US EPA

2298673 

Journal Article 

Synthesis and characterization of arsenolipids: Naturally occurring arsenic compounds in fish and algae 

Taleshi, MS; Seidler-Egdal, RK; Jensen, KB; Schwerdtle, T; Francesconi, KA 

2014 

1 

Organometallics
ISSN: 0276-7333
EISSN: 1520-6041 

33 

6 

1397-1403 

English 

24683287 

10.1021/om4011092 

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.