New tetrodotoxin analogs from the newt Cynops ensicauda

Yasumoto, Takeshi; Yotsu, Mari; Murata, Michio; Naoki, Hideo

doi:10.1021/ja00215a078

Cited by 148 publications

(73 citation statements)

References 5 publications

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“…However, the TTX biosynthetic pathway has yet to be elucidated. A number of TTX biosynthesis pathway proposals have been documented (Woodward and Gougoutas, 1964;Yasumoto et al, 1988;Kotaki et al, 1993;Chau et al, 2011). It was speculated that TTX is assembled by a hybrid polyketide synthase (PKS)/non-ribosomal peptide synthetase (NRPS) enzyme complex which possibly incorporates an amidinotransferase (AMT) (Chau et al, 2011), however, no supporting or experimental evidence has been published for the biosynthesis of TTX.…”

Section: Introductionmentioning

confidence: 99%

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Liu

Fang

et al. 2015

Toxicon

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Section: Introductionmentioning

confidence: 99%

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Liu

Fang

et al. 2015

Toxicon

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“…The extract was successively treated on charcoal, Bio-Gel P-2, Bio-Rex 70 and Hitachi Gel 3011 C, as previously described for I and other analogs. 1) Elution of 6 was monitored by fluorometric HPLC analysis. The final purification of 6 was accomplished under the same chromatographic conditions as those for analysis, and the eluates were desalted in a Hitachi Gel 3011 C column.…”

mentioning

confidence: 99%

Isolation and Structural Assignment of 11-Nortetrodotoxin-6(S)-ol from the Puffer Arothron nigropunctatus

Yotsu

Khora

et al. 1992

Bioscience, Biotechnology, and Biochemistry

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“…1). Yasumoto and his co-workers first isolated these toxins and another TTX derivative, 11-deoxytetrodotoxin, from pufferfish and/or newts as minor components, and estimated that a series of oxidations took place at C11 in these animals (Endo et al 1988;Khora and Yasumoto 1989;Yasumoto et al 1988). Because the A. floridus specimens mainly contained 11-oxoTTX as well as TTX, the oxidation might be more progressive in this crab than in other TTX-bearing animals.…”

Section: -1 Detection Of Ttx or Its Derivatives In Several Aquatic mentioning

confidence: 96%

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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New tetrodotoxin analogs from the newt Cynops ensicauda

Cited by 148 publications

References 5 publications

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Isolation and Structural Assignment of 11-Nortetrodotoxin-6(S)-ol from the Puffer Arothron nigropunctatus

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

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New tetrodotoxin analogs from the newt Cynops ensicauda

Cited by 148 publications

References 5 publications

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Production level of tetrodotoxin in Aeromonas is associated with the copy number of a plasmid

Isolation and Structural Assignment of 11-Nortetrodotoxin-6(S)-ol from the Puffer Arothron nigropunctatus

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

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