Efficient synthesis of eriodictyol from l-tyrosine in escherichia coli

Applied and Environmental Microbiology

Volumn 80, Issue 10, 2014, Pages 3072-3080

  Zhu, Saijie ^a,b   Wu, Junjun ^a,b   Du, Guocheng ^a   Zhou, Jingwen ^a,b   Chen, Jian ^a,b  

^a JIANGNAN UNIVERSITY   (China)

^b Synergetic Innovation Center of Food Safety and Nutrition   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE EXPRESSION; PLANTS (BOTANY); PROTEINS;

ANTI-INFLAMMATORIES; ANTI-OXIDANT ACTIVITIES; CHALCONE ISOMERASE; CHALCONE SYNTHASE; CYTOCHROME P450; EFFICIENT SYNTHESIS; FUSION PROTEINS; TYROSINE AMMONIA LYASE;

FLAVONOIDS;

ALCOHOL; BIOACCUMULATION; BIOENGINEERING; COLIFORM BACTERIUM; ENZYME ACTIVITY; GENE EXPRESSION; HYDROXYL RADICAL; SECONDARY METABOLITE;

ERIODICTYOL; ESCHERICHIA COLI PROTEIN; FLAVANONE DERIVATIVE; MALONYL COENZYME A; TYROSINE;

BIOSYNTHESIS; ENZYMOLOGY; ESCHERICHIA COLI; EVALUATION STUDY; GENETICS; METABOLIC ENGINEERING; METABOLISM;

ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; FLAVANONES; MALONYL COENZYME A; METABOLIC ENGINEERING; TYROSINE;

EID: 84899085998     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.03986-13     Document Type: Article

References (46)

