Brevetoxins: Structure, Toxicology, and Origin

Furey, Ambrose; Fernández, Javier García; O'Callaghan, Keith; Lehane, Mary; Amandi, Mónica Fernández; James, Kevin J.

doi:10.1002/9780470277874.ch2

Cited by 17 publications

(16 citation statements)

References 85 publications

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“…The cellular amounts of these toxins for all clones tested here far exceeded those reported by McNabb et al (2006) and were more consistent with the results reported by Errera et al (2009). These results also emphasize that remarkably the Wilson clone has retained its toxin production in spite of being maintained in cultivation for over 56 years, contrasting some observations related to loss of toxicity with time reported for other toxic species maintained in cultivation (Furey et al, 2007;Baden, personal communication).…”

Section: Discussionsupporting

confidence: 88%

The brevetoxin and brevenal composition of three Karenia brevis clones at different salinities and nutrient conditions

Lekan

Tomas

2010

Harmful Algae

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Section: Discussionsupporting

confidence: 88%

The brevetoxin and brevenal composition of three Karenia brevis clones at different salinities and nutrient conditions

Lekan

Tomas

2010

Harmful Algae

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“…Recently, increased mortality and abnormalities of larvae resulting from 2-to 4-cell embryos exposed to whole and lysed K. brevis (1.5 Â 10 3 -3 Â 10 3 cells ml À1 ) with a concomitant decrease in larval shell length were reported for M. mercenaria and C. virginica (Rolton et al, 2014). Overall, lysed cells of K. brevis had a more pronounced effect on quahog and oyster larvae than did whole cells; however, the production of brevetoxins in K. papilionacea, and in K. brevisulcata, Karenia concordia, Karenia cristata, and Karenia selliformis, has not yet been confirmed by LC-MS (Landsberg, 2002;Haywood et al, 2004;Furey et al, 2007;Ramsdell, 2008;Brand et al, 2012) and the role PbTx could have played in the toxicity of K. papilionacea is therefore unclear.…”

Section: Harmful Algal Species Treatmentsmentioning

confidence: 71%

“…No morphological anomalies were observed in embryos or in larvae, thereby excluding lytic activity in favor of toxicity of brevetoxins (PbTx) and/or other organic compounds, although K. mikimotoi is known to produce hemolysin activated via cell contact (Neely and Campbell, 2006;Zou et al, 2010). Brevetoxins (PbTx) responsible for the neurotoxic shellfish poisoning (NSP) in humans are produced by Karenia brevis, and other Kareniacea, including K. papilionacea, are suspected to produce PbTx or PbTx-like compounds (Furey et al, 2007;Ramsdell, 2008;Brand et al, 2012). The PbTx are potent lipophilic neurotoxins that bind with high affinity to voltage-gated sodium channels causing increased sodium influx and depolarization of cell membrane (Watkins et al, 2008).…”

Section: Harmful Algal Species Treatmentsmentioning

confidence: 98%

Differential inimical effects of Alexandrium spp. and Karenia spp. on cleavage, hatching, and two larval stages of Japanese pearl oyster Pinctada fucata martensii

Basti

Nagai

Go³

et al. 2015

Harmful Algae

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“…We also investigated the occurrence of brevetoxins which, although never reported in the Mediterranean sea, are usually associated with poisonings due to marine aerosols [5]. None of the above toxins was detected in the plankton sample [4].…”

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confidence: 99%

Putative palytoxin and its new analogue, ovatoxin-a, in Ostreopsis ovata collected along the ligurian coasts during the 2006 toxic outbreak

Ciminiello

Dell’Aversano

Fattorusso

et al. 2008

J. Am. Soc. Mass Spectrom.

195

158

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In this article we report on the liquid chromatography tandem mass spectrometry (LC-MS) investigation of plankton samples collected in the summer of 2006 along the Ligurian coasts, coinciding with a massive bloom of the tropical microalga Ostreopsis ovata. LC-MS analyses indicated the occurrence of putative palytoxin along with a much more abundant palytoxinlike compound never reported so far, which we named ovatoxin-a. On the basis of molecular formula, fragmentation pattern, and chromatographic behavior, the structure of ovatoxin-a appeared to be strictly related to that of palytoxin. We report also on the analysis of cultured O. ovata, which was necessary to unequivocally demonstrate that putative palytoxin and ovatoxin-a contained in field samples were actually produced by O. ovata itself. They have only occasionally caused cases of human sufferings, until, in summer 2005, a massive proliferation of O. ovata broke out with alarming proportion in Liguria, nearby Genoa, Italy. This phenomenon caught the attention of both national and international media, which delivered breaking news on the event, as hundreds of people required medical attention after exposure to marine aerosol. The symptoms shown by all the patients included fever associated with serious respiratory distress and, in some cases, conjunctivitis. The toxic outbreak reached its climax in coincidence with the highest concentration of O. ovata in seawater and disappeared as the population of this microalga started fading away.We collected a concentrated plankton sample off Genoa coasts during the toxic outbreak and analyzed it for the most common phycotoxins found in the Mediterranean sea, such as okadaic acid, spirolides, azaspiracids, yessotoxins, paralytic shellfish poisoning toxins, and domoic acid [3,4]. We also investigated the occurrence of brevetoxins which, although never reported in the Mediterranean sea, are usually associated with poisonings due to marine aerosols [5]. None of the above toxins was detected in the plankton sample [4].Some Ostreopsis species produce palytoxin (Figure 1) [6 -8], a complex polyhydroxylated compound and one of the most potent marine biotoxins, or palytoxin analogues such as ostreocin-D [9 -11] and mascarenotoxins [12]. Structure of ostreocin-D was assigned to based on NMR data [9,10], and verified by negative-ion fast-atom bombardment collision-induced dissociation tandem mass spectrometry [11]. The charge-remote fragmentations were facilitated by a negative charge introduced to the terminal amino group or to a hydroxyl group at the other terminus of the molecule by reaction of pure ostreocin-D with 2-sulfobenzoic acid cyclic anhydride. Mascarenotoxins [12] were purified and identified as palytoxin-like compounds based on comparison of their mass spectrum profiles and fragmentation patterns with those of a reference standard of palytoxin. Other analogues of palytoxin, namely homo-, bishomo-, neo-, and deoxy-palytoxin were isolated from the soft coral Palythoa tuberculosa [13] but theywere not yet proven to...

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Brevetoxins: Structure, Toxicology, and Origin

Cited by 17 publications

References 85 publications

The brevetoxin and brevenal composition of three Karenia brevis clones at different salinities and nutrient conditions

The brevetoxin and brevenal composition of three Karenia brevis clones at different salinities and nutrient conditions

Differential inimical effects of Alexandrium spp. and Karenia spp. on cleavage, hatching, and two larval stages of Japanese pearl oyster Pinctada fucata martensii

Putative palytoxin and its new analogue, ovatoxin-a, in Ostreopsis ovata collected along the ligurian coasts during the 2006 toxic outbreak

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