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Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli

  • Original Paper
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Journal of Industrial Microbiology & Biotechnology

Abstract

Biological synthesis of plant secondary metabolites has attracted increasing attention due to their proven or assumed beneficial properties and health-promoting effects. Phenylpropanoids are the precursors to a range of important plant metabolites such as the secondary metabolites belonging to the flavonoid/stilbenoid class of compounds. In this study, engineered Escherichia coli containing artificial phenylpropanoid biosynthetic pathways utilizing tyrosine as the initial precursor were established for production of plant-specific metabolites such as ferulic acid, naringenin, and resveratrol. The construction of the artificial pathway utilized tyrosine ammonia lyase and 4-coumarate 3-hydroxylase from Saccharothrix espanaensis, cinnamate/4-coumarate:coenzyme A ligase from Streptomyces coelicolor, caffeic acid O-methyltransferase and chalcone synthase from Arabidopsis thaliana, and stilbene synthase from Arachis hypogaea.

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References

  1. Austin MB, Noel JP (2003) The chalcone synthase superfamily of type III polyketide synthases. Nat Prod Rep 20:79–110

    Article  PubMed  CAS  Google Scholar 

  2. Beekwilder J, Wolswinkel R, Jonker H, Hall R, de Vos CH, Bovy A (2006) Production of resveratrol in recombinant microorganisms. Appl Environ Microbiol 72:5670–5672

    Article  PubMed  CAS  Google Scholar 

  3. Berner M, Krug D, Bihlmaier C, Vente A, Muller R, Bechthold A (2006) Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J Bacteriol 188:2666–2673

    Article  PubMed  CAS  Google Scholar 

  4. Davis MS, Solbiati J, Cronan JE Jr (2000) Overproduction of acetyl-CoA carboxylase activity increases the rate of fatty acid biosynthesis in Escherichia coli. J Biol Chem 275:28593–28598

    Article  PubMed  CAS  Google Scholar 

  5. Do CT, Pollet B, Thevenin J, Sibout R, Denoue D, Barriere Y, Lapierre C, Jouanin L (2007) Both caffeoyl Coenzyme A 3-O-methyltransferase 1 and caffeic acid O-methyltransferase 1 are involved in redundant functions for lignin, flavonoids and sinapoyl malate biosynthesis in Arabidopsis. Planta 226:1117–1129

    Article  PubMed  CAS  Google Scholar 

  6. Dueber JE, Wu GC, Malmirchegini GR, Moon TS, Petzold CJ, Ullal AV, Prather KL, Keasling JD (2009) Synthetic protein scaffolds provide modular control over metabolic flux. Nat Biotechnol 27:753–759

    Article  PubMed  CAS  Google Scholar 

  7. Fowler ZL, Koffas MA (2009) Biosynthesis and biotechnological production of flavanones: current state and perspectives. Appl Microbiol Biotechnol 83:799–808

    Article  PubMed  CAS  Google Scholar 

  8. Gao X, Wang P, Tang Y (2010) Engineered polyketide biosynthesis and biocatalysis in Escherichia coli. Appl Microbiol Biotechnol 88(6):1233–1242

    Article  PubMed  CAS  Google Scholar 

  9. Grotewold E (2007) The Science of Flavonoids. Springer, New York

    Google Scholar 

  10. Horinouchi S (2009) Combinatorial biosynthesis of plant medicinal polyketides by microorganisms. Curr Opin Chem Biol 13:197–204

    Article  PubMed  CAS  Google Scholar 

  11. Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S (2003) Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Appl Environ Microbiol 69:2699–2706

    Article  PubMed  CAS  Google Scholar 

  12. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, Fong HH, Farnsworth NR, Kinghorn AD et al (1997) Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275:218–220

    Article  PubMed  CAS  Google Scholar 

  13. Kaneko M, Hwang EI, Ohnishi Y, Horinouchi S (2003) Heterologous production of flavanones in Escherichia coli: potential for combinatorial biosynthesis of flavonoids in bacteria. J Ind Microbiol Biotechnol 30:456–461

    Article  PubMed  CAS  Google Scholar 

  14. Kaneko M, Ohnishi Y, Horinouchi S (2003) Cinnamate:coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3(2). J Bacteriol 185:20–27

