Arsenic-containing hydrocarbons: natural compounds in oil from the fish capelin, Mallotus villosus

Taleshi, Mojtaba S.; Jensen, Kenneth B.; Raber, Georg; Edmonds, John S.; Gunnlaugsdóttir, Helga; Francesconi, Kevin A.

doi:10.1039/b808049f

Cited by 109 publications

(116 citation statements)

References 8 publications

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“…2. Arsenic-hydrocarbons in Wakame and Hijiki; As-HC332 & As-HC360, previously identified in fish oil [7] and sashimi tuna, [9] were present in both Wakame and Hijiki. The homologue As-HC388 is first reported here where it was shown to be present in Wakame (but not Hijiki).…”

Section: Asmentioning

confidence: 97%

“…[1] Although most of the arsenic compounds identified so far have been water-soluble species, the early work on arsenic marine chemistry focussed on lipidsoluble compounds, so called arsenolipids. [2][3][4] Identification of these arsenolipids proved difficult, however, and it was not until 1988 that an arsenolipid was first rigorously characterised and identified as an arsenosugar-containing phospholipid [5] (see Table 1, compound As-PL958).Subsequently, the range of naturally occurring arsenolipids has been extended with the discovery of arsenic-containing fatty acids in fish oils, [6] and arsenic-containing hydrocarbons in fish oils, [7] fish liver, [8] sashimi tuna [9] and fish meal. [10] The origin of these compounds was presumed to be algae.…”

mentioning

confidence: 99%

“…Subsequently, the range of naturally occurring arsenolipids has been extended with the discovery of arsenic-containing fatty acids in fish oils, [6] and arsenic-containing hydrocarbons in fish oils, [7] fish liver, [8] sashimi tuna [9] and fish meal. [10] The origin of these compounds was presumed to be algae.…”

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confidence: 99%

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Arsenosugar phospholipids and arsenic hydrocarbons in two species of brown macroalgae

et al. 2012

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Environmental context. Although organoarsenic compounds occur in marine organisms at high concentrations, the origin and role of these compounds is unknown. Arsenic-containing lipids (arsenolipids) are newly discovered compounds in fish. We identify a range of arsenolipids in algae and propose that algae are the origin of these unusual arsenic compounds in marine ecosystems.Abstract. Fourteen arsenolipids, including 11 new compounds, were identified and quantified in two species of brown algae, Wakame (Undaria pinnatifida) and Hijiki (Hizikia fusiformis), by high resolution mass spectrometry, high performance liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry. Both algal species contained arsenosugar-phospholipids as the major type of arsenolipid, and arsenic-hydrocarbons were also significant components, particularly in Hijiki. The origin of the various arsenolipids, and the possible significance of their relative quantities, is briefly discussed. Arsenic-containing organic compounds are abundant in marine ecosystems where they are thought to play a pivotal role in the cycling and detoxification of potentially toxic inorganic arsenic (arsenate) present in seawater. [1] Although most of the arsenic compounds identified so far have been water-soluble species, the early work on arsenic marine chemistry focussed on lipidsoluble compounds, so called arsenolipids. [2][3][4] Identification of these arsenolipids proved difficult, however, and it was not until 1988 that an arsenolipid was first rigorously characterised and identified as an arsenosugar-containing phospholipid [5] (see Table 1, compound As-PL958).Subsequently, the range of naturally occurring arsenolipids has been extended with the discovery of arsenic-containing fatty acids in fish oils, [6] and arsenic-containing hydrocarbons in fish oils, [7] fish liver, [8] sashimi tuna [9] and fish meal. [10] The origin of these compounds was presumed to be algae. We report the arsenolipid profiles of two species of brown algae, determined mainly by high performance liquid chromatography-mass spectrometry (HPLC-MS), and we briefly discuss the possible biosynthetic origin of these unusual compounds.Samples of Wakame (Undaria pinnatifida, 40 AE 3 mg As g À1 dry mass) and Hijiki (Hizikia fusiformis, 113 AE 5 mg As g À1 dry mass), A obtained from a Japanese commercial source, were extracted with a mixture of chloroform and methanol using a modification B of the classical procedure of Bligh and Dyer. [11] The lipid fraction containing 6.7 % (Wakame) and 1.6 % (Hijiki)A Determination of arsenic contents. Total arsenic analyses were performed on portions of the dry powders, extracts or combined fractions from the silica columns by ICP-MS (Agilent 7500ce) in helium collision cell mode following a microwave-assisted acid mineralisation step. The method was validated by analysis of reference material NIES No. 9 Sargasso (certified As content 115 AE 5 mg As g À1 ); we obtained 116 AE 2 mg As g À1 (n ¼ 3). BExtraction and purification of arsenolipid...

