Synthesis of a novel biologically active amide ester of 7,10-dihydroxy-8(E)-octadecanoic acid (DOD) using lipase

Authors: CHOI, IN-HAE - Kyungpook National University; JUNG, JI-HYE - Kyungpook National University; Hou, Ching; KIM, HAK-RYUL - Kyungpook National University

Submitted to: American Oil Chemists' Society Meeting
Publication Type: Abstract Only
Publication Acceptance Date: 5/1/2016
Publication Date: 5/3/2016
Citation: Choi, I.H., Jung, J.H., Hou, C.T., Kim, H.R. 2016. Synthesis of a novel biologically active amide ester of 7,10-dihydroxy-8(E)-octadecanoic acid (DOD) using lipase [abstract]. American Oil Chemists' Society.

Interpretive Summary:

Technical Abstract: Hydroxy fatty acids (HFA) are known to have industrial potential because of their special properties such as high viscosity and reactivity. Among the hydroxy fatty acids, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) was successfully produced from oleic acid and lipid containing oleic acid by a bacterial strain Pseudomonas aeruginosa PR3. Recently we have shown that DOD presented strong antimicrobial activity against broad range of pathogenic bacteria. In this study, we tried to modify DOD molecules by lipase-catalyzed esterification with triethanolamine (TEA) to exert enhanced biological activity. Structure of a novel DOD-TEA ester was confirmed by GC-MS, NMR, FT-IR analysis. Antibacterial activity of DOD-TEA ester was determined against several food-born pathogenic bacteria. We found out that antibacterial activity of DOD-TEA ester was highly enhanced compared to those with DOD.