Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex

Microbial Cell Factories

Volumn 11, Issue 1, 2014, Pages

  Lin, Yuheng ^a   Yan, Yajun ^a  

^a University of Georgia   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYPHENYLACETATE 3 HYDROXYLASE; CAFFEIC ACID; LEVODOPA; LYASE; OXYGENASE; PARA COUMARIC ACID; TYROSINE AMMONIA LYASE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; BACTERIAL METABOLISM; BACTERIAL STRAIN; BACTERIUM CULTURE; BIOTECHNOLOGICAL PRODUCTION; CARBON SOURCE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; METABOLIC ENGINEERING; NONHUMAN; PROTEIN EXPRESSION;

ESCHERICHIA COLI; PROKARYOTA; RHODOBACTER; RHODOBACTER CAPSULATUS;

EID: 84938746622     PISSN: None     EISSN: 14752859     Source Type: Journal    
DOI: 10.1186/1475-2859-11-42     Document Type: Article

References (37)

1. Mori H, Iwahashi H: Antioxidant activity of caffeic acid through a novel mechanism under uva irradiation. J Clin Biochem Nutr 2009, 45:49-55.
2. Gulcin I: Antioxidant activity of caffeic acid (3,4-dihydroxycinnamic acid). Toxicology 2006, 217:213-220.
3. Ikeda K, Tsujimoto K, Uozaki M, Nishide M, Suzuki Y, Koyama AH, Yamasaki H: Inhibition of multiplication of herpes simplex virus by caffeic acid. Int J Mol Med 2011, 28:595-598.
4. Rajendra-Prasad N, Karthikeyan A, Karthikeyan S, Reddy BV: Inhibitory effect of caffeic acid on cancer cell proliferation by oxidative mechanism in human HT-1080 fibrosarcoma cell line. Mol Cell Biochem 2011, 349:11-19.
5. Chao PC, Hsu CC, Yin MC: Anti-inflammatory and anti-coagulatory activities of caffeic acid and ellagic acid in cardiac tissue of diabetic mice. Nutr Metab (Lond) 2009, 6:33.
6. Wu J, Omene C, Karkoszka J, Bosland M, Eckard J, Klein CB, Frenkel K: Caffeic acid phenethyl ester (CAPE), derived from a honeybee product propolis, exhibits a diversity of anti-tumor effects in pre-clinical models of human breast cancer. Cancer Lett 2011, 308:43-53.
7. Celik S, Erdogan S, Tuzcu M: Caffeic acid phenethyl ester (CAPE) exhibits significant potential as an antidiabetic and liver-protective agent in streptozotocin-induced diabetic rats. Pharmacol Res 2009, 60:270-276.
8. Bourgaud F, Hehn A, Larbat R, Doerper S, Gontier E, Kellner S, Matern U: Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes. Phytochem Rev 2006, 5:293-308.
9. Kojima M, Takeuchi W: Detection and characterization of p-coumaric acid hydroxylase in mung bean, Vigna mungo, seedlings. J Biochem 1989, 105:265-270.
10. Kim YH, Kwon T, Yang HJ, Kim W, Youn H, Lee JY, Youn B: Gene engineering, purification, crystallization and preliminary X-ray diffraction of cytochrome P450 p-coumarate-3-hydroxylase (C3H), the Arabidopsis membrane protein. Protein Expr Purif 2011, 79:149-155.
11. Kneusel RE, Matern U, Nicolay K: Formation of trans-caffeoyl-CoA from trans-4-coumaroyl-CoA by Zn2 + -dependent enzymes in cultured plant cells and its activation by an elicitor-induced pH shift. Arch Biochem Biophys 1989, 269:455-462.
12. Berner M, Krug D, Bihlmaier C, Vente A, Muller R, Bechthold A: Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothrix espanaensis. J Bacteriol 2006, 188:2666-2673.
13. Wang J, Lu DQ, Zhao H, Ling XQ, Jiang B, Ouyang PK: Application of response surface methodology optimization for the production of caffeic acid from tobacco waste. Af J Biotechnol 2009, 8:1416-1424.
14. Yoshimoto M, Kurata-Azuma R, Fujii M, Hou DX, Ikeda K, Yoshidome T, Osako M: Enzymatic production of caffeic acid by koji from plant resources containing caffeoylquinic acid derivatives. Biosci Biotechnol Biochem 2005, 69:1777-1781.
15. Sachan A, Ghosh S, Sen SK, Mitra A: Co-production of caffeic acid and p-hydroxybenzoic acid from p-coumaric acid by Streptomyces caeruleus MTCC 6638. Appl Microbiol Biotechnol 2006, 71:720-727.
