Regiospecific modifications of naringenin for astragalin production in Escherichia coli

Biotechnology and Bioengineering

Volumn 110, Issue 9, 2013, Pages 2525-2535

  Malla, Sailesh ^a,c   Pandey, Ramesh Prasad ^b   Kim, Byung Gee ^a   Sohng, Jae Kyung ^b  

^a Seoul National University   (South Korea)

^b SunMoon University   (South Korea)

^c Chalmers University of Technology   (Denmark)

Author keywords

E. coli; Flavonoids; Glycosylation; Heterologous expression; Kaempferol 3 O glucoside

Indexed keywords

ARABIDOPSIS THALIANA; BIOSYNTHETIC PATHWAY; D GLUCOSE 6 PHOSPHATES; E. COLI; ESCHERICHIA COLI BL21; GLUCOSE 6 PHOSPHATES; HETEROLOGOUS EXPRESSION; KAEMPFEROL-3-O-GLUCOSIDE;

AMINO ACIDS; ENZYME ACTIVITY; ESCHERICHIA COLI; FLAVONOIDS; GLYCOSYLATION; ORGANIC COMPOUNDS; PLANTS (BOTANY);

GLUCOSE;

ASTRAGALIN; FLAVONOID; GLUCOSE; GLUCOSE 6 PHOSPHATE ISOMERASE; KAEMPFEROL; NARINGENIN; URIDINE DIPHOSPHATE GLUCOSE; URIDINE TRIPHOSPHATE GLUCOSE 1 PHOSPHATE URIDYLYLTRANSFERASE;

ARABIDOPSIS THALIANA; ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; DISSOCIATION; ESCHERICHIA COLI; GENE OVEREXPRESSION; GLYCOSYLATION; LARGE SCALE PRODUCTION; NOCARDIA; NOCARDIA FARCINIA; NONHUMAN; SOYBEAN;

E. COLI; FLAVONOIDS; GLYCOSYLATION; HETEROLOGOUS EXPRESSION; KAEMPFEROL-3-O-GLUCOSIDE;

ARABIDOPSIS PROTEINS; BIOREACTORS; ESCHERICHIA COLI; FERMENTATION; FLAVANONES; FLAVONOIDS; KAEMPFEROLS; METABOLIC NETWORKS AND PATHWAYS; MIXED FUNCTION OXYGENASES; MUTATION; RECOMBINANT PROTEINS; STEREOISOMERISM;

ARABIDOPSIS THALIANA; ESCHERICHIA COLI; GLYCINE MAX; NOCARDIA;

EID: 84880810277     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.24919     Document Type: Article

References (43)

