Production of bioactive hydroxyflavones by using monooxygenase from Saccharothrix espanaensis

Journal of Biotechnology

Volumn 176, Issue 1, 2014, Pages 11-17

  Lee, Hyejin ^a   Kim, Bong Gyu ^a   Ahn, Joong Hoon ^a  

^a Konkuk University   (South Korea)

Author keywords

Biocatalyst; Flavonoids; Hydroxylation; Monooxygenase

Indexed keywords

ANTI-OXIDANT ACTIVITIES; CO-EXPRESSION; FINE CHEMICALS; HYDROXYFLAVONES; HYDROXYL GROUPS; MONOOXYGENASES; REGIO-SELECTIVE; STRUCTURAL MODIFICATIONS;

BIOCATALYSTS; ENZYMES; ESCHERICHIA COLI; HYDROXYLATION;

FLAVONOIDS;

3' HYDROXYDAIDZEIN; APIGENIN; CYTOCHROME P450 REDUCTASE; DAIDZEIN; ERIODICTYOL; FLAVONOID; GENISTEIN; HYPOLAETIN; KAEMPFEROL; LUTEOLIN; NARINGENIN; QUERCETIN; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ARTICLE; BACTERIUM; BIOCATALYSIS; CONTROLLED STUDY; ESCHERICHIA COLI; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; MOLECULAR WEIGHT; NONHUMAN; PRIORITY JOURNAL; SACCHAROTHRIX ESPANAENSIS; SYNTHESIS;

BIOCATALYST; FLAVONOIDS; HYDROXYLATION; MONOOXYGENASE;

ACTINOMYCETALES; BACTERIAL PROTEINS; BIOCATALYSIS; ESCHERICHIA COLI; FLAVONOIDS; HYDROXYLATION; MIXED FUNCTION OXYGENASES; NADPH-FERRIHEMOPROTEIN REDUCTASE; ORYZA SATIVA; PLANT PROTEINS;

EID: 84896751799     PISSN: 01681656     EISSN: 18734863     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2014.02.002     Document Type: Article

References (39)

1. Ballou D.P., Entsch B., Cole L.J. Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases. Biochem. Biophys. Res. Commun. 2005, 338:590-598.
2. Berner M., Krug D., Bihlmaier C., Vente A., Müller R., Bechthold A. Genes and enzymes involved in caffeic acid biosynthesis in the actinomycete Saccharothix espanaensis. J. Bacteriol. 2006, 188:2666-2673.
3. Brugliera F., Barri-Rewell G., Holton T.A., Mason J.G. Isolation and characterization of a flavonoid 3'-hydroxylase cDNA clone corresponding to the Ht1 locus of Petunia hybrida. Plant J. 1999, 19:441-451.
4. Cho J.-H., Park Y., Ahn J.-H., Lim Y., Rhee S. Structural and Functional Insights of O-methyltransferase from Bacillus cereus. J. Mol. Biol. 2008, 382:987-997.
5. Duetz W.A., van Beilen J.B., Witholt B. Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. Curr. Opin. Biotechnol. 2001, 12:419-425.
6. de Vetten N., ter Horst J., van Schaik H.-P., de Boer A., Mol J., Koes R. A cytochrome b5 is required for full activity of flavonoid 3',5'-hydroxylase, a cytochrome P450 involved in the formation of blue flower colors. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:778-783.
7. Esaki H., Onozaki H., Morimitsu Y., Kawakishi S., Osawa T. Potent antioxidative isoflavones isolated from soybeans fermented with Aspergillus saitoi. Biosci. Biotechnol. Biochem. 1998, 62:740-746.
8. Esaki H., Kawakishi S., Morimitsu Y., Osawa T. New potent antioxidative o-dihydroxyisoflavones in fermented Japanese soybean products. Biosci. Biotechnol. Biochem. 1999, 63:1637-1639.
9. Halbwirth H., Stich K. An NADPH and FAD dependent enzyme catalyzes hydroxylation of flavonoids in position 8. Phytochemistry 2006, 67:1080-1087.
10. Holton T.A., Brugliera F., Lester D.R., Tanaka Y., Hyland C.D., Menting J.G.T., Lu C.Y., Farcy E., Stevenson T.W., Cornish E.C. Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993, 366:276-279.
11. Jung N.R., Joe E.J., Kim B.-G., Ahn B.C., Park J.C., Chong Y., Ahn J.-H. Change of Bacillus cereus flavonoid O-triglucosyltransferase into flavonoid O-monoglucosyltransferase by error-prone polymerase chain reaction. J. Microbiol. Biotechnol. 2010, 20:1393-1396.
12. Kasai N., Ikushiro S.-I., Hirosue S., Arisawa A., Ichinose H., Wariishi H., Ohta M., Sakaki T. Enzymatic properties of cytochrome P450 catalyzing 3'-hydroxylation of naringenin from the white-rot fungus Phanerochaete chrysosporim. Biochem. Biophys. Res. Commun. 2009, 387:103-108.
13. Kim B.G., Shin K.H., Lee Y., Hur H.-G., Lim Y., Ahn J.-H. Multiple regiospecific methylations of a flavonoid by plant O-methyltransferases expressed in E. coli. Biotechnol. Lett. 2005, 27:1861-1864.
14. Kim B.G., Kim H., Hur H.G., Lim Y., Ahn J.H. Regioselectivity of 7-O-methyltransferase of poplar to flavones. J. Biotechnol. 2006, 138:155-162.
15. Kim B.G., Jung B.-R., Lee Y., Hur H.-G., Lim Y., Ahn J.-H. Regiospecific Flavonoid 7-O-Methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli. J. Agric. Food Chem. 2006, 54:823-828.
16. Kim B.G., Kim J.H., Min S.Y., Shin K.H., Kim J.H., Kim H.I., Ryu S.N., Ahn J.-H. Anthocyanin content in rice is related to expression level of anthocyanin biosynthetic genes. J. Plant Biol. 2007, 50:156-160.
17. Kim B.-G., Sung S.H., Chong Y., Lim Y., Ahn J.-H. Plant flavonoid O-methyltransferases: substrate specificity and application. J. Plant Biol. 2010, 53:321-329.
18. Kim B.G., Kim H.J., Ahn J.-H. Production of bioactive flavonol rhamnosides by expression of plant genes in Escherichia coli. J. Agric. Food Chem. 2012, 60:11143-11148.
19. Kim D.H., Kim B.G., Lee H.J., Lim Y., Hur H.G., Ahn J.-H. Enhancement of isoflavone synthase activity by co-expression of P450 reductase from rice. Biotechnol. Lett. 2005, 27:1291-1294.
20. Kim D.H., Kim B.G., Jung N.R., Ahn J.-H. Production of genistein from naringenin using Escherichia coli containing isoflavone synthase-cytochrome P450 reductase fusion protien. J. Microbiol. Biotechnol. 2009, 19:1612-1616.
21. Ko J.H., Kim B.G., Ahn J.-H. Glycosylation of flavonoids with a glycosyltransferase from Bacillus cereus. FEMS Microbiol. Lett. 2006, 258:263-268.
22. Koeller K.M., Wong C.H. Enzymes for chemical synthesis. Nature 2001, 409:232-240.
23. Latunde-Dada A.O., Cabello-Hurtado F., Czittrich N., Didierjean L., Schopfer C., Hertkorn N., Werck-Reichhart D., Ebel J. Flavonoid 6-hydroxylase from soybean (Glycine max), a novel plant P-450 monooxygenase. J. Biol. Chem. 2001, 276:1688-1695.
24. Leonard E., Yan Y., Koffas M.A.G. Functional expression of a P450 flavonoid hydroxylase for the biosynthesis of plant-specific hydroxylated flavonols in Escherichia coli. Metab. Eng. 2006, 8:172-181.
25. Lee D.E., Lee K.W., Byun S., Jung S.K., Song N., Lim S.H., Heo Y.-S., Kim J.E., Kang N.J., Kim B.Y., Bowden T.G., Bode A.M., Lee H.J., Dong Z. 7,3',4'-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J. Biol. Chem. 2011, 286:14246-14256.
26. Lee H., Kim Y.O., Kim H., Kim S.Y., Noh H.S., Kang S.S., Cho G.A., Choi W.S., Suk K. Flavonoid wogonin from medicinal herb is neuroprotective by inhibiting inflammatory activation of microglia. J. Federat. Am. Soc. Exp. Biol. 2003, 17:1943-1944.
27. Lee H.J., Kim B.G., Ahn J.-H. Molecular cloning and characterization of Bacillus cereus O-methyltransferase. J. Microbiol. Biotechnol. 2006, 16:619-622.
28. Li Z., van Beilen J.B., Duetz W.A., Schmid A., de Raadt A., Griengl H., Witholt B. Oxidative biotransformations using oxygenases. Curr. Opin. Chem. Biol. 2002, 6:136-144.
29. Lim E.-K., Ashford D.A., Hou B., Jackson R.G., Bowles D.J. Arabidopsis glycosyltransferases as biocatalysts in fermentation for regioselective synthesis of diverse quercetin glucosides. Biotechnol. Bioeng. 2004, 87:623-631.
30. Lin Y., Yan Y. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell Fact. 2012, 11:42.
31. Lo Y.-L., Wanga W., Ho C.-T. 7,3',4'-Trihydroxyisoflavone modulates multidrug resistance transporters and induces apoptosis via production of reactive oxygen species. Toxicology 2012, 302:221-232.
32. Min L.-W. New therapeutic aspects of flavones: the anticancer properties of Scutellaria and its main active constituents wogonin, baicalein and baicalin. Cancer Treat. Rev. 2009, 35:57-68.
33. Moroney M.A., Alcarz M.J., Forder R.A., Carey F., Hoult J.R.S. Selectivity of neutrophil 5-lipoxugeanse and cyclo-oygenase inhibition by an anti-inflammatory flavonoid glycoside and related aglycone flavononids. J. Pharm. Pharmacol. 1988, 40:787-792.
34. Prieto M.A., Perez-Aranda A., Garcia J.L. Characterization of an Escherichia coli aromatic hydroxylase with a broad substrate range. J. Bacteriol. 1993, 175:2162-2167.
35. Urlacher V.B., Eiben S. Cytochrome P450 monooxygenases: perspectives for synthetic application. Trends Biotechnol. 2006, 24:324-330.
36. Urlacher V.B., Girhard M. Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol. 2012, 30:26-36.
37. van Berkel W.J.H., Kamerbeek N.M., Fraaije M.W. Flavoprotein monooxygenase, a diverse class of oxidative biocatalysis. J. Biotechnol. 2006, 124:670-689.
38. van Beilen J.B., Duetz W.A., Schmid A., Witholt B. Practical issues in the application of oxygenases. Trends Biotechnol. 2003, 21:170-177.
39. Winkel-Shirley B. Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology, and biotechnology. Plant Physiol. 2001, 126:485-493.