Structure of neosaxitoxin

Shimizu, Yuzuru; Hsu, Chien-Ping; Fallon, William E.; Oshima, Yasukatsu; Miura, Iwao; Nakanishi, Koji

doi:10.1021/ja00489a060

Cited by 86 publications

(64 citation statements)

References 5 publications

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“…In the carbon resonance spectrum of BR-2, the chemical shifts resembled those of STX cited from the literature ( Table 5) (Rogers and Rapoport 1980). The downfield shift by b effect at C-6 of neoSTX (Shimizu et al 1978) was not recognized at C-4 and C-5 of BR-2; thus there was little possibility of 7-N-or 9-N-hydroxy formation. Similarly, the chemical shifts of BR-1 agreed with those of neoSTX.…”

Section: -2a Separation Of Carbamoyl-n-hydroxy Deriva-supporting

confidence: 51%

“…The chemical structure was clarified by an X-ray diffraction analysis in 1975 (Schantz et al 1975). Subsequently, many derivatives with the same skeleton as STX, such as 1-N-hydroxy derivative [neosaxitoxin (neoSTX)] (Shimizu et al 1978), 11-sulfate derivatives [gonyautoxins (GTXs)] (Noguchi et al 1981;Shimizu et al 1976), N-sulfo-carbamoyl derivatives (Kobayashi and Shimizu 1981;Harada et al 1982a), and decarbamoyl derivatives (Harada et al 1983) were successively found in several species of dinoflagellates and toxified bivalves (Fig. 25).…”

Section: -1 Diversity Of Psp Componentsmentioning

confidence: 99%

“…It is interesting that SEA, the first natural analgue of STX that has a substituent other than the hydroxylsulfate at C-11, seems to be rather specific to the A. floridus living in some restricted regions. Comparison of 13 C NMR data of BR-2 and 1 with those of STX (Rogers and Rapoport 1980) and neoSTX (Shimizu et al 1978).…”

Section: -2b Separation Of Carboxymethyl Derivative Frommentioning

confidence: 99%

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Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions

Arakawa¹,

Takatani²,

Taniyama³

et al. 2017

Aqua-BioSci. Monogr. (ABSM)

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Keywordsunit) is defined as the amount of toxin required to kill a 20-g male mouse within 30 min after intraperitoneal administration], and the minimum lethal dose (MLD) for humans is estimated to be approximately 10000 MU (ª2 mg) (Noguchi and Ebesu 2001).The main symptoms of human intoxication include numbness of lips, tongue and the limbs, paresthesia, dysarthria, respiratory distress, and death is caused by respiratory failure in the most critical cases (Noguchi and Ebesu 2001). According to Toda et al. (2012), 651 incidents of TTX poisoning due to pufferfish have occurred in Japan, involving 976 patients and 56 deaths during the 22 years from 1989 to 2010. Many cases occurred during the winter season in coastal prefectures of the Seto Inland Sea, with "komonfugu" Takifugu poecilonotus, "mafugu" Takifugu porphyreus, "higanfugu" Takifugu pardalis, "shosaifugu" Takifugu Abstract Our many years of studies have provided a lot of information regarding distribution, accumulation mechanism, and physiologic functions of the natural toxins harbored by pufferfish. We detected tetrodotoxin (TTX) and/or its derivatives in several species of aquatic organisms including marine bacteria. This, along with the fact that pufferfish became non-toxic when they were reared with non-toxic feed, indicated that the toxification of pufferfish is of exogenous origin. Subsequently, we revealed by various TTX administration experiments using non-toxic cultured pufferfish that the TTX administered into the muscle or digestive tract rapidly transferred to the liver and skin, and that the toxin transfer to the gonads was largely different between male and female, suggesting the involvement of maturation in the internal kinetics of TTX. On the other hand, we visualized micro-distribution of TTX in the tissues of various TTX-bearing organisms using an immunohistochemical technique, giving a crucial insight to elucidate physiologic functions of TTX including the function as a defensive or offensive agent. Furthermore, we found that Southeast Asian freshwater pufferfish possess paralytic shellfish poison (PSP) as a main toxin, and that boxfish and Bangladeshi freshwater pufferfish bear a palytoxin (PLTX)-like toxin, and cause a rhabdomyolysis, which overturned the common sense that pufferfish toxin equals TTX.

