De novo biosynthesis of Gastrodin in Escherichia coli

Metabolic Engineering

Volumn 35, Issue , 2016, Pages 138-147

  Bai, Yanfen ^a,b,c   Yin, Hua ^a,b   Bi, Huiping ^a,b   Zhuang, Yibin ^a,b   Liu, Tao ^a,b   Ma, Yanhe ^a  

^a Chinese Academy of Sciences   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Chorismate; Directed evolution; Escherichia coli; Gastrodin; Glycosyltransferase; Metabolic engineering

Indexed keywords

BIOCHEMISTRY; BIOSYNTHESIS; ESCHERICHIA COLI; METABOLISM; PLANTS (BOTANY); SYNTHESIS (CHEMICAL);

4-HYDROXYBENZOIC ACIDS; ALCOHOL DEHYDROGENASE; CATALYTIC PROPERTIES; CHORISMATE; DIRECTED EVOLUTION; GASTRODIN; GLYCOSYL TRANSFERASE; MICROBIAL SYNTHESIS;

METABOLIC ENGINEERING;

4 HYDROXYBENZOIC ACID; 4 HYDROXYBENZYL ALCOHOL; ALCOHOL DEHYDROGENASE; ALCOHOL DERIVATIVE; BENZYL DERIVATIVE; CARBOXYLIC ACID REDUCTASE; GASTRODIN; GLYCOSYLTRANSFERASE; OXIDOREDUCTASE; UBIQUINONE; UNCLASSIFIED DRUG; BACTERIAL PROTEIN; BENZYL ALCOHOL DERIVATIVE; GLUCOSIDE; PLANT PROTEIN;

ARTICLE; BACTERIAL STRAIN; BIOSYNTHESIS; CONTROLLED STUDY; DIRECTED MOLECULAR EVOLUTION; ENZYMATIC ASSAY; ENZYME ACTIVITY; ESCHERICHIA COLI; EXTRACTION; GENE OVEREXPRESSION; NOCARDIA; NOCARDIA IOWENSIS; NONHUMAN; PRIORITY JOURNAL; RHODIOLA; SCREENING; ENZYMOLOGY; GENETICS; METABOLISM;

BACTERIAL PROTEINS; BENZYL ALCOHOLS; ESCHERICHIA COLI; GLUCOSIDES; GLYCOSYLTRANSFERASES; NOCARDIA; OXIDOREDUCTASES; PLANT PROTEINS; RHODIOLA;

EID: 84955325204     PISSN: 10967176     EISSN: 10967184     Source Type: Journal    
DOI: 10.1016/j.ymben.2016.01.002     Document Type: Article

References (46)

