Improved pinocembrin production in Escherichia coli by engineering fatty acid synthesis

Journal of Industrial Microbiology and Biotechnology

Volumn 43, Issue 4, 2016, Pages 557-566

  Cao, Weijia ^a   Ma, Weichao ^a   Zhang, Bowen ^a   Wang, Xin ^a   Chen, Kequan ^a   Li, Yan ^a   Ouyang, Pingkai ^a  

^a NANJING TECH UNIVERSITY   (China)

Author keywords

Cerulenin; Fatty acid synthesis; Flavonoid; Malonyl CoA; Pinocembrin

Indexed keywords

CERULENIN; MALONYL COENZYME A; PINOCEMBRINE; 3 OXOACYL ACYL CARRIER PROTEIN SYNTHASE; FATTY ACID; FATTY ACID SYNTHASE; FLAVANONE DERIVATIVE;

ARTICLE; BIOMASS; BIOSYNTHESIS; CELL DENSITY; CONTROLLED STUDY; ESCHERICHIA COLI; FATTY ACID SYNTHESIS; FERMENTATION; METABOLIC ENGINEERING; NONHUMAN; PROMOTER REGION; PROTEIN EXPRESSION; BIOREACTOR; GENETICS; METABOLISM;

3-OXOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE; BIOREACTORS; BIOSYNTHETIC PATHWAYS; ESCHERICHIA COLI; FATTY ACID SYNTHASES; FATTY ACIDS; FLAVANONES; MALONYL COENZYME A; METABOLIC ENGINEERING;

EID: 84961177528     PISSN: 13675435     EISSN: 14765535     Source Type: Journal    
DOI: 10.1007/s10295-015-1725-3     Document Type: Article

References (41)

