Abstract
Myricetin is an important flavonol whose medically important properties include activities as an antioxidant, anticarcinogen, and antimutagen. The solubility, stability, and other biological properties of the compounds can be enhanced by conjugating aglycon with sugar moieties. The type of sugar moiety also plays a significant role in the biological and physical properties of the natural product glycosides. Reconstructed Escherichia coli containing thymidine diphosphate-α-l-rhamnose sugar gene cassette and Arabidopsis-derived glycosyltransferase were used for rhamnosylation of myricetin. Myricetin (100 μM) was exogenously supplemented to induced cultures of engineered E. coli. The formation of target product—myricetin-3-O-α-l-rhamnoside—was confirmed by chromatographic and NMR analyses. The yield of product was improved by using various mutants and methylated cyclodextrin as a molecular carrier for myricetin in combination with E. coli M3G3. The maximal yield of product is 55.6 μM (3.31-fold higher than the control E. coli MG3) and shows 55.6 % bioconversion of substrate under optimized conditions.
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References
Nirmala, P., & Ramanathan, M. (2011). Journal of Experimental Therapeutics and Oncology, 9, 101–108.
Robak, J., & Gryglewski, R. J. (1988). Biochemical Pharmacology, 37, 837–841.
Abalea, V., Cillard, J., Dubos, M. P., Sergent, O., Cillard, P., & Morel, I. (1999). Free Radical Biology and Medicine, 26, 1457–1466.
Meotti, F. C., Senthilmohan, R., Harwood, D. T., Missau, F. C., Pizzolatti, M. G., & Kettle, A. J. (2008). Free Radical Biology and Medicine, 44, 109–120.
Pereira, M., Siba, I. P., Chioca, L. R., Correia, D., Vital, M. A., Pizzolatti, M. G., et al. (2011). Progress in Neuro-Psychopharmacology & Biological Psychiatry, 35, 1636–1644.
Shimosaki, S., Tsurunaga, Y., Itamura, H., & Nakamura, M. (2011). Natural Product Research, 25, 374–380.
Sun, G. B., Qin, M., Ye, J. X., Pan, R. L., Meng, X. B., Wang, M., Luo, Y., Li, Z. Y., Wang, H. W., & Sun, X. B. (2013). Toxicology and Applied Pharmacology. doi:10.1016/j.taap.2013.04.015.
Ren, G., Hou, J., Fang, Q., Sun, H., Liu, X., Zhang, L., et al. (2012). Glycoconjugate Journal, 29, 425–432.
Weis, M., Lim, E. K., Bruce, N., & Bowles, D. (2006). Angewandte Chemie International Edition, 45, 3534–3538.
Thibodeaux, C. J., & Melacon, C. E. (2008). Angewandte Chemie International Edition, 47, 9814–9859.
Jones, P., Messner, B., Nakajima, J., Schaffner, A. R., & Saito, K. (2003). Journal of Biological Chemistry, 278, 43910–43918.
Lim, E. K., Ashford, D. A., & Bowles, D. J. (2006). ChemBioChem, 7, 1181–1185.
Lim, E. K., Ashford, D. A., Hou, B., Jackson, R. G., & Bowles, D. J. (2004). Biotechnology and Bioengineering, 87, 623–631.
Trantas, E., Panopoulos, N., & Ververidis, F. (2009). Metabolic Engineering, 11, 355–366.
Yoon, J. A., Kim, B. G., Lee, W. J., Lim, Y., Chong, Y., & Ahn, J. H. (2012). Applied and Environmental Microbiology, 78, 4256–4262.
Williams, G. J., Yang, J., Zhang, C., & Thorson, J. S. (2011). ACS Chemical Biology, 6, 95–100.
Kren, V., & Martínková, L. (2001). Current Medicinal Chemistry, 8, 1303–1328.
Pandey, R. P., Malla, S., Simkhada, D., Kim, B. G., & Sohng, J. K. (2012). Applied Microbiology and Biotechnology, 97, 1889–1901.
Simkhada, D., Kim, E. M., Lee, H. C., & Sohng, J. K. (2009). Molecules and Cells, 28, 397–401.
Simkhada, D., Lee, H. C., & Sohng, J. K. (2010). Biotechnology and Bioengineering, 107, 154–162.
Sambrook, J., Fritsch, E. F., & Maniatis, T. (1989). Molecular cloning: a laboratory manual (2nd ed.). Cold Spring Harbor: Cold Spring Harbor Laboratory Press.
http://openwetware.org/wiki/NanoBio:_Protocol_for_gene_knockout
Liu, S. Y., & Rosazza, J. P. (1998). Applied and Environmental Microbiology, 64, 3972–3976.
Liu, S. Y., & Rosazza, P. N. (1995). Journal of Liquid Chromatography, 18, 4081–4095.
Shen, Y., Wang, M., Zhang, L., Ma, Y., Ma, B., Zheng, Y., et al. (2011). Applied Microbiology and Biotechnology, 90, 1995–2003.
Bergonzi, M. C., Bilia, A. R., Di Bari, L., Mazzi, G., & Vincieri, F. F. (2007). Bioorganic and Medicinal Chemistry Letters, 17, 5744–5748.
Donova, M. V., Nikolayeva, V. M., Dovbnya, D. V., Gulevskaya, S. A., & Suzina, N. E. (2007). Microbiology, 153, 1981–1992.
Ma, S. X., Chen, W., Yang, X. D., Zhang, N., Wang, S. J., Liu, L., et al. (2012). Journal of Pharmaceutical and Biomedical Analysis, 67–68, 193–200.
Truong, V. T., Boyer, R. R., McKinney, J. M., O’Keefe, S. F., & William, R. C. (2010). Journal of Food Protection, 73, 92–96.
Wen, J., Liu, B., Yuan, E., Ma, Y., & Zhu, Y. (2010). Molecules, 15, 4401–4407.
Xiao, Y., Yang, L., Mao, P., Yuan, J., Deng, Y., & Qu, L. (2012). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 85, 298–302.
Ficarra, R., Tommassini, S., Raneri, D., Calabro, M. L., Di Bella, M. R., Rustichelli, C., et al. (2002). Journal of Pharmaceutical and Biomedical Analysis, 29, 1005–1014.
Kim, B. G., Kim, H. J., & Ahn, J. H. (2012). Journal of Agriculture and Food Chemistry, 60, 11143–11148.
Acknowledgments
This work was supported by grant from the Next-Generation BioGreen 21 Program (SSAC, grant#: PJ00948302), Rural Development Administration and supported by the Intelligent Synthetic Biology Center of Global Frontier Project funded by the Ministry of Education, Science and Technology (2011-0031960), Republic of Korea; grants from the National Foundation for Science and Technology Development—(NAFOSTED), Vietnam (Grant no: 104.01-2010.22).
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Thuan, N.H., Pandey, R.P., Thuy, T.T.T. et al. Improvement of Regio-Specific Production of Myricetin-3-O-α-l-Rhamnoside in Engineered Escherichia coli . Appl Biochem Biotechnol 171, 1956–1967 (2013). https://doi.org/10.1007/s12010-013-0459-9
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DOI: https://doi.org/10.1007/s12010-013-0459-9