Biotechnological production of plant-specific hydroxylated phenylpropanoids

Biotechnology and Bioengineering

Volumn 111, Issue 9, 2014, Pages 1895-1899

  Lin, Yuheng ^a   Yan, Yajun ^a  

^a University of Georgia   (United States)

Author keywords

Escherichia coli; Esculetin; Non P450 hydroxylase; ortho hydroxylation; Phenylpropanoids; Piceatannol

Indexed keywords

ESCULETIN; NARINGENIN; PICEATANNOL; RESVERATROL; UMBELLIFERONE; UNSPECIFIC MONOOXYGENASE; 3,3',4,5'-TETRAHYDROXYSTILBENE; 7-HYDROXYCOUMARIN; STILBENE DERIVATIVE; UMBELLIFERONE DERIVATIVE;

ANIMAL CELL; BIOCATALYSIS; BIOSYNTHESIS; BIOTECHNOLOGICAL PRODUCTION; EDITORIAL; ELECTROSPRAY MASS SPECTROMETRY; ENZYME MECHANISM; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; KINETICS; NONHUMAN; PLANT; WHOLE CELL; GENETICS; METABOLIC ENGINEERING; METABOLISM;

ESCHERICHIA COLI;

ESCHERICHIA COLI; METABOLIC ENGINEERING; STILBENES; UMBELLIFERONES;

EID: 84904973763     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.25237     Document Type: Editorial

References (20)

1. Bavaresco L, Fregoni M, Trevisan M, Mattivi F, Vrhovsek U, Falchetti R. 2002. The occurrence of the stilbene piceatannol in grapes. Vitis 41(3):133-136.
2. Brisdelli F, D'Andrea G, Bozzi A. 2009. Resveratrol: A natural polyphenol with multiple chemopreventive properties. Curr Drug Metab 10(6):530-546.
3. Huang Q, Lin Y, Yan Y. 2013. Caffeic acid production enhancement by engineering a phenylalanine over-producing Escherichia coli. Biotechnol Bioeng 110(12):3188-3196.
4. Kim SH, Hisano T, Takeda K, Iwasaki W, Ebihara A, Miki K. 2007. Crystal structure of the oxygenase component (HpaB) of the 4-hydroxyphenylacetate 3-monooxygenase from Thermus thermophilus HB8. J Biol Chem 282(45):33107-33117.
5. Lee N, Kim EJ, Kim BG. 2012. Regioselective hydroxylation of trans-resveratrol via inhibition of tyrosinase from Streptomyces avermitilis MA4680. ACS Chem Biol 7(10):1687-1692.
6. Lim CG, Fowler ZL, Hueller T, Schaffer S, Koffas MA. 2011. High-yield resveratrol production in engineered Escherichia coli. Appl Environ Microbiol 77(10):3451-3460.
7. Lin Y, Sun X, Yuan Q, Yan Y. 2013. Combinatorial biosynthesis of plant-specific coumarins in bacteria. Metab Eng 18:69-77.
8. Lin Y, Yan Y. 2012. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb Cell Fact 11(1):42.
9. 2 by NAD(P)H-flavin oxidoreductase and 4-hydroxyphenylacetate 3-monooxygenase. Biochemistry (Mosc) 42(24):7509-7517.
10. Masamoto Y, Murata Y, Baba K, Shimoishi Y, Tada M, Takahata K. 2004. Inhibitory effects of esculetin on melanin biosynthesis. Biol Pharm Bull 27(3):422-425.
11. Pandey BP, Lee N, Choi KY, Jung E, Jeong DH, Kim BG. 2011. Screening of bacterial cytochrome P450s responsible for regiospecific hydroxylation of (iso)flavonoids. Enzyme Microb Technol 48(4-5):386-392.
12. Piotrowska H, Kucinska M, Murias M. 2012. Biological activity of piceatannol: Leaving the shadow of resveratrol. Mutat Res 750(1):60-82.
13. Potter GA, Patterson LH, Wanogho E, Perry PJ, Butler PC, Ijaz T, Ruparelia KC, Lamb JH, Farmer PB, Stanley LA, Burke MD. 2002. The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br J Cancer 86(5):774-778.
14. Prieto MA, Garcia JL. 1994. Molecular characterization of 4-hydroxyphenylacetate 3-hydroxylase of Escherichia coli. A two-protein component enzyme. J Biol Chem 269(36):22823-22829.
15. Prieto MA, Perez-Aranda A, Garcia JL. 1993. Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range. J Bacteriol 175(7):2162-2167.
16. Urlacher VB, Girhard M. 2012. Cytochrome P450 monooxygenases: An update on perspectives for synthetic application. Trends Biotechnol 30(1):26-36.
17. 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(5):578-587.
18. Xun L, Sandvik ER. 2000. Characterization of 4-hydroxyphenylacetate 3-hydroxylase (HpaB) of Escherichia coli as a reduced flavin adenine dinucleotide-utilizing monooxygenase. Appl Environ Microbiol 66(2):481-486.
19. Yang JY, Della-Fera MA, Hartzell DL, Nelson-Dooley C, Hausman DB, Baile CA. 2006. Esculetin induces apoptosis and inhibits adipogenesis in 3T3-L1 cells. Obesity (Silver Spring) 14(10):1691-1699.
20. Yun ES, Park SK, Kim BS, Chae YZ, Cho SM, Yi H, Cho HJ, Shin HC. 2012. Determination of the esculetin contents of medicinal plants by liquid chromatography-tandem mass spectrometry. Biomed Chromatogr 26(10):1247-1251.