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http://dx.doi.org/10.4014/jmb.1401.01031

Construction of Artificial Biosynthetic Pathways for Resveratrol Glucoside Derivatives  

Choi, Oksik (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
Lee, Jae Kyoung (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
Kang, Sun-Young (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
Pandey, Ramesh Prasad (Institute of Biomolecule Reconstruction, Department of Pharmaceutical Engineering, Sun Moon University)
Sohng, Jae-Kyung (Institute of Biomolecule Reconstruction, Department of Pharmaceutical Engineering, Sun Moon University)
Ahn, Jong Seog (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
Hong, Young-Soo (Chemical Biology Research Center, Korea Research Institute of Bioscience and Biotechnology)
Publication Information
Journal of Microbiology and Biotechnology / v.24, no.5, 2014 , pp. 614-618 More about this Journal
Abstract
Resveratrol, which is a polyphenolic antioxidant, is dose-dependent when used to provide health benefits, to enhance stress resistance, and to extend lifespans. However, even though resveratrol has therapeutic benefits, its clinical therapeutic effect is limited owing to its low oral bioavailability. An Escherichia coli system was developed that contains an artificial biosynthetic pathway that produces resveratrol glucoside derivatives, such as resveratrol-3-Oglucoside (piceid) and resveratrol-4'-O-glucoside (resveratroloside), from simple carbon sources. This artificial biosynthetic pathway contains a glycosyltransferase addition (YjiC from Bacillus) with resveratrol biosynthetic genes. The produced glucoside compounds were verified through the presence of a product peak(s) and also through LC/MS analyses. The strategy used in this research demonstrates the first harnessing of E. coli for de novo synthesis of resveratrol glucoside derivatives from a simple sugar medium.
Keywords
Artificial biosynthesis; resveratrol; glycosylation; piceid;
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1 Torres P, Poveda A, Jimenez-Barbero J, Parra JL, Comelles F, Ballesteros AO, Plou FJ. 2011. Enzymatic synthesis of $\alpha$- glucosides of resveratrol with surfactant activity. Adv. Synth. Catal. 353: 1077-1086.   DOI   ScienceOn
2 Walle T. 2011. Bioavailability of resveratrol. Ann N. Y. Acad. Sci. 1215: 9-15.   DOI   ScienceOn
3 Wang Y, Chen S, Yu O. 2011. Metabolic engineering of flavonoids in plants and microorganisms. Appl. Microbiol. Biotechnol. 91: 949-956.   DOI
4 Watts KT, Lee PC, Schmidt-Dannert C. 2006. Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol. 6: 22.   DOI
5 Wu CZ, Jang JH, Woo M, Ahn JS, Kim JS, Hong Y-S. 2012. Enzymatic glycosylation of nonbenzoquinone geldanamycin analogs via Bacillus UDP-glycosyltransferase. Appl. Environ. Microbiol. 78: 7680-7686.   DOI
6 Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, et al. 1997. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275: 218-220.   DOI   ScienceOn
7 Kaneko M, Ohnishi Y, Horinouchi S. 2003. Cinnamate:coenzyme A ligase from the filamentous bacterium Streptomyces coelicolor A3(2). J. Bacteriol. 185: 20-27.   DOI
8 Kang SY, Choi O, Lee JK, Hwang BY, Uhm TB, Hong Y-S. 2012. Artificial biosynthesis of phenylpropanoic acids in a tyrosine overproducing Escherichia coli strain. Microb. Cell Fact. 11: 153.   DOI
9 Khater F, Fournand D, Vialet S, Meudec E, Cheynier V, Terrier N. 2012. Identification and functional characterization of cDNAs coding for hydroxybenzoate/hydroxycinnamate glucosyltransferases co-expressed with genes related to proanthocyanidin biosynthesis. J. Exp. Bot. 63: 1201-1214.   DOI
10 Ko JH, Kim BG, Ahn J-H. 2006. Glycosylation of flavonoids with a glycosyltransferase from Bacillus cereus. FEMS Microbiol. Lett. 258: 263-268.   DOI   ScienceOn
11 Ozaki S, Imai H, Iwakiri T, Sato T, Shimoda K, Nakayama T, Hamada H. 2012. Regioselective glucosidation of transresveratrol in Escherichia coli expressing glucosyltransferase from Phytolacca americana. Biotechnol. Lett. 34: 475-481.   DOI
12 Pandey RP, Li TF, Kim EH, Yamaguchi T, Park YI, Kim JS, Sohng JK. 2013. Enzymatic synthesis of novel phloretin glucosides. Appl. Environ. Microbiol. 79: 3516-3521.   DOI   ScienceOn
13 Baur JA, Sinclair DA. 2006. Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 5: 493-506.   DOI   ScienceOn
14 Pandey RP, Parajuli P, Koirala N, Park JW, Sohng JK. 2013. Probing 3-hydroxyflavone for in vitro glycorandomization of flavonols by YjiC. Appl. Environ. Microbiol. 79: 6833-6838.   DOI   ScienceOn
15 Su D, Cheng Y, Liu M, Liu D, Cui H, Zhang B, et al. 2013. Comparision of piceid and resveratrol in antioxidation and antiproliferation activities in vitro. PLoS One 8: e54505.   DOI
16 Ahn BC, Kim BG, Jeon YM, Lee EJ, Lim Y, Ahn J-H. 2009. Formation of flavone di-O-glucosides using a glycosyltransferase from Bacillus cereus. J. Microbiol. Biotechnol. 19: 387-390.   DOI
17 Camont L, Cottart CH, Rhayem Y, Nivet-Antoine V, Djelidi R, Collin F, et al. 2009. Simple spectrophotometric assessment of the trans-/cis-resveratrol ratio in aqueous solutions. Anal. Chim. Acta 634: 121-128.   DOI   ScienceOn
18 Choi O, Wu CZ, Kang SY, Ahn JS, Uhm TB, Hong Y-S. 2011. Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli. J. Ind. Microbiol. Biotechnol. 38: 1657-1665.   DOI   ScienceOn
19 Cichewicz RH, Kouzi SA. 1998. Biotransformation of resveratrol to piceid by Bacillus cereus. J. Nat. Prod. 61: 1313-1314.   DOI   ScienceOn
20 Gurung RB, Kim EH, Oh TJ, Sohng JK. 2013. Enzymatic synthesis of apigenin glucosides by glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13. Mol Cells 36: 355-361.   DOI
21 Shim H, Hong W, Ahn BC. 2003. Enzymatic preparation of phenolic glucosides by Streptococcus mutans. Bull. Kor. Chem. Soc. 24: 1680-1682.   DOI   ScienceOn