Arsenic‐Containing Phosphatidylcholines: A New Group of Arsenolipids Discovered in Herring Caviar

Viczek, Sandra Antonia; Jensen, Kenneth B.; Francesconi, Kevin A.

doi:10.1002/ange.201512031

Cited by 17 publications

(9 citation statements)

References 26 publications

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“…67 Two new groups of arsenolipids, arsenic-containing phosphatidylcholines (AsPC) and arsenic-containing phosphatidylethanolamine (AsPE) from herring caviar, were characterized. 68 In total, more than 20 arsenosugars and 70 arsenolipids have been identified in marine organisms that live in low phosphate and high salt environments. These organoarsenicals are not toxic for the marine plants and animals, but their function in these marine organisms is not known.…”

Section: Arsenic Metabolism: From Genes To Biogeochemical Processesmentioning

confidence: 99%

Linking Genes to Microbial Biogeochemical Cycling: Lessons from Arsenic

Zhu

Xue

Kappler

et al. 2017

Environ. Sci. Technol.

266

140

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The biotransformation of arsenic is highly relevant to the arsenic biogeochemical cycle. Identification of the molecular details of microbial pathways of arsenic biotransformation coupled with analyses of microbial communities by meta-omics can provide insights into detailed aspects of the complexities of this biocycle. Arsenic transformations couple to other biogeochemical cycles, and to the fate of both nutrients and other toxic environmental contaminants. Microbial redox metabolism of iron, carbon, sulfur, and nitrogen affects the redox and bioavailability of arsenic species. In this critical review we illustrate the biogeochemical processes and genes involved in arsenic biotransformations. We discuss how current and future metagenomic-, metatranscriptomic-, metaproteomic-, and metabolomic-based methods will help to decipher individual microbial arsenic transformation processes, and their connections to other biogeochemical cycle. These insights will allow future use of microbial metabolic capabilities for new biotechnological solutions to environmental problems. To understand the complex nature of inorganic and organic arsenic species and the fate of environmental arsenic will require integrating systematic approaches with biogeochemical modeling. Finally, from the lessons learned from these studies of arsenic biogeochemistry, we will be able to predict how the environment changes arsenic, and, in response, how arsenic biotransformations change the environment.

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Section: Arsenic Metabolism: From Genes To Biogeochemical Processesmentioning

confidence: 99%

Linking Genes to Microbial Biogeochemical Cycling: Lessons from Arsenic

Zhu

Xue

Kappler

et al. 2017

Environ. Sci. Technol.

266

140

View full text Add to dashboard Cite

show abstract

“…Concerning lipid fraction, several studies on brown algae have been focused on minor arsenosugar phospholipids [16][17][18], arsenic-including hydrocarbons [19,20], and free polyunsaturated fatty acids [21,22]. While the knowledge of glycolipids (GL) and PL is foremost in red algae [23], these compounds have been only partially investigated in brown algae [24].…”

Section: Introductionmentioning

confidence: 99%

Lipidomics of the Edible Brown Alga Wakame (Undaria pinnatifida) by Liquid Chromatography Coupled to Electrospray Ionization and Tandem Mass Spectrometry

