Pinnatoxin A: a toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata

Uemura, Daisuke; Chou, Tong; Haino, Takeharu; Nagatsu, Akito; Fukuzawa, Seketsu; Zheng, Shu-zhen; Chen, Haisheng

doi:10.1021/ja00108a043

Cited by 264 publications

(167 citation statements)

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“…Pinnatoxins are cyclic imine toxins and of them pinnatoxin A was the first to be characterised (Uemura et al 1995). Pinnatoxins BÁD were then isolated from P. muricata in Japan (Chou et al 1996;Takada et al 2001).…”

Section: Introductionmentioning

confidence: 99%

The first report ofVulcanodinium rugosum(Dinophyceae) from the South China Sea with a focus on the life cycle

Zeng

Smith

et al. 2012

New Zealand Journal of Marine and Freshwater Research

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An individual non-motile (NM) cell was isolated from a surface sediment sample collected in Guangxi, China and subsequently established as a dinoflagellate strain in culture. The motile cells are 22.5Á32.5 mm long and 20.0Á30.0 mm wide, with a plate formula of Po, X, 4?, 3a, 7ƒ, 6c, 5(?)s, 5ƒ?, 2ƒƒ, fitting the description of Vulcanodinium rugosum. The Chinese strain shares 99.8%, 97.4% and 96.7% similarity (LSU sequence) with those from Australasia, France and Japan. Asexual division of V. rugosum takes place either in the thecate motile stage or within a NM division cell. Motile cells divided by binary fission inside the parent cell and transformed to NM division cells within 24 h. The NM cell underwent one to three consecutive divisions within the parent wall. The divisions were not always synchronous and neither was the release of motile cells from the NM cells. It generally took 4 to 6 days for the NM cells to complete one division. NM cells survived for 1 month at 4 8C in the dark, suggesting that they might play an important role in species dispersal. A novel pinnatoxin was detected at 20 pg cell(1 and no other known pinnatoxins (AÁG) were detected.

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Section: Introductionmentioning

confidence: 99%

The first report ofVulcanodinium rugosum(Dinophyceae) from the South China Sea with a focus on the life cycle

Zeng

Smith

et al. 2012

New Zealand Journal of Marine and Freshwater Research

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“…The relative and absolute stereochemistry has not been established to date, but a tentative assignment based on NMR studies has been reported [13]. In common with the pinnatoxins [14], the spirolides possess a seven-membered spiro-linked cyclic imine together with the novel 1,7,9-trioxadispiro[4.1.5.2]tetradecane bis-spiroacetal ring system. The 6,5,5-bis-spiroacetal unit of the spirolides B (22) and D (23) is challenging due to the presence of two five-membered rings, for which the anomeric effect is considerably reduced as compared with six-membered rings.…”

Section: Methodsmentioning

confidence: 99%

“…Aldehyde 26 provided the substituents required for the substituted tetrahydrofuran ring of the 6,5,5-bis-spiroacetal ring system and these were introduced in a stereocontrolled manner by crotyl metallation of a protected 3-hydroxypropanal that afforded the desired homoallylic alcohol 25 in 82% yield and >97% d.e. The R,R configuration was selected both by analogy with pinnatoxin A [14] and the relative stereochemistry of the spirolides proposed by Falk et al [13]. The resultant homoallylic alcohol 25 was then converted into aldehyde 26 in good yield using standard transformations.…”

Section: Methodsmentioning

confidence: 99%

Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview

Brimble

2004

Molecules

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Abstract:The use of iodobenzene diacetate and iodine under photolytic conditions provides and efficient method for the oxidative cyclization of spiroacetals bearing an hydroxyalkyl side chain to bis-spiroacetals. An overview is provided of the use of this reaction for the synthesis of several bis-spiroacetal containing natural products such as the polyether antibiotics salinomycin and CP44,161 and the shellfish toxins, the spirolides.

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“…Pntx (A-G) and Pttx (A-C) were initially found in Japan and New Zealand (Chou et al, 1996;takada et al, 2001a;Uemura et al, 1995). the source of Pntx and Pttx currently is thought to be the dinoflagellate Vulcanodinium rugosum (Rhodes et al, 2010;Selwood et al, 2010;Nézan and Chomérat, 2011;Rhodes et al, 2011;Smith et al, 2011), and Pttx may be biotransformation products of Pntx .…”

Section: Ciguatera Fish Poisoning (Cfp) Toxinsmentioning

confidence: 99%

A roadmap for hazard monitoring and risk assessment of marine biotoxins on the basis of chemical and biological test systems

Daneshian

2013

ALTEX

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Summary Aquatic food accounts for over 40% of global animal food products, and the potential contamination with toxins of algal origin -marine biotoxins -poses a health threat for consumers. The gold standards to assess toxins in aquatic food have traditionally been in vivo methodssingle marine biotoxins or combinations of marine biotoxins and intoxication symptomatology as well as monitoring the "success" of controls implemented during fishery and aquaculture production, processing, and retailing. For this reason, a workshop was organized in ermatingen, Switzerland by the Center for Alternatives to Animal testing -europe (CAAteurope) within the framework of the transatlantic think tank for toxicology (t 4 ).In contrast to other food products where hygiene and potential contamination with microbes or mold toxins is the prime issue, the emphasis in aquatic products (shellfish and finfish) is, beyond viral and bacterial contaminations, primarily placed on potential contamination with marine biotoxins owing to the numerous and recurring human intoxications.The gold standards to assess toxins in aquatic food have traditionally been in vivo methods, i.e., the mouse and the rat bioassays. Besides the ethical issues of in vivo bioassays there are specific difficulties, e.g., different exposure route (i.p. versus oral), low inter-species comparability, high intra-species variability, and questionable extrapolation of quantitative risk to humans, thus highlighting the need for the development of more reliable detection and quantification methods. Based on this reasoning, the european Food Safety Authority (eFSA) advocates the use of an analytical method, i.e., LC-MS (Liquid Chromatography coupled Mass Spectrometry), as a substitute for in vivo bioassays for almost all classes of marine toxins. However, although lC-MS is a very sensitive method that has the advantages of being able to detect multiple toxins in a single analysis and being good for confirming the identity of toxins, the quality of quantitative analysis is dependent on the availability of calibration standards. While many new toxin structural analogues have been detected and identified using LC-MS, this technique -as with most other methods -is not good at detecting new toxin types. When new toxin analogues are detected but accurate standards are not yet available, only an approximate quantitation is possible using estimated response factors.For the purpose of risk assessment of food, however, it is imperative to focus on the possible adverse effects, independent of whether they stem from one toxin or a combination of toxins. As toxicity is defined by functional and structural changes of biological systems, the development of a human-relevant in vitro system for appropriate risk assessment of marine biotoxins in seafood stands to reason. Moreover, poor correlation of human intoxications, of acute symptomatology and long-term adverse effects, and of predictive in vitro, in vivo, and analytical detection methodologies of marine biotoxins stems not least from a...

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Pinnatoxin A: a toxic amphoteric macrocycle from the Okinawan bivalve Pinna muricata

Cited by 264 publications

References 0 publications

The first report ofVulcanodinium rugosum(Dinophyceae) from the South China Sea with a focus on the life cycle

The first report ofVulcanodinium rugosum(Dinophyceae) from the South China Sea with a focus on the life cycle

Radical Oxidative Cyclization of Spiroacetals to Bis-spiroacetals: An Overview

A roadmap for hazard monitoring and risk assessment of marine biotoxins on the basis of chemical and biological test systems

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