Eicosapentaenoic acid is an ω-3 fatty acid abundantly available in marineorganisms. (±)17(18)-DiHETE is one of the major metabolites produced when eicosapentaenoic acid (EPA) is incubated with various rat tissue homogenates or cynomolgus monkey seminal vesicles. The route of production of (±)17(18)-DiHETE likely proceeds through cytochrome P450-catalyzed epoxidation at the ω-3 double bond followed by conversion to the vicinal diols by epoxide hydrolase. EPA is also metabolized preferentially by Gaeumannomyces graminis to (±)17(18)-DiHETE.
Eicosapentaenoic acid is an ω-3 polyunsaturated fatty acid that is abundant in marineorganisms and fish oils. EPA is metabolized, in part, through cytochrome P450-catalyzed epoxidation followed by conversion to the vicinal diols by epoxide hydrolases. (±)5(6)-DiHETE is a possible metabolite produced from EPA following epoxidation of the α-5 double bond. The biological activity of (±)5(6)-DiHETE has not been documented.
One of the first organisms in which quorum sensing was observed were Myxobacteria, a group of gram-negative bacteria, found mainly in soil and also common to marine and freshwater systems. The cellular membranes of autotrophic bacteria contain mono-unsaturated fatty acids. The specific composition and abundance of membrane fatty acids can be used to identify specific genera of bacterial populations in natural environments (e.g., mining lakes, etc.). δ2-cis-Hexadecenoic acid is an unusual fatty acid unique to some Myxococcus species.
Arsenobetaine, an organoarsenical and compatible solute, is discovered in numerous marine animals like lobsters and crabs, and terrestrial organisms such as earthworms and lichens. It protects against B. subtilis cell death caused by high osmolarity or extreme temperatures at 1 mM concentration. Notably, arsenobetaine exhibits non-toxicity to mice with an LD50 of 10 g/kg.