Tetrodotoxin. VII. On the Structures of Tetrodotoxin and its Derivatives

Tsuda, Kyosuke; Ikuma, Susumu; Kawamura, Masaaki; Tachikawa, Ryuji; Saito, Kiyoshi; Tamura, Chihiro; Amakasu, Osamu

doi:10.1248/cpb.12.1357

Cited by 234 publications

(102 citation statements)

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“…IR-spectra of KBr pellet were acquired using IR spectrophotometer, which was used by Onoue et al for determination the IR spectrum of pufferfish toxin [49]. On the other hand, Tsuda et al reported the IR spectrum of a TTX-HCl salt by the "Nujol" method [2]. Here we introduce another method as mentioned below.…”

Section: Infrared (Ir) Spectrometrymentioning

confidence: 99%

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Instrumental Analysis of Tetrodotoxin

Asakawa¹,

Shida²,

Miyazawa³

et al. 2012

Chromatography - The Most Versatile Method of Chemical Analysis

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Section: Infrared (Ir) Spectrometrymentioning

confidence: 99%

“…In 1950, TTX was isolated for the first time as a crystalline prism from toxic pufferfish ovaries by Yokoo [1]. Its structure was elucidated by three groups in 1964 [2][3][4]. TTX is a powerful and specific sodium channel blocker [5].…”

Section: Introductionmentioning

confidence: 99%

Instrumental Analysis of Tetrodotoxin

Asakawa¹,

Shida²,

Miyazawa³

et al. 2012

Chromatography - The Most Versatile Method of Chemical Analysis

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“…It can be isolated from the pufferfish as a unique compound having polyfunctional groups and peculiar structure. 1 We are studying the synthesis of optically active TTX from D-glucose by means of intramolecular nitroaldol condensation. As a result of many efforts, we succeeded in obtaining potential key compounds, (1R,2R,3S,4S,5S,6S,7R,9S)-6-azido-7-cyano-3-C-hydroxymethyl-3,3′-di-O-isopropylidene-9-methoxy-2,4,5-tris(O-methoxymethyl)-2,3,4,5-tetrahydroxy-8-oxabicyclo[4.3.0]nonane (2) and its 9-epimer (2′) for total synthesis of optically active TTX.…”

mentioning

confidence: 99%

Crystal Structure of (1R,2R,3S,4S,5S,6S,7R,9S)-6-Azido-7-cyano-3-C-hydroxy-methyl-3,3′-di-O-isopropylidene-9-methoxy-2,4,5-tris(O-methoxymethyl)-2,3,4,5-tetrahydroxy-8-oxabicyclo[4.3.0]nonane, toward Tetrodotoxin

et al. 1999

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“…TTX is a potent neurotoxin of low molecular weight, whose unique structure was determined by three groups in 1964 (Goto et al 1965;Tsuda et al 1964;Woodward 1964). Various TTX derivatives have so far been separated from pufferfish, newts, frogs, and/or some other TTX-bearing organisms (Yotsu-Yamashita 2001;YotsuYamashita et al 2013) (Fig.…”

Section: Introductionmentioning

confidence: 99%

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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Tetrodotoxin. VII. On the Structures of Tetrodotoxin and its Derivatives

Cited by 234 publications

References 0 publications

Instrumental Analysis of Tetrodotoxin

Instrumental Analysis of Tetrodotoxin

Crystal Structure of (1R,2R,3S,4S,5S,6S,7R,9S)-6-Azido-7-cyano-3-C-hydroxy-methyl-3,3′-di-O-isopropylidene-9-methoxy-2,4,5-tris(O-methoxymethyl)-2,3,4,5-tetrahydroxy-8-oxabicyclo[4.3.0]nonane, toward Tetrodotoxin

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

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Tetrodotoxin. VII. On the Structures of Tetrodotoxin and its Derivatives

Cited by 234 publications

References 0 publications

Instrumental Analysis of Tetrodotoxin

Instrumental Analysis of Tetrodotoxin

Crystal Structure of (1R,2R,3S,4S,5S,6S,7R,9S)-6-Azido-7-cyano-3-C-hydroxy-methyl-3,3′-di-O-isopropylidene-9-methoxy-2,4,5-tris(O-methoxymethyl)-2,3,4,5-tetrahydroxy-8-oxabicyclo[4.3.0]nonane, toward Tetrodotoxin

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

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