1. Ahn E.K., Jeon H.J., Lim E.J., Jung H.J., Park E.H. Anti-inflammatory and anti-angiogenic activities of Gastrodia elata Blume. J. Ethnopharmacol. 2007, 110:476-482.
2. Ajikumar P.K., Xiao W.H., Tyo K.E., Wang Y., Simeon F., Leonard E., Mucha O., Phon T.H., Pfeifer B., Stephanopoulos G. Isoprenoid pathway optimization for Taxol precursor overproduction in Escherichia coli. Science 2010, 330:70-74.
3. Bai Y.F., Bi H.P., Zhuang Y.B., Liu C., Cai T., Liu X.N., Zhang X.L., Liu T., Ma Y.H. Production of salidroside in metabolically engineered Escherichia coli. Sci. Rep. 2014, 4:6640.
4. Bongaerts J., Kramer M., Muller U., Raeven L., Wubbolts M. Metabolic engineering for microbial production of aromatic amino acids and derived compounds. Metab. Eng. 2001, 3:289-300.
5. Chang A., Singh S., Phillips G.N., Thorson J.S. Glycosyltransferase structural biology and its role in the design of catalysts for glycosylation. Curr. Opin. Biotech. 2011, 22:800-808.
6. Duan X.H., Li Z.L., Yang D.S., Zhang F.L., Lin Q., Dai R. Study on the chemical constituents of Gastrodia elata. Zhongyaocai 2013, 36:1608-1611.
7. Gallage N.J., Hansen E.H., Kannangara R., Olsen C.E., Motawia M.S., Jorgensen K., Holme I., Hebelstrup K., Grisoni M., Moller B.L. Vanillin formation from ferulic acid in Vanilla planifolia is catalysed by a single enzyme. Nat. Commun. 2014, 5:4037.
8. Gantt R.W., Peltier-Pain P., Thorson J.S. Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules. Nat. Prod. Rep. 2011, 28:1811-1853.
9. Gao H.M. Gastrodia elata Blume. Dietary Chinese Herbs: Chemistry, Pharmacology and Clinical Evidence 2015, 127-133. Springer-Verlag Wien. Y.Z. Liu, Z.M. Wang, J.Z. Zhang (Eds.).
10. Han Y.J., Je J.H., Kim S.H., Ahn S.M., Kim H.N., Kim Y.R., Choi Y.W., Shin H.K., Choi B.T. Gastrodia elata shows neuroprotective effects via activation of PI3K signaling against oxidative glutamate toxicity in HT22 Cells. Am. J. Chin. Med. 2014, 42:1007-1019.
11. Harle J., Gunther S., Lauinger B., Weber M., Kammerer B., Zechel D.L., Luzhetskyy A., Bechthold A. Rational design of an aryl-C-glycoside catalyst from a natural product O-Glycosyltransferase. Chem. Biol. 2011, 18:520-530.
12. He A.M., Li T., Daniels L., Fotheringham I., Rosazza J.P.N. Nocardia sp carboxylic acid reductase: cloning, expression, and characterization of a new aldehyde oxidoreductase family. Appl. Env. Microb. 2004, 70:1874-1881.
13. Hoffmeister D., Wilkinson B., Foster G., Sidebottom P.J., Ichinose K., Bechthold A. Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem. Biol. 2002, 9:287-295.
14. Hsieh C.L., Chiang S.Y., Cheng K.S., Lin Y.H., Tang N.Y., Lee C.J., Pon C.Z., Hsieh C.T. Anticonvulsive and free radical scavenging activities of Gastrodia elata Bl. in kainic acid-treated rats. Am. J. Chin. Med. 2001, 29:331-341.
15. Jung J.W., Yoon B.H., Oh H.R., Ahn J.H., Kim S.Y., Park S.Y., Ryu J.F. Anxiolytic-Like effects of Gastrodia elata and its phenolic constituents in mice. Pharm. Bull. 2006, 29:261-265.
16. Kikuchi Y., Tsujimoto K., Kurahashi O. Mutational analysis of the feedback sites of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase of Escherichia coli. Appl. Env. Microb. 1997, 63:761-762.
17. Krauth C., Fedoryshyn M., Schleberger C., Luzhetskyy A., Bechthold A. Engineering a function into a glycosyltransferase. Chem. Biol. 2009, 16:28-35.
18. Leonard E., Yan Y., Fowler Z.L., Li Z., Lim C.G., Lim K.H., Koffas M.A.G. Strain improvement of recombinant Escherichia coli for efficient production of plant flavonoids. Mol. Pharm. 2008, 5:257-265.
19. Li H.B., Chen F. Preparative isolation and purification of gastrodin from the Chinese medicinal plant Gastrodia elata by high-speed counter-current chromatography. J. Chromatogr. A. 2004, 1052:229-232.
20. Lim C.G., Fowler Z.L., Hueller T., Schaffer S., Koffas M.A.G. High-yield resveratrol production in engineered Escherichia coli. Appl. Env. Microb. 2011, 77:3451-3460.
21. Lin Y.H., Shen X.L., Yuan Q.P., Yan Y.J. Microbial biosynthesis of the anticoagulant precursor 4-hydroxycoumarin. Nat. Commun. 2013, 4:2603.
22. Lin Y.H., Yan Y.J. Biosynthesis of caffeic acid in Escherichia coli using its endogenous hydroxylase complex. Microb. Cell. Fact. 2012, 11:42.
