Microbial Synthesis of Linoleate 9S-Lipoxygenase Derived Plant C18 Oxylipins from C18 Polyunsaturated Fatty Acids,Journal of Agricultural and Food Chemistry

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Microbial Synthesis of Linoleate 9S-Lipoxygenase Derived Plant C18 Oxylipins from C18 Polyunsaturated Fatty Acids
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2019-02-27 00:00:00 , DOI: 10.1021/acs.jafc.8b05857
Jung-Ung An _{1,

2} , In-Gyu Lee ₁ , Yoon-Joo Ko ₃ , Deok-Kun Oh ₁

Affiliation

Plant oxylipins, including hydroxy fatty acids, epoxy hydroxy fatty acids, and trihydroxy fatty acids, which are biosynthesized from C18 polyunsaturated fatty acids (PUFAs), are involved in pathogen-specific defense mechanisms against fungal infections. However, their quantitative biotransformation by plant enzymes has not been reported. A few bacteria produce C18 trihydroxy fatty acids, but the enzymes and pathways related to the biosynthesis of plant oxylipins in bacteria have not been reported. In this study, we first report the biotransformation of C18 PUFAs into plant C18 oxylipins by expressing linoleate 9S-lipoxygenase with and without epoxide hydrolase from the proteobacterium Myxococcus xanthus in recombinant Escherichia coli. Among the nine types of plant oxylipins, 12,13-epoxy-14-hydroxy-cis,cis-9,15-octadecadienoic acid was identified as a new compound by NMR analysis, and 9,10,11-hydroxy-cis,cis-6,12-octadecadienoic acid and 12,13,14-trihydroxy-cis,cis-9,15-octadecadienoic were suggested as new compounds by LC-MS/MS analysis. This study shows that bioactive plant oxylipins can be produced by microbial enzymes.

中文翻译：

从C18多不饱和脂肪酸微生物合成亚油酸酯9 S-脂氧合酶衍生的植物C18氧化脂

由C18多不饱和脂肪酸（PUFA）生物合成的植物羟基磷脂，包括羟基脂肪酸，环氧羟基脂肪酸和三羟基脂肪酸，参与了针对真菌感染的病原体特异性防御机制。然而，尚未报道它们通过植物酶的定量生物转化。少数细菌会产生C18三羟基脂肪酸，但尚未报道与细菌中植物脂蛋白生物合成有关的酶和途径。在这项研究中，我们首先通过表达亚油酸9报告C18多不饱和脂肪酸的生物转化成植物C18氧脂素小号脂肪氧合酶与不从变形菌环氧化物水解酶粘细菌在重组大肠杆菌。在九个类型的植物氧脂素，12,13-环氧-14-羟基的顺式，顺式-9,15十八碳二烯酸，鉴定为通过NMR分析的新化合物，以及9,10,11羟基顺式，顺式通过LC-MS / MS分析，建议将-6,12-十八碳二烯酸和12,13,14-三羟基顺式，顺式-9,15-十八碳二烯酸作为新化合物。这项研究表明，具有生物活性的植物脂蛋白可以通过微生物酶产生。

更新日期：2019-02-27

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