Absolute stereochemistry of palytoxin

Moore, Richard E.; Bartolini, G.; Barchi, Joseph J.; Bothner‐By, Aksel A.; Dadok, Josef; Ford, Jennifer B.

doi:10.1021/ja00377a064

Cited by 85 publications

(19 citation statements)

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“…Recently several analogues, ostreocin-D (42-hydroxy-3, 26-didemethyl-9,44-dideoxypalytoxin) and mascarenotoxins were identified in O. siamensis . PTX is regarded as one of the most potent toxins so far known [108], the LD 50 s 24 h after intravenous injection vary from 0.025 μg/kg in rabbits and about the same in dogs to 0.45 μg/kg in mice, with monkeys, rats and guinea pigs around 0.9 μg/kg. Toxic symptoms include fever inaction, ataxia, drowsiness, and weakness of limbs followed by death.…”

Section: Palytoxin (Ptx)mentioning

confidence: 99%

Neurotoxins from Marine Dinoflagellates: A Brief Review

2008

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Abstract:Dinoflagellates are not only important marine primary producers and grazers, but also the major causative agents of harmful algal blooms. It has been reported that many dinoflagellate species can produce various natural toxins. These toxins can be extremely toxic and many of them are effective at far lower dosages than conventional chemical agents. Consumption of seafood contaminated by algal toxins results in various seafood poisoning syndromes: paralytic shellfish poisoning (PSP), neurotoxic shellfish poisoning (NSP), amnesic shellfish poisoning (ASP), diarrheic shellfish poisoning (DSP), ciguatera fish poisoning (CFP) and azaspiracid shellfish poisoning (ASP). Most of these poisonings are caused by neurotoxins which present themselves with highly specific effects on the nervous system of animals, including humans, by interfering with nerve impulse transmission. Neurotoxins are a varied group of compounds, both chemically and pharmacologically. They vary in both chemical structure and mechanism of action, and produce very distinct biological effects, which provides a potential application of these toxins in pharmacology and toxicology. This review summarizes the origin, structure and clinical symptoms of PSP, NSP, CFP, AZP, yessotoxin and palytoxin produced by marine dinoflagellates, as well as their molecular mechanisms of action on voltage-gated ion channels.

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Section: Palytoxin (Ptx)mentioning

confidence: 99%

Neurotoxins from Marine Dinoflagellates: A Brief Review

2008

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“…Zoanthus solanderi typically inhabits a lower vertical zone where it is much more likely to encounter predators and spatial competitors (Karlson 1980, Sebens 1982b and is more likely to have evolved allelochemical defenses than Z. sociatus (Karlson 1980). 1982, Moore et al 1982 detailed studies have indicated extremely high levels of toxicity associated with the presence of eggs in Palythoa tuberculosa (Kimura et al 1972). The occurrence of powerful allelochemicals in zoanthids has long been recognized (Scheuer 1964, Attaway 1968, Hashimoto et al 1969, Moore and Scheuer 1971, Chaetal.…”

Section: Reciprocal Transplant Experimentsmentioning

confidence: 99%

Size‐Dependent Growth in Two Zoanthid Species: A Constrast in Clonal Strategies

Karlson¹

1988

Ecology

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The widespread occurrence of genet fragmentation among modular, clonal organisms results in size-dependent life history patterns that are often independent of clonal age. In this study the size dependence of clonal growth rates was experimentally evaluated using two common coral reef cnidarians that inhabit shallow reef environments at Discovery Bay, Jamaica. As a result of the turbulent conditions associated with storms, these organisms commonly undergo fragmentation. The growth of aggregations of these clonal fragments in three small size classes (ranging over three orders of magnitude) was statistically evaluated against a null, exponential model that predicts that relative growth rates of small aggregations are size independent. Growth rates for Zoanthus solanderi were consistent with this model. Z. sociatus, on the other hand, exhibited size-dependent relative growth rates. The smallest aggregations of this species had the highest relative growth rates, which were sufficiently high to more than compensate for losses due to mortality.These results are consistent with other life history and distributional differences between these two species. Zoanthus sociatus has a higher rate of mortality, does not undergo sexual reproduction until reaching a larger aggregation size, and commonly has a higher vertical distribution (which may represent a spatial refuge from subtidal predators) than does Z. solanderi. The comparatively rapid relative growth rates of small aggregations of Z. sociatus may be the result of spatial constraints on growth in large aggregations and/or of higher relative energy allocations to growth in small aggregations.The incorporation of fragmentation into the life history strategy of clonal organisms has a range of predicted consequences. Among some organisms, fragmentation and associated adaptations may be rare and oflittle consequence. Among organisms that frequently fragment as a result of physical disturbances, natural selection should favor repair and regenerative processes as well as resistance to this source of mortality. At the extreme, fragmentation need not be associated with death and injury. Adaptations at the developmental and physiological level may involve genetically programmed production of asexual fragments and size-dependent shifts in energy allocations to growth, sexual reproduction, and energy reserves. The degree of interdependence of the processes controlling the dynamics of genets and fragmented modules may well depend on the relative importance of such adaptations.

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“…Palytoxin (PTX) consists of a long aliphatic, partially unsaturated chain with interspersed cyclic ether, hydroxyl and carboxyl groups (Moore et al, 1982). It is one of the most potent toxins known and acts by impairing the function of excitable cells such as neuronal cells (Dubois & Cohen, 1977; Pichon, 1982) and cardiac cells (Sauviat et al, 1987).…”

Section: Introductionmentioning

confidence: 99%

3,4 Dichlorobenzamil‐sensitive, monovalent cation channel induced by palytoxin in cultured aortic myocytes

Renterghem

Frelin

1993

British J Pharmacology

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1 Smooth muscle cells were dispersed from rat aorta and then cultured. The action of palytoxin on rat aortic myocytes was analysed by measurement of 22Na+ uptake and single channel recording techniques. 2 Palytoxin induced an increase in 22Na+ uptake, with a concentration of 50 nM producing halfmaximal activation. The action of palytoxin was inhibited by amiloride derivatives and by ouabain. The concentrations of inhibitor producing half-maximal inhibition were 10 JIM for 3,4 dichlorobenzamil, 30 JAM for benzamil, 100 JAM for phenamil and 1 mm for ouabain. 3 In outside-out patches, palytoxin induced single channel currents that reversed near 0 mV with NaCl or KCI in the extracellular solution, but were outward with N-methyl-D-glucamine chloride or CaCl2 ( 10 mM), indicating that palytoxin induced a cation channel permeable to Na+ and K+ (PK/PNa = 1.2) but not to Ca2+ (PK/PCa > 30) or to N-methyl-D-glucamine (NMDG) (PK/PNMDG> 11). The unit channel conductance was 11 -14 pS. 4 A high (>0.1 mM) extracellular concentration of Ca2+ was necessary to observe channel activation by palytoxin. A high (150 mM) extracellular concentration of K+ partially prevented and reversed channel activation by palytoxin. 5 The channel activity was fully blocked by 3,4 dichlorobenzamil (20 JAM) and partially blocked by phenamil (50 JM). It was not reduced by ouabain (200 JAM).

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Absolute stereochemistry of palytoxin

Cited by 85 publications

References 0 publications

Neurotoxins from Marine Dinoflagellates: A Brief Review

Neurotoxins from Marine Dinoflagellates: A Brief Review

Size‐Dependent Growth in Two Zoanthid Species: A Constrast in Clonal Strategies

3,4 Dichlorobenzamil‐sensitive, monovalent cation channel induced by palytoxin in cultured aortic myocytes

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