Bio-fermentation of modified flavonoids: An example of in vivo diversification of secondary metabolites

Phytochemistry

Volumn 65, Issue 1, 2004, Pages 31-41

  Willits, Michael G ^a   Giovanni, Maïté ^b   Prata, Rogerio T N ^a   Kramer, Catherine M ^a   De Luca, Vincenzo ^c   Steffens, John C ^a   Graser, Gerson ^a  

^a SYNGENTA BIOTECHNOLOGY INC   (United States)

^b CEMAGREF   (France)

^c BROCK UNIVERSITY   (Canada)

Author keywords

Arabidopsis thaliana; Cruciferae; Drug discovery; Flavonoids; Labiatae; Mentha x piperita; Natural products; O Glucosyltransferases; O Methyltransferases; Plant secondary metabolites

Indexed keywords

FLAVONOID; FLAVONOL; GLUCOSIDE; GLUCOSYLTRANSFERASE; METHYLTRANSFERASE; QUERCETIN; VEGETABLE PROTEIN;

ARABIDOPSIS; ARTICLE; BACTERIUM CULTURE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DNA MODIFICATION; DRUG STRUCTURE; ENZYME SUBSTRATE; ENZYME SYNTHESIS; ESCHERICHIA COLI; FERMENTATION; GENE EXPRESSION; IN VITRO STUDY; MENTHA; METABOLITE; METHYLATION; NONHUMAN; NUCLEOTIDE SEQUENCE; ONION; PROTEIN EXPRESSION;

ALLIUM; ALLIUM CEPA; ARABIDOPSIS; ARABIDOPSIS THALIANA; BRASSICACEAE; ESCHERICHIA COLI; LAMIACEAE; MENTHA; MENTHA PIPERITA; MENTHA X PIPERITA;

EID: 0742287178     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2003.10.005     Document Type: Article

References (35)