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Section: -2a Separation Of Carbamoyl-n-hydroxy Deriva-supporting

confidence: 51%

Section: -1 Diversity Of Psp Componentsmentioning

confidence: 99%

Section: -2b Separation Of Carboxymethyl Derivative Frommentioning

confidence: 99%

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Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions

Arakawa¹,

Takatani²,

Taniyama³

et al. 2017

Aqua-BioSci. Monogr. (ABSM)

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“…), phylum Cnidaria (soft corals, Sarcoph ton elegans, Sinularia, dura ; sea anemone, Actinia australis), and phylum Brachiopoda, (Lingula sp.). Of particular interest among negative species are the bivalve molluscs, Saxidomus giganteus and M tilus edulis, which are known to accumulate STX from toxic marine dinoflagellates (Shimizu et al 1978 ;Schantz 1986), but they do not appear to produce saxiphilin (table 2).…”

Section: Resultsmentioning

confidence: 99%

Phylogenetic survey of soluble saxitoxin-binding activity in pursuit of the function and molecular evolution of saxiphilin, a relative of transferrin

Llewellyn

Bell

Moczydlowski

1997

Proc. R. Soc. Lond. B

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Saxiphilin is a soluble protein of unknown function which binds the neurotoxin, saxitoxin (STX), with high affinity. Molecular characterization of saxiphilin from the North American bullfrog, Rana catesbeiana, has previously shown that it is a member of the transferrin family. In this study we surveyed various animal species to investigate the phylogenetic distribution of saxiphilin, as detected by the presence of soluble [$H]STX binding activity in plasma, haemolymph or tissue extracts. We found that saxiphilin activity is readily detectable in a wide variety of arthropods, fish, amphibians, and reptiles. The pharmacological characteristics of [$H]STX binding activity in phylogenetically diverse species indicates that a protein homologous to bullfrog saxiphilin is likely to be constitutively expressed in many ectothermic animals. The results suggest that the saxiphilin gene is evolutionarily as old as an ancestral gene encoding bilobed transferrin, an Fe$ + -binding and transport protein which has been identified in several arthropods and all the vertebrates which have been studied.

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“…The pH is the most critical variable in achieving effective separations. Based on the work of Shimizu et al (18) with NEO, the pKs of the N-I hydroxyl, C-8 guanidinium, and C-2 guanidinium groups are approximately 6.8, 8.7, and 1 1.7, respectively. The charge contributions of these groups along with those of the sulfate groups yield net negative charges for the Cx toxins at pH 7.5 (mobile phase A).…”

Section: Resultsmentioning

confidence: 99%

Paralytic Shellfish Toxins in Protogonyaulax tamarensis and Protogonyaulax catenella in Axenic Culture

Boczar¹,

Beitler²,

Liston³

et al. 1988

Plant Physiol.

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Paralytic shellfish toxin concentrations were measured and individual toxin profiles were monitored in axenic batch cultures of Protogonyaulax tamarensis and Protogonyaulax catenella. High pressure liquid chromatographic methods were used that allowed the separation of all 12 known paralytic shellfish poisons, including toxins Cl, C2, and C3, from a single sample. In isolates of both Protogonyaulax species, total toxin levels were relatively low after inoculation, increased rapidly in early to midexponential growth to a value 100 to 300% of that at the initial time point, then decreased by 86 to 95% as the culture aged. Although the concentrations of individual toxins per cell followed the same general pattern as that seen for total moles of toxin per cell, variability in toxin profile with culture age was observed. In P. tamarensis, the mole percent of neosaxitoxin increased substantially from 8 to 44% as total toxin levels per cell decreased. A concomitant decrease in the mole percent of saxitoxin with culture age was noted. Although not as precipitous, changes in the mole percent of specific toxins from P. catenella were also observed. The mole percent of gonyautoxins I and IV increased, while that of gonyautoxins II and III decreased. These data suggest that the toxin profile in isolates of Protogonyaulax can change, sometimes significantly, with changing environmental variables. Protogonyaulax species produce an array ofchemically similar neurotoxins that differ in their biological toxicity (8,17).

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Structure of neosaxitoxin

Cited by 86 publications

References 5 publications

Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions

Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions

Phylogenetic survey of soluble saxitoxin-binding activity in pursuit of the function and molecular evolution of saxiphilin, a relative of transferrin

Paralytic Shellfish Toxins in Protogonyaulax tamarensis and Protogonyaulax catenella in Axenic Culture

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Structure of neosaxitoxin

Cited by 86 publications

References 5 publications

Toxins of Pufferfish—Distribution, Accumulation Mechanism, and Physiologic Functions

Toxins of Pufferfish—Distribution, Accumulation Mechanism, and Physiologic Functions

Phylogenetic survey of soluble saxitoxin-binding activity in pursuit of the function and molecular evolution of saxiphilin, a relative of transferrin

Paralytic Shellfish Toxins in Protogonyaulax tamarensis and Protogonyaulax catenella in Axenic Culture

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Product

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Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions

Toxins of Pufferfish—Distribution, Accumulation　Mechanism, and Physiologic Functions