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PubMed1999

A case-control study of sporadic infection with O157 and non-O157 verocytotoxin-producing Escherichia coli.

Potential risk factors for sporadic verocytotoxin-producing Escherichia coli (VTEC) infection in Belgium were investigated in a matched case-control study. Thirty-seven cases, 8 infected with O157 VTEC strains (all eaeA-positive), 29 with non-O157 VTEC strains (13 eaeA-positive and 16 eaeA-negative) and 69 matched controls were interviewed. In a conditional logistic regression analysis, consumption of fish appeared to be a risk factor for infection (adjusted odds ratio (OR) 3.25, P = 0.04). Contact with dogs (OR 0.27, P = 0.04) and consumption of shellfish (OR 0.19, P = 0.05) showed a negative association, corresponding to a decrease in risk. These findings might be explained if low level environmental exposure to VTEC induces protective immunity. Eating raw meat, a frequent habit in Belgium, or hamburgers, or eating in a fast-food restaurant was not more frequently reported by cases than controls. The exposures causing sporadic infections with VTEC, in particular non-O157 strains, may be very different from those which led to outbreaks, and may account for more cases overall.

Adolescent↗
PubMed2005

Neurobehavioral effects of harmful algal bloom (HAB) toxins: a critical review.

Human exposure to naturally occurring marine toxins has been associated with a range of neurobehavioral abnormalities. The toxins are produced by harmful algal blooms (HABs) and are typically contracted through seafood consumption. The primary target of many of the HAB toxins is the neurologic system, and the neurobehavioral symptoms associated with the HAB illnesses have influenced public health policy. The HAB-related illnesses most frequently linked to neuropsychological disturbance are Amnesic Shellfish Poisoning, Ciguatera Fish Poisoning, and Possible Estuarine Associated Syndrome, which is associated with exposure to the Pfiesteria piscicida organism. Although the neurophysiologic mechanisms underlying many of the HAB illnesses have been well delineated, the literature examining the neuropsychological impairments is unclear and needs to be defined. This review is intended to introduce an emerging area of study linking HAB illnesses with neuropsychological changes.

Amnesia↗
PubMed1999

Development of an ultrasensitive immunoassay for rapid measurement of okadaic acid and its isomers.

This report highlights the characteristics of an okadaic acid immunoassay with limits of detection in the subfemtomole range. Two different immunoassay formats were investigated and their characteristics compared in relation to linear ranges, limits of detection, and cross-reactivity with other seafood toxins present in water and/or mussel samples. The developed ELISA system can be manipulated to quantitatively measure total diarrhetic shellfish poisoning (DSP) content or for okadaic acid and dinophysistoxin-1 individual concentrations by variation of the format of the immunoassay. Real mussel samples were validated in percentage recovery test. Calibration curves were established, and aliquots of real samples were tested. Very good recoveries were attained, highlighting the validity of the ELISA system to accurately determine the DSP concentration in mussel samples.

Animals↗
PubMed2002

UV-irradiated DNA matrixes selectively bind endocrine disruptors with a planar structure.

DNA has unique chemical properties and is readily purified from salmon milts and shellfish gonads. DNA has few commercial uses and is generally discarded as an industrial waste. Recently, we prepared water-insoluble and nuclease-resistant DNA-films by UV irradiation. The DNA-films removed DNA-intercalating compounds. Here, we immobilized double-stranded DNA onto porous glass beads by UV irradiation and prepared DNA-immobilized glass bead columns. The DNA-immobilized columns effectively accumulated more DNA-intercalating materials than the DNA-films. The DNA-immobilized columns bound endocrine disruptors with a planar structure, such as dioxin-derivatives, polychlorobiphenyl (PCB)-derivatives, and benzo[a]pyrene. Bisphenol A and diethylstilbestrol, which lack a planar structure, did not bind to the DNA-immobilized columns. These results suggest that DNA-immobilized glass bead columns could selectively remove chemical compounds with a planar structure by intercalation into the double-stranded DNA. DNA-immobilized glass beads and DNA-films prepared by UV irradiation have the potential to serve as useful biomaterials for medical, engineering, and environmental applications.

Binding Sites↗
PubMed2005

Total mercury, methyl mercury, and selenium levels in the red meat of small cetaceans sold for human consumption in Japan.

