Metabolic engineering for resveratrol derivative biosynthesis in escherichia coli

Molecules and Cells

Volumn 38, Issue 4, 2015, Pages 318-326

  Jeong, Yu Jeong ^a   Woo, Su Gyeong ^a   An, Chul Han ^a,b   Jeong, Hyung Jae ^a   Hong, Young Soo ^a   Kim, Young Min ^c   Ryu, Young Bae ^a   Rho, Mun Chual ^a   Lee, Woo Song ^a   Kim, Cha Young ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Chungnam National University   (South Korea)

^c Chonnam National University   (South Korea)

Author keywords

Metabolic engineering; Pinostilbene; Resveratrol; Resveratrol O methyltransferase; Stilbene synthase

Indexed keywords

CINNAMIC ACID; METHYLTRANSFERASE; PARA COUMARIC ACID; RESVERATROL; STILBENE; SYNTHETASE; ACYLTRANSFERASE; PINOSTILBENE; RECOMBINANT PROTEIN; STILBENE DERIVATIVE; STILBENE SYNTHASE;

AMINO ACID SEQUENCE; ARTICLE; BACTERIAL CELL; BACTERIAL STRAIN; BIOSYNTHESIS; ENZYME ACTIVITY; ESCHERICHIA COLI; GENE EXPRESSION; GRAPE; HETEROLOGOUS EXPRESSION; IN VITRO STUDY; METABOLIC ENGINEERING; NONHUMAN; PEANUT; PLANT GENE; PROCESS OPTIMIZATION; PROTEIN EXPRESSION; RHUBARB; STREPTOMYCES COELICOLOR; GENETICS; METABOLISM; MOLECULAR MODEL; PROCEDURES;

ACYLTRANSFERASES; ESCHERICHIA COLI; METABOLIC ENGINEERING; METHYLTRANSFERASES; MODELS, MOLECULAR; RECOMBINANT PROTEINS; STILBENES;

EID: 84937466233     PISSN: 10168478     EISSN: 02191032     Source Type: Journal    
DOI: 10.14348/molcells.2015.2188     Document Type: Article

References (26)

