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Synthesis of Methylated Anthranilate Derivatives Using Engineered Strains of Escherichia coli

  • Lee, Hye Lim (Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Song-Yi (Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Eun Ji (Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University) ;
  • Han, Da Ye (Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Bong-Gyu (Department of Forest Resources, Gyeongnam National University of Science and Technology) ;
  • Ahn, Joong-Hoon (Department of Integrative Bioscience and Biotechnology, Bio/Molecular Informatics Center, Konkuk University)
  • 투고 : 2019.04.15
  • 심사 : 2019.06.03
  • 발행 : 2019.06.28

초록

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, $185.3{\mu}M$ N-methylanthranilate and $95.2{\mu}M$ methyl N-methylanthranilate were synthesized. This is the first report about the synthesis of anthranilate derivatives in E. coli.

키워드

참고문헌

  1. Balderas-Hernandez VE, Sabido-Ramos A, Silva P, Cabrera-Valladares N, Hernandez-Chavez G, Baez-Viveros JL, et al. 2009. Metabolic engineering for improving anthranilate synthesis from glucose in Escherichia coli. Microb. Cell Fact. 8: 19. https://doi.org/10.1186/1475-2859-8-19
  2. Radwanski ER, Last RL.1995. Tryptophan biosynthesis and metabolism: biochemical and molecular genetics. Plant Cell 7: 921-934. https://doi.org/10.1105/tpc.7.7.921
  3. Kutchan TM. 1995. Alkaloid biosynthesis-The basis for metabolic engineering of medicinal plants. Plant Cell 7: 1059-1070. https://doi.org/10.2307/3870057
  4. Pillet J, Chambers AH, Barbey C, Bao Z, Plotto A, Bai J, et al. 2017. Identification of a methyltransferase catalyzing the final step of methyl anthranilate synthesis in cultivated strawberry. BMC Plant Biol. 17: 147. https://doi.org/10.1186/s12870-017-1088-1
  5. Radulovic NS, Miltojevic A B, McDermott M , Waldren S, Parnell JA, Pinheiro MMG, et al. 2011. Identification of a new antinociceptive alkaloid N-methylantranilate from the essential oil of Choisya ternate Kunth. J. Ethnopharmacol. 135: 610-619. https://doi.org/10.1016/j.jep.2011.03.035
  6. Moio L, Etievant PX. 1995. 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: 392-398.
  7. Chambers AH, Evans SA, Folta KM. 2013. Methyl anthranilate and ${\gamma}$-decalactone inhibit strawberry pathogen growth and achene germination. J. Agri. Food Chem. 61: 12625-12633. https://doi.org/10.1021/jf404255a
  8. Clark L, Shah PS, Mason JR. 1991. Chemical repellency in birds: relationship between chemical structure and avoidance response. J. Exp. Zool. 260: 310-322. https://doi.org/10.1002/jez.1402600306
  9. Radulovic NS, Miltojevic AB, Randjelovic PJ, Stojanovic NM, Boylan F. 2013. Effects of methyl and isopropyl Nmethylanthranilates from Choisya ternata Kunth (Rutaceae) on experimental anxiety and depression in mice. Phytother. Res. 27: 1334-1338. https://doi.org/10.1002/ptr.4877
  10. Correa E, Quinones W, Echeverri F. 2016. Methyl-Nmethylanthranilate, a pungent compound from Citrus reticulata Blanco leaves. Pharm. Biol. 54: 569-571. https://doi.org/10.3109/13880209.2015.1044618
  11. Fuleki, T. 1972. Changes in the chemical composition of Concord grapes grown in Ontario during ripening in the 1970 season. Can. J. Plant Sci. 52: 863-868. https://doi.org/10.4141/cjps72-149
  12. Avery ML, Decker DG, Humphrey JS, Aronov E, Linscombe SD, Way MO. 1995. Methyl anthranilate as a rice seed treatment to deter birds. J. Wildl. Manag. 59: 50-56. https://doi.org/10.2307/3809115
  13. Cummings JL, Avery ML, Pochop PA, Davis Jr. JE, Decker DG, Krupa HW, et al. 1995. Evaluation of a methyl anthranilate formulation for reducing bird damage to blueberries. Crop. Prot. 14: 257-259. https://doi.org/10.1016/0261-2194(95)00016-F
  14. Rohde B , Hans J, Martens S , Baumert A, Hunziker P , Matern U. 2008. Anthranilate N-methyltransferase, a branchpoint enzyme of acridone biosynthesis. Plant J. 53: 541-553. https://doi.org/10.1111/j.1365-313X.2007.03360.x
  15. Wang J, De Luca V. 2005. The biosynthesis and regulation of biosynthesis of C oncord grape fruite sters, including 'foxy' methylanthranilate. Plant J. 44: 606-619. https://doi.org/10.1111/j.1365-313X.2005.02552.x
  16. Coleman JP, Hudson LL, McKnight SL, Farrow JM, Calfee MW, Lindsey CA, et al. 2008. Pseudomonas aeruginosa PqsA is an anthranilate-coenzyme A ligase. J. Bacteriol. 190: 1247-1255. https://doi.org/10.1128/JB.01140-07
  17. Jeandet P, Vasserot Y, Chastang T, Courot E. 2013. Engineering microbial cells for the biosynthesis of natural compounds of pharmaceutical significance. BioMed Res. Int. 2013: 13.
  18. Song MK, Lee SJ, Kang YY, Lee Y, Mok H, Ahn J-H. 2017. Biological synthesis and anti-inflammatory activity of arylalkylamine. Appl. Biol. Chem. 60: 597-602. https://doi.org/10.1007/s13765-017-0315-7
  19. Lee SJ, Sim GY, Kang H, Yeo WS, Kim B-G, Ahn J-H. 2018. Synthesis of avenanthramides using engineered Escherichia coli. Microb. Cell Fact. 17: 46. https://doi.org/10.1186/s12934-018-0896-9
  20. Choo HJ, Kim EJ, Kim SY, Lee Y, Kim B-G, Ahn J-H. 2018. Microbial synthesis of hydroxytyrosol and hydroxysalidroside. Appl. Biol. Chem. 61: 295-301. https://doi.org/10.1007/s13765-018-0360-x
  21. Kim M, Kim H, Lee W, Lee Y, Kwon SW, Lee J. 2015. Quantitative shotgun proteomics analysis of rice anther proteins after exposure to high temperature. Int. J. Genomics 2015: 238704.
  22. Pittard AJ, Davidson BE. 1991. TyrR protein of Escherichia coli and its role as repressor and activator. Mol. Microbiol. 5: 1585-1592. https://doi.org/10.1111/j.1365-2958.1991.tb01904.x
  23. Shoeman R, Redfield B, Coleman T, Greene RC, Smith AA, Brot N, et al. 1985. 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: 3601-3605. https://doi.org/10.1073/pnas.82.11.3601

피인용 문헌

  1. Microbial Engineering for Production ofN‐Functionalized Amino Acids and Amines vol.15, pp.7, 2019, https://doi.org/10.1002/biot.201900451
  2. Synthesis of 4-Hydroxybenzoic Acid Derivatives in Escherichia coli vol.68, pp.36, 2019, https://doi.org/10.1021/acs.jafc.0c03149
  3. Synthesis of acridone derivatives via heterologous expression of a plant type III polyketide synthase in Escherichia coli vol.19, 2019, https://doi.org/10.1186/s12934-020-01331-2