Controlled formation of mono- and dihydroxy-resolvins from EPA and DHA using soybean 15-lipoxygenase[S]

Journal of Lipid Research

Eleanor P. Dobson¹  Colin J. Barrow¹  Jaroslav A. Kralovec²  Jacqui L. Adcock³ 

[1] Centre for Chemistry and Biotechnology, Deakin University, Geelong, Victoria 3220, Australia;Ocean Nutrition Canada Ltd., Dartmouth, Nova Scotia B2Y 4T6, Canada;To whom correspondence should be addressed [e-mail];

关键词: polyunsaturated fatty acids;    eicosanoid;    docosanoid;    eicosapentaenoic acid;    docosahexaenoic acid;   

DOI  :  

来源: DOAJ

【 摘 要 】

Resolvins and protectins are important anti-inflammatory and pro-resolution compounds derived from the enzymatic oxidation of omega-3 fatty acids all-cis-5,8,11,14,17-eicosapentaenoic acid (EPA) and all-cis-4,7,10,13,16,19-docosahexaenoic acid (DHA). We have developed a simple, controlled method to synthesize an array of resolvin and protectin analogs from fatty acid starting materials using soybean 15-lipoxygenase. The conditions were optimized for the production of both mono- and dihydroxy derivatives, with enzyme concentration and pH found to have a significant effect on the reaction products. The methods were applied to five biologically important omega-3 and omega-6 fatty acid substrates. Mono- and dihydroxy compounds were successfully synthesized from all substrates and the products were characterized by normal phase (NP) HPLC, GC-MS, TOF-MS, UV-visible (UV-vis) spectroscopy, and NMR spectroscopy. The methods could be further applied to any polyunsaturated fatty acids containing the cis-1,4,7,10-undecatetraene moiety to produce a range of novel compounds with potential biological activity.

【 授权许可】

Unknown