1. Albrecht M., Shinichi T., Steiger S., Zheng-Yu W., Sandmann G. Novel hydroxycarotenoids with improved antioxidative properties produced by gene combination in Escherichia coli. Nat. Biotechnol. 18:2000;843-846.
2. Arend J., Warzecha H., Hefner T., Stöckigt J. Utilizing genetically engineered bacteria to produce plant-specific glucosides. Biotechnol. Bioeng. 76:2001;126-131.
3. Brunet G., Ibrahim R.K. O-Methylation of flavonoids by cell-free extracts of calamondin orange. Phytochemistry. 19:1980;741-746.
4. Buckingham J. Dictionary of Natural Products on CD. 2000;Chapman & Hall/CRC Press, England.
5. Christensen A.B., Gregersen P.L., Olsen C.E., Collinge D.B. A flavonoid 7-O-methyltransferase is expressed in barley leaves in response to pathogen attack. Plant Mol. Biol. 36:1998;219-227.
6. Cordell G.A. Biodiversity and drug discovery - a symbiotic relationship. Phytochemistry. 55:2000;463-480.
7. Di Carlo G., Mascolo N., Izzo A.A., Capasso F. Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci. 65:1999;337-353.
8. Facchini P.J., De Luca V. Expression in Escherichia coli and partial characterization of two tyrosine/dopa decarboxylases from opium poppy. Phytochemistry. 38:1995;1119-1126.
9. Facchini P.J. Plant secondary metabolism. out of the evolutionary abyss Trends Plant Sci. 4:1999;382-384.
10. Ford C.M., Boss P.K., Høj P.B. Cloning and characterization of Vitis vinifera UDP-glucose:flavonoid 3-O-glucosyltransferase, a homologue of the enzyme encoded by the maize Bronze-1 locus that may primarily serve to glucosylate anthocyanidins in vivo. J. Biol. Chem. 273:1998;9224-9233.
11. Frick S., Kutchan T.M. Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J. 17:1999;329-339.
12. Frick S., Ounaroon A., Kutchan T.M. Combinatorial biochemistry in plants. the case of O-methyltransferases Phytochemistry. 56:2001;1-4.
13. Graham T.L. Flavonoid and flavonol glycoside metabolism in Arabidopsis. Plant Physiol. Biochem. 36:1998;135-144.
14. Harborne J.B., Baxter H. Handbook of Natural Flavonoids. 2 vols. 1999;John Wiley & Sons, Chichester.
15. Harborne J.B., Williams C.A. Advances in flavonoid research since 1992. Phytochemistry. 55:2000;481-504.
16. He X.-Z., Reddy J.T., Dixon R.A. Stress responses in alfalfa (Medicago sativa L.). XXII. cDNA cloning and characterization of an elicitor-inducible isoflavone 7-O-methyltransferase. Plant Mol. Biol. 36:1998;43-54.
17. Hirotani M., Kuroda R., Suzuki H., Yoshikawa T. Cloning and expression of UDP-glucose. flavonoid 7-O-glucosyltransferase from hairy root cultures of Scutellaria baicalensis Planta. 210:2000;1006-1013.
18. Hollmann P.C.H., Arts I.C.W. Flavonols, flavones and flavanols - nature, occurrence and dietary burden. J. Sci. Food Agric. 80:2000;1081-1093.
19. Ibrahim R.K., Varin L. Flavonoid enzymology. Lea P.J. Methods in Plant Biochemistry, Vol. 9. 1993;Academic Press, London.
20. Ibrahim R.K. Plant O-methyltransferase signatures. Trends Plant Sci. 2:1997;249-250.
21. Ibrahim R.K., Bruneau A., Bantignies B. Plant O-methyltransferases. molecular analysis, common signature and classification Plant Mol. Biol. 36:1998;1-10.
22. Kramer C.M., Prata R.T.N., Willits M.G., De, Luca V., Steffens J.C., Graser G. Cloning and regiospecificity studies of two flavonoid glucosyltransferases from Allium cepa. Phytochemistry. 64:2003;1069-1076.
23. Kutchan T.M. Expression of enzymatically active cloned strictosidine synthase from the higher plant Rauvolfia serpentina in Escherichia coli. FEBS Lett. 257:1989;127-130.
24. Lagrimini L.M., Burkhart W., Moyer M., Rothstein S. Molecular cloning of complementary DNA encoding the lignin-forming peroxidase from tobacco. molecular analysis and tissue-specific expression Proc. Natl. Acad. Sci. U.S.A. 84:1987;7542-7546.
25. Lange B.M., Wildung M.R., Stauber E.J., Sanchez C., Pouchnik D., Croteau R. Probing essential oil biosynthesis and secretion by functional evaluation of expressed sequence tags from mint glandular trichomes. Proc. Natl. Acad. Sci. U.S.A. 97:2000;2934-2939.
26. Luque T., Okano K., O'Reilly D.R. Characterization of a novel silkworm (Bombyx mori) phenol UDP-glucosyltransferase. Eur. J. Biochem. 269:2002;819-825.
27. O'Neil M.J., Lewis J.A. The renaissance of plant research in the pharmaceutical industry. Kinghorn A.D., Balandrin M.F. Human Medicinal Agents from Plants, ACS Symposium Series No. 534. 1993;48 American Chemical Society, Washington, DC.
28. Rozen, S., Skaletsky, H.J., 1998. Primer3. Code available at http://www-genome.wi.mit.edu/genome_software/other/primer3.html .
29. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning: A Laboratory Manual. 1989;Cold Spring Harbor Laboratory Press, NY.
30. Sneader W. Drug Discovery: The Evolution of Modern Medicines. 1985;John Wiley & Sons, Chichester.
31. Veit M., Pauli G.F. Major flavonoids from Arabidopsis thaliana leaves. J. Nat. Prod. 62:1999;1301-1303.
32. Vidgren J., Svensson L.A., Liljas A. Crystal structure of catechol O-methyltransferase. Nature. 368:1994;354-358.
33. Vogt T., Jones P. Glycosyltransferases in plant natural product synthesis. characterization of a supergene family Trends Plant Sci. 5:2000;380-386.
34. Voirin B., Bayet C., Colson M. Demonstration that flavone aglycones accumulate in the peltate glands of Mentha x piperita leaves. Phytochemistry. 34:1993;85-87.
35. Voirin B., Bayet C., Faure O., Jullien F. Free flavonoid aglycones as markers of parentage in Mentha aquatica, M. citrata, M. spicata and M. x piperita. Phytochemistry. 50:1999;1189-1193.