Tetrodotoxin and paralytic shellfish toxins in Philippine crabs.

Yasumura, Daisuke; Oshima, Yasukatsu; Yasumoto, Takeshi; Alcala, Angel C.; Alcala, Lawton C.

doi:10.1271/bbb1961.50.593

Cited by 32 publications

(3 citation statements)

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“…In addition, some species of starfish on which these gastropods feed also contained TTX [56]. Toxic crabs [31,57,58], flatworms [59,60,61], a horseshoe crab [62], ribbon worms and arrow worms [63] have also been identified as TTX-containing animals. The two species of Japanese nemerteans, the palaeonemertean Tubulanus punctatus and the heteronemertean Lineus fuscoviridis , also contained TTX [29].…”

Section: Discussionmentioning

confidence: 99%

Highly Toxic Ribbon Worm Cephalothrix simula Containing Tetrodotoxin in Hiroshima Bay, Hiroshima Prefecture, Japan

Asakawa

Ito

Kajihara

2013

Toxins

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In 1998, during a toxicological surveillance of various marine fouling organisms in Hiroshima Bay, Japan, specimens of the ribbon worm, Cephalothrix simula (Nemertea: Palaeonemertea) were found. These ribbon worms contained toxins with extremely strong paralytic activity. The maximum toxicity in terms of tetrodotoxin (TTX) was 25,590 mouse units (MU) per gram for the whole worm throughout the monitoring period. The main toxic component was isolated and recrystallized from an acidified methanolic solution. The crystalline with a specific toxicity of 3520 MU/mg was obtained and identified as TTX by high performance liquid chromatography (HPLC)-fluorescent detection (FLD) (HPLC-FLD), electrospray ionization-mass spectrometry (ESI-MS), infrared (IR), nuclear magnetic resonance (NMR) and gas chromatography–mass spectrometry (GC-MS). The highest toxicity of C. simula exceeded the human lethal dose per a single worm. A toxicological surveillance of C. simula from 1998 to 2005 indicated approximately 80% of the individuals were ranked as “strongly toxic” (≥1000 MU/g). Forty-eight percent of the specimens possessed toxicity scores of more than 2000 MU/g. Seasonal variations were observed in the lethal potency of C. simula. Specimens collected on January 13, 2000 to December 26, 2000 showed mean toxicities of 665–5300 MU/g (n = 10). These data prompted a toxicological surveillance of ribbon worms from other localities with different habitats in Japan, including Akkeshi Bay (Hokkaido) under stones on rocky intertidal beaches, as well as Otsuchi (Iwate) among calcareous tubes of serpulid polychaetes on rocky shores. Within twelve species of ribbon worms examined, only C. simula possessed extremely high toxicity. Therefore, C. simula appears to show generally high toxicity irrespective of their locality and habitat.

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Section: Discussionmentioning

confidence: 99%

Highly Toxic Ribbon Worm Cephalothrix simula Containing Tetrodotoxin in Hiroshima Bay, Hiroshima Prefecture, Japan

Asakawa

Ito

Kajihara

2013

Toxins

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“…Tetrodotoxin (TTX) [1,2,3] is a well-known voltage-gated Na + channel blocker [4,5], found in a wide variety of marine animals, such as pufferfish [6], crabs [7,8], flatworms [9,10], snails [11], starfish [12], blue-ringed octopus [13], and sea slugs [14], and also found in some species of amphibians, frogs [15] and newts [16]. TTX in marine animals is thought to come from external origin, since TTX-producing marine bacteria have been reported [17,18], and pufferfish has been experimentally shown to have an ability to accumulate TTX administrated dietarily [19,20] and intramuscularly [21,22,23].…”

Section: Introductionmentioning

confidence: 99%

First Identification of 5,11-Dideoxytetrodotoxin in Marine Animals, and Characterization of Major Fragment Ions of Tetrodotoxin and Its Analogs by High Resolution ESI-MS/MS