1. Adam KP. 1999. Phenolic constituents of the fern Phegopteris connectilis. Phytochemistry 52:929-934.
2. Beninger CW, Hosfield GL. 1999. Astragalin (kaempferol 3-O-glucoside) and proanthocyanidins are the main flavonoid compounds of four Phaseolus vulgaris L. Seed coat color genotypes, Proceeding/symposium.
3. Beninger CW, Hosfield GL. 1999. Flavonoid composition of three genotypes of dry bean (Phaseolus vulgaris) differing in seedcoat color. J Am Soc Hortic Sci 124:514-518.
4. Bowles D, Isayenkova J, Lim EK, Poppenberger B. 2005. Glycosyltransferases: Managers of small molecules. Curr Opin Plant Biol 8:254-263.
5. Bugg TDH. 2003. Dioxygenase enzymes: Catalytic mechanisms and model. Tetrahedron 59:7075-7101.
6. Correia H, González-Paramás A, Amaral MT, Santos-Buelga C, Batista MT. 2006. Polyphenolic profile characterization of Agrimonia eupatoria L. by HPLC with different detection devices. Biomed Chromatogr 20:88-94.
7. Datsenko KA, Wanner BL. 2000. One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products. Proc Natl Acad Sci U S A 97:6640-6645.
8. Ebada SS, Ayoub NA, Singab ANB, Al-azizi MM. 2008. Phytophenolics from Peltophorum africanum Sond.(Fabaceae) with promising hepatoprotective activity. Pharmacogn Mag 4:287-293.
9. Fraenkel DG. 1968. The accumulation of glucose-6-phosphate from glucose and its effect in an Escherichia coli mutant lacking phosphoglucose isomerase and glucose-6-phosphate dehydrogenase. J Biol Chem 243:6541-6457.
10. Hall D, Yuan XX, Murata J, De Luca V. 2012. Molecular cloning and biochemical characterization of the UDP-glucose: Flavonoid 3-O-glucosyltransferase from Concord grape (Vitis labrusca). Phytochemistry 74:90-99.
11. Harborne JB, Williams CA. 2000. Advances in flavonoid research since 1992. Phytochemistry 55:481-504.
12. Hiraoka A, Hasegawa M. 1975. Flavonoid glycosides from five Cyathea species. Bot Mag 88:127-130.
13. Hwang EI, Kaneko M, Ohnishi Y, Horinouchi S. 2003. Production of plant-specific flavanones by Escherichia coli containing an artificial gene cluster. Appl Environ Microbiol 69:2699-2706.
14. Keseler IM, Bonavides-Martínez C, Collado-Vides J, Gama-Castro S, Gunsalus RP, Johnson DA, Krummenacker M, Nolan LM, Paley S, Paulsen IT, Peralta-Gil M, Santos-Zavaleta A, Shearer AG, Karp PD. 2009. EcoCyc: A comprehensive view of Escherichia coli biology. Nucleic Acids Res 37:D464-D470.
15. Kim BG, Sung SH, Ahn JH. 2012. Biological synthesis of quercetin 3-O-N-acetylglucosamine conjugate using engineered Escherichia coli expressing UGT78D2. Appl Microbiol Biotechnol 93:2447-2453.
16. Kim JH, Shin KH, Ko JH, Ahn JH. 2006. Glucosylation of flavonols by Escherichia coli expressing glucosyltransferase from rice (Oryza sativa). J Biosci Bioeng 102:135-137.
17. Ko JH, Kim BG, Ahn JH. 2006. Glycosylation of flavonoids with a glycosyltransferase from Bacillus cereus. FEMS Microbiol Lett 258:263-268.
18. Kovganko NV, Kashkan ZhN, Krivenok SN, Potapovich MV, Eremin AN, Metelitsa DI. 2004. Bioactive compounds in the flora of Belarus. 2. Astragalin, an effective protector of catalase from ultrasonic inactivation in aqueous solutions. Chem Nat Compd 40:71-74.
19. Kovinich N, Saleem A, Arnason JT, Miki B. 2010. Functional characterization of a UDP-glucose:flavonoid 3-O-glucosyltransferase from the seed coat of black soybean (Glycine max (L.) Merr.). Phytochemistry 71:1253-1263.
20. Lin YM, Anderson H, Flavin MT, Pai YH, Mata-Greenwood E, Pengsuparp T, Pezzuto JM, Schinazi RF, Hughes SH, Chen FC. 1997. In vitro anti-HIV activity of biflavonoids isolated from Rhus succedanea and Garcinia multiflora. J Nat Prod 60:884-888.
21. Malla S, Koffas MA, Kazlauskas RJ, Kim BG. 2012. Production of 7-O-methyl aromadendrin, a medicinally valuable flavonoid, in Escherichia coli. Appl Environ Microbiol 78:684-694.
