Open AccessSelective Production of 9R-Hydroxy-10E,12Z,15Z-Octadecatrienoic Acid from α-Linolenic Acid in Perilla Seed Oil Hydrolyzate by a Lipoxygenase from Nostoc Sp. SAG 25.82
Author(s) -
Kyoung-Rok Kim,
Jung-Ung An,
Seon Hwa Lee,
DeokKun Oh
Publication year - 2015
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0137785
Subject(s) - linoleic acid , lipoxygenase , linolenic acid , fatty acid , food science , biochemistry , enzyme , polyunsaturated fatty acid , alpha linolenic acid , hydrolysis , perilla frutescens , chemistry , biology , docosahexaenoic acid
Hydroxy fatty acids (HFAs) derived from omega-3 polyunsaturated fatty acids have been known as versatile bioactive molecules. However, its practical production from omega-3 or omega-3 rich oil has not been well established. In the present study, the stereo-selective enzymatic production of 9 R -hydroxy-10 E ,12 Z ,15 Z -octadecatrienoic acid (9 R -HOTE) from α-linolenic acid (ALA) in perilla seed oil (PO) hydrolyzate was achieved using purified recombinant 9 R -lipoxygenase (9 R -LOX) from Nostoc sp. SAG 25.82. The specific activity of the enzyme followed the order linoleic acid (LA) > ALA > γ-linolenic acid (GLA). A total of 75% fatty acids (ALA and LA) were used as a substrate for 9 R -LOX from commercial PO by hydrolysis of Candida rugosa lipase. The optimal reaction conditions for the production of 9 R -HOTE from ALA using 9 R -LOX were pH 8.5, 15°C, 5% (v/v) acetone, 0.2% (w/v) Tween 80, 40 g/L ALA, and 1 g/L enzyme. Under these conditions, 9 R -LOX produced 37.6 g/L 9 R -HOTE from 40 g/L ALA for 1 h, with a conversion yield of 94% and a productivity of 37.6 g/L/h; and the enzyme produced 34 g/L 9 R -HOTE from 40 g/L ALA in PO hydrolyzate for 1 h, with a conversion yields of 85% and a productivity of 34 g/L/h. The enzyme also converted 9 R -hydroxy-10 E ,12 Z -octadecadienoic acid (9 R -HODE) from 40 g/L LA for 1.0 h, with a conversion yield of 95% and a productivity of 38.4 g/L. This is the highest productivity of HFA from both ALA and ALA-rich vegetable oil using LOX ever reported. Therefore, our result suggests an efficient method for the production of 9 R -HFAs from LA and ALA in vegetable oil using recombinant LOX in biotechnology.