    Article  PubMed  CAS  Google Scholar 

  15. Katsuyama Y, Miyahisa I, Funa N, Horinouchi S (2007) One-pot synthesis of genistein from tyrosine by coincubation of genetically engineered Escherichia coli and Saccharomyces cerevisiae cells. Appl Microbiol Biotechnol 73:1143–1149

    Article  PubMed  CAS  Google Scholar 

  16. Lee JS, Kim DH, Liu KH, Oh TK, Lee CH (2005) Identification of flavonoids using liquid chromatography with electrospray ionization and ion trap tandem mass spectrometry with an MS/MS library. Rapid Commun Mass Spectrom 19:3539–3548

    Article  PubMed  CAS  Google Scholar 

  17. Leonard E, Lim KH, Saw PN, Koffas MA (2007) Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl Environ Microbiol 73:3877–3886

    Article  PubMed  CAS  Google Scholar 

  18. Leonard E, Yan Y, Fowler ZL, Li Z, Lim CG, Lim KH, Koffas MA (2008) Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids. Mol Pharm 5:257–265

    Article  PubMed  CAS  Google Scholar 

  19. Miroux B, Walker JE (1996) Over-production of proteins in Escherichia coli: mutant hosts that allow synthesis of some membrane proteins and globular proteins at high levels. J Mol Biol 260:289–298

    Article  PubMed  CAS  Google Scholar 

  20. Miyahisa I, Funa N, Ohnishi Y, Martens S, Moriguchi T, Horinouchi S (2006) Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Appl Microbiol Biotechnol 71:53–58

    Article  PubMed  CAS  Google Scholar 

  21. Miyahisa I, Kaneko M, Funa N, Kawasaki H, Kojima H, Ohnishi Y, Horinouchi S (2005) Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Appl Microbiol Biotechnol 68:498–504

    Article  PubMed  CAS  Google Scholar 

  22. Signorelli P, Ghidoni R (2005) Resveratrol as an anticancer nutrient: molecular basis, open questions and promises. J Nutr Biochem 16:449–466

    Article  PubMed  CAS  Google Scholar 

  23. Trantas E, Panopoulos N, Ververidis F (2009) Metabolic engineering of the complete pathway leading to heterologous biosynthesis of various flavonoids and stilbenoids in Saccharomyces cerevisiae. Metab Eng 11:355–366

    Article  PubMed  CAS  Google Scholar 

  24. Watts KT, Lee PC, Schmidt-Dannert C (2004) Exploring recombinant flavonoid biosynthesis in metabolically engineered Escherichia coli. ChemBioChem 5:500–507

    Article  PubMed  CAS  Google Scholar 

  25. Watts KT, Lee PC, Schmidt-Dannert C (2006) Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol 6:22

    Article  PubMed  Google Scholar 

  26. Weisshaar B, Jenkins GI (1998) Phenylpropanoid biosynthesis and its regulation. Curr Opin Plant Biol 1:251–257

    Article  PubMed  CAS  Google Scholar 

  27. Winkel-Shirley B (2001) Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol 126:485–493

    Article  PubMed  CAS  Google Scholar 

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Acknowledgments

This work was supported in part by the 21C Frontier Microbial Genomics and Application Center, Basic Science Research Program, and Global R&D Center program, the Ministry of Science and Technology, Republic of Korea, and by a grant from KRIBB Research Initiative Program. The authors would also like to thank Joon-Tae Park for assistance in the LC–MS experiment.

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Authors and Affiliations

  1. Korea Research Institute of Bioscience and Biotechnology, 685-1 Yangcheong-ri Ochang-eup, Chungbuk, 363-883, Republic of Korea

    Oksik Choi, Cheng-Zhu Wu, Sun Young Kang, Jong Seog Ahn & Young-Soo Hong

  2. Biological Sciences, Chunbuk National University, Jeollabuk-do, 561-756, Republic of Korea

    Oksik Choi & Tai-Boong Uhm

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  1. Oksik Choi
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  2. Cheng-Zhu Wu
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  3. Sun Young Kang
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  4. Jong Seog Ahn
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  6. Young-Soo Hong
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Correspondence to Young-Soo Hong.

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Choi, O., Wu, CZ., Kang, S.Y. et al. Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli . J Ind Microbiol Biotechnol 38, 1657–1665 (2011). https://doi.org/10.1007/s10295-011-0954-3

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  • DOI: https://doi.org/10.1007/s10295-011-0954-3

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