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Section: Asmentioning

confidence: 97%

mentioning

confidence: 99%

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Arsenosugar phospholipids and arsenic hydrocarbons in two species of brown macroalgae

et al. 2012

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“…Combined use of elemental and molecular mass spectrometry is helpful to identify the arsenic-containing non-polar compounds and elucidate their structure. By using combined HPLC-ICP-MS and HPLC-electrospray ionization (ESI)-MS, novel arsenic-containing long-chain fatty acids [21] and hydrocarbons [22] were identified in fish oil. Furthermore, the response factor of known concentration of arsenic (e.g.…”

Section: Speciation Of Asmentioning

confidence: 99%

Recent advances in speciation analysis of mercury, arsenic and selenium

2012

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Mercury (Hg), arsenic (As) and selenium (Se) are ubiquitous in the environment and exist in a variety of species, which have great influence on their transport, bioaccumulation and toxicity. This review presents the recent research progress in speciation analysis of Hg, As, and Se, with emphasis on enhanced cold vapor generation as interface for liquid chromatography and atomic spectrometry, speciation of volatile species in gas phase, and isotope dilution technique to improve the precision and accuracy of speciation. Hyphenated techniques to characterize the complexes of Hg and As with phytochelatins and chromatographic separation coupled with multi-collector-inductively coupled plasma mass spectrometry to measure species-specific isotopic ratios, are also briefly discussed. Mercury (Hg) and arsenic (As) are among the most highly toxic elements for humans and ecosystems and can cause serious environmental and human health problems even at low concentrations [1,2]. Selenium (Se) is an "essential toxin" for human health. It has been recognized as an important antioxidant and anti-cancer element. However, Se can also pose negative impact such as defective skin and hair loss [3]. The adsorption/uptake, transport, bioaccumulation, metabolism and toxicity of these elements strongly depend on their chemical species present in environmental and biological samples. In the environment, one species can transform to another through chemical or biological processes. For example, in anaerobic sediments, sulfur-reducing or iron-reducing bacteria can methylate inorganic mercury into highly toxic methylmercury (MeHg) [4,5]. Therefore, speciation analysis of Hg, As and Se is of great importance in order to elucidate the biogeochemcal cycle and toxicology of these elements. Speciation analysis mainly involves chromatographic separation (gas chromatography (GC) or high performance liquid chromatography (HPLC)) hyphenated with element-specific spectrometry or molecular mass spectrometry. This review presents the recent advances in speciation analysis of Hg, As, and Se based on chromatographic separation, with emphasis on enhanced cold vapor generation (CVG) as interface for LC and atomic spectrometry, speciation of volatile Hg, As and Se in gas phase, and isotope dilution technique to improve the precision and accuracy of speciation. Hyphenated techniques to characterize the complexes of Hg and As with phytochelatins and chromatographic separation coupled with multi-collector-inductively coupled plasma mass spectrometry (MC-ICP-MS) to measure species-specific isotopic ratios, are also briefly introduced.

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“…[12,17,18] Recent findings of Meyer et al [19] have shown that AsHCs show different toxicity depending on the structure of the AsHC and can have similar cytotoxicity to inorganic arsenic (iAs). These new findings underline the relevance of accurately identifying AsLps but also the need to understand better how they are formed and which factors influence their formation.…”

Section: Introductionmentioning

confidence: 99%

Environmental effects on arsenosugars and arsenolipids in Ectocarpus (Phaeophyta)

et al. 2016

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Environmental context. Arsenolipids, which are present in seaweed, can show high toxicity, emphasising the need for more information on these compounds. We investigated the effects of different stress factors on the arsenic compounds formed by cultures of brown algae, and compared the results with those from field-collected samples. We show that the arsenolipid and arsenosugar profiles differ depending on the experimental conditions, and that a deficiency in phosphate has a direct positive effect on the biosynthesis of arseniccontaining phospholipids.Abstract. Seaweeds have recently been shown to contain a significant proportion of arsenic in the form of arsenolipids (AsLp). Three strains of the filamentous brown alga Ectocarpus species were grown in the laboratory with different simulations of environmental stress: control conditions (1/2 Provasoli-enriched seawater), low nitrate (30 % of the amount of nitrates in the control), low phosphate (30 % of the amount of phosphate in the control) and under oxidative stress levels (2 mM H 2 O 2 ). Generally, the major AsLp was an arsenic-containing hydrocarbon, AsHC360 (50-80 %), but additionally, several arsenic-containing phospholipids (AsPL) were identified and quantified using high-performance liquid chromatography-inductively coupled plasma mass spectrometry and electrospray ionisation mass spectrometry (HPLC-ICP-MS/ ESI-MS). The AsLps in cultures were compared with AsLps in Ectocarpus found in its natural habitat as well as with other brown filamentous algae. The AsLp and arsenosugar profiles differed depending on the experimental conditions. Under low phosphate conditions, a significant reduction of phosphorus-containing arsenosugars was noticed, and a significant increase of phosphate-containing AsLps was found when compared with the controls. Strains grown under oxidative stress showed a significant increase in AsLps as well as clear physiological changes.

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Arsenic-containing hydrocarbons: natural compounds in oil from the fish capelin, Mallotus villosus

Abstract: Arsenic-containing hydrocarbons have been identified for the first time as natural components of fish oil.

Cited by 109 publications

References 8 publications

Arsenosugar phospholipids and arsenic hydrocarbons in two species of brown macroalgae

Arsenosugar phospholipids and arsenic hydrocarbons in two species of brown macroalgae

Recent advances in speciation analysis of mercury, arsenic and selenium

Environmental effects on arsenosugars and arsenolipids in Ectocarpus (Phaeophyta)

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