et al. 2021

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The lipidome of a brown seaweed commonly known as wakame (Undaria pinnatifida), which is grown and consumed around the world, including Western countries, as a healthy nutraceutical food or supplement, was here extensively examined. The study was focused on the characterization of phospholipids (PL) and glycolipids (GL) by liquid chromatography (LC), either hydrophilic interaction LC (HILIC) or reversed-phase LC (RPLC), coupled to electrospray ionization (ESI) and mass spectrometry (MS), operated both in high and in low-resolution mode. Through the acquisition of single (MS) and tandem (MS/MS) mass spectra more than 200 PL and GL of U. pinnatifida extracts were characterized in terms of lipid class, fatty acyl (FA) chain composition (length and number of unsaturations), and regiochemistry, namely 16 SQDG, 6 SQMG, 12 DGDG, 5 DGMG, 29 PG, 8 LPG, 19 PI, 14 PA, 19 PE, 8 PE, 38 PC, and 27 LPC. The FA (C16:0) was the most abundant saturated acyl chain, whereas the monounsaturated C18:1 and the polyunsaturated C18:2 and C20:4 chains were the prevailing ones. Odd-numbered acyl chains, iJ., C15:0, C17:0, C19:0, and C19:1, were also recognized. While SQDG exhibited the longest and most unsaturated acyl chains, C18:1, C18:2, and C18:3, in the sn-1 position of glycerol, they were preferentially located in the sn-2 position in the case of PL. The developed analytical approach might pave the way to extend lipidomic investigations also for other edible marine algae, thus emphasizing their potential role as a source of bioactive lipids.

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“… 1 In the past decade, about 70 arsenolipids have been discovered from algae, fish oil, and caviar (Supporting Information Table S1 ). Reported arsenolipids typically include phosphatidyl-arsenosugar (AsPL), 2 arsenic-containing fatty acids (AsFAs), 3 arsenic-containing hydrocarbons (AsHCs), 4 trimethylarsenio fatty alcohols (TMAsFOHs), 5 arsenic-containing phosphatidylcholines (AsPCs), and arsenic-containing phosphatidylethanolamines (AsPEs). 6 Recent studies have found that several arsenolipids elicited cytotoxicity comparable to that of arsenite in the human bladder and liver cells.…”

Section: Introductionmentioning

confidence: 99%

Discovery and Identification of Arsenolipids Using a Precursor-Finder Strategy and Data-Independent Mass Spectrometry

Liu

Huang

et al. 2021

Environ. Sci. Technol.

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Arsenolipids are a class of lipid-soluble arsenic species. They are present in seafoods and show high potentials of cytotoxicity and neurotoxicity. Hindered by traditional low-throughput analytical techniques, the characterization of arsenolipids is far from complete. Here, we report on a sensitive and high-throughput screening method for arsenolipids in krill oil, tuna fillets, hairtail heads, and kelp. We demonstrate the detection and identification of 23 arsenolipids, including novel arsenic-containing fatty acids (AsFAs), hydroxylated AsFAs, arsenic-containing hydrocarbons (AsHCs), hydroxylated AsHCs, thiolated trimethylarsinic acids, and arsenic-containing lysophosphatidylcholines not previously reported. The new method incorporated precursor ion scan (PIS) into data-independent acquisition. High-performance liquid chromatography (HPLC) electrospray ionization quadrupole time-of-flight mass spectrometry (ESI–qToF–MS) was used to perform the sequential window acquisition of all theoretical spectra (SWATH). Comprehensive HPLC–MS and MS/MS data were further processed using a fragment-guided chromatographic computational program Precursorfinder developed here. Precursorfinder achieved efficient peak-picking, retention time comparison, hierarchical clustering, and wavelet coherence calculations to assemble fragment features with their target precursors. The identification of arsenolipids was supported by coeluting the HPLC–MS peaks detected with the characteristic fragments of arsenolipids. Method validation using available arsenic standards and the successful identification of previously unknown arsenolipids in seafood samples demonstrated the applicability of the method for environmental research.

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Arsenic‐Containing Phosphatidylcholines: A New Group of Arsenolipids Discovered in Herring Caviar

Cited by 17 publications

References 26 publications

Linking Genes to Microbial Biogeochemical Cycling: Lessons from Arsenic

Linking Genes to Microbial Biogeochemical Cycling: Lessons from Arsenic

Lipidomics of the Edible Brown Alga Wakame (Undaria pinnatifida) by Liquid Chromatography Coupled to Electrospray Ionization and Tandem Mass Spectrometry

Discovery and Identification of Arsenolipids Using a Precursor-Finder Strategy and Data-Independent Mass Spectrometry

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