We surveyed the total mercury (T-Hg) and methyl mercury (M-Hg) levels in red meat products (n = 160) from small cetacean species sold for human consumption in markets throughout Japan from 2000 to 2003. Genetic identification showed that the red meat products originated from nine species: false killer whale, bottlenose dolphin, short-finned pilot whale, striped dolphin, rough-toothed dolphin, Risso's dolphin, pantropical spotted dolphin, Baird's beaked whale, and Dall's porpoise. T-Hg and M-Hg concentrations in all red meat products exceeded the provisional permitted levels of T-Hg (0.4 microg/wet g) and M-Hg (0.3 microg/ wet g) in fish and shellfish set by the Japanese government, respectively. The average M-Hg level in the most contaminated species (false killer whale) was 11.5 microg/wet g, and that in the least contaminated species (Dall's porpoise) was about 1.0 microg/wet g, exceeding or equaling the Codex guideline of M-Hg in predatory fishes (1.0 microg/wet g). Contamination levels of T-Hg and M-Hg differed considerably among samples of the nine species and among individuals of a particular species. The highest M-Hg was about 26 microg/ wet g in a sample from a striped dolphin, 87-times higher than the permitted level. The consumption of only 4 g of this product would exceed the provisional tolerable weekly intake of M-Hg for someone of 60 kg body weight (1.6 microg/kg-bw/ week). Although a high correlation between T-Hg and selenium (Se) was observed in these products, the molar ratio of T-Hg to Se was substantially higher than 1. The consumption of red meat from small cetaceans, therefore, could pose a health problem for not only pregnant women but also for the general population.

Animals↗
PubMed2006

Antibodies with broad specificity to azaspiracids by use of synthetic haptens.

The development of general, sensitive, portable, and quantitative assays for the azaspiracid (AZA) class of marine toxins is urgently needed. Use of a synthetic hapten containing rings F-I of AZA to generate antibodies that cross-react with the AZAs via their common C28-C40 domain and use of these antibodies in ELISA and immunoaffinity columns are reported. This approach has many advantages over using intact azaspiracids (AZAs) derived from environmental samples or total synthesis as haptens for antibody development. A derivative of the levorotatory C28-C40 azaspiracid domain (1) was synthesized efficiently using a one-pot Staudinger reduction/intramolecular aza-Wittig reaction-imine capture sequence to form the H-I ring spiroaminal and a double intramolecluar hetero-Michael addition to assemble the F-G ring ketal. Conjugation of the hapten 1 to cBSA and immunization in sheep generated antibodies that recognized and bound to ovalbumin-conjugated 1 in the absence of AZA1. This binding was inhibited by 1 in a concentration-dependent manner. A mixture of AZA1, AZA2, AZA3, and AZA6 caused a degree of inhibition of antibody binding consistent with its total AZA content, rather than just its content of AZA1. This result suggests that the antibodies also have a similar affinity for AZA2, AZA3, and AZA6 as they do for AZA1 and that such antibodies are suitable for analysis of AZAs in shellfish samples.

Antibodies↗
PubMed2003

Concentrations of arsenic, cadmium, mercury, and lead in common foods and estimated daily intake by children, adolescents, adults, and seniors of Catalonia, Spain.

This study was designed to estimate the dietary intake of arsenic (As), cadmium (Cd), mercury (Hg), and lead (Pb) by the general population of Catalonia, Spain. The concentrations of these elements were determined in food samples randomly acquired in seven cities of Catalonia between June and August 2000. A total of 11 food groups were included in the study. As, Cd, Hg, and Pb levels were measured by ICP-MS and AAS. The dietary intake of these elements was determined by a total diet study. Calculations were carried out on the basis of recent data on the consumption of the selected food items. Trace element intake was estimated for five population groups: children, adolescents, male and female adults, and seniors. The highest dietary intakes of As (223.6 microg/day), Cd (15.7 microg/day), Hg (21.2 microg/day), and Pb (28.4 microg/day) corresponded to male adults. For all analyzed elements, fish and shellfish was the group showing the highest contribution to the respective intakes. In comparison with previous results, a general decrease in As, Cd, Hg, and Pb intake has occurred. The dietary intake of these elements was also compared with the provisional tolerable weekly intake (PTWI). Dietary intakes of As, Cd, Hg, and Pb by the population of Catalonia are currently well below the respective PTWIs.

Adolescent↗
PubMed2003

Utilization of Folin-Ciocalteu phenol reagent for the detection of certain nitrogen compounds.

