Arsenobetaine and other arsenic species in mushrooms

Byrne, A. R.; Šlejkovec, Zdenka; Stijve, T.; Fay, Laurent B.; Gössler, Walter; Gailer, Jürgen; Lrgolic, K. J.

doi:10.1002/aoc.590090403

Cited by 111 publications

(50 citation statements)

References 16 publications

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“…Only 10% of the extraction yield achieved with orthophosphoric acid and 12% of the extraction yield achieved with water can be reached with methanol/water (9 1). These results correspond to the findings of Byrne et al, 25 who reported higher extraction yields with water than with methanol/water (9 1) in a mushroom sample containing almost all of its arsenic as inorganic arsenic. Almost no differences were observed in the extractability of DMA, the phosphate-, the sulfate-, and the sulfonate-riboses.…”

supporting

confidence: 91%

Comparison of three methods for the extraction of arsenic compounds from the NRCC standard reference material DORM‐2 and the brown alga Hijiki fuziforme

Kuehnelt

Irgolic

Goessler

2001

Applied Organom Chemis

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The NRCC standard reference material DORM-2 and the marine brown alga Hijiki fuziforme were extracted with water, methanol/water (9 1), and 1.5 M orthophosphoric acid. The extracts from DORM-2 were analyzed by HPLC-ICP-MS for arsenobetaine, arsenocholine, trimethylarsine oxide, and the tetramethylarsonium cation and the extracts from H. fuziforme for arsenous acid, arsenic acid, dimethylarsinic acid, methylarsonic acid, and four arsenoriboses. Almost no differences between the three extractants were observed when DORM-2 was investigated. Only arsenobetaine was slightly better extracted with 1.5 M orthophosphoric acid or methanol/water (9 1) than with water. The sum of all extractable compounds (arsenobetaine, the tetramethylarsonium cation, and a formerly unknown compound recently identified as the trimethyl(2-carboxyethyl)arsonium ion) accounted for 94% of the total arsenic when 1.5 M orthophosphoric acid was used, for 92% when methanol/water (9 1) was used, and for 87% when water was used. Significant differences in the extraction yields obtained for the alga were observed for arsenic acid and one of the arsenoriboses ('glycerol-ribose'). Orthophosphoric acid removed twice as much of this ribose from the algal material than water and three times more than methanol/water (9 1). Arsenic acid was 1.2 times better extracted with orthophosphoric acid than with water and ten times better than with methanol/water (9 1). Almost no differences in the extraction yields were found for dimethylarsinic acid and the other three riboses. Orthophosphoric acid extracted 76%, water 65%, and methanol/water 33% of the total arsenic from H. fuziforme.

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supporting

confidence: 91%

Comparison of three methods for the extraction of arsenic compounds from the NRCC standard reference material DORM‐2 and the brown alga Hijiki fuziforme

Kuehnelt

Irgolic

Goessler

2001

Applied Organom Chemis

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“…Also, the question has arisen as to whether more complex organoantimony species, such as stibiobetaine, might be produced in the environment; other workers have detected arsenobetaine in some arsenic-accumulating terrestrial fungi. 27 It might be worth examining P. schweinitzii to see if such species are present.…”

Section: Discussionmentioning

confidence: 99%

Antimony biomethylation by the wood rotting fungus Phaeolus schweinitzii

Andrewes

Cullen

Polishchuk

et al. 2001

Applied Organom Chemis

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The wood rotting fungus, Phaeolus schweinitzii, efficiently transforms the antimony(III) compounds potassium antimony tartrate and antimony trioxide to nonvolatile dimethylantimony and trimethylantimony species. The organoantimony species were detected in potato dextrose broth media samples by using hydride generation-gas chromatography-atomic absorption spectroscopy (HG-GC-AAS). The average concentrations of trimethylantimony species after 40 days incubation with potassium antimony tartrate were approximately 35 mg, 155 mg and 520 mg Sb/l, for substrate concentrations of 10 mg, 100 mg and 1000 mg Sb/l respectively. Thus, the maximum yield of trimethylantimony species was approximately 0.4%. When antimony trioxide (saturated solution, 4 mg Sb/l) was used as a substrate, the average concentration of trimethylantimony species was 150 mg Sb/l after 40 days. The HG-GC-AAS response for the dimethylantimony species was less than that for the trimethylantimony species; however, quantification was not possible because of the lack of an appropriate standard. In comparison, cultures of P. schweinitzii incubated with 1 mg As/l as sodium arsenite contained approximately 200 mg As/l as trimethylarsenic species, i.e. 20% yield. Biomethylation of antimony(V) was inefficient: cultures contained only 3 mg Sb/l as trimethylantimony species after incubation with 100 mg Sb/l as potassium hexahydroxyantimonate. No organoantimony species were detected in control cultures that contained only medium and inorganic antimony compounds. The identities of the organoantimony species were confirmed by using GC-Mass Spectrometry.

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“…These structural types are not present in bacteria and fungi. However, methylarsonate and dimethylarsinate were found in several edible mushrooms (collected in Switzerland and Slovenia) and, as well, arsenobetaine (35). These materials occur in a wide range of terrestrial mushrooms and lichens; other compounds include arsenocholine and the tetramethylarsonium ion (140,145,146,150,220) and small amounts of some arsenoribofuranosides (140).…”

Section: Biomethylation and Bioalkylationmentioning

confidence: 99%

Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth

Bentley

Chasteen

2002

Microbiol Mol Biol Rev

513

316

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A significant 19th century public health problem was that the inhabitants of many houses containing wallpaper decorated with green arsenical pigments experienced illness and death. The problem was caused by certain fungi that grew in the presence of inorganic arsenic to form a toxic, garlic-odored gas. The garlic odor was actually put to use in a very delicate microbiological test for arsenic. In 1933, the gas was shown to be trimethylarsine. It was not until 1971 that arsenic methylation by bacteria was demonstrated. Further research in biomethylation has been facilitated by the development of delicate techniques for the determination of arsenic species. As described in this review, many microorganisms (bacteria, fungi, and yeasts) and animals are now known to biomethylate arsenic, forming both volatile (e.g., methylarsines) and nonvolatile (e.g., methylarsonic acid and dimethylarsinic acid) compounds. The enzymatic mechanisms for this biomethylation are discussed. The microbial conversion of sodium arsenate to trimethylarsine proceeds by alternate reduction and methylation steps, with S-adenosylmethionine as the usual methyl donor. Thiols have important roles in the reductions. In anaerobic bacteria, methylcobalamin may be the donor. The other metalloid elements of the periodic table group 15, antimony and bismuth, also undergo biomethylation to some extent. Trimethylstibine formation by microorganisms is now well established, but this process apparently does not occur in animals. Formation of trimethylbismuth by microorganisms has been reported in a few cases. Microbial methylation plays important roles in the biogeochemical cycling of these metalloid elements and possibly in their detoxification. The wheel has come full circle, and public health considerations are again important

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Arsenobetaine and other arsenic species in mushrooms

Cited by 111 publications

References 16 publications

Comparison of three methods for the extraction of arsenic compounds from the NRCC standard reference material DORM‐2 and the brown alga Hijiki fuziforme

Comparison of three methods for the extraction of arsenic compounds from the NRCC standard reference material DORM‐2 and the brown alga Hijiki fuziforme

Antimony biomethylation by the wood rotting fungus Phaeolus schweinitzii

Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth

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