Production of 7,8-Dihydroxy Unsaturated Fatty Acids from Plant Oils by Whole Recombinant Cells Expressing 7,8-Linoleate Diol Synthase from Glomerella cingulata

Abstract

The reaction conditions for the production of 7S,8S-dihydroxy-9,12(Z,Z)-octadecadienoic acid from linoleic acid by recombinant Escherichia coli expressing 7,8-linoleate diol synthase from Glomerella cingulata were optimized using response surface methodology. The optimal reaction conditions were pH 7.0, 18.6 °C, 10.8% (v/v) dimethyl sulfoxide, 44.9 g/L cells, and 14.3 g/L linoleic acid, with agitation at 256 rpm. Under these conditions, recombinant cells produced 7,8-dihydroxy unsaturated fatty acids in the range of 7.0-9.8 g/L from 14.3 g/L linoleic acid, 14.3 g/L oleic acid, and plant oil hydrolysates such as waste oil and olive oil containing 14.3 g/L linoleic acid or oleic acid. To the best of the authors' knowledge, this is the first report on the biotechnological production of 7,8-dihydroxy unsaturated fatty acids.

Simultaneous Enzyme/Whole‐Cell Biotransformation of C18 Ricinoleic Acid into (R)‐3‐Hydroxynonanoic Acid, 9‐Hydroxynonanoic Acid, and 1,9‐Nonanedioic Acid

“…Furthermore, the high specific whole‐cell biotransformation rates with the insoluble reactants in a solid form indicated that solid‐type fatty acids could be good substrates even for the complex biotransformations like the simultaneous enzyme/whole‐cell biotransformation of dihydroxy fatty acid. This study can be used for the biotransformation of poly‐hydroxy fatty acids such as 10,13‐dihydroxyoctadecanoic acid,, 7,8‐dihydroxy‐9,12‐octadecadienoic acid, 7, 10‐dihydroxy‐8‐octadecenoic acid, and 5,8‐dihydroxy‐9,12,15‐octadecatrienoic acid …”

Production of 6,8‐Dihydroxy Fatty Acids by Recombinant Escherichia coli Expressing T879A Variant 6,8‐Linoleate Diol Synthase from Penicillium oxalicum

“…S1, Supporting Information), while the maximum activity of the purified enzyme was observed at pH 6.5 and 25°C (Seo et al, ). Activities for the biotransformation of linoelic acid into DiHODE by recombinant E. coli expressing 5,8‐LDS from A. nidulans (Seo et al, ), 7,8‐LDS from G. cingulate (Seo et al, ), and 8,11‐LDS from P. chrysogenum (Kim et al, ) have been shown to be maximal at pH 7.5 and 35°C, pH 7.0 and 19°C, and pH 7.0 and 25°C, respectively. Thermal stability was evaluated by determining residual enzyme activity after pre‐incubation for 30 min at temperatures ranging from 20 to 45°C (Fig.…”

“…A diverse range of DiHFA have been produced by recombinant Escherichia coli cells. These include 5,8‐dihydroxy‐9( Z )‐octadecenoic acid (5,8‐DiHOME), 5,8‐dihydroxy‐9,12( Z , Z )‐octadecadienoic acid (5,8‐DiHODE), and 5,8‐dihydroxy‐9,12,15( Z , Z , Z )‐octadecatrienoic acid (5,8‐DiHOTrE) produced by recombinant E. coli expressing 5,8‐LDS from A. nidulans (Seo et al, ); 7,8‐DiHOME, 7,8‐DiHODE, and 7,8‐DiHOTrE by cells expressing 7,8‐LDS from Glomerella cingulate (Seo et al, ); and 8,11‐DiHODE and 8,11‐DiHOTrE by cells expressing 8,11‐LDS from Penicillium chrysogenum (Kim et al, ). Recombinant E. coli has been used for DiHFA production because cell reactions are more stable and economical than enzymatic reactions (Sim et al, ).…”

Production of 8,11‐dihydroxy fatty acids from oleic and palmitoleic acids by Escherichia coli cells expressing variant 6,8‐linoleate diol synthases from Penicillium oxalicum

“…Recombinant E . coli cells expressing 5,8‐LDS from Aspergillus nidulans , 25–27 6,8‐LDS from Penicillium oxalicum , 28 and 7,8‐LDS from Glomerella cingulate 29 convert not only linoleic acid into 5,8‐, 6,8‐, and 7,8‐DiHODEs, respectively, via 8‐hydroperoxy‐9,12( Z , Z )‐octadecadienoic acid (HPODE) but also oleic acid into 5,8‐, 6,8‐, and 7,8‐DiHOMEs, respectively, via 8‐hydroperoxy‐9( Z )‐octadecenoic acid (HPOME). Furthermore, recombinant E .…”