To determine in more detail the reaction of Folin-Ciocalteu phenol reagent with nitrogen compounds, a number of hydroxylamine-related compounds and a large number of guanidine-containing compounds were tested. In general, guanidine compounds did not react strongly unless they were hydroxyamino or hydrazino derivatives. The non-hydroxyamino paralytic shellfish poison saxitoxin, however, reacted to a significant extent. This may be due to the presence of a five-membered ring structure and its analogy to 2-aminopurines, which react strongly. A number of simpler amines were also tested. Tertiary aliphatic amines, but not primary, secondary, or quaternary amines, reacted strongly with the reagent. Primary, secondary, and tertiary aromatic amines all reacted strongly with the reagent. Reactivity was extended to pyrroles and indole derivatives but not to imidazole and benzimidazole derivatives. Defining the reactivity of Folin-Ciocalteau phenol reagent with nitrogen compounds extends the usefulness of the reagent for the detection and determination of certain nitrogen compounds in basic extracts by colorimetric means and by thin-layer chromatography.

Amides↗
PubMed2006

Identification of fatty acid esters of pectenotoxin-2 seco acid in blue mussels (Mytilus edulis) from Ireland.

Pectenotoxins from marine dinoflagellates of the genus Dinophysis are rapidly hydrolyzed by many shellfish to give pectenotoxin-2 seco acid, which isomerizes to 7-epi-pectenotoxin-2 seco acid. Three series of fatty acid esters of pectenotoxin-2 seco acid (PTX-2 seco acid) and 7-epi-PTX-2 seco acid were detected by LC-MS analysis of extracts from blue mussels (Mytilus edulis) from Ireland. The locations of the fatty acid ester linkages were identified by a combination of LC-MSn in positive- and negative-ion modes, LC-MS analysis of the products from reaction of the esters with sodium periodate, and NMR analysis of purified samples of the two most abundant ester derivatives. The 37-O-acyl esters of PTX-2 seco acid were the most abundant, followed by the corresponding 11-O-acyl esters, accompanied by low levels of the 33-O-acyl esters. The most abundant fatty acid esters in the fractionated sample were, in order, the 16:0, 22:6, 14:0, 16:1, 18:4, and 20:5 fatty acids, although a wide array of other PTX-2 seco acid fatty acid esters were also present at low levels.

Animals↗
PubMed2006

Concentrations of perfluorooctanesulfonamides in Canadian total diet study composite food samples collected between 1992 and 2004.

Canadian Total Diet Study composite samples collected from 1992 to 2004 (n = 151) were analyzed for a series of perfluorooctanesulfonamides that are likely breakdown products or manufacturing residuals associated with perfluorooctylsulfonyl phosphate esters. These esters have been incorporated into coatings for paper and paperboard used in food packaging. N-Ethylperfluorooctanesulfonamide (N-EtPFOSA), perfluorooctanesulfonamide, N,N-diethylperfluorooctanesulfonamide, N-methylperfluorooctanesulfonamide, and N,N-dimethylperfluorooctanesulfonamide were extracted using solvent extraction and quantified by gas chromatography-mass spectrometry. Perfluorooctanesulfonamides were detected in the picograms per gram to low nanograms per gram of wet weight range in all food groups tested-baked goods and candy, dairy, eggs, fast food, fish, meat, and foods to be prepared in packaging. The highest concentrations of total perfluorooctanesulfonamides were observed in fast food composites (from less than the method detection limit to 27300 pg/g of wet weight). Concentrations of N-EtPFOSA appeared to decrease over the sampling period (1992-2004) in French fries and other fast food composites; no such trend was apparent in freshwater fish, marine fish, and shellfish composites. A basic estimate of dietary exposure to perfluorooctanesulfonamides suggests that Canadians (>12 years old) are exposed to approximately 73 ng/person/day from these foods.

Canada↗
PubMed1999

Further studies on the analysis of DSP toxin profiles in galician mussels.

Further studies on mussel samples from Galicia, Spain, have revealed the presence of okadaic acid (OA), dinophysistoxin 2 (DTX2), and the fatty acid acyl esters of both of these toxins as the "DTX3" complex. Measurements were performed with an improved in situ method for the formation of 9-anthryldiazomethane (ADAM) derivatives followed by liquid chromatography with fluorescence detection. Base hydrolysis of DTX3 toxins gave free OA and DTX2, which were determined following ADAM derivatization. Results were confirmed by liquid chromatography/mass spectrometry analyses, and in most of the samples, free DTX2 was the most abundant toxin. However, the OA/DTX2 ratio in the DTX3 conjugated form was different, with OA being the most abundant in all cases. This difference could be due to different rates of metabolism of OA and DTX2 to the acyl esters or due to contamination of the shellfish by the two toxins at different points in time, resulting in less acyl ester formation for one toxin versus the other. The second possibility would be reasonable if two different source organisms were producing the toxins.

