Investigation of two distinct flavone synthases for plant-specific flavone biosynthesis in Saccharomyces cerevisiae

Applied and Environmental Microbiology

Volumn 71, Issue 12, 2005, Pages 8241-8248

  Leonard, Effendi ^a   Yan, Yajun ^a   Lim, Kok Hong ^a   Koffas, Mattheos A G ^a  

^a the State University of New York   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; DRUG PRODUCTS; ENZYME KINETICS; PLANTS (BOTANY); YEAST;

FLAVONE SYNTHASES; LUTEOLIN; YEAST STRAIN;

ENZYMES;

ACETIC ACID; APIGENIN; CHALCONE SYNTHASE; CHRYSIN; CINNAMATE 4 MONOOXYGENASE; CYTOCHROME P450 REDUCTASE; ERIODICTYOL; FLAVONE; FLAVONE SYNTHASE; FLAVONE SYNTHASE I; FLVAONE SYNTHASE II; GLUCOSE; ISOMERASE; LONG CHAIN FATTY ACID COENZYME A LIGASE; LUTEOLIN; NARINGENIN; PARA COUMARIC ACID; PHENYLPROPANOID ACID; PINOCEMBRINE; PROPIONIC ACID DERIVATIVE; RAFFINOSE; SYNTHETASE; UNCLASSIFIED DRUG;

SECONDARY METABOLITE;

ARTICLE; BIOSYNTHESIS; DOSE RESPONSE; FUNGAL METABOLISM; FUNGAL STRAIN; NONHUMAN; PLANT; SACCHAROMYCES CEREVISIAE; YEAST;

CYTOCHROME P-450 ENZYME SYSTEM; FLAVONES; FLAVONOIDS; GENOTYPE; KINETICS; MIXED FUNCTION OXYGENASES; PLANTS; SACCHAROMYCES CEREVISIAE; SACCHAROMYCES CEREVISIAE PROTEINS;

SACCHAROMYCES CEREVISIAE;

EID: 29144455444     PISSN: 00992240     EISSN: None     Source Type: Journal    
DOI: 10.1128/AEM.71.12.8241-8248.2005     Document Type: Article

References (39)

