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Synthesis and Characterization of Arsenolipids: Naturally Occurring Arsenic Compounds in Fish and Algae

  • Arsenic-containing lipids (arsenolipids) are natural products present in fish and algae. Because these compounds occur in foods, there is considerable interest in their human toxicology. We report the synthesis and characterization of seven arsenic-containing lipids, including six natural products. The compounds comprise dimethylarsinyl groups attached to saturated long-chain hydrocarbons (three compounds), saturated long-chain fatty acids (two compounds), and monounsaturated long chain fatty acids (two compounds). The arsenic group was introduced through sodium dimethylarsenide or bis(dimethylarsenic) oxide. The latter route provided higher and more reproducible yields, and consequently, this pathway was followed to synthesize six of the seven compounds. Mass spectral properties are described to assist in the identification of these compounds in natural samples. The pure synthesized arsenolipids will be used for in vitro experiments with human cells to test their uptake, biotransformation, and possible toxic effects.

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Author:Mojtaba S. Taleshi, Rune K. Seidler-Egdal, Kenneth B. Jensen, Tanja Schwerdtle, Kevin A. Francesconi
ISSN:0276-7333 (print)
ISSN:1520-6041 (online)
Parent Title (English):Organometallics
Publisher:American Chemical Society
Place of publication:Washington
Document Type:Article
Year of first Publication:2014
Year of Completion:2014
Release Date:2017/03/27
First Page:1397
Last Page:1403
Funder:Austrian Science Fund (FWF) [I550-N17]; DFG [SCHW903/4-1]; Carlsbergfoundation
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Ernährungswissenschaft
Peer Review:Referiert