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Enrichment of Arachidonic Acid for the Enzymatic Synthesis of Arachidonoyl Ethanolamide
Author(s) -
Wang Xiaosan,
Wang Xingguo,
Wang Tong
Publication year - 2013
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-013-2247-7
Subject(s) - arachidonic acid , chemistry , urea , fatty acid , anandamide , lipase , biochemistry , ethanolamine , fractionation , polyunsaturated fatty acid , linoleic acid , chromatography , enzyme , cannabinoid receptor , receptor , agonist
Arachidonoyl ethanolamide is an endogenous cannabinoid neurotransmitter that potentially has therapeutic properties. In this study, we report an enzymatic method to synthesize this bioactive ethanolamide. First, free fatty acids were obtained from arachidonic acid‐rich oil and then arachidonic acid was enriched by urea inclusion and AgNO 3 solution fractionation. Arachidonic acid content was increased from 40.2 to 78.4 % with 27.6 ± 1.8 % total fatty acid mass yield (w/w, relative to total free fatty acid) after urea inclusion. Purification of arachidonic acid by AgNO 3 solution fractionation was optimized, and under the optimal conditions, a product with 90.7 % arachidonic acid was obtained with 80.4 % mass yield (w/w, relative to total free fatty acid). Finally, arachidonoyl ethanolamide was synthesized by reacting the purified arachidonic acid with ethanolamine in hexane using Novozym 435 lipase of Novozymes America (Blair, NE), which resulted in the formation of 88.4 ± 0.6 % arachidonoyl ethanolamide with 72.7 ± 2.2 % mass yield. The main novelties of this study are the enrichment of polyunsaturated fatty acids by AgNO 3 solution fractionation which has received little attention in recent years, and this is the first time the synthesis of arachidonoyl ethanolamide is reported.