Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Chlorogenic Acid and p-Coumaroyl Shikimates from Glucose Using Engineered Escherichia coli

  • Cha, Mi Na (Department of Bioscience and Biotechnology, Bio, Molecular Informatics Center, Konkuk University) ;
  • Kim, Hyeon Jeong (Department of 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 Bioscience and Biotechnology, Bio, Molecular Informatics Center, Konkuk University)
  • Received : 2014.03.13
  • Accepted : 2014.04.27
  • Published : 2014.08.28
Download PDF
⟨ Previous Next ⟩

Abstract

Chlorogenic acid and hydroxylcinnamoyl shikimates are major dietary phenolics as well as antioxidants, with recently discovered biological, activities including protection against chemotheraphy side effects and prevention of cardiovascular disease and cancer. Certain fruits and vegetables produce these compounds, although a microbial system can also be utilized for synthesis of chlorogenic acid and hydroxylcinnamoyl shikimates. In this study, we engineered Escherichia coli to produce chlorogenic acid and p-coumaroyl shikimates from glucose. For the synthesis of chlorogenic acid, two E. coli strains were used; one strain for the synthesis of caffeic acid from glucose and the other strain for the synthesis of chlorogenic acid from caffeic acid and quinic acid. The final yield of chlorogenic acid using this approach was approximately 78 mg/l. To synthesize p-coumaroyl shikimates, wild-type E. coli as well as several mutants were tested. Mutant E. coli carrying deletions in three genes (tyrR, pheA, and aroL) produced 236 mg/l of p-coumaroyl shikimates.

Keywords

References

  1. Clifford MN. 1999. Chlorogenic acids and other cinnamates - nature, occurrence and dietary burden. J. Sci. Food Agric. 79: 362-372. https://doi.org/10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D
  2. Draths KM, Knop DR, Frost JW. 1999. Shikimic acid and quinic acid: replacing isolation from plant sources with recombinant microbial biocatalysis. J. Am. Chem. Soc. 121: 1603-1604. https://doi.org/10.1021/ja9830243
  3. Dixon RA, Paiva NL. 1995. Stress-induced phenylpropanoid metabolism. Plant Cell 7: 1085-1097. https://doi.org/10.1105/tpc.7.7.1085
  4. E l-Seedi HR, El-Seed AMA, Khalifa SAM, Görassonu, Bohlin L, Borg-Karlson AK, Verpoorte R. 2012. Biosynthesis, natural sources, dietary intake, pharmacokinetic properties, and biological activities of hydroxycinnamic acids. J. Agric. Food Chem. 60: 10877-10895. https://doi.org/10.1021/jf301807g
  5. E ly B, Pittard J. 1979. Aromatic amino acid biosynthesis: regulation of shikimate kinase in Escherichia coli K-12. J. Bacterol. 138: 933-943.
  6. Goup y PM, Varoquaux PJA, Nicolas JJ, Macheix JJ. 1990. Identification and localization of hydroxycinnamoyl and flavonol derivatives from endive (Cichorium endivia L cv Geante Maraichere) leaves. J. Agric. Food Chem. 38: 2116-2121. https://doi.org/10.1021/jf00102a003
  7. Herrmann K. 1989. Occurrence and content of hydroxycinnamic acid and hydoxybenzoic acid compounds in foods. Crit. Rev. Food Sci. Nutr. 28: 315-347. https://doi.org/10.1080/10408398909527504
  8. Hoff mann L, Maury S, Martz F, Geoffroy P, Legrand M. 2003. Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. J. Biol. Chem. 278: 95-103. https://doi.org/10.1074/jbc.M209362200
  9. Ka ng S-Y, Choi O, Lee JK, Hwang BY, Im T-B, Hong Y-S. 2012. Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli s train. Microb. Cell Fact. 11: 153. https://doi.org/10.1186/1475-2859-11-153
  10. Kim BG, Jung WD, Mok H, Ahn J-H. 2013. Production of hydroxycinnamoyl-shikimates and chlorogenic acid in Escherichia coli: production of hydroxycinnamic acid conjugates. Microb. Cell Fact. 12: 15. https://doi.org/10.1186/1475-2859-12-15
  11. Kim MJ, Kim B-G, Ahn J-H. 2013. Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli. Appl. Microbiol. Biotechnol. 97: 7195-7204. https://doi.org/10.1007/s00253-013-5020-9
  12. Kramer M, Bongaerts J, Bovenberg R, Kremer S, Muller U, Orf S, et al. 2003. Metabolic engineering for microbial production of shikimic acid. Met. Eng. 5: 277-283. https://doi.org/10.1016/j.ymben.2003.09.001
  13. Lin Y, Yan Y. 2012. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell Fact. 11: 42. https://doi.org/10.1186/1475-2859-11-42
  14. L indner HA, Nadeau G, Matte A, Michel G, Ménard R, Cygler M. 2005. Site-directed mutagenesis of the active site region in the quinate/shimate 5-dehydrogenase YdiB of Escherichia coli. J. Biol. Chem. 280: 7162-7169. https://doi.org/10.1074/jbc.M412028200
  15. Lütke-Eversloh T, Stephanopoulos G. 2007. L-Tyrosine production by deregulated strains of Escherichia coli. Appl. Microbiol. Biotechnol. 75: 103-110. https://doi.org/10.1007/s00253-006-0792-9
  16. Rumbero-Sanchez A, Vazquez P. 1991. Quinic acid esters from Isertia haenkeana. Phytochemistry 30: 311-313. https://doi.org/10.1016/0031-9422(91)84144-H
  17. Stev enson PC, Anderson JC, Blaney M, Simmonds MSJ. 1993. Developmental inhibition of Spodoptera litura (Fab) larvae by a novel caffeoylquinic acid from wild groundnut Arachis paraguariensis (Chod et Hassl). J. Chem. Ecol. 19: 2917-2933. https://doi.org/10.1007/BF00980592
  18. Upadhyay R, Rao LJM. 2013. An outlook on chlorogenic acids - occurrence, chemistry, technology, and biological activities. Crit. Rev. Food Sci. Nutr. 53: 968-984. https://doi.org/10.1080/10408398.2011.576319
  19. Vogt T. 2010. Phenylpropanoid biosynthesis. Mol. Plant 3: 2-20. https://doi.org/10.1093/mp/ssp106
  20. Winkel-Shirley B. 2001. Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol. 126: 485-493. https://doi.org/10.1104/pp.126.2.485
  21. Zhang H, Stephanopoulos G. 2013. Engineering E. coli for caffeic acid biosynthesis from renewable sugars. Appl. Microbiol. Biotechnol. 97: 3333-3341. https://doi.org/10.1007/s00253-012-4544-8

Cited by

  1. Exploiting members of the BAHD acyltransferase family to synthesize multiple hydroxycinnamate and benzoate conjugates in yeast vol.15, pp.None, 2014, https://doi.org/10.1186/s12934-016-0593-5
  2. Puccinellia maritima, Spartina maritime, and Spartina patens Halophytic Grasses: Characterization of Polyphenolic and Chlorophyll Profiles and Evaluation of Their Biological Activities vol.24, pp.20, 2019, https://doi.org/10.3390/molecules24203796
  3. Recent Advances in Metabolically Engineered Microorganisms for the Production of Aromatic Chemicals Derived From Aromatic Amino Acids vol.8, pp.None, 2014, https://doi.org/10.3389/fbioe.2020.00407
  4. Metabolic engineering of Escherichia coli for production of chemicals derived from the shikimate pathway vol.47, pp.6, 2014, https://doi.org/10.1007/s10295-020-02288-2
  5. De Novo Biosynthesis of Chlorogenic Acid Using an Artificial Microbial Community vol.69, pp.9, 2014, https://doi.org/10.1021/acs.jafc.0c07588
  6. Cell-free Biosynthesis of Chlorogenic Acid Using a Mixture of Chassis Cell Extracts and Purified Spy-Cyclized Enzymes vol.69, pp.28, 2021, https://doi.org/10.1021/acs.jafc.1c03309
  7. Biosynthesis of resveratrol derivatives and evaluation of their anti-inflammatory activity vol.64, pp.1, 2014, https://doi.org/10.1186/s13765-021-00607-4