Precursor-directed biosynthesis of stilbene methyl ethers in Escherichia coli

Biotechnology Journal

Volumn 2, Issue 10, 2007, Pages 1286-1293

  Katsuyama, Yohei ^a   Funa, Nobutaka ^a   Horinouchi, Sueharu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Combinatorial biosynthesis; O Methylated stilbenes; O Methyltransferase from Oryza sativa; Stilbene

Indexed keywords

1 (4' FLUOROPHENYL) 2 (3,5 DIMETHOXYPHENYL)ETHANE; 2 [2 (3,5 DIMETHOXYPHENYL)VINYL]FURAN; 2 [2 (3,5 DIMETHOXYPHENYL)VINYL]THIOPHENE; 3 [2 (3,5 DIMETHOXYPHENYL)VINYL]PYRIDINE; ACRYLIC ACID; CARBOXYLIC ACID; COMPLEMENTARY DNA; COUMARIC ACID; PHENYLALANINE; PINOSTILBENE; PINOSYLVIN; PINOSYLVIN DIMETHYL ETHER; PINOSYLVIN MONOMETHYL ETHER; PLANT EXTRACT; PTEROSTILBENE; RESVERATROL; STILBENE DERIVATIVE; STILBENE DIMETHYL ETHER DERIVATIVE; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; DRUG DETERMINATION; DRUG STRUCTURE; ENZYME SPECIFICITY; ESCHERICHIA COLI; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; RICE; STRUCTURE ANALYSIS;

CLONING, MOLECULAR; ESCHERICHIA COLI; ETHERS; GENETIC ENGINEERING; METHYLTRANSFERASES; ORYZA SATIVA; RECOMBINANT PROTEINS; STILBENES;

ESCHERICHIA COLI; ORYZA SATIVA;

EID: 35748972666     PISSN: 18606768     EISSN: None     Source Type: Journal    
DOI: 10.1002/biot.200700098     Document Type: Article

References (21)

1. Ulrich, S., Wolter, F., Stein, J. M., Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis. Mol. Nutr. Food Res. 2005, 49, 452-461.
2. Baur, J. A., Sinclair, D. A., Therapeutic potential of resveratrol: the in vivo evidence. Nat. Rev. Drug Discov. 2006, 5, 493-506.
3. Jang, M., Cai, L., Udeani, G. O., Slowing, K. V. et al., Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 1997, 275, 218-220.
4. Baur, J. A., Pearson, K. J., Price, N. L., Jamieson, H. A. et al., Resveratrol improves health and survival of mice on a high-calorie diet. Nature 2006, 444, 337-342.
5. Becker, J. V., Armstrong, G. O., van der Merwe, M. J., Lambrechts, M. G. et al., Metabolic engineering of Saccharomyces cerevisiae for the synthesis of the wine-related antioxidant resveratrol. FEMS Yeast Res. 2003, 4, 79-85.
6. Beekwilder, J., Wolswinkel, R., Jonker, H., Hall, R. et al., Production of resveratrol in recombinant microorganisms. Appl. Environ. Microbiol. 2006, 72, 5670-6672.
7. Zhang, Y., Li, S. Z., Li, J., Pan, X. et al., Using unnatural protein fusions to engineer resveratrol biosynthesis in yeast and mammalian cells. J. Am. Chem. Soc. 2006, 128, 13030-13031.
8. Walle, T., Hsieh, F., DeLegge, M. H., Oatis, J. E. Jr, Walle, U.K., High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 2004, 32, 1377-1382.
9. She, Q. B., Ma, W. Y., Wang, M., Kaji, A. et al., Inhibition of cell transformation by resveratrol and its derivatives: differential effects and mechanisms involved. Oncogene 2003, 22, 2143-2150.
10. Cai, Y. J., Wei, Q. Y., Fang, J. G., Yang, L. et al., The 3,4-dihydroxyl groups are important for trans-resveratrol analogs to exhibit enhanced antioxidant and apoptotic activities. Anticancer Res. 2004. 24, 999-1002.
11. Murias, M., Jager, W., Handler, N., Erker, T. et al., Antioxidant, prooxidant and cytotoxic activity of hydroxylated resveratrol analogues: structure-activity relationship. Biochem. Pharmacol. 2005, 15, 903-912.
12. Tolomeo, M., Grimaudo, S., Di Cristina, A., Roberti, M. et al., Pterostilbene and 3′-hydroxypterostilbene are effective apoptosis-inducing agents in MDR and BCR-ABL-expressing leukemia cells. Int. J. Biochem. Cell Biol. 2005, 37, 1709-1726.
13. Suh, N., Paul, S., Hao, X., Simi, B. et al., Pterostilbene, an active constituent of blueberries, suppresses aberrant crypt foci formation in the azoxymethane-induced colon carcinogenesis model in rats. Clin. Cancer Res. 2007, 13, 350-355.
14. Mikstacka, R., Przybylska, D., Rimando, A. M., Baer-Dubowska, W., Inhibition of human recombinant cytochromes P450 CYP1A1 and CYP1B1 by trans-resveratrol methyl ethers. Mol. Nutr. Food Res. 2007, 51, 517-524.
15. Suga, T., Ohta, S., Munesada, S., Ide, N. et al., Endogenous pine wood nematicidal substances in pines, Pinus massoniana, P. strobus and P. palustris. Phytochemistry 1993, 6, 1395-1401.
16. Miyahisa, I., Kaneko, M., Funa, N., Kawasaki, H. et al., Efficient production of (2S)-flavanones by Escherichia coli containing an artificial biosynthetic gene cluster. Appl. Microbiol. Biotechnol. 2005, 68, 498-504.
17. Yamaguchi, T., Kurosaki, F., Suh, D.-Y., Sankawa, U. et al., Cross-reaction of chalcone synthase and stilbene synthase overexpressed in Escherichia coli. FEBS Lett. 1999, 460, 457-461.
18. Miyahisa, I., Funa, N., Ohnishi, Y., Martens, S. et al., Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. Appl. Microbiol. Biotechnol. 2006, 71, 53-58.
19. Chiron, H., Drouet, A., Claudot, A. C., Eckerskorn, C. et al., Molecular cloning and functional expression of a stress-induced multifunctional O-methyltransferase with pinosylvin methyltransferase activity from Scots pine (Pinus sylvestris L.). Plant Mol. Biol. 2000, 44, 733-745.
20. Gonzaléz, M. J. T. G., Pinto, M. M. M., Kijjoa, A., Anantachoke, C., Herz, W., Stilbenes and other constituents of Knema austrosiamensis. Phytochemistry 1993, 2, 433-438.
21. Katsuyama, Y., Funa, N., Miyahisa, I., Horinouchi, S., Synthesis of unnatural flavonoids and stilbenes by exploiting the plant biosynthetic pathway in Escherichia coli. Chem. Biol. 2007, 14, 613-621.