Synthesis of Methylated Anthranilate Derivatives Using Engineered Strains of Escherichia coli
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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.
Abstract
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.
참고문헌 (23)
- Balderas-Hernández VE, "Metabolic engineering for improving anthranilate synthesis from glucose in Escherichia coli", Microb. Cell Fact, 8, pp.19~ (2009)
- Radwanski ER, "Tryptophan biosynthesis and metabolism : biochemical and molecular genetics", Plant Cell, 7, pp.921~934 (1995)
- Kutchan TM, "Alkaloid biosynthesis-The basis for metabolic engineering of medicinal plants", Plant Cell, 7, pp.1059~1070 (1995)
- Pillet J, "Identification of a methyltransferase catalyzing the final step of methyl anthranilate synthesis in cultivated strawberry", BMC Plant Biol, 17, pp.147~ (2017)
- Radulović NS, "Identification of a new antinociceptive alkaloid N-methylantranilate from the essential oil of Choisya ternate Kunth", J. Ethnopharmacol, 135, pp.610~619 (2011)
- Moio L, "Ethyl anthranilate, ethyl cinnamate, 2, 3-dihydrocinnamate, and methyl anthranilate : four important odorants Identified in Binot Noir Wines of Burgundy", Am. J. Enol. Viticult, 46, pp.392~398 (1995)
- Chambers AH, "Methyl anthranilate and γ-decalactone inhibit strawberry pathogen growth and achene germination", J. Agri. Food Chem, 61, pp.12625~12633 (2013)
- Clark L, "Chemical repellency in birds : relationship between chemical structure and avoidance response", J. Exp. Zool, 260, pp.310~322 (1991)
- Radulović NS, "Effects of methyl and isopropyl Nmethylanthranilates from Choisya ternata Kunth(Rutaceae)on experimental anxiety and depression in mice", Phytother. Res, 27, pp.1334~1338 (2013)
- Correa E, "Methyl-Nmethylanthranilate, a pungent compound from Citrus reticulata Blanco leaves", Pharm. Biol, 54, pp.569~571 (2016)
- Fuleki, T., "Changes in the chemical composition of Concord grapes grown in Ontario during ripening in the 1970 season", Can. J. Plant Sci, 52, pp.863~868 (1972)
- Avery ML, "Methyl anthranilate as a rice seed treatment to deter birds", J. Wildl. Manag, 59, pp.50~56 (1995)
- Cummings JL, "Evaluation of a methyl anthranilate formulation for reducing bird damage to blueberries", Crop. Prot, 14, pp.257~259 (1995)
- Rohde B, "Anthranilate N-methyltransferase, a branchpoint enzyme of acridone biosynthesis", Plant J, 53, pp.541~553 (2008)
- Wang J, "The biosynthesis and regulation of b iosynthesis of C oncord g rape f ruit e sters, including ‘foxy’ methylanthranilate", Plant J, 44, pp.606~619 (2005)
- Coleman JP, "Pseudomonas aeruginosa PqsA is an anthranilate-coenzyme A ligase", J. Bacteriol, 190, pp.1247~1255 (2008)
- Jeandet P, "Engineering microbial cells for the biosynthesis of natural compounds of pharmaceutical significance", BioMed Res. Int, 2013, pp.13~ (2013)
- 송민경, "Biological synthesis and anti-inflammatory activity of arylalkylamine", Applied Biological Chemistry, 60(6), pp.597~602 (2017), 한국응용생명화학회
- Lee SJ, "Synthesis of avenanthramides using engineered Escherichia coli", Microb. Cell Fact, 17, pp.46~ (2018)
- 추혜정, "Microbial synthesis of hydroxytyrosol and hydroxysalidroside", Applied Biological Chemistry, 61(3), pp.295~301 (2018), 한국응용생명화학회
- Kim M, "Quantitative shotgun proteomics analysis of rice anther proteins after exposure to high temperature", Int. J. Genomics, 2015, pp.238704~ (2015)
- Pittard AJ, "TyrR protein of Escherichia coli and its role as repressor and activator", Mol. Microbiol, 5, pp.1585~1592 (1991)
- Shoeman R, "Regulation of methionine synthesis in Escherichia coli : effect of metJ gene product and Sadenosylmethionine on the expression of the metF gene", Proc. Natl. Acad. Sci. USA, 82, pp.3601~3605 (1985)