22. Mao Z, Shin HD, Chen RR. 2006. Engineering the E. coli UDP-glucose synthesis pathway for oligosaccharide synthesis. Biotechnol Prog 22:369-374.
23. Matsumoto M, Kotani M, Fujita A, Higa S, Kishimoto T, Suemura M, Tanaka T. 2002. Oral administration of persimmon leaf extract ameliorates skin symptoms and transepidermal water loss in atopic dermatitis model mice, NC/Nga. Br J Dermatol 146:221-227.
24. Middleton E, Jr., Kandaswami C, Theoharides TC. 2000. The effects of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacol Rev 52:673-751.
25. Morita T, El-Kazzaz W, Tanaka Y, Inada T, Aiba H. 2003. Accumulation of glucose-6-phosphate or fructose-6-phosphate is responsible for destabilization of glucose transporter mRNA in Escherichia coli. J Biol Chem 278:15608-15614.
26. Owens DK, Alerding AB, Crosby KC, Bandara AB, Westwood JH, Winkel BS. 2008. Functional analysis of a predicted flavonol synthase gene family in Arabidopsis. Plant Physiol 147:1046-1061.
27. Pandey RP, Malla S, Simkhada D, Kim BG, Sohng JK. 2013. Production of 3-O-xylosyl quercetin in Escherichia coli. Appl Microbiol Biotechnol 97:1889-1901.
28. Paquette S, Møller BL, Bak S. 2003. On the origin of family 1 plant glycosyltransferases. Phytochemistry 62:399-413.
29. Parejo I, Viladomat F, Bastida J, Schmeda-Hirschmann G, Burillo J, Codina C. 2004. Bioguided isolation and identification of the nonvolatile antioxidant compounds from fennel (Foeniculum vulgare Mill.) waste. J Agric Food Chem 52:1890-1897.
30. Park HJ, Young HS, Park KY, Rhee SH, Chung HY, Choi JS. 1991. Flavonoids from the whole plants of Orostachys japonicus. Arch Pharmacal Res 14:167-171.
31. Parveen Z, Deng Y, Saeed MK, Dai R, Ahamad W, Yu YH. 2007. Antiinflammatory and analgesic activities of Thesium chinense Turcz extracts and its major flavonoids, kaempferol and kaempferol-3-O-glucoside. Yakugaku Zasshi 27:1275-1279.
32. Parveen Z, Deng Y, Saeed MK, Dai R, Ahmad W, Yu Y, Yasmeen T. 2006. Optimizations of conditions for maximum recovery of astragalin from Thesium chinense Turcz. J Appl Sci 6:2829-2832.
33. Peterson J, Dwyer J. 1998. Flavonoids: Dietary occurrence and biochemical activity. Nutr Res 18:1995-2018.
34. Prescott AG, Stamford NP, Wheeler G, Firmin JL. 2002. In vitro properties of a recombinant flavonol synthase from Arabidopsis thaliana. Phytochemistry 60:589-593.
35. Ren G, Hou J, Fang Q, Sun H, Liu X, Zhang L, Wang PG. 2012. Synthesis of flavonol 3-O-glycoside by UGT78D1. Glycoconj J 29:425-432.
36. Ross JA, Kasum CM. 2002. Dietary flavonoids: Bioavailability, metabolic effects, and safety. Annu Rev Nutr 22:19-34.
37. Sambrook J, Russell DW. 2001. Molecular Cloning: A laboratory manual, third ed. Cold Spring Harbor, NY: Cold Spring Harbor Laboratory.
38. Stracke R, De Vos RC, Bartelniewoehner L, Ishihara H, Sagasser M, Martens S, Weisshaar B. 2009. Metabolomic and genetic analyses of flavonol synthesis in Arabidopsis thaliana support the in vivo involvement of leucoanthocyanidin dioxygenase. Planta 229:427-445.
39. Tang LJ, Zhang SF, Yang JZ, Gao WT. 2004. New synthetic methods of flavones. Chin J Org Chem 24:882-889.
40. Tsuchiya H, Sato M, Miyazaki T, Fujiwara S, Tanigaki S, Ohyama M, Tanaka T, Iinuma M. 1996. Comparative study on the antibacterial activity of phytochemical flavanones against methicillin-resistant Staphylococcus aureus. J Ethnopharmacol 50:27-34.
41. Ververidis F, Trantas E, Douglas C, Vollmer G, Kretzschmar G, Panopoulos N. 2007. Biotechnology of flavonoids and other phenylpropanoid-derived natural products. Part I: Chemical diversity, impacts on plant biology and human health. Biotechnol J 2:1214-1234.
42. Vogt T, Jones P. 2000. Glycosyltransferases in plant natural product synthesis: Characterization of a supergene family. Trends Plant Sci 5:380-386.
43. Xu P, Vansiri A, Bhan N, Koffas MAG. 2012. ePathBrick: A synthetic biology platform for engineering metabolic pathways in E. coli. ACS Synth Biol 1:256-266.