1. Baur, J.A., Pearson, K.J., Price, N.L., Jamieson, H.A., Lerin, C., Kalra, A., Prabhu, V.V., Allard, J.S., Lopez-Lluch, G., Lewis, K., et al. (2006). Resveratrol improves health and survival of mice on a high-calorie diet. Nature 444, 337-342.
2. Becker, J.V., Armstrong, G.O., van der Merwe, M.J., Lambrechts, M.G., Vivier, M.A., and Pretorius, I.S. (2003). Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol. FEMS Yeast Res. 4, 79-85.
3. Beekwilder, J., Wolswinkel, R., Jonker, H., Hall, R., de Vos, C.H., and Bovy, A. (2006). Production of resveratrol in recombinant microorganisms. Appl. Environ. Microbiol. 72, 5670-5672.
4. Choi, O., Wu, C.Z., Kang, S.Y., Ahn, J.S., Uhm, T.B., and 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.
5. Delaunois, B., Cordelier, S., Conreux, A., Clément, C., and Jeandet, P. (2009). Molecular engineering of resveratrol in plants. Plant Biotechnol. J. 7, 2-12.
6. Foust, C.M. (1992). Rhubarb: The wondrous drug. (Princeton, NJ, USA: Princeton University Press).
7. Frémont, L. (2000). Biological effects of resveratrol. Life Sci. 66, 663-673.
8. Horinouchi, S. (2009). Combinatorial biosynthesis of plant medicinal polyketides by microorganisms. Curr. Opin. Chem. Biol. 73, 197-204.
9. Jeong, Y.J., An, C.H., Woo, S.G., Jeong, H.J., Kim, Y.-M., Park, S.-J., Yoon, B.D., and Kim, C.Y. (2014). Production of pinostilbene compounds by the expression of resveratrol O-methyltransferase genes in Escherichia coli. Enzyme Microb. Tech. 54, 8-14.
10. Kaneko, M., Ohnishi, Y., and Horinouchi, S. (2003). Cinnamate: coenzyme A ligase from the filamentous bacterium Streptomy-ces coelicolor A3(2). J. Bacteriol. 785, 20-27.
11. Kashiwada, Y., Nonaka, G., Nishioka, I., Nishizawa, M., and Yamagishi, T. (1988). Studies on rhubarb (Rhein Rhizoma). XIV. Isolation and characterization of stilbene glucosides from Chinese rhubarb. Chem. Pharm. Bull. 36, 1545-1549.
12. Katsuyama, Y., Funa, N., Miyahisa, I., and Horinouchi, S. (2007). Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli. Chem. Biol. 74, 613-621.
13. Lee, S.K., Nam, K.A., Hoe, Y.H., Min, H.Y., Kim, E.Y., Ko, H., Song, S., Lee, T., and Kim, S. (2003). Synthesis and evaluation of cy-totoxicity of stilbene analogues. Arch. Pharm. Res. 26, 253-257.
14. Lee, S.W., Hwang, B.S., Kim, M.H., Park, C.S., Lee, W.S., Oh, H.M., and Rho, M.C. (2012). Inhibition of LFA-1/ICAM-1- mediated cell adhesion by stilbene derivatives from Rheum undulatum. Arch. Pharm. Res. 35, 1763-1770.
15. Melchior, F., and Kindl, H. (1990). Grapevine stilbene synthase cDNA only slightly differing from chalcone synthase cDNA is expressed in Escherichia coli into a catalytically active enzyme. FEBS Lett. 268, 17-20.
16. Remsberg, C.M., Yáñez, J.A., Ohgami, Y., Vega-Villa, K.R., Rimando, A.M., and Davies, N.M. (2008). Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, an-ticancer, antiinflammatory, antioxidant and analgesic activity. Phytother. Res. 22, 169-179.
17. Rimando, A.M., Pan, Z., Polashock, J.J., Dayan, F.E., Mizuno, C.S., Snook, M.E., Liu, C.J., and Baerson, S.R. (2012). In planta production of the highly potent resveratrol analogue pterostilbene via stilbene synthase and O-methyltransferase co-expression. Plant Biotechnol. J. 70, 269-283.
18. Sambrook, J., Fritsch, E.F., and Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual. (2nd ed). Vol. 123. (NY, USA: Cold Spring Harbor Laboratory Press).
19. Schmidlin, L., Poutaraud, A., Claudel, P., Mestre, P., Prado, E., Santos-Rosa, M., Wiedemann-Merdinoglu, S., Karst, F., Merdinoglu, D., and Hugueney, P. (2008). A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine. Plant Physiol. 748, 1630-1639.
20. Sparvoli, F., Martin, C., Scienza, A., Gavazzi, G., and Tonelli, C. (1994). Cloning and molecular analysis of structural genes involved in flavonoid and stilbene biosynthesis in grape (Vitis vinif-era L.). Plant Mol. Biol. 24, 743-755.
21. Ulrich, S., Wolter, F., and Stein, J.M. (2005). Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis. Mol. Nutr. Food. Res. 49, 452-461.
22. Ververidis, F., Trantas, E., Douglas, C., Vollmer, G., Kretzschmar, G., and Panopoulos, N. (2007). Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part II: Reconstruction of multienzyme pathways in plants and microbes. Biotechnol. J. 2, 1235-1249.
23. Walle, T., Hsieh, F., DeLegge, M.H., Oatis, J.E, and Walle, U.K. (2004). High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 32, 1377-1382.
24. Wang, T.T., Schoene, N.W., Kim, Y.S., Mizuno, C.S., and Rimando, A.M. (2010). Differential effects of resveratrol and its naturally occurring methylether analogs on cell cycle and apoptosis in human androgen-responsive LNCaP cancer cells. Mol. Nutr. Food Res. 54, 335-344.
25. Watts, K.T., Lee, P.C., and Schmidt-Dannert, C. (2006). Biosynthesis of plant-specific stilbene polyketides in metabolically engineered Escherichia coli. BMC Biotechnol. 6, 22.
26. Zhang, Y., Li, S.Z., Li, J., Pan, X., Cahoon, R.E., Jaworski, J.G., Wang, X., Jez, J.M., Chen, F., and Yu, O. (2006). Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and Mammalian cells. J. Am. Chem. Soc. 728, 13030-13031