N-Docosanoyl Taurine

Several different arachidonoyl amino acid conjugates, including N-arachidonoyl dopamine and N-arachidonoyl-L-serine, have been isolated and characterized from bovine brain. N-Docosanoyl taurine is one of several novel taurine-conjugated fatty acids discovered during mass spectrometry lipidomic analysis of brain and spinal cord from wild-type and fatty acid amide hydrolase (FAAH) knockout mice. The levels of N-docosanoyl taurine were elevated ~12 fold in FAAH-/- mice compared to wild-type mice, indicating that FAAH utilizes N-docosanoyl taurine as a substrate. However, in vitro experiments with purified FAAH indicate that related N-fatty acyl taurines and ethanolamines of similar chain length are hydrolyzed 2,000-50,000 times more slowly by FAAH compared to oleoyl ethanolamide. N-acyl taurines bearing polyunsaturated acyl chains can activate members of the transient receptor potential (TRP) family of calcium channels, including TRPV1 and TRPV4.