LC–MS/MS analysis of okadaic acid analogues and other lipophilic toxins in single-cell isolates of several Dinophysis species collected in Hokkaido, Japan

Suzuki, Toshiyuki; Miyazono, Akira; Baba, Katsuhisa; Sugawara, Rieko; Kamiyama, Takashi

doi:10.1016/j.hal.2008.06.001

Cited by 82 publications

(70 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(Cembella 1989, Caroppo et al 1999 nor in single-cell isolates analyzed by liquid chromatography coupled to mass spectrometry (LC-MS) (Suzuki et al 2009). In contrast, Miles et al (2004) showed traces of lipophilic toxins in P. rotundatum cells picked from net-haul samples dominated by other Dinophysis spp.…”

Section: Abstract: Phalacroma Rotundatum · Dinophysis Spp · Diarrhementioning

confidence: 99%

“…In contrast, Miles et al (2004) showed traces of lipophilic toxins in P. rotundatum cells picked from net-haul samples dominated by other Dinophysis spp. The possibility of false positives -due to interfering false peaks deriving from fluorescence reagents and biological matrices -has been suggested to explain discrepancies among different cellular toxin content observed in the same species using different analytical methods (Suzuki et al 2009). An intriguing question concerning the mixotrophic species of Dinophysis has been whether the toxins are synthesized de novo or are derived from their prey.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…An intriguing question concerning the mixotrophic species of Dinophysis has been whether the toxins are synthesized de novo or are derived from their prey. Recently, de novo production of okadaic acid (OA) derivatives and pectenotoxins in the mixotroph D. acuminata and the lack of toxins in its prey -the ciliate Myrionecta rubra -has been proved in laboratory cultures (Kamiyama & Suzuki 2009).Phalacroma rotundatum was observed to feed on tintinnid ciliates (Elbrächter 1991) and to become replete of digestive vacuoles after feeding on laboratory cultures of the ciliate Tiarina fusus (Hansen 1991). Jacobson & Andersen (1994) observed vacuoles in field specimens of P. rotundatum under light (differential interference contrast [DIC]) microscopy.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Considerations on the toxigenic nature and prey sources of Phalacroma rotundatum

González-Gil

Pizarro²,

Paz³

et al. 2011

Aquat. Microb. Ecol.

View full text Add to dashboard Cite

The heterotrophic dinoflagellate Phalacroma rotundatum (Claparède & Lachman)Kofoid & Michener is considered a toxic species, but there is controversy about its toxigenic nature. In the present study, about one-third of the toxin analyses done with liquid chromatography-mass spectrometry (LC-MS) of P. rotundatum specimens picked from field populations in Galicia (NW Spain) between 2003 and 2005 revealed traces of lipophilic toxins -okadaic acid (OA) and/or dinophysistoxin-2 (DTX2) and/or pectenotoxin-2 (PTX2) (if any) -that mimicked the toxin profile of cooccurring toxigenic mixotrophic species of Dinophysis (D. acuminata, D. acuta, and D. caudata). Thus, during the period of study, P. rotundatum was never a relevant contributor to diarrhetic shellfish poisoning (DSP) toxins contaminating shellfish resources in Galicia. Observations of phycoerythrin-like autofluorescence in P. rotundatum and in its co-occurring potential ciliate prey -Tiarina cf. fususled to the suspicion that P. rotundatum had taken up toxins by feeding on this ciliate prey that had previously fed on Dinophysis spp. Nevertheless, toxins in P. rotundatum specimens with orange autofluorescence were under detection levels, and the source of these orange pigments may be a prey different from Dinophysis spp. (e.g. Myrionecta spp.). New results here add evidence to suggest that P. rotundatum does not produce toxins de novo, but acts as a vector from toxin-containing prey to shellfish, and that M. rubra may be one of its potential ciliate prey. Conclusive testing of these hypotheses is now under investigation with laboratory cultures of Dinophysis and Phalacroma spp. and M. rubra. KEY WORDS: Phalacroma rotundatum · Dinophysis spp. · Diarrhetic shellfish poisoning · DSP · Pectenotoxins · PTX · Lipophilic shellfish toxinsResale or republication not permitted without written consent of the publisher Aquat Microb Ecol 64: 197-203, 2011 toxins either in dense net-hauls where P. rotundatum was not accompanied by other Dinophysis spp. (Cembella 1989, Caroppo et al. 1999 nor in single-cell isolates analyzed by liquid chromatography coupled to mass spectrometry (LC-MS) (Suzuki et al. 2009). In contrast, Miles et al. (2004) showed traces of lipophilic toxins in P. rotundatum cells picked from net-haul samples dominated by other Dinophysis spp. The possibility of false positives -due to interfering false peaks deriving from fluorescence reagents and biological matrices -has been suggested to explain discrepancies among different cellular toxin content observed in the same species using different analytical methods (Suzuki et al. 2009). An intriguing question concerning the mixotrophic species of Dinophysis has been whether the toxins are synthesized de novo or are derived from their prey. Recently, de novo production of okadaic acid (OA) derivatives and pectenotoxins in the mixotroph D. acuminata and the lack of toxins in its prey -the ciliate Myrionecta rubra -has been proved in laboratory cultures (Kamiyama & Suzuki 2009).Phalacroma rotundatum was ...

show abstract

Section: Abstract: Phalacroma Rotundatum · Dinophysis Spp · Diarrhementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Considerations on the toxigenic nature and prey sources of Phalacroma rotundatum

González-Gil

Pizarro²,

Paz³

et al. 2011

Aquat. Microb. Ecol.