Animals↗
PubMed1999

Determination of domoic acid in phytoplankton by high-performance liquid chromatography of the 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate derivative.

Domoic acid is the toxin that can cause amnesic shellfish poisoning. In this work, a new precolumn derivatization reagent, 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate, was used to react with domoic acid to form a stable unsymmetrical urea derivative, which was readily analyzed by reversed-phase HPLC with fluorescence detection. The one-step derivatizing method is rapid and straightforward. The method was applied to detect domoic acid in phytoplankton using a 3.9 x 150 mm Nova-Pak, 4 microm, C(18) column.

Aminoquinolines↗
PubMed2004

Self-association of okadaic acid upon complexation with potassium ion.

Okadaic acid (OA) is a toxin responsible for diarrhetic shellfish poisoning and is an extremely useful tool for studying processes that are regulated by phosphorylation, although the exact mechanism of action is still undetermined. We report on a study that proved the existence of OA in an unusual dimeric form when complexed with potassium ion. The proposed structure of this dimer is based on spectroscopic and conformational studies.

Animals↗
PubMed2003

Studies of the biosynthesis of DTX-5a and DTX-5b by the dinoflagellate Prorocentrum maculosum: regiospecificity of the putative Baeyer-Villigerase and insertion of a single amino acid in a polyketide chain.

The biosynthetic origins of the diarrhetic shellfish poisoning toxins DTX-5a and DTX-5b have been elucidated by supplementing cultures of the producing organism Prorocentrum maculosum with stable isotope labeled precursors and determining the incorporation patterns by 13C NMR spectroscopy. The amino acid residue in the sulfated side chain is found to originate from glycine, and oxygen insertion in the chain is shown to occur after polyketide formation.

Amino Acids↗
PubMed2003

Sulfonyl-stabilized oxiranyllithium-based approach to polycyclic ethers. Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.

Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, marine polycyclic ether toxins causative of diarrheic shellfish poisoning, has been accomplished. The A-ring fragment was constructed by coupling of an appropriately functionalized sulfonyl-stabilized oxiranyl anion and a triflate prepared from an erythritol derivative. An iterative protocol of the oxiranyl anion strategy was also applied for the construction of the DEF-ring fragment. The triflate derivatives of the A-ring and the DEF-ring fragments were connected with lithium acetylide. The resulting acetylene derivative was further transformed into the hexacyclic ABCDEF fragment via oxidation of the acetylene unit to 1,2-diketone, double methyl acetal formation, and reductive etherification.

Ethers↗
PubMed1998

Identification and Characterization of Pectenotoxin (PTX) 4 and PTX7 as Spiroketal Stereoisomers of Two Previously Reported Pectenotoxins.

Pectenotoxins (PTXs) isolated from the scallop Patinopecten yessoensis were shown to be involved in an episode of diarrhetic shellfish poisoning (DSP). A total of eight analogues (PTX1-PTX7 and PTX10) have been isolated to date, and the structures of four of these analogues (PTX1, PTX2, PTX3, and PTX6) have already been elucidated. Here, we report the characterization of PTX4 and PTX7 as 7-epi-PTX1 and 7-epi-PTX6, respectively, on the basis of NMR data and an acid-catalyzed chemical interconversion. The structures of two new artifacts, PTX8 and PTX9, produced following this treatment are also reported.

Journal Article↗
PubMed2006

Adsorption and activity of a domoic acid binding antibody fragment on mesoporous silicates.

The adsorption of an anti-domoic acid single-chain Fv (scFv) antibody fragment onto a range of mesoporous silicate supports was investigated. The scFv fragment adsorbed to all materials investigated, and pI had an apparently large effect on coating, with the greatest-and fastest-adsorption found on the most negatively charged silicates. Maximal coating levels attainable did not reflect the pore diameters of the materials. The immobilized antibody was functional on all materials and bound its antigen, a naturally occurring neurotoxin produced by shellfish, in a rapidly saturating manner that suggested the antibody adsorbed in a multilayer on the mesoporous particles. The antigen:antibody ratio decreased from 1:1.3 to <1:10 with increasing concentration of immobilized antibody, and the immobilized scFv exhibited no detectable reduction in domoic acid binding over a 42-day incubation period.

Adsorption↗