1. An JH, Kim YS (1998) A gene cluster encoding malonyl-CoA decarboxylase (MatA), malonyl-CoA synthetase (MatB) and a putative dicarboxylate carrier protein (MatC) in Rhizobium trifolii—cloning, sequencing, and expression of the enzymes in Escherichia coli. Eur J Biochem 257:395–402
2. Chemler JA, Lock LT, Koffas MA, Tzanakakis ES (2007) Standardized biosynthesis of flavan-3-ols with effects on pancreatic beta-cell insulin secretion. Appl Microbiol Biotechnol 77:797–807. doi:10.1007/s00253-007-1227-y
3. Chemler JA, Yan Y, Koffas MA (2006) Biosynthesis of isoprenoids, polyunsaturated fatty acids and flavonoids in Saccharomyces cerevisiae. Microb Cell Fact 5:20. doi:10.1186/1475-2859-5-20
4. Choi O, Wu CZ, Kang SY, Ahn JS, Uhm TB, Hong YS (2011) Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J Ind Microbiol Biotechnol 38:1657–1665. doi:10.1007/s10295-011-0954-3
5. Cushnie TP, Lamb AJ (2011) Recent advances in understanding the antibacterial properties of flavonoids. Int J Antimicrob Agents 38:99–107. doi:10.1016/j.ijantimicag.2011.02.014
6. Edwards P, Nelsen JS, Metz JG, Dehesh K (1997) Cloning of the fabF gene in an expression vector and in vitro characterization of recombinant fabF and fabB encoded enzymes from Escherichia coli. FEBS Lett 402:62–66. doi:10.1016/s0014-5793(96)01437-8
7. Forkmann G, Martens S (2001) Metabolic engineering and applications of flavonoids. Curr Opin Biotechnol 12:155–160
8. Fowler ZL, Gikandi WW, Koffas MA (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. doi:10.1128/aem.00270-09
9. Garwin JL, Klagesg AL, Cronan JE (1980) Structural, enzymatic, and genetic studies of β-ketoacyl-acyl carrier protein synthases I and II of Escherichia coli. J Biol Chem 255:11949–11956
10. 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
11. Jantan I, Raweh SM, Sirat HM, Jamil S, Mohd Yasin YH, Jalil J, Jamal JA (2008) Inhibitory effect of compounds from Zingiberaceae species on human platelet aggregation. Phytomedicine 15:306–309. doi:10.1016/j.phymed.2007.08.002
12. 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. doi:10.1007/s10295-003-0061-1
13. 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. doi:10.1128/aem.00200-07
14. 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. doi:10.1021/mp7001472
15. Lim CG, Fowler ZL, Hueller T, Schaffer S, Koffas MA (2011) High-yield resveratrol production in engineered Escherichia coli. Appl Environ Microbiol 77:3451–3460. doi:10.1128/aem.02186-10
16. Liu D, Xiao Y, Evans BS, Zhang F (2015) Negative feedback regulation of fatty acid production based on a malonyl-CoA sensor-actuator. ACS Synth Biol 4:132–140. doi:10.1021/sb400158w
17. Liu R, Gao M, Yang ZH, Du GH (2008) Pinocembrin protects rat brain against oxidation and apoptosis induced by ischemia-reperfusion both in vivo and in vitro. Brain Res 1216:104–115. doi:10.1016/j.brainres.2008.03.049
18. Magnuson K, Jackowski S, Rock CO, Cronan JE Jr (1993) Regulation of fatty acid biosynthesis in Escherichia coli. Microbiol Rev 57:522–542
19. Mavel S, Dikic B, Palakas S, Emond P, Greguric I, de Gracia AG, Mattner F, Garrigos M, Guilloteau D, Katsifis A (2006) Synthesis and biological evaluation of a series of flavone derivatives as potential radioligands for imaging the multidrug resistance-associated protein 1 (ABCC1/MRP1). Bioorg Med Chem 14:1599–1607. doi:10.1016/j.bmc.2005.10.009
20. 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. doi:10.1007/s00253-005-1916-3
21. Moche M, Schneider G, Edwards P, Dehesh K, Lindqvist Y (1999) Structure of the complex between the antibiotic cerulenin and its target, beta-ketoacyl-acyl carrier protein synthase. J Biol Chem 274:6031–6034. doi:10.1074/jbc.274.10.6031
22. Neidhardt FC, Bloch PL, Smith DF (1974) Culture medium for enterobacteria. J Bacteriol 119:736–747
23. Olsen JG, Kadziola A, von Wettstein-Knowles P, Siggaard-Andersen M, Lindquist Y, Larsen S (1999) The X-ray crystal structure of beta-ketoacyl acyl carrier protein synthase I. FEBS Lett 460:46–52. doi:10.1016/s0014-5793(99)01303-4
24. Pasetto S, Pardi V, Murata RM (2014) Anti-HIV-1 activity of flavonoid myricetin on HIV-1 infection in a dual-chamber in vitro model. PLoS One 9:e115323. doi:10.1371/journal.pone.0115323
25. Rasul A, Millimouno FM, Ali Eltayb W, Ali M, Li J, Li X (2013) Pinocembrin: a novel natural compound with versatile pharmacological and biological activities. Biomed Res Int 2013:379850. doi:10.1155/2013/379850
26. Santos CN, Koffas M, Stephanopoulos G (2011) Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab Eng 13:392–400. doi:10.1016/j.ymben.2011.02.002
27. Shi LL, Chen BN, Gao M, Zhang HA, Li YJ, Wang L, Du GH (2011) The characteristics of therapeutic effect of pinocembrin in transient global brain ischemia/reperfusion rats. Life Sci 88:521–528. doi:10.1016/j.lfs.2011.01.011
28. Subrahmanyam S, Cronan JE Jr (1998) Overproduction of a functional fatty acid biosynthetic enzyme blocks fatty acid synthesis in Escherichia coli. J Bacteriol 180:4596–4602
29. Takamura Y, Nomura G (1988) Changes in the intracellular concentration of acetyl-CoA and malonyl-CoA in relation to the carbon and energy metabolism of Escherichia coli K12. J Gen Microbiol 134:2249–2253
30. van Summeren-Wesenhagen PV, Marienhagen J (2015) Metabolic engineering of Escherichia coli for the synthesis of the plant polyphenol pinosylvin. Appl Environ Microbiol 81:840–849. doi:10.1128/aem.02966-14
31. Wang Y, Chen S, Yu O (2011) Metabolic engineering of flavonoids in plants and microorganisms. Appl Microbiol Biotechnol 91:949–956. doi:10.1007/s00253-011-3449-2
32. Wu H, Lee J, Karanjikar M, San KY (2015) Simultaneous utilization of glucose and mannose from woody hydrolysate for free fatty acid production by metabolically engineered Escherichia coli. Bioresour Technol 185:431–435. doi:10.1016/j.biortech.2015.03.007
33. Wu H, San KY (2014) Efficient odd straight medium chain free fatty acid production by metabolically engineered Escherichia coli. Biotechnol Bioeng 111:2209–2219. doi:10.1002/bit.25296
34. 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. doi:10.1016/j.ymben.2012.11.009
35. Xiong AS, Yao QH, Peng RH, Duan H, Li X, Fan HQ, Cheng ZM, Li Y (2006) PCR-based accurate synthesis of long DNA sequences. Nat Protoc 1:791–797. doi:10.1038/nprot.2006.103
36. Xu P, Ranganathan S, Fowler ZL, Maranas CD, Koffas MA (2011) Genome-scale metabolic network modeling results in minimal interventions that cooperatively force carbon flux towards malonyl-CoA. Metab Eng 13:578–587. doi:10.1016/j.ymben.2011.06.008
37. Xu P, Vansiri A, Bhan N, Koffas MA (2012) ePathBrick: a synthetic biology platform for engineering metabolic pathways in E. coli. ACS Synth Biol 1:256–266. doi:10.1021/sb300016b
38. Yu X, Liu T, Zhu F, Khosla C (2011) In vitro reconstitution and steady-state analysis of the fatty acid synthase from Escherichia coli. Proc Natl Acad Sci USA 108:18643–18648. doi:10.1073/pnas.1110852108
39. 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. doi:10.1016/j.ymben.2009.01.005
40. Zhang F, Ouellet M, Batth TS, Adams PD, Petzold CJ, Mukhopadhyay A, Keasling JD (2012) Enhancing fatty acid production by the expression of the regulatory transcription factor FadR. Meta Eng 14:653–660. doi:10.1016/j.ymben.2012.08.009
41. Zhou J, Du G, Chen J (2014) Novel fermentation processes for manufacturing plant natural products. Curr Opin Biotechnol 25:17–23. doi:10.1016/j.copbio.2013.08.009