title: Synthesis and Characterization of Arsenolipids: Naturally Occurring Arsenic Compounds in Fish and Algae.
abstract: 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.
authors.affiliation: Faculty of Marine Science, Marine Chemistry, University of Mazandaran , Babolsar, Iran ; Institute of Chemistry-Analytical Chemistry, University of Graz , Universitaetsplatz 1, Graz, Austria.
authors.forename: Mojtaba S
authors.initials: MS
authors.lastname: Taleshi
authors.affiliation: Institute of Chemistry-Analytical Chemistry, University of Graz , Universitaetsplatz 1, Graz, Austria.
authors.forename: Rune K
authors.initials: RK
authors.lastname: Seidler-Egdal
authors.affiliation: Institute of Chemistry-Analytical Chemistry, University of Graz , Universitaetsplatz 1, Graz, Austria.
authors.forename: Kenneth B
authors.initials: KB
authors.lastname: Jensen
authors.affiliation: Institute of Nutritional Sciences, University of Potsdam , Arthur-Scheunert-Allee 114-116 14558 Nuthetal, OT Bergholz-Rehbrücke, Germany.
authors.forename: Tanja
authors.initials: T
authors.lastname: Schwerdtle
authors.affiliation: Institute of Chemistry-Analytical Chemistry, University of Graz , Universitaetsplatz 1, Graz, Austria.
authors.forename: Kevin A
authors.initials: KA
authors.lastname: Francesconi