16. Yan Y, Chemler J, Huang L, Martens S, Koffas MA: Metabolic engineering of anthocyanin biosynthesis in Escherichia coli. Appl Environ Microbiol 2005, 71:3617-3623.
17. Yan Y, Kohli A, Koffas MA: Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Appl Environ Microbiol 2005, 71:5610-5613.
18. Yan Y, Huang L, Koffas MA: Biosynthesis of 5-deoxyflavanones in microorganisms. Biotechnol J 2007, 2:1250-1262.
19. Yan Y, Li Z, Koffas MA: High-yield anthocyanin biosynthesis in engineered Escherichia coli. Biotechnol Bioeng 2008, 100:126-140.
20. Choi O, Wu CZ, Kang SY, Ahn JS, Uhm TB, Hong YS: Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J Ind Microbiol Biotechnol 2011, 38:1657-1665.
21. Santos CN, Koffas M, Stephanopoulos G: Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab Eng 2011, 13:392-400.
22. Nakagawa A, Minami H, Kim JS, Koyanagi T, Katayama T, Sato F, Kumagai H: A bacterial platform for fermentative production of plant alkaloids. Nat Commun 2011, 2:326.
23. Munoz AJ, Hernandez-Chavez G, de Anda R, Martinez A, Bolivar F, Gosset G: Metabolic engineering of Escherichia coli for improving L -3,4-dihydroxyphenylalanine (L -DOPA) synthesis from glucose. J Ind Microbiol Biotechnol 2011, 38:1845-1852.
24. Leonard E, Runguphan W, O'Connor S, Prather KJ: Opportunities in metabolic engineering to facilitate scalable alkaloid production. Nat Chem Biol 2009, 5:292-300.
25. Xue Z, McCluskey M, Cantera K, Sariaslani FS, Huang L: Identification, characterization and functional expression of a tyrosine ammonia-lyase and its mutants from the photosynthetic bacterium Rhodobacter sphaeroides. J Ind Microbiol Biotechnol 2007, 34:599-604.
26. Louie TM, Xie XS, Xun L: Coordinated production and utilization of FADH2 by NAD(P)H-flavin oxidoreductase and 4-hydroxyphenylacetate 3-monooxygenase. Biochemistry 2003, 42:7509-7517.
27. Prieto MA, Perez-Aranda A, Garcia JL: Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range. J Bacteriol 1993, 175:2162-2167.
28. Liebgott PP, Amouric A, Comte A, Tholozan JL, Lorquin J: Hydroxytyrosol from tyrosol using hydroxyphenylacetic acid-induced bacterial cultures and evidence of the role of 4-HPA 3-hydroxylase. Res Microbiol 2009, 160:757-766.
29. Noel JP, Louie GV, Bowman ME, Moore BS, Moffitt MC: Substrate switched ammonia lyases and mutases. United States Patent Application 2009. No. 2009/0011400 A1
30. Chavez-Bejar MI, Lara AR, Lopez H, Hernandez-Chavez G, Martinez A, Ramirez OT, Bolivar F, Gosset G: Metabolic engineering of Escherichia coli for L-tyrosine production by expression of genes coding for the chorismate mutase domain of the native chorismate mutase-prephenate dehydratase and a cyclohexadienyl dehydrogenase from Zymomonas mobilis. Appl Environ Microbiol 2008, 74:3284-3290.
31. Lutke-Eversloh T, Stephanopoulos G: L-tyrosine production by deregulated strains of Escherichia coli. Appl Microbiol Biotechnol 2007, 75:103-110.
32. Shen CR, Liao JC: Metabolic engineering of Escherichia coli for 1-butanol and 1-propanol production via the keto-acid pathways. Metab Eng 2008, 10:312-320.
33. Lutz R, Bujard H: Independent and tight regulation of transcriptional units in Escherichia coli via the LacR/O, the TetR/O and AraC/I1-I2 regulatory elements. Nucleic Acids Res 1997, 25:1203-1210.
34. Sambrook J, Fritsch EF, Maniatis T: Molecular cloning: a laboratory manual. 2nd edition. NY: Cold Spring Harbor Laboratory; 1989.
35. Datsenko KA, Wanner BL: One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci USA 2000, 97:6640-6645.
36. Heckman KL, Pease LR: Gene splicing and mutagenesis by PCR-driven overlap extension. Nat Protoc 2007, 2:924-932.
37. Lutke-Eversloh T, Stephanopoulos G: Feedback inhibition of chorismate mutase/prephenate dehydrogenase (TyrA) of Escherichia coli: generation and characterization of tyrosine-insensitive mutants. Appl Environ Microbiol 2005, 71:7224-7228.