Arsenic Fatty Acids Are Human Urinary Metabolites of Arsenolipids Present in Cod Liver

Schmeisser, Ernst; Rumpler, Alice; Kollroser, Manfred; Rechberger, Gerald; Goessler, Walter; Francesconi, Kevin A.

doi:10.1002/anie.200502706

Cited by 63 publications

(55 citation statements)

References 16 publications

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“…[9][10][11] Sulfur derivatives such as thio-organoarsenates are rarely encountered, [12] while thioarsenic acid is known to be derived from the metabolism of cod-liver arsenolipids in humans. [13] The presence of arsenic in drinking water is a major problem in certain countries, and efforts are directed at removing it, especially As III , with chelating agents. [14] Abstract: The 1 H and 13 C NMR chemical shifts and coupling constants of a series of organoarsenic compounds were calculated with DFT methods and compared with available experimental spectra.…”

Section: Introductionmentioning

confidence: 99%

“…[13] The presence of arsenic in drinking water is a major problem in certain countries, and efforts are directed at removing it, especially As III , with chelating agents. [14] Abstract: The 1 H and 13 C NMR chemical shifts and coupling constants of a series of organoarsenic compounds were calculated with DFT methods and compared with available experimental spectra. We show that non-relativistic methods successfully model the NMR spectra of these molecules; relativistic spin-orbit effects are small but appreciable for 13 C shifts, and their inclusion is beneficial.…”

Section: Introductionmentioning

confidence: 99%

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Computational NMR Spectroscopy of Organoarsenicals and the Natural Polyarsenic Compound Arsenicin A

Tähtinen

Saielli

Guella

et al. 2008

Chemistry A European J

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The (1)H and (13)C NMR chemical shifts and coupling constants of a series of organoarsenic compounds were calculated with DFT methods and compared with available experimental spectra. We show that non-relativistic methods successfully model the NMR spectra of these molecules; relativistic spin-orbit effects are small but appreciable for (13)C shifts, and their inclusion is beneficial. Application of the same methods of calculation to the intriguing natural polyarsenic compound arsenicin A allowed several viable alternative structures to be ruled out and thereby confirmed the previously suggested adamantane-like structure of arsenicin A. These results not only reinforce the known predictive power of DFT NMR calculations, but also open the way for the investigation of other naturally occurring molecules with unusual structures outside the scope of empirical methods.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Computational NMR Spectroscopy of Organoarsenicals and the Natural Polyarsenic Compound Arsenicin A

Tähtinen

Saielli

Guella

et al. 2008

Chemistry A European J

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“…The gastrointestinal microflora probably play a role in the conversion of arsenosugars to bioavailable metabolites as demonstrated in vitro with mice caecum contents by Conklin et al (2006) and by in vivo experiments carried out in sheep (Hansen et al, 2003). The human metabolism of arsenolipids also results in the formation of dimethylarsinate, which is then excreted in the urine (Schmeisser et al, 2006). …”

Section: Metabolismmentioning

confidence: 99%

“…Arsenosugars and arsenolipids are metabolised by humans to dimethylarsinate (Raml et al, 2009;Schmeisser et al, 2006), but no other information is available regarding their toxicity.…”

Section: Organic Arsenicmentioning

confidence: 99%

Scientific Opinion on Arsenic in Food

2009

EFSA Journal

877

220

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The EFSA Panel on Contaminants in the Food Chain (CONTAM Panel) assessed the risks to human health related to the presence of arsenic in food. More than 100,000 occurrence data on arsenic in food were considered with approximately 98 % reported as total arsenic. Making a number of assumptions for the contribution of inorganic arsenic to total arsenic, the inorganic arsenic exposure from food and water across 19 European countries, using lower bound and upper bound concentrations, has been estimated to range from 0.13 to 0.56 µg/kg bodyweight (b.w.) per day for average consumers, and from 0.37 to 1.22 µg/kg b.w. per day for 95 th percentile consumers. Dietary exposure to inorganic arsenic for children under three years of age is in general estimated to be from 2 to 3-fold that of adults. The CONTAM Panel concluded that the provisional tolerable weekly intake (PTWI) of 15 µg/kg b.w. established by the Joint FAO/WHO Expert Committee on Food Additives (JECFA) is no longer appropriate as data had shown that inorganic arsenic causes cancer of the lung and urinary bladder in addition to skin, and that a range of adverse effects had been reported at exposures lower than those reviewed by the JECFA. The CONTAM Panel modelled the dose-response data from key for providing consumption information and calculating exposure, the partners of the EFSA project on the "Individual food consumption data and exposure" coordinated by Ghent University (Department of Public Health, University Hospital, Ghent University, Belgium), and RIKILT (Institute of Food Safety, Wageningen, The Netherlands) for the accessibility of the exposure assessment tools. 4 Table of contents shows now the fourth level of subheadings. 5 An error in the interpretation of the total number of the population in the study of Rahman et al. (2006a) was discovered (Table 41). The BMDL was recalculated and as a consequence it was not considered a potential reference point. The text in the opinion, Table 43 and Appendix were revised accordingly. In addition, the header of the "total number of cases" was replaced by "total number of individuals" in Tables 40-42 and the erroneous units were corrected to µg/L in the text below SUMMARYArsenic is a metalloid that occurs in different inorganic and organic forms, which are found in the environment both from natural occurrence and from anthropogenic activity. The inorganic forms of arsenic are more toxic as compared to the organic arsenic but so far most of the occurrence data in food collected in the framework of official food control are still reported as total arsenic without differentiating the various arsenic species. The need for speciation data is evident because several investigations have shown that especially in seafood most of the arsenic is present in organic forms that are less toxic. Consequently, a risk assessment not taking into account the different species but considering total arsenic as being present exclusively as inorganic arsenic would lead to a considerable overestimation of the health risk rel...