1. Akashi, T., M. Fukuchi-Mizulani, T. Aoki, Y. Ueyama, K. Yonekura-Sakakibara, Y. Tanaka, T. Kusumi, and S. Ayabe. 1999. Molecular cloning and biochemical characterization of a novel cytochrome P450, flavone synthase II, that catalyzes direct conversion of flavanones to flavones. Plant Cell Physiol. 40:1182-1186.
2. Bell, S. G., R. J. Sowden, and L. L. Wong. 2001. Engineering the heme monooxygenase cytochrome P450(cam) for monoterpene oxidation. Chem. Commun. 7:635-636.
3. Blake, J. A. R., M. Pritchard, S. H. Ding, G. C. M. Smith, B. Burchell, C. R. Wolf, and T. Friedberg. 1996. Coexpression of a human P450 (CYP3A4) and P450 reductase generates a highly functional monooxygenase system in Escherichia coli. FEES Lett. 397:210-214.
4. Brewer, C. B., and J. A. Peterson. 1986. Single-turnover kinetics of oxycytochrome P-450 Cam with reduced putidaredoxin. Fed. Proc. 45:1506.
5. Brewer, C. B., and J. A. Peterson. 1986. Single turnover studies with oxycytochrome P-450 Cam. Arch. Biochem. Biophys. 249:515-521.
6. Daran-Lapujade, P., M. L. Jansen, J. M. Daran, W. van Gulik, J. H. de Winde, and J. T. Pronk. 2004. Role of transcriptional regulation in controlling fluxes in central carbon metabolism of Saccharomyces cerevisiae. A chemostat culture study. J. Biol. Chem. 279:9125-9138.
7. Gietz, R. D., and R. H. Schiestl. 1995. Transforming yeast with DNA. Methods Mol. Cell. Biol. 5:255-269.
8. Gietz, R. D., R. H. Schiestl, A. R. Willems, and R. A. Woods. 1995. Studies on the transformation of intact yeast cells by the Liac/S-DNA/PEG procedure. Yeast 11:355-360.
9. Guthrie, C., G. R. Fink, M. I. Simon, and J. N. Abelson (ed.). 1991. Guide to yeast genetics and molecular biology. Methods Enzymol. 194:1-863.
10. Harbone, A. J. 1998. Phytochemical methods: a guide to modern techniques of plant analysis, 3rd ed. Springer, New York, N.Y.
11. Hotze, M., G. Schroder, and J. Schroder. 1995. Cinnamate 4-hydroxylase from Catharanthus roseus, and a strategy for the functional expression of plant cytochrome P450 proteins as translational fusions with P450 reductase in Escherichia coli. FEES Lett. 374:345-350.
12. Hwang, E. I., M. Kaneko, Y. Ohnishi, and S. Horinouchi. 2003. Production of plant-specific flavanones by Eschenchia coli containing an artificial gene cluster. Appl. Environ. Microbiol. 69:2699-2706.
13. Iwata, H., K. Fujita, H. Kushida, A. Suzuki, Y. Konno, K. Nakamura, A. Fujino, and T. Kamataki. 1998. High catalytic activity of human cytochrome P450 co-expressed with human NADPH-cytochrome P450 reductase in Escherichia coli. Biochem. Pharmacol. 55:1315-1325.
14. James, E. S., and J. E. Cronan. 2004. Expression of two Eschenchia coli acetyl-CoA carboxylase subunits is autoregulated. J. Biol. Chem. 279:2520-2527.
15. Jiang, H., K. V. Wood, and J. A. Morgan. 2005. Metabolic engineering of the phenylpropanoid pathway in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 71:2962-2969.
16. Kaltenbach, M., G. Schröder, E. Schmelzer, V. Lutz, and J. Schroder. 1999. Flavonoid hydroxylase from Catharanthus roseus: cDNA, heterologous expression, enzyme properties and cell-type specific expression in plants. Plant J. 19:183-193.
17. Lebeau, J., R. Neviere, and R. Cotelle. 2001. Beneficial effects of different flavonoids on functional recovery after ischemia and reperfusion in isolated rat heart. Bioorg. Med. Chem. Lett. 11:23-27.
18. Li, S. J., and J. E, Cronan. 1993. Growth rate regulation of Eschenchia coli acetyl coenzyme A carboxylase, which catalyzes the first committed step of lipid biosynthesis. J. Bacteriol. 175:332-340.
19. Lukacin, R., U. Matern, K. T. Junghanns, M. L. Heskamp, L. Britsch, G. Forkmann, and S. Martens. 2001. Purification and antigenicity of flavone synthase I from irradiated parsley cells. Arch. Biochem. Biophys. 393:177-183.
20. Martens, S., and G. Forkmann. 1999. Cloning and expression of flavone synthase II from Gerbera hybrids. Plant J. 20:611-618.
21. Martens, S., and G. Forkmann. 1998. Genetic control of flavone synthase II activity in flowers of Gerbera hybrids. Phytochemistry 49:1953-1958.
22. Martens, S., G. Forkmann, U. Matern, and R. Lukacin. 2001. Cloning of parsley flavone synthase I. Phytochemistry 58:43-46.
23. Middleton, E., Jr., C. Kandaswami, and T. C. Theoharides. 2000. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 52:673-751.
24. Miksicek, R. J. 1995. Estrogenic flavonoids-structural requirements for biological activity. Proc. Soc. Exp. Biol. Med. 208:44-50.
25. Parikh, A., E. M. J. Gillam, and F. P. Guengerich. 1997. Drug metabolism by Escherichia coli expressing human cytochromes P450. Nat. Biotechnol. 15: 784-788.
26. Pompon, D., B. Louerai, A. Bronine, and P. Urban. 1996. Yeast expression of animal and plant P450s in optimized redox environments. Methods Enzymol. 272:51-64.
27. Ross, J. A., and C. M. Kasum. 2002. Dietary flavonoids: bioavailability, metabolic effects, and safety. Annu. Rev. Nutr. 22:19-34.
28. Rump, A. F. E., M. Schussler, D. Acar, A. Cordes, M. Theisohn, R. Rosen, W. Klaus, and U. Fricke. 1994. Functional and antiischemic effects of luteolin-7-glucoside in isolated rabbit hearts. Gen. Pharmacol. 25:1137-1142.
29. Sambrook, J., E. F. Fritsch, and T. Maniatis. 1989. Molecular cloning: a laboratory manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.
30. Schoenbohm, C., S. Martens, C. Eder, G. Forkmann, and B. Weisshaar. 2000. Identification of the Arabidopsis thaliana flavonoid 3′-hydroxylase gene and functional expression of the encoded P450 enzyme. Biol. Chem. 381: 749-753.
31. Schussler, M., J. Holzl, A. F. E. Rump, and U. Fricke. 1995. Functional and antiischaemic effects of monoacetyl-vitexinrhamnoside in different in vitro models. Gen. Pharmacol. 26:1565-1570.
32. Sieber, V., C. A. Martinez, and F. H. Arnold. 2001. Libraries of hybrid proteins from distantly related sequences. Nat. Biotechnol. 19:456-460.
33. Staral, V. J., and J. C. Escalante-Semerena. 2004. Acetyl-coenzyme A synthetase (AMP forming). Cell. Mol. Life Sci. 61:2020-2030.
34. Verduyn, C., E. Postma, W. A. Scheffers, and J. P. Vandijken. 1992. Effect of benzoic acid on metabolic fluxes in yeasts-a continuous culture study on the regulation of respiration and alcoholic fermentation. Yeast 8:501-517.
35. Viola, H., C. Wasowski, M. L. Destein, C. Wolfman, R. Silveira, F. Dajas, J. H. Medina, and A. C. Paladini. 1995. Apigenin, a component of Matricaria recutita flowers, is a central benzodiazepine receptors ligand with anxiolytic effects. Planta Med. 61:213-216.
36. Wolfman, C., H. Viola, A. Paladini, F. Dajas, and J. H. Medina. 1994. Possible anxiolytic effects of chrysin, a central benzodiazepine receptor ligand isolated from Passiflora coerulea. Pharmacol. Biochem. Behav. 47:1-4.
37. Wolfman, C., H. Viola, C. Wasowski, M. L. Destein, R. Silveira, F. Dajas, J. H. Medina, and A. C. Paladini. 1995. Apigenin, a component of Matricaria recutita (L.) flowers, is a central benzodiazepine receptor ligand with anxiolytic effects. J. Neurochem. 65:5167-5167.
38. Yan, Y., J. Chemler, L. Huang, S. Martens, and M. A. Koffas. 2005. Metabolic engineering of anthocyanin biosynthesis in Escherichia call. Appl. Environ. Microbiol. 71:3617-3623.
39. Yan, Y., A. Kohli, and M. A. Koffas. 2005. Biosynthesis of natural flavanones in Saccharomyces cerevisiae. Appl. Environ. Microbiol. 71:5610-5613.