Production of three phenylethanoids, tyrosol, hydroxytyrosol, and salidroside, using plant genes expressing in Escherichia coli

Scientific Reports

Volumn 7, Issue 1, 2017, Pages

  Chung, Daeun ^a   Kim, So Yeon ^a   Ahn, Joong Hoon ^a  

^a Konkuk University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3,4-DIHYDROXYPHENYLETHANOL; 4-HYDROXYPHENYLETHANOL; GLUCOSIDE; GLYCOSYLTRANSFERASE; PHENETHYL ALCOHOL; PHENOL DERIVATIVE; SALIDROSIDE;

ANALOGS AND DERIVATIVES; BIOSYNTHESIS; CHEMISTRY; CLASSIFICATION; ENZYMOLOGY; ESCHERICHIA COLI; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; RHODIOLA;

ESCHERICHIA COLI; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GLUCOSIDES; GLYCOSYLTRANSFERASES; PHENOLS; PHENYLETHYL ALCOHOL; RHODIOLA;

EID: 85019987593     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/s41598-017-02042-2     Document Type: Article

References (36)

1. Uttara, B., Singh, A. V., Zamboni, P. & Mahajan, R. T. Oxidative stress and neurodegenerative diseases: A review of upstream and downstream antioxidant therapeutic options. Curr. Neuropharmacol. 7, 65-74, doi:10.2174/157015909787602823 (2009).
2. Stark, A. H. & Madar, Z. Olive oil as a functional food: epidemiology and nutritional approaches. Nutr. Rev. 60, 170-176, doi:10.1301/002966402320243250 (2002).
3. St-Laurent-Thibault, C., Arseneault, M., Longpré, F. & Ramassamy, C. Tyrosol and hydroxytyrosol, two main components of olive oil, protect N2a cells against amyloid-β-induced toxicity. Involvement of the NF-κB signaling. Curr. Alzheimer. Res. 8, 543-551, doi:10.2174/156720511796391845 (2011).
4. Yousef, G. G. et al. Comparative phytochemical characterization of three Rhodiola species. Phytochemistry 67, 2380-2391, doi:10.1016/j.phytochem.2006.07.026 (2006).
5. Cifani, C. et al. Effect of salidroside, active principle of Rhodiola rosea extract, on binge eating. Physiol. Behav. 101, 555-562, doi:10.1016/j.physbeh.2010.09.006 (2010).
6. Palumbo, D. R., Occhiuto, F., Spadaro, F. & Circosta, C. Rhodiola rosea extract protects human cortical neurons against glutamate and hydrogen peroxide-induced cell death through reduction in the accumulation of intracellular calcium. Phytother, Res. 26, 878-83, doi:10.1002/ptr.v26.6 (2012).
7. Zhang, L. et al. Neuroprotective effects of salidroside against beta-amyloid-induced oxidative stress in SH-SY5Y human neuroblastoma cells. Neurochem. Int. 57, 547-555, doi:10.1016/j.neuint.2010.06.021 (2010).
8. Zhang, J. K. et al. Protection by salidroside against bone loss via inhibition of oxidative stress and bone-resorbing mediators. PLoS One 8, e57251, doi:10.1371/journal.pone.0057251 (2013).
9. Ma, L. Q. et al. Effects of overexpression of endogenous phenylalanine ammonia-lyase (PALrs1) on accumulation of salidroside in Rhodiola sachalinensis. Plant Biol. (Stuttg) 10, 323-333, doi:10.1111/j.1438-8677.2007.00024.x (2008).
10. Zhang, J. X. et al. A tyrosine decarboxylase catalyzes the initial reaction of the salidroside biosynthesis pathway in Rhodiola sachalinensis. Plant Cell Rep 30, 1443-1453, doi:10.1007/s00299-011-1053-7 (2011).
11. Qualley, A. V. et al. Completion of the core β-oxidative pathway of benzoic acid biosynthesis in plants. Proc. Natl. Acad. Sci. USA 109, 16383-16388, doi:10.1073/pnas.1211001109 (2012).
12. Ma, L. Q. et al. Molecular cloning and overexpression of a novel UDP-glucosyltransferase elevating salidroside levels in Rhodiola sachalinensis. Plant Cell Rep. 26, 989-999, doi:10.1007/s00299-007-0317-8 (2007).
13. Bai, Y. et al. Production of salidroside in metabolically engineered Escherichia coli. Sci. Rep. 4, 6640, doi:10.1038/srep06640 (2014).
14. Satoh, Y. et al. Engineering of a tyrosol-producing pathway, utilizing simple sugar and the central metabolic tyrosine, in Escherichia coli. J. Agric. Food. Chem. 60, 979-984, doi:10.1021/jf203256f (2012).
15. Kaminaga, Y. et al. Plant phenylacetaldehyde synthase is a bifunctional homotetrameric enzyme that catalyzes phenylalanine decarboxylation and oxidation. J. Biol. Chem. 281, 23357-23366, doi:10.1074/jbc.M602708200 (2006).