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“…AB, AC, TMAP, and TETRA were prepared according to McShane. [32] TMAO, [33] 301 DMAP, [28] and Gly [34] were synthesized as previously reported. Thio-Gly was prepared from the oxo-Gly as 302 described elsewhere.…”

mentioning

confidence: 99%

Arsenic speciation in bodily fluids of harbor seals (Phoca vitulina) and harbor porpoises (Phocoena phocoena)

Kuenstl

Griesel²,

Prange³

et al. 2009

Environ. Chem.

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11 12Environmental context. Marine mammals as top predators ingest a lot of arsenic from their food. In this 13 study liver samples and body fluids of marine mammals from the North and Baltic Seas were investigated 14 for arsenic speciation in order to get some information about their feeding habits. Only organic arsenic 15 compounds with low toxicity were detected in all investigated samples. Although a high quantitative 16 variability was observed, the same compounds were determined in all fluids examined. 18Abstract. The total arsenic concentrations in whole blood of harbor seals (Phoca vitulina) and in liver 19 tissues of harbor porpoises (Phocoena phocoena) were determined using TXRF (total-reflection X-ray 20 fluorescence spectrometry). The total arsenic concentration found in whole blood was lower for fish-fed ). In porpoise liver the arsenic concentrations were higher from carcases found in the North Sea (217- ). 25Furthermore the total arsenic content and arsenic species in urine, plasma, and gastric juice of seals and 26 the urine of porpoises, which were collected from animals at different areas in the North and Baltic Seas, 27were determined using ICPMS (inductively coupled plasma mass spectrometry . The arsenic is almost entirely present in inorganic forms.[1] 49Marine organisms are known to accumulate and convert inorganic arsenic to organic arsenic compounds. 50Mammals such as porpoises and seals living in the marine environment and feeding exclusively on marine 51 organisms are in an exceptional position. As top predators they could accumulate arsenic due to their 52 position in the food web. Goessler et al., reported in 1997 the arsenic concentrations and speciation in a 53 three organism marine food chain starting with a seaweed followed by two gastropods. They showed that 54 arsenic was accumulated and metabolized within this food chain.[2] These results were in contrast to those 55of Kubota et al., who found lower arsenic concentrations in marine mammals (seals and porpoises) 56 compared to those of lower tropic level marine organisms from other studies.[3] Furthermore Kubota et al. 57investigated a possible correlation between arsenic accumulation and gender, age (or body length), or 58 feeding habits in liver tissues of 16 different marine mammal species. The determined arsenic 59concentrations varied widely among species and individuals ranging from 100 to 7680 µg kg -1 dry mass. 60Marine mammals feeding on fish contained lower arsenic concentrations compared to animals feeding on 61cephalopods and crustaceans but no trend with gender or age could be seen.[3] 62Seals feed with regional and seasonal variations on fish, crustaceans, and cephalopods, [4] in contrast to 63 harbor porpoises, which feed mainly on fish and less frequently on molluscs and squids.[5] 64Arsenic contents in tissues of field-collected marine mammals, fish, and invertebrates have been reported 65 in quantities ranges from less than 1000 up to 30000 µg As kg -1 dry mass. [6][7] Total arsenic content in 66 whole blood of...

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Arsenic Fatty Acids Are Human Urinary Metabolites of Arsenolipids Present in Cod Liver

Abstract: Is fish a healthy food? Arsenolipids present in cod liver are metabolized by humans to arsenic‐containing fatty acids. Four of these metabolites were identified in human urine after consumption of cod liver and characterized by mass spectrometry and chromatography.

Cited by 63 publications

References 16 publications

Computational NMR Spectroscopy of Organoarsenicals and the Natural Polyarsenic Compound Arsenicin A

Computational NMR Spectroscopy of Organoarsenicals and the Natural Polyarsenic Compound Arsenicin A

Scientific Opinion on Arsenic in Food

Arsenic speciation in bodily fluids of harbor seals (Phoca vitulina) and harbor porpoises (Phocoena phocoena)

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