et al. 2013

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Even though tetrodotoxin (TTX) is a widespread toxin in marine and terrestrial organisms, very little is known about the biosynthetic pathway used to produce it. By describing chemical structures of natural analogs of TTX, we can start to identify some of the precursors that might be important for TTX biosynthesis. In the present study, an analog of TTX, 5,11-dideoxyTTX, was identified for the first time in natural sources, the ovary of the pufferfish and the pharynx of a flatworm (planocerid sp. 1), by comparison with totally synthesized (−)-5,11-dideoxyTTX, using high resolution ESI-LC-MS. Based on the presence of 5,11-dideoxyTTX together with a series of known deoxy analogs, 5,6,11-trideoxyTTX, 6,11-dideoxyTTX, 11-deoxyTTX, and 5-deoxyTTX, in these animals, we predicted two routes of stepwise oxidation pathways in the late stages of biosynthesis of TTX. Furthermore, high resolution masses of the major fragment ions of TTX, 6,11-dideoxyTTX, and 5,6,11-trideoxyTTX were also measured, and their molecular formulas and structures were predicted to compare them with each other. Although both TTX and 5,6,11-trideoxyTTX give major fragment ions that are very close, m/z 162.0660 and 162.1020, respectively, they are distinguishable and predicted to be different molecular formulas. These data will be useful for identification of TTXs using high resolution LC-MS/MS.

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“…The Xanthid crabs Zosimus aeneus , Atergatis floridus, and Platypodia granulosa inhabiting tropical and subtropical area are known to contain potent neurotoxins [3]. In Z. aeneus , the species most frequently implicated in human poisoning, the occurrence of saxitoxin (STX) analogues [4–6] and tetrodotoxin (TTX) [7] has been confirmed. Paralytic shellfish poison (PSP), a most hazardous marine toxin, mainly originates in toxic marine dinoflagellates species of the genera Alexandrium , Gymnodinium, and Pyrodinium , which are accumulated in many species of marine organisms such as crabs and filter-feeding organisms such as bivalve mollusks [8–13].…”

Section: Introductionmentioning

confidence: 99%

Toxicity Assessment of the Xanthid CrabDemania cultripesfrom Cebu Island, Philippines

Asakawa

Gomez-Delan

Tsuruda

et al. 2010

Journal of Toxicology

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Several cases of poisoning resulting in human fatalities and stemming from the ingestion of coral reef crabs have been reported from the Indo-Pacific region. We assessed the toxicity of the unidentified xanthid crab collected from the Camotes Sea off the eastern coast of Cebu Island, central Visayas region of Philippines from the food hygienic point of view. All seven specimens, which were identified with Demania cultripes, collected in 2006 were toxic to mice irrespective of the season of collection and induced paralytic symptoms typical of tetrodotoxin (TTX) and paralytic shellfish poison (PSP). The activity was expressed in mouse unit (MU) being defined as the amount of TTX to kill a 20 g ddY male mice in 30 min after i.p. injection. Toxicity scores for viscera and appendages of specimens were 18.2 ± 16.0 (mean ± S.D.) and 4.4 ± 2.6 MU/g, respectively. The highest individual toxicity scores observed for viscera and appendages were 52.1 and 7.7 MU/g, respectively. The frequency of toxic samples was 100%. Toxin profiles as determined by high-performance liquid chromatography-fluorescent detection analysis (HPLC-FLD) revealed that TTX was the main toxic principle accounting for about 90% of the total toxicity along with 4-epi TTX and 4,9-anhydroTTX. Furthermore, gas chromatography-mass spectrometry (GC-MS) analysis revealed mass fragment ion peaks at m/z 376, 392 and 407, which were characteristic of the quinazoline skeleton (C9-base) specific to TTX. In addition, only a small amount of PSP containing gonyautoxins1–4 and hydroxysaxitoxin was detected. To our knowledge, this is the first report presenting evidence of occurrence of TTX and PSP in the xanthid crab D. cultripes inhabiting waters surrounding Cebu Island. From food hygienic point of view, people in coastal areas should be warned of the potential hazard of this crab in order to prevent its intentional or accidental consumption.

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Tetrodotoxin and paralytic shellfish toxins in Philippine crabs.

Abstract: The frequent occurrence of lethal specimens of Zosimus aeneus and Atergatis floridus on southern Negros Island, Philippines, was confirmed by mouse lethality tests. Among eight D. Yasumura et al.

Cited by 32 publications

References 0 publications

Highly Toxic Ribbon Worm Cephalothrix simula Containing Tetrodotoxin in Hiroshima Bay, Hiroshima Prefecture, Japan

Highly Toxic Ribbon Worm Cephalothrix simula Containing Tetrodotoxin in Hiroshima Bay, Hiroshima Prefecture, Japan

First Identification of 5,11-Dideoxytetrodotoxin in Marine Animals, and Characterization of Major Fragment Ions of Tetrodotoxin and Its Analogs by High Resolution ESI-MS/MS

Toxicity Assessment of the Xanthid CrabDemania cultripesfrom Cebu Island, Philippines

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