16. Torrens-Spence, M. et al. Biochemical evaluation of a parsley tyrosine decarboxylase results in a novel 4-hydroxyphenylacetaldehyde synthase enzyme. Biochem. Biophys. Res. Commun. 418, 211-216, doi:10.1016/j.bbrc.2011.12.124 (2012).
17. Torrens-Spence, M. et al. Biochemical evaluation of the decarboxylation-deamination activities of plant aromatic amino acid decarboxylase. J. Biol. Chem. 288, 2376-2387, doi:10.1074/jbc.M112.401752 (2013).
18. Lütke-Eversloh, T. & Stephanopoulos, G. L-Tyrosine production by deregulated strains of Escherichia coli. Appl. Microbiol. Biotechnol. 75, 103-110, doi:10.1007/s00253-006-0792-9 (2007).
19. Juminaga, D. et al. Modular engineering of L-tyrosine production in Escherichia coli. Appl. Environ. Microbiol. 78, 89-98, doi:10.1128/AEM.06017-11 (2012).
20. Lim, E. K. et al. Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J. Biol. Chem. 276, 4344-4349, doi:10.1074/jbc.M007263200 (2001).
21. Lim, E.-K. et al. The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and benzoates. J. Biol. Chem. 277, 586-592, doi:10.1074/jbc.M109287200 (2002).
22. Lim, E.-K., Higgins, G. S., Li, Y. & Bowles, D. J. Regioselectivity of glucosylation of caffeic acid by a UDP-glucose:glucosyltransferase is maintained in planta. Biochem. J. 373, 987-992, doi:10.1042/bj20021453 (2003).
23. Lim, E.-K., Jackson, R. G. & Bowles, D. J. Identification and characterization of Araabidopsis glycosyltransferase capable of glucosylating coniferyl aldehyde and sinapyl aldehyde. FEBS Letters 579, 2802-2806, doi:10.1016/j.febslet.2005.04.016 (2005).
24. Caputi, L., Lim, E.-K. & Bowles, D. J. Discovery of new biocatalysts for the glycosylation of terpenoid scaffolds. Chem, Eur. J. 14, 6656-6662, doi:10.1002/chem.v14:22 (2008).
25. Xu, L. & Sandvik, E. R. Chrarcterization of 4-hydroxyphenylacetate 3-hydroxylase (HpaB) of Escherichia coli as a reduced flavin adenine dinucleotide-utilizing monoxygenase. App. Environ. Microbiol. 66, 481-486, doi:10.1128/AEM.66.2.481-486.2000 (2000).
26. Berner, M. et al. Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothix espanaensis. J. Bacteriol. 188, 2666-2673, doi:10.1128/JB.188.7.2666-2673.2006 (2006).
27. Lin, Y. & Yan, Y. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microbial. Cell Fact. 11, 42, doi:10.1186/1475-2859-11-42 (2012).
28. Lee, H., Kim, B.-G. & Ahn, J.-H. Production of bioactive hydroxyflavones by using monooxygenase from. Saccharothrix espanaensis. J. Biotech. 176, 11-17, doi:10.1016/j.jbiotec.2014.02.002 (2014).
29. Jones, J. A. et al. Optimization of naringenin and p-coumaric acid hydroxylation using the native E. coli hydroxylase complex, HpaBC. Biotechnol Prog. 32, 21-25, doi:10.1002/btpr.2185 (2016).
30. Satoh, Y. et al. Engineering of L-tyrosine oxidation in Escherichia coli and microbial production of hydroxytyrosol. Met. Eng. 14, 603-610, doi:10.1016/j.ymben.2012.08.002 (2012).
31. Jin, S. H. et al. Overexpression of glucosyltransferase UGT85A1 influences trans-zeatin homeostasis and trans-zeatin responses likely through O-glucosylation. Planta 237, 991-999, doi:10.1007/s00425-012-1818-4 (2013).
32. Wang, L. et al. Comparing the acceptor promiscuity of a Rosa hybrida glucosyltransferase RhGT1 and an engineered microbial glucosyltransferase OleD(PSA) toward a small flavonoid library. Carbohydr, Res. 368, 73-77, doi:10.1016/j.carres.2012.12.012 (2013).
33. Kim, B. G. et al. Cloning and expression of the isoflavone synthase gene (IFS-Tp) from. Trifolium pratense. Mol. Cells 15, 301-306 (2003).
34. Yoon, J.-A. et al. Production of a novel quercetin glycoside through metabolic engineering of Escherichia coli. Appl. Env. Microbiol. 78, 4256-4262, doi:10.1128/AEM.00275-12 (2012).
35. Kim, B. G., Kim, H. J. & Ahn, J.-H. Production of bioactive flavonoid rhamnosides by expression of plant genes in Escherichia coli. J. Agri. Food Chem. 60, 11143-11148, doi:10.1021/jf302123c (2012).
36. Kim, M. J., Kim, B.-G. & Ahn, J.-H. Biosynthesis of bioactive O-methylated flavonoids in Escherichia coli. Appl. Microbiol. Biot 97, 7195-7204, doi:10.1007/s00253-013-5020-9 (2013).