23. Liu J., Mori A. Antioxidant and free-radical scavenging activities of Gastrodia-Elata Bl and Uncaria-Rhynchophylla (Miq) Jacks. Neuropharmacology 1992, 31:1287-1298.
24. Nakagawa A., Minami H., Kim J.S., Koyanagi T., Katayama T., Sato F., Kumagai H. A bacterial platform for fermentative production of plant alkaloids. Nat. Commun. 2011, 2:326.
25. Nakano M.M., Corbell N., Besson J., Zuber P. Isolation and characterization of sfp: a gene that functions in the production of the lipopeptide biosurfactant, surfactin in Bacillus subtilis. Mol. Gen. Genet. 1992, 232:313-321.
26. Ojemann L.M., Nelson W.L., Shin D.S., Rowe A.O., Buchanan R.A. Tian ma, an ancient Chinese herb, offers new options for the treatment of epilepsy and other conditions. Epilepsy Behav. 2006, 8:376-383.
27. Osmani S.A., Bak S., Moller B.L. Substrate specificity of plant UDP-dependent glycosyltransferases predicted from crystal structures and homology modeling. Phytochemistry 2009, 70:325-347.
28. Park S., Kim D.S., Kang S. Gastrodia elata Blume water extracts improve insulin resistance by decreasing body fat in diet-induced obese rats: vanillin and 4-hydroxybenzaldehyde are the bioactive candidates. Eur. J. Nutr. 2011, 50:107-118.
29. Patnaik R., Liao J.C. Engineering of Escherichia coli central metabolism for aromatic metabolite production with near theoretical yield. Appl. Env. Microb. 1994, 60:3903-3908.
30. Podstolski A., Havkin-Frenkel D., Malinowski J., Blount J.W., Kourteva G., Dixon R.A. Unusual 4-hydroxybenzaldehyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry 2002, 61:611-620.
31. Ro D.K., Paradise E.M., Ouellet M., Fisher K.J., Newman K.L., Ndungu J.M., Ho K.A., Eachus R.A., Ham T.S., Kirby J., Chang M.C., Withers S.T., Shiba Y., Sarpong R., Keasling J.D. Production of the antimalarial drug precursor artemisinic acid in engineered yeast. Nature 2006, 440:940-943.
32. Santos C.N.S., Koffas M., Stephanopoulos G. Optimization of a heterologous pathway for the production of flavonoids from glucose. Metab. Eng. 2011, 13:392-400.
33. Siebert M., Severin K., Heide L. Formation of 4-Hydroxybenzoate in Escherichia coli: characterization of the Ubic gene and its encoded enzyme chorismate pyruvate-lyase. Microbiol-Sgm. 1994, 140:897-904.
34. Tang W.C., Eisenbrand G. Chinese drugs of plant origin: chemistry, pharmacology, and use in traditional and modern medicine 1992, 545-548. Springer-Verlag, Berlin Heidelberg.
35. Thodey K., Galanie S., Smolke C.D. A microbial bio-manufacturing platform for natural and semisynthetic opioids. Nat. Chem. Biol. 2014, 10:837.
36. Wang M.W., Hao X., Chen K. Biological screening of natural products and drug innovation in China. Philos. Trans. R. Soc. Lond. B. Biol. Sci. 2007, 362:1093-1105.
37. Wang X.Q. Structure, mechanism and engineering of plant natural product glycosyltransferases. FEBS Lett. 2009, 583:3303-3309.
38. Williams G.J., Thorson J.S. A high-throughput fluorescence-based glycosyltransferase screen and its application in directed evolution. Nat. Protoc. 2008, 3:357-362.
39. Williams G.J., Zhang C., Thorson J.S. Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution. Nat. Chem. Biol. 2007, 3:657-662.
40. Wu C.R., Hsieh M.T., Huang S.C., Peng W.H., Chang Y.S., Chen C.F. Effects of Gastrodia elata and its active constituents on scopolamine-induced amnesia in rats. Planta Med. 1996, 62:317-321.
41. Yan Y.J., Li Z., Koffas M.A.G. High-yield anthocyanin biosynthesis in engineered Escherichia coli. Biotechnol. Bioeng. 2008, 100:126-140.
42. Yang X.D., Zhu J., Yang R., Liu J.P., Li L., Zhang H.B. Phenolic constituents from the rhizomes of Gastrodia elata. Nat. Prod. Res. 2007, 21:180-186.
43. Yao Y.F., Wang C.S., Qiao J.J., Zhao G.R. Metabolic engineering of Escherichia coli for production of salvianic acid A via an artificial biosynthetic pathway. Metab. Eng. 2013, 19:79-87.
44. Zhang H.R., Pereira B., Li Z.J., Stephanopoulos G. Engineering Escherichia coli coculture systems for the production of biochemical products. Proc. Natl. Acad. Sci. USA 2015, 112:8266-8271.
45. Zhou J. Bioactive glycosides from Chinese medicines. Mem. Inst. Oswaldo Cruz. 1991, 86(Suppl 2):231-234.
46. Zhou J., Yang Y.B., Yang C.R. Chemical studies on Gastrodia elata Blume. II. Synthesis of gastrodin and its derivatives. Acta Chim. Sin. 1980, 38:7.