View full text Add to dashboard Cite

show abstract

“…Detection of DTX-1 in picked cells from Kesennuma Bay (Japan) using liquid chromatography with fluorescence detection (LC-FLD) was the first record of toxin production by this species (Lee et al, 1989). However, these toxins were not detected later in D. tripos isolates from Japan analyzed by liquid chromatography-tandem mass spectrometry (LC-MS/MS) (Suzuki et al, 2009). More recently, the presence of PTX-2 in D. tripos was detected for the first time in field samples and cultures from Galician Rías also using LC-MS analyses (Rodríguez et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Co-occurrence of Dinophysis tripos and pectenotoxins in Argentinean shelf waters

et al. 2015

View full text Add to dashboard Cite

A New Diol Ester Derivative of Dinophysistoxin‐1 from Cultures of Prorocentrum lima Collected in South Korea

Lee

Hwang

Kim

et al. 2015

Bulletin Korean Chem Soc

View full text Add to dashboard Cite

Keywords: Prorocentrum lima, Dinophysistoxin-1, DTX-1 diol ester, Cytotoxicity Marine dinoflagellates have been widely studied because of their rich chemodiversity and biologically toxic compounds extracted from them. These organisms are considered the cause of most occurrences of food poisoning from seafood. 1-3 Among these, the genera Prorocentrum and Dinophysis were well known to produce diarrhetic shellfish poisoning (DSP) toxins such as the okadaic acid (OA), pectenotoxin-2 (PTX-2), and dinophysistoxin-1 (DTX-1), leading to disastrous influences on the shellfish industry worldwide due to their effect on human health. [4][5][6] Shellfish are believed to become toxic by accumulating the toxins through filterfeeding the algae of the two genera. Furthermore, many research works have also revealed the existence of a wide range of OA analogs from the large-scale cultivation or filter-feeding bivalve molluscs, such as scallops, clams, and mussels. The OA analogs are largely classified into 7-O-fatty acid esters, which are found only in shellfish, and diol esters, where the carboxylic group of OA is esterified with C 6 to C 10 diols. All of these constituents may be very important in the study of toxin production and toxin profile of shellfish or harmful algae in coast areas. [7][8][9] Recently, during the monitoring of toxic compounds from the benthic Prorocentrum lima spawned around Jeju island, Korea, an unidentified DTX-1 analog (1) was isolated from the toxic fractions of the cultures of P. lima and structurally characterized. This new compound is characterized by a lipid-soluble C 9 diol ester of DTX-1. As shown in Figure 1, most of the lipid-soluble diol esters previously reported in the literature are commonly derived from the OA parent compound. [10][11][12][13][14][15] Interestingly, on the other hand, 1 came from the DTX-1 compound. The 7-O-fatty acid esters of DTX-1, collectively named as DTX-3, have been found, 4 but, to our knowledge, diol esters of DTX-1, such as compound 1, have not been reported. In this paper, we present the cultivation method of P. lima, the characterization of compound 1, and its bioactivity.The methanolic extract of P. lima, exhibiting strong cytotoxicity during a brine shrimp lethality test, showed in the liquid chromatography-mass spectrometry (LC-MS) analysis the presence of two well-known DSP toxins: OA and DTX-1.Interestingly, a major peak in the LC-MS chromatogram was deduced to belong to a derivative of DTX-1 by its fragmented ion peak of m/z 841 in the MS/MS spectrum, which is identical to the mass value of the sodiated DTX-1. In order to isolate the corresponding compound, unialgal P. lima was cultivated up to a volume of 200 L. After harvesting the cultures by centrifugation, the cells were extracted using methanol, and the extract was chromatographed on a Sephadex LH20 column, yielding six fractions. Compound 1 was isolated and purified by reversed-phase HPLC from the mixture of the two fractions that are responsible for a strong cytotoxicity.Compound 1 was isolated a...

show abstract

LC–MS/MS analysis of okadaic acid analogues and other lipophilic toxins in single-cell isolates of several Dinophysis species collected in Hokkaido, Japan

Cited by 82 publications

References 31 publications

Considerations on the toxigenic nature and prey sources of Phalacroma rotundatum

Considerations on the toxigenic nature and prey sources of Phalacroma rotundatum

Co-occurrence of Dinophysis tripos and pectenotoxins in Argentinean shelf waters

A New Diol Ester Derivative of Dinophysistoxin‐1 from Cultures of Prorocentrum lima Collected in South Korea

Contact Info

Product

Resources

About