Synthesis of avenanthramides using engineered Escherichia coli

Lee, Su Jin; Sim, Geun Young; Kang, Hyunook; Yeo, Won Seok; Kim, Bong-Gyu; Ahn, Joong‐Hoon

doi:10.1186/s12934-018-0896-9

Cited by 17 publications

(16 citation statements)

References 41 publications

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“…Analysis of the reaction products was carried out using Thermo Ultimate 3000 HPLC [23]. Mass spectrometry and proton nuclear magnetic resonance (NMR) were performed as previously described [24,25]…”

Section: Production and Analysis Of Metabolitesmentioning

confidence: 99%

Biosynthesis of fraxetin from three different substrates using engineered Escherichia coli

Choi

Ahn

2020

Appl Biol Chem

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Fraxetin, which is a simple coumarin, is a phytochemical present in medicinal plants, such as Fraxinus rhynchophylla, and Cortex Fraxini. In plants, it serves as a controller of iron homeostasis. The health-enhancing activities of fraxetin, such as anticancer, neuroprotective and antibacterial activities, are known. Scopoletin 8-hydroxylase (S8H) is a key enzyme involved in the synthesis of fraxetin from scopoletin. Scopoletin can be synthesized either from esculetin by O-methylation or from ferulic acid by feruloyl CoA 6′-hydroxylase (F6′H) and 4-coumaric acid CoA ligase (4CL). To enable fraxetin synthesis, the fraxetin biosynthesis pathway was introduced into Escherichia coli. Three distinct routes, from ferulic acid, esculetin, and scopoletin, were designed for the synthesis of fraxetin. In the first approach, E. coli strain harboring S8H was used and found to synthesize 84.8 μM fraxetin from 100 μM scopoletin. Two E. coli strains were used for the other two approaches because these approaches required at least two enzymatic reactions. Through this approach, 41.4 μM fraxetin was synthesized from 100 μM esculetin, while 33.3 μM fraxetin was synthesized from 100 μM ferulic acid.

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Section: Production and Analysis Of Metabolitesmentioning

confidence: 99%

Biosynthesis of fraxetin from three different substrates using engineered Escherichia coli

Choi

Ahn

2020

Appl Biol Chem

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“…Lee and colleagues optimized the synthesis of nine AVAs in Escherichia coli , using different hydroxycinnamic acids, and providing a new strategy to produce both natural and synthetic AVAs [20], whose biological activities may be explored.…”

Section: Chemical Structure Of Avas and Their Derivativesmentioning

confidence: 99%

Overview of the Anticancer Profile of Avenanthramides from Oat

Turrini

Maffei

Milelli

et al. 2019

IJMS

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Cancer represents one of the leading causes of death worldwide. Progresses in treatment of cancer have continued at a rapid pace. However, undesirable side effects and drug resistance remain major challenges for therapeutic success. Natural products represent a valuable starting point to develop new anticancer strategies. Polyphenols, well-known as antioxidant, exert anticancer effects through the modulation of multiple pathways and mechanisms. Oat (Avena sativa L., Poaceae) is a unique source of avenanthramides (AVAs), a group of polyphenolic alkaloids, considered as its signature compounds. The present review aims to offer a comprehensive and critical perspective on the chemopreventive and chemotherapeutic potential of AVAs. AVAs prevent cancer mainly by blocking reactive species. Moreover, they exhibit potential therapeutic activity through the modulation of different pathways including the activation of apoptosis and senescence, the block of cell proliferation, and the inhibition of epithelial mesenchymal transition and metastatization. AVAs are promising chemopreventive and anticancer phytochemicals, which need further clinical trials and toxicological studies to define their efficacy in preventing and reducing the burden of cancer diseases.

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“…Culture filtrate was extracted with ethyl acetate and the organic layer was dried and dissolved in DMSO. The dissolved sample was analyzed using high-performance liquid chromatography (HPLC) [19]. N-Methylanthranilate was detected at 250 nm.…”

Section: Production Of Methylated Anthranilatesmentioning

confidence: 99%

Synthesis of Methylated Anthranilate Derivatives Using Engineered Strains of Escherichia coli

Lee

Kim

et al. 2019

Journal of Microbiology and Biotechnology

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Anthranilate derivatives have been used as flavoring and fragrant agents for a long time. Recently, these compounds are gaining attention due to new biological functions including antinociceptive and analgesic activities. Three anthranilate derivatives, N-methylanthranilate, methyl anthranilate, and methyl N-methylanthranilate were synthesized using metabolically engineered stains of Escherichia coli. NMT encoding N-methyltransferase from Ruta graveolens, AMAT encoding anthraniloyl-coenzyme A (CoA):methanol acyltransferase from Vitis labrusca, and pqsA encoding anthranilate coenzyme A ligase from Pseudomonas aeruginosa were cloned and E. coli strains harboring these genes were used to synthesize the three desired compounds. E. coli mutants (metJ, trpD, tyrR mutants), which provide more anthranilate and/or S-adenosyl methionine, were used to increase the production of the synthesized compounds. MS/MS analysis was used to determine the structure of the products. Approximately, 185.3 µM N-methylanthranilate and 95.2 µM methyl N-methylanthranilate were synthesized. This is the first report about the synthesis of anthranilate derivatives in E. coli.

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Synthesis of avenanthramides using engineered Escherichia coli

Cited by 17 publications

References 41 publications

Biosynthesis of fraxetin from three different substrates using engineered Escherichia coli

Biosynthesis of fraxetin from three different substrates using engineered Escherichia coli

Overview of the Anticancer Profile of Avenanthramides from Oat

Synthesis of Methylated Anthranilate Derivatives Using Engineered Strains of Escherichia coli

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