1. Ververidis F, Trantas E, Douglas C, Vollmer G, Kretzschmar G, Panopoulos N. 2007. Biotechnology of flavonoids and other phenylpropanoidderived natural products. Part I. Chemical diversity, impacts on plant biology and human health. Biotechnol. J. 2:1214-1234. http://dx.doi.org/10.1002/biot.200700084.
2. Wang Y, Chen S, Yu O. 2011. Metabolic engineering of flavonoids in plants and microorganisms. Appl. Microbiol. Biotechnol. 91:949-956. http://dx.doi.org/10.1007/s00253-011-3449-2.
3. Chemler JA, Lock LT, Koffas MAG, Tzanakakis ES. 2007. Standardized biosynthesis of flavan-3-ols with effects on pancreatic beta-cell insulin secretion. Appl. Microbiol. Biotechnol. 77:797-807. http://dx.doi.org/10.1007/s00253-007-1227-y.
4. Broadhurst CL, Polansky MM, Anderson RA. 2000. Insulin-like biological activity of culinary and medicinal plant aqueous extracts in vitro. J. Agric. Food Chem. 48:849-852. http://dx.doi.org/10.1021/jf9904517.
5. Sinclair DA. 2005. Toward a unified theory of caloric restriction and longevity regulation. Mech. Ageing Dev. 126:987-1002. http://dx.doi.org/10.1016/j.mad.2005.03.019.
6. Koopman F, Beekwilder J, Crimi B, van Houwelingen A, Hall RD, Bosch D, van Maris AJ, Pronk JT, Daran JM. 2012. De novo production of the flavonoid naringenin in engineered Saccharomyces cerevisiae. Microb. Cell Fact. 11:155. http://dx.doi.org/10.1186/1475-2859-11-155.
7. Mora-Pale M, Sanchez-Rodriguez SP, Linhardt RJ, Dordick JS, Koffas MAG. 2013. Metabolic engineering and in vitro biosynthesis of phytochemicals and non-natural analogues. Plant Sci. 210:10-24. http://dx.doi.org/10.1016/j.plantsci.2013.05.005.
8. Rossato MF, Trevisan G, Walker CIB, Klafke JZ, de Oliveira AP, Villarinho JG, Zanon RB, Royes LFF, Athayde ML, Gomez MV. 2011. Eriodictyol: a flavonoid antagonist of the TRPV1 receptor with antioxidant activity. Biochem. Pharmacol. 81:544-551. http://dx.doi.org/10.1016/j.bcp.2010.11.004.
9. Zhang WY, Lee JJ, Kim Y, Kim IS, Han JH, Lee SG, Ahn MJ, Jung SH, Myung CS. 2012. Effect of eriodictyol on glucose uptake and insulin resistance in vitro. J. Agric. Food Chem. 60:7652-7658. http://dx.doi.org/10.1021/jf300601z.
10. Yoo JM, Kim JH, Park SJ, Kang YJ, Kim TJ. 2012. Inhibitory effect of eriodictyol on IgE/Ag-induced type I hypersensitivity. Biosci. Biotechnol. Biochem. 76:1285-1290. http://dx.doi.org/10.1271/bbb.110952.
11. Selepe MA, Van Heerden FR. 2013. Application of the Suzuki-Miyaura reaction in the synthesis of flavonoids. Molecules 18:4739-4765. http://dx.doi.org/10.3390/molecules18044739.
12. Pandey RP, Malla S, Simkhada D, Kim B-G, Sohng JK. 2013. Production of 3-O-xylosyl quercetin in Escherichia coli. Appl. Microbiol. Biotechnol. 97:1889-1901. http://dx.doi.org/10.1007/s00253-012-4438-9.
13. Leonard E, Lim KH, Saw PN, Koffas MAG. 2007. Engineering central metabolic pathways for high-level flavonoid production in Escherichia coli. Appl. Environ. Microbiol. 73:3877-3886. http://dx.doi.org/10.1128/AEM.00200-07.
14. Leonard E, Yan Y, Fowler ZL, Li Z, Lim CG, Lim KH, Koffas MAG. 2008. Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids. Mol. Pharm. 5:257-265. http://dx.doi.org/10.1021/mp7001472.
15. Fowler ZL, Gikandi WW, Koffas MAG. 2009. Increased malonyl coenzyme A biosynthesis by tuning the Escherichia coli metabolic network and its application to flavanone production. Appl. Environ. Microbiol. 75: 5831-5839. http://dx.doi.org/10.1128/AEM.00270-09.
16. Wu J, Du G, Zhou J, Chen J. 2013. Metabolic engineering of Escherichia coli for (2S)-pinocembrin production from glucose by a modular metabolic strategy. Metab. Eng. 16:48-55. http://dx.doi.org/10.1016/j.ymben.2012.11.009.
17. Fowler ZL, Koffas MAG. 2009. Biosynthesis and biotechnological production of flavanones: current state and perspectives. Appl. Microbiol. Biotechnol. 83:799-808. http://dx.doi.org/10.1007/s00253-009-2039-z.
18. 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. http://dx.doi.org/10.1007/s10295-003-0061-1.
19. Kim DH, Kim BG, Jung N, Ahn JH. 2009. Production of genistein from naringenin using Escherichia coli containing isoflavone synthasecytochrome P450 reductase fusion protein. J. Microbiol. Biotechnol. 19: 1612-1616. http://dx.doi.org/10.4014/jmb.0905.05043.
20. Hotze M, Schröder G, Schröder J. 1995. Cinnamate 4-hydroxylase from Catharanthus roseus and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli. FEBS Lett. 374:345-350. http://dx.doi.org/10.1016/0014-5793(95)01141-Z.
21. Amor I, Hehn A, Guedone E, Ghedira K, Engasser JM, Chekir-Ghedrira L, Ghoul M. 2010. Biotransformation of naringenin to eriodictyol by Saccharomyces cerevisiae functionally expressing flavonoid 3' hydroxylase. Nat. Prod. Commun. 5:1893-1898.
22. Harada H, Shindo K, Iki K, Teraoka A, Okamoto S, Yu F, Hattan J, Utsumi R, Misawa N. 2011. Efficient functional analysis system for cyanobacterial or plant cytochromes P450 involved in sesquiterpene biosynthesis. Appl. Microbiol. Biotechnol. 90:467-476. http://dx.doi.org/10.1007/s00253-010-3062-9.
