FaGT2: A multifunctional enzyme from strawberry (Fragaria x ananassa) fruits involved in the metabolism of natural and xenobiotic compounds

Planta

Volumn 226, Issue 2, 2007, Pages 417-428

  Landmann, Christian ^a   Fink, Barbara ^a   Schwab, Wilfried ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Fragaria; Glucose ester; Glucosyltransferase; Substrate specificity; Xenobiotics

Indexed keywords

FURAN DERIVATIVE; FURANEOL; GLUCOSYLTRANSFERASE; MAGNESIUM; UNCLASSIFIED DRUG; VEGETABLE PROTEIN; XENOBIOTIC AGENT;

ARTICLE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVATION; ENZYMOLOGY; FRUIT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; METABOLISM; MOLECULAR GENETICS; NUCLEOTIDE SEQUENCE; PHYSIOLOGY; STRAWBERRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME ACTIVATION; FRAGARIA; FRUIT; FURANS; GