Browse > Article
http://dx.doi.org/10.1007/s10059-009-0135-7

Metabolic Engineering of Escherichia coli for the Biological Synthesis of 7-O-Xylosyl Naringenin  

Simkhada, Dinesh (Department of Pharmaceutical, Institute of Biomolecule Reconstruction, Sun Moon University)
Kim, EuiMin (Department of Pharmaceutical, Institute of Biomolecule Reconstruction, Sun Moon University)
Lee, Hei Chan (Department of Pharmaceutical, Institute of Biomolecule Reconstruction, Sun Moon University)
Sohng, Jae Kyung (Department of Pharmaceutical, Institute of Biomolecule Reconstruction, Sun Moon University)
Publication Information
Molecules and Cells / v.28, no.4, 2009 , pp. 397-401 More about this Journal
Abstract
Flavonoids are a group of polyphenolic compounds that have been recognized as important due to their physiological and pharmacological roles and their health benefits. Glycosylation of flavonoids has a wide range of effects on flavonoid solubility, stability, and bioavailability. We previously generated the E. coli BL21 (DE3) ${\Delta}pgi$ host by deleting the glucose-phosphate isomerase (Pgi) gene in E. coli BL21 (DE3). This host was further engineered for whole-cell biotransformation by integration of galU from E. coli K12, and expression of calS8 (UDP-glucose dehydrogenase) and calS9 (UDP-glucuronic acid decarboxylase) from Micromonospora echinospora spp. calichensis and arGt-4 (7-O-glycosyltransferase) from Arabidopsis thaliana to form E. coli (US89Gt-4), which is expected to produce glycosylated flavonoids. To test the designed system, the engineered host was fed with naringenin as a substrate, and naringenin 7-O-xyloside, a glycosylated naringenin product, was detected. Product was verified by HPLC-LC/MS and ESI-MS/MS analyses. The reconstructed host can be applied for the production of various classes of glycosylated flavonoids.
Keywords
7-O-xylosyl naringenin; glycosylation; metabolic engineering; naringenin; UDP-D-xylose;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
연도 인용수 순위
1 Bililign, T., Shepard, E.M., Ahlert, J., and Thorson, J.S. (2002). On the origin of deoxypentoses: Evidence to support a glucose progenitor in the biosynthesis of calicheamicin. ChemBioChem 11, 1143-1146   PUBMED
2 Cao, G., Sofic, E., and Prior, R.L. (1997). Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic. Biol. Med. 22, 749-760   DOI   ScienceOn
3 Chen, L.J., Games, D.E., Jones, J., and Kidwell, H. (2003). Separation and identification of flavonoids in an extract from the seeds of Oroxylum indicum by CCC. J. Liq. Chromatogr. Relat. Technol. 26, 1623-1636   DOI   ScienceOn
4 Ferreres, F., Llorach, R., and Gil-Izquierdo, A. (2004). Characterization of the interglycosidic linkage in di-, tri-, tetra- and pentaglycosylated flavonoids and differentiation of positional isomers by liquid chromatography/electrospray ionization tandem mass spectrometry. J. Mass. Spectrum. 39, 1-15   DOI   ScienceOn
5 Hu, Y., and Walker, S. (2002). Remarkable structural similarities between diverse glycosyltransferases. Chem. Biol. 9, 1287-1296   DOI   ScienceOn
6 Kim, H.P., Son, K.H., Chang, H.W., and Kang, S.S. (2004). Antiinflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci. 96, 229-245   DOI   ScienceOn
7 Kim, J.H., Kim, B.G., Park, Y., Ko, J.H., Lim, C.E., Lim, J., Lim, Y., and Ahn, J-H. (2006). Characterization of flavonoid 7-O-glucosyltrans- ferase from Arabidopsis thaliana. Biosci. Biotechnol. Biochem. 70, 1471-1477   DOI   ScienceOn
8 Ko, J.H., Kim, B.G., and Ahn, J.-H. (2006). Glycosylation of flavonoids with a glycosyltransferase from Bacillus cereus. FEMS Microbiol. Lett. 258, 263-268   DOI   ScienceOn
9 So, F.V., Guthrie, A.F., Chambers, A.F., Moussa, M., and Carroll, K.K. (1996). Inhibition of human breast cancer cell proliferation and delay of mammary tumorogenesis by flavonoids and citrus juices. Nutr. Cancer 26, 167-181   DOI   ScienceOn
10 Stobiecki, M. (2000). Application of mass spectrometry for identifycation and structural studies of flavonoid glycosides. Photochemistry 54, 237-256   DOI   PUBMED   ScienceOn
11 Tahara, S. (2007). A journey of twenty-five years through the ecological biochemistry of flavonoids. Biosci. Biotechnol. Biochem. 71, 1387-1404   DOI   ScienceOn