23. Chang MC, Eachus RA, Trieu W, Ro DK, Keasling JD. 2007. Engineering Escherichia coli for production of functionalized terpenoids using plant P450s. Nat. Chem. Biol. 3:274-277. http://dx.doi.org/10.1038/nchembio875.
24. Alonso-Gutierrez J, Chan R, Batth TS, Adams PD, Keasling JD, Petzold CJ, Lee TS. 2013. Metabolic engineering of Escherichia coli for limonene and perillyl alcohol production. Metab. Eng. 19:33-41. http://dx.doi.org/10.1016/j.ymben.2013.05.004.
25. Lim CG, Fowler ZL, Hueller T, Schaffer S, Koffas MAG. 2011. Highyield resveratrol production in engineered Escherichia coli. Appl. Environ. Microbiol. 77:3451-3460. http://dx.doi.org/10.1128/AEM.02186-10.
26. Xu P, Ranganathan S, Fowler ZL, Maranas CD, Koffas MAG. 2011. Genome-scale metabolic network modeling results in minimal interventions that cooperatively force carbon flux towards malonyl-CoA. Metab. Eng. 13:578-587. http://dx.doi.org/10.1016/j.ymben.2011.06.008.
27. Grote A, Hiller K, Scheer M, Münch R, Nörtemann B, Hempel DC, Jahn D. 2005. JCat: a novel tool to adapt codon usage of a target gene to its potential expression host. Nucleic Acids Res. 33:W526-W531. http://dx.doi.org/10.1093/nar/gki376.
28. Datsenko KA, Wanner BL. 2000. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc. Natl. Acad. Sci. U. S. A. 97:6640-6645. http://dx.doi.org/10.1073/pnas.120163297.
29. Gande R, Dover LG, Krumbach K, Besra GS, Sahm H, Oikawa T, Eggeling L. 2007. The two carboxylases of Corynebacterium glutamicum essential for fatty acid and mycolic acid synthesis. J. Bacteriol. 189:5257- 5264. http://dx.doi.org/10.1128/JB.00254-07.
30. 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. http://dx.doi.org/10.1007/s00253-005-1916-3.
31. Leonard E, Yan Y, Koffas MAG. 2006. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylatedflavonols in Escherichia coli. Metab. Eng. 8:172-181. http://dx.doi.org/10.1016/j.ymben.2005.11.001.
32. Guermeur Y, Geourjon C, Gallinari P, Deléage G. 1999. Improved performance in protein secondary structure prediction by inhomogeneous score combination. Bioinformatics 15:413-421. http://dx.doi.org/10.1093/bioinformatics/15.5.413.
33. Yamanaka M, Hara K, Kudo J. 2005. Bactericidal actions of a silver ion solution on Escherichia coli, studied by energy-filtering transmission electron microscopy and proteomic analysis. Appl. Environ. Microbiol. 71: 7589-7593. http://dx.doi.org/10.1128/AEM.71.11.7589-7593.2005.
34. Neidhardt FC, Bloch PL, Smith DF. 1974. Culture medium for enterobacteria. J. Bacteriol. 119:736-747.
35. Zha W, Rubin-Pitel SB, Shao Z, Zhao H. 2009. Improving cellular malonyl-CoA level in Escherichia coli via metabolic engineering. Metab. Eng. 11:192-198. http://dx.doi.org/10.1016/j.ymben.2009.01.005.
36. Cheng X, Liu F, Yan T, Zhou X, Wu L, Liao K, Wang G, Hao H. 2012. Metabolic profile, enzyme kinetics, and reaction phenotyping of β-lapachone metabolism in human liver and intestine in vitro. Mol. Pharm. 9:3476-3485. http://dx.doi.org/10.1021/mp300296m.
37. Rathnasingh C, Raj SM, Lee Y, Catherine C, Ashok S, Park S. 2012. Production of 3-hydroxypropionic acid via malonyl-CoA pathway using recombinant Escherichia coli strains. J. Biotechnol. 157:633-640. http://dx.doi.org/10.1016/j.jbiotec.2011.06.008.
38. Bhan N, Xu P, Khalidi O, Koffas MAG. 15 November 2013. Redirecting carbon flux into malonyl-CoA to improve resveratrol titers: proof of concept for genetic interventions predicted by OptForce computational framework. Chem. Eng. Sci. http://dx.doi.org/10.1016/j.ces.2012.10.009.
39. Santos CNS, Koffas MAG, Stephanopoulos G. 2011. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab. Eng. 13:392- 400. http://dx.doi.org/10.1016/j.ymben.2011.02.002.
40. Jones KL, Kim S-W, Keasling J. 2000. Low-copy plasmids can perform as well as or better than high-copy plasmids for metabolic engineering of bacteria. Metab. Eng. 2:328-338. http://dx.doi.org/10.1006/mben.2000.0161.
41. Wu J, Liu P, Fan Y, Bao H, Du G, Zhou J, Chen J. 2013. Multivariate modular metabolic engineering of Escherichia coli to produce resveratrol from L-tyrosine. J. Biotechnol. 167:404-411. http://dx.doi.org/10.1016/j.jbiotec.2013.07.030.
42. Novy R, Yaeger K, Held D, Mierendorf R. 2002. Coexpression of multiple target proteins in E. coli. inNovations 15:2-6.
43. Held D, Yaeger K, Novy R. 2003. New coexpression vectors for expanded compatibilities in E. coli. inNovations 18:4-6.
44. Selzer G, Som T, Itoh T, Tomizawa J. 1983. The origin of replication of plasmid p15A and comparative studies on the nucleotide sequences around the origin of related plasmids. Cell 32:119-129. http://dx.doi.org/10.1016/0092-8674(83)90502-0.
45. Leonard E, Chemler J, Lim KH, Koffas MA. 2006. Expression of a soluble flavone synthase allows the biosynthesis of phytoestrogen derivatives in Escherichia coli. Appl. Microbiol. Biotechnol. 70:85-91. http://dx.doi.org/10.1007/s00253-005-0059-x.
46. Carta R, Tola G. 1996. Solubilities of L-cystine, L-tyrosine, L-leucine, and glycine in aqueous solutions at various pHs and NaCl concentrations. J. Chem. Eng. Data 41:414-417. http://dx.doi.org/10.1021/je9501853.