Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase

Lee, Jin; Ko, Yoon-Joo; Park, Jin-Byung; Oh, Deok-Kun

doi:10.1039/d4gc00308j

Cited by 3 publications

(1 citation statement)

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“…The ndings suggested that the most effective ratios of cells to substrate for producing RvE4 and its enantiomer were 1:4 and 1:3 (g L −1 per mM), respectively. SP825 was chosen as the absorbent resin for converting EPA into RvE4 and its enantiomer due to its superior binding capacity for ARA compared to other tested resins, including HP20, SP2MG, SP207, SP825, and SP850 (Lee et al 2024).…”

Section: Optimization Of Cell Substrate and Resin Concentrations To E...mentioning

confidence: 99%

Biotransformation of eicosapentaenoic acid into the dihydroxyeicosapentaenoic acids resolvin E4 and its enantiomer by 15S- and 15R-lipoxygenases expressed in Escherichia coli

Lee,

Park,

Shin

et al. 2024

Preprint

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Objectives To enhance the production of resolvin E4 (RvE4) or its enantiomer from eicosapentaenoic acid (EPA), Archangium violaceum 15S-lipoxygenase (15S-LOX) or Sorangium cellulosum 15R-LOX was expressed in Escherichia coli with solvent, polymer, and adsorbent resin, respectively. Results The concentrations of cells and substrate and the types and concentrations of solvent, polymer, and resin were optimized for the biotransformation of EPA into RvE4 (5S,15S-dihydroxyeicosapentaenoic acid) and its enantiomer (5R,15R-dihydroxyeicosapentaenoic acid). Under optimized conditions, A. violaceum 15S-LOX and S. cellulosum 15R-LOX expressed in E. coli converted 6.0 mM (1.8 g L−1) EPA into 4.3 mM (1.4 g L−1) RvE4 and 5.8 mM (1.9 g L−1) RvE4 enantiomer in 60 min, with productivities of 4.3 and 5.8 mM h−1 and molar conversions of 72 and 97%, respectively. The concentrations of RvE4 and its enantiomer resulting from the conversion of EPA with solvent, polymer, and resin were 3.1- and 5.3-fold higher than those without additives, respectively. Conclusions The concentrations, productivities, and conversions of RvE4 and its enantiomer were increased by optimizing the concentrations of cells and substrate and the types and concentrations of solvent, polymer, and adsorbent resin.

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Section: Optimization Of Cell Substrate and Resin Concentrations To E...mentioning

confidence: 99%

Biotransformation of eicosapentaenoic acid into the dihydroxyeicosapentaenoic acids resolvin E4 and its enantiomer by 15S- and 15R-lipoxygenases expressed in Escherichia coli

Lee,

Park,

Shin

et al. 2024

Preprint

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Bioconversion of eicosapentaenoic acid into 5S,15S- and 5R,15R-dihydroxyeicosapentaenoic acids by double-dioxygenating 15S- and 15R-lipoxygenases

Lee,

Park,

Shin

et al. 2025

Journal of Bioscience and Bioengineering

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Recent Advances and Challenges in the Production of Hydroxylated Natural Products Using Microorganisms

Sun,

Zeng,

Chen

et al. 2024

Fermentation

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Hydroxylation reaction is a significant source of structural diversity in natural products (NPs), playing a crucial role in improving the bioactivity, solubility, and stability of natural product molecules. This review summarizes the latest research progress in the field of natural product hydroxylation, focusing on several key hydroxylases involved in the biosynthesis of NPs, including cytochrome P450 monooxygenases, α-ketoglutarate-dependent hydroxylases, and flavin-dependent monooxygenases. These enzymes achieve selective hydroxylation modification of various NPs, such as terpenoids, flavonoids, and steroids, through different catalytic mechanisms. This review systematically summarizes the recent advances on the hydroxylation of NPs, such as amino acids, steroids, terpenoids, lipids, and phenylpropanoids, demonstrating the potential of synthetic biology strategies in constructing artificial biosynthetic pathways and producing hydroxylated natural product derivatives. Through metabolic engineering, enzyme engineering, genetic engineering, and synthetic biology combined with artificial intelligence-assisted technologies, a series of engineered strains have been successfully constructed for the efficient production of hydroxylated NPs and their derivatives, achieving efficient synthesis of hydroxylated NPs. This has provided new avenues for drug development, functional food, and biomaterial production and has also offered new ideas for the industrial production of these compounds. In the future, integrating artificial synthetic pathway design, enzyme directed evolution, dynamic regulation, and artificial intelligence technology is expected to further expand the application of enzyme-catalyzed hydroxylation reactions in the green synthesis of complex NPs, promoting research on natural product hydroxylation to new heights.

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Biotransformation of C20- and C22-polyunsaturated fatty acids and fish oil hydrolyzates to R,R-dihydroxy fatty acids as lipid mediators using double-oxygenating 15R-lipoxygenase

Abstract: C20- and C22-dihydroxy fatty acids (DiHFAs) are bioactive lipid mediators (LMs) in humans. Among them, leukotrienes are inflammatory mediators, whereas resolvins generated by M2 macrophages in humans are anti-inflammatory mediators....

Cited by 3 publications

References 43 publications

Biotransformation of eicosapentaenoic acid into the dihydroxyeicosapentaenoic acids resolvin E4 and its enantiomer by 15S- and 15R-lipoxygenases expressed in Escherichia coli

Biotransformation of eicosapentaenoic acid into the dihydroxyeicosapentaenoic acids resolvin E4 and its enantiomer by 15S- and 15R-lipoxygenases expressed in Escherichia coli

Bioconversion of eicosapentaenoic acid into 5S,15S- and 5R,15R-dihydroxyeicosapentaenoic acids by double-dioxygenating 15S- and 15R-lipoxygenases

Recent Advances and Challenges in the Production of Hydroxylated Natural Products Using Microorganisms

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