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.
Highlights
The presence of arsenic in lipid extracts of fish and algae was first reported in the late 1960s,1 but their structures remained unknown
Subsequent biochemical studies in 1978 showed that arsenic-containing lipids in unicellular algae comprised three main lipid types,[2] and the same compounds were reported in clam tissues as a consequence of an algal−clam symbiosis.[3]
It was clear that the third lipid type was not a phospholipid, no additional information could be gleaned from the biochemical experiments
Summary
The presence of arsenic in lipid extracts of fish and algae was first reported in the late 1960s,1 but their structures remained unknown. Treatment with (Me2As)2O in the usual way gave the desired arsenic-containing carboxylic acid (4, As-FA 374) in 32% overall yield (Scheme 2). The synthesis of seven arsenolipids reported here provides material for an evaluation of the bioavailability and toxicity of a novel group of arseniccontaining natural products that accumulate in fatty fish and algae.
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