12 Valenzuela, A., Sanhueza, J., and Nieto, S. (2003). Natural antioxidants in functional foods: from food safety to health benefits. Grasas Aceites 54, 295-303
13 He, X.M., and Liu, H-W. (2002). Formation of unusual sugars: mechanistic studies and biosynthetic studies and biosynthetic applications. Annu. Rev. Biochem. 71, 701-754   DOI   ScienceOn
14 Middleton, E., and Kandaswami, C. (1992). Effects of flavonoids on immune and inflammatory cell functions. Biochem. Pharmacol. 43, 1167-1179   DOI   ScienceOn
15 Fraenkel, D.G. (1968). The accumulation of glucose 6-phosphate from glucose and its effect in an Escherichia coli mutant lacking glucose phosphate isomeraseand glucose 6-phosphate dehydrogenase. J. Biol. Chem. 243, 6451-6457
16 Ma, Y.L., Li, Q.M., Van den Heuvel, H., and Claeys, M. (1997). Characterization of flavone and flavonol aglycones by collisioninduced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrum 11, 1357-1364   DOI   ScienceOn
17 Simkhada, D., Oh, T.J., Pageni, B.B., Lee, H.C., Liou, K.K., and Sohng, J.K. (2009). Characterization of CalS9 in the biosynthesis of UDP-xylose and production of xylosyl-attached hybrid compound. Appl. Microbiol. Biotechnol. 83, 885-895   DOI   ScienceOn
18 Asres, K., Seyoum, A., Veeresham, C., Bucar, F., and Gibbons, S. (2005). Naturally derived anti-HIV agents. Phytother. Res. 19, 557-581   DOI   ScienceOn
19 Yochum, L., Kushi, L.H., Meyer, K., and Folsom, A.R. (1999). Dietary flavonoid intake and risk of cardiovascular disease in postmenopausal women. Am. J. Epidemiol. 149, 943-949   DOI   PUBMED   ScienceOn
20 Cushnie, T.P.T., and Lamb, A.J. (2005). Antimicrobial activity of flavonoids. Int. J. Antimicrob. Agent. 26, 343-356   DOI   ScienceOn
21 Borrelli, F., and Izzo, A.A. (2000). The plant kingdom as a source of anti-ulcer remedies. Phytother. Res. 14, 581-591   DOI   ScienceOn
22 Brugliera, F., Holton, T.A., Stevenson, T.W., Farcy, E., Lu, C., and Cornish, E.C. (1992). Isolation and characterization of a cDNA clone corresponding to the Rt locus of Petunia hybrida. Plant J. 5, 81-92   DOI   ScienceOn
23 Bowles, D., Lim, E-K., Poppenberger B., and Vaistij F.E. (2006). Glycosyltransferase of lipophilic small molecules. Annu. Rev. Plant Biol. 57, 567-597   DOI   PUBMED   ScienceOn
24 Tanaka, T. (1997). Chemoprevention of human cancer: biology and therapy. Crit. Rev. Oncol. Hematol. 25, 139-174   DOI   PUBMED   ScienceOn
25 Tijburg, L.B.M., Mattern, T., Folts, J.D., Weisgerber, U.M., and Katan, M.B. (1997). Tea flavonoids and cardiovascular diseases: a review. Crit. Rev. Food Sci. 37, 771-785   DOI   ScienceOn
26 Kris-Etherton, P.M., Lefevre, M., Beecher, G.R., Gross, M.D., Keen, C.L., and Etherton, T.D. (2004). Bioactive compounds in nutrition and health-research methodologies for stablishing biological function: the antioxidant and anti-inflammatory effects of flavonoids on atherosclerosis. Ann. Rev. Nutr. 24, 511-538   DOI   ScienceOn
27 Buslig, B.S., and Manthey, J.A. (2002). Eds; Flavonoids in cell function. (New York, NY: Kluwer Academic/Plenum Publishers)
28 Benavente-Garcia, O., Castillo, J., Marín, F.R., Ortuno, A., and Del Rio, J.A. (1997). Uses and properties of Citrus flavonoids. J. Agric. Food Chem. 45, 4505-4515   DOI   ScienceOn
29 Boue, M.S., Carter-Wientjes, H.C., Shih, Y.B., and Cleveland, E.T. (2003). Identification of flavone aglycones and glycosides in soybean pods by liquid chromatography-tandem mass spectrometry. J. Chromatogr. A 991, 61-68
30 Lee, Y.U., Kawasaki, I., Lim, Y., Oh, W.S., Paik, Y.K., and Shim, Y.H. (2008). Inhibition of developmental processes by Flavone in Caenorhabditis elegans and its application to the pinewood nematode, Bursaphelenchus xylophilus. Mol. Cells 26, 171-174   PUBMED
31 Manach, C., and Donovan, J.L. (2004). Pharmacokinetics and metabolism of dietary flavonoids in humans. Free Radic. Res. 38, 771-785   DOI   ScienceOn
32 Kris-Etherton, P.M., Hecker, K.D., Bonanome, A., Coval, S.M., Binkoski, A.E., Hilpert, K.F., and Etherton, T.D. (2002). Bioactive compounds in foods: Their role in the prevention of cardiovascular disease and cancer. Am. J. Med. 113, 71-88   DOI   ScienceOn