were of analytical reagent grade or higher purity.The Hanks' balanced salt solution (HBSS) used for cell washing consisted of 137 mM NaCl, 5.6 mM KCl, 1.26 mM CaCl 2 , 0.81 mM MgSO 4 , 0.38 mM Na 2 HPO 4 , 0.44 mM KH 2 PO 4 and 4.2 mM NaHCO 3 . The pH of the HBSS was adjusted to 7.4 with 0.1 M HCl and NaOH.

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Isolation and structure of yessotoxin, a novel polyether compound implicated in diarrhetic shellfish poisoning

Cited by 360 publications

References 10 publications

Growth and bioactive secondary metabolites of arctic Protoceratium reticulatum (Dinophyceae)

Growth and bioactive secondary metabolites of arctic Protoceratium reticulatum (Dinophyceae)

Selective disruption of the E-cadherin–catenin system by an algal toxin

Effect of yessotoxin on cytosolic calcium levels in human hepatocellular carcinoma cells in vitro

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