Isolation and structure of a new brevetoxin analog, brevetoxin B2, from greenshell mussels from New Zealand

Murata, Kazuya; Satake, Masayuki; Naoki, Hideo; Kaspar, Heinrich F.; Yasumoto, Takeshi

doi:10.1016/s0040-4020(97)10336-2

Cited by 78 publications

(53 citation statements)

References 15 publications

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“…In shellfish tissue, PbTx-3 remains largely intact, whereas PbTx-2 is rapidly converted to PbTx-3 and cysteine conjugates (Plakas et al 2002). Studies of cockle (Austrovenus stutchburyi), mussel (Perna canaliculus), and Pacific oyster (Crassostrea gigas) tissues in New Zealand after an NSP event indicated that the predominant brevetoxin forms in the tissue were metabolites of PbTx-2, including PbTx-3, brevetoxin-B 1 , cysteine conjugates, and fatty acid conjugates (Ishida et al 1995;Morohashi et al 1999;Murata et al 1998). Differences were observed in brevetoxin metabolite composition between the mollusks wherein oysters contained more PbTx-3 and cysteine conjugates and cockles contained brevetoxin-B 1 (Ishida et al 1995).…”

Section: Discussionmentioning

confidence: 99%

The type B brevetoxin (PbTx-3) adversely affects development, cardiovascular function, and survival in Medaka (Oryzias latipes) embryos.

Colman

Ramsdell

2003

Environ Health Perspect

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Brevetoxins are produced by the red tide dinoflagellate Karenia brevis. The toxins are lipophilic polyether toxins that elicit a myriad of effects depending on the route of exposure and the target organism. Brevetoxins are therefore broadly toxic to marine and estuarine animals. By mimicking the maternal route of exposure to the oocytes in finfish, we characterized the adverse effects of the type B brevetoxin brevetoxin-3 (PbTx-3) on embryonic fish development and survival. The Japanese rice fish, medaka (Oryzias latipes), was used as the experimental model in which individual eggs were exposed via microinjection to various known concentrations of PbTx-3 dissolved in an oil vehicle. Embryos injected with doses exceeding 1.0 ng/egg displayed tachycardia, hyperkinetic twitches in the form of sustained convulsions, spinal curvature, clumping of the erythrocytes, and decreased hatching success. Furthermore, fish dosed with toxin were often unable to hatch in the classic tail-first fashion and emerged head first, which resulted in partial hatches and death. We determined that the LD 50 (dose that is lethal to 50% of the fish) for an injected dose of PbTx-3 is 4.0 ng/egg. The results of this study complement previous studies of the developmental toxicity of the type A brevetoxin brevetoxin-1 (PbTx-1), by illustrating in vivo the differing affinities of the two congeners for cardiac sodium channels. Consequently, we observed differing cardiovascular responses in the embryos, wherein embryos exposed to PbTx-3 exhibited persistent tachycardia, whereas embryos exposed to PbTx-1 displayed bradycardia, the onset of which was delayed.

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Section: Discussionmentioning

confidence: 99%

The type B brevetoxin (PbTx-3) adversely affects development, cardiovascular function, and survival in Medaka (Oryzias latipes) embryos.

Colman

Ramsdell

2003

Environ Health Perspect

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“…In 1992Á93, more than 180 cases of human illness that fitted the symptoms of neurotoxic shellfish poisoning (NSP) occurred after consumption of contaminated shellfish mainly collected from the coastline from Northland to the Bay of Plenty (Jasperse 1993;Chang et al 1995;MacKenzie et al 1995). High levels of the metabolites of brevetoxins (BTXs) were detected in shellfish samples collected at that time (Ishida et al 1995;Murata et al 1998;Morohashi et al 1999). Karenia cf brevis (similar morphology to *Corresponding author.…”

Section: á1mentioning

confidence: 99%

The toxic effects of three dinoflagellate species from the genusKareniaon invertebrate larvae and finfish

Shi

McNabb

Rhodes

et al. 2012

New Zealand Journal of Marine and Freshwater Research

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“…The predominantly occurring brevetoxin in algae, PbTx-2, is rapidly reduced to the more stable PbTx-3. Following the neurotoxic shellfish poisoning in New Zealand (Mackenzie et al 1996;Satake et al 1996), four brevetoxin metabolites were described, including a taurine conjugate, an S-cysteine conjugate, and fatty acid esters (Ishida et al 1996;Morohashi et al 1995Morohashi et al , 1999Murata et al 1998). Subsequently, Poli et al (2000) reported brevetoxin activity consistent with metabolites from shellfish from Florida coastal waters, and Plakas et al (2002) identified these as cysteine conjugates.…”

Section: Discussionmentioning

confidence: 99%

Measurement of brevetoxin levels by radioimmunoassay of blood collection cards after acute, long-term, and low-dose exposure in mice.

Woofter

Dechraoui

Garthwaite

et al. 2003

Environ Health Perspect

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We developed a radioimmunoassay (RIA) using a sheep anti-brevetoxin antiserum to evaluate detection of brevetoxin on blood collection cards from mice treated with the brevetoxin congener PbTx-3. The RIA has high affinity for PbTx-3 [half-maximal effective concentration (EC(50)) +/- SE = 1.2 +/- 0.2 nM; n = 10] and recognizes both type 1 and type 2 brevetoxins, but not ciguatoxin. Direct comparison of the RIA with a radiolabeled [(3)H]-PbTx-3 receptor-binding assay (RBA) revealed excellent sensitivity, congener selectivity, and minimal interference from blood matrix. We first analyzed blood samples from an acute time course exposure, using a maximal nonlethal dose [180 microg/kg body weight (bw)] for 0.5, 1, 2, 4, and 24 hr. Mean blood brevetoxin levels were 36 nM at 30 min and stayed above 20 nM during the 1-4 hr time points. We next analyzed blood brevetoxin levels after longer exposure (0.5, 1, 2, 3, 4, or 7 days). Mean blood brevetoxin levels were 26.0 nM at 0.5 days, decreased to 8.2 nM at 1.0 day, and maintained a significant level (p < 0.05) of 1.3 nM at day 2. We next determined the lowest measurable dose using increasing concentrations of PbTx-3 (10-300 micro g/kg bw). Analysis of the blood samples at 60 min revealed a linear relationship between administered and internal doses (r(2) = 0.993). All doses of brevetoxin administered were detectable at 1 hr, with significant levels found for the lowest administered dose of 10 micro g/kg bw--a dose that was 10-fold lower than the lowest observable effect level. This RIA provides an optimal first-tier detection of brevetoxin from blood collection cards and, used in combination with the RBA and liquid chromatography-mass spectrometry, should provide a complete panel of methods to biomonitor brevetoxin exposure.

show abstract

Isolation and structure of a new brevetoxin analog, brevetoxin B2, from greenshell mussels from New Zealand

Cited by 78 publications

References 15 publications

The type B brevetoxin (PbTx-3) adversely affects development, cardiovascular function, and survival in Medaka (Oryzias latipes) embryos.

The type B brevetoxin (PbTx-3) adversely affects development, cardiovascular function, and survival in Medaka (Oryzias latipes) embryos.

The toxic effects of three dinoflagellate species from the genusKareniaon invertebrate larvae and finfish

Measurement of brevetoxin levels by radioimmunoassay of blood collection cards after acute, long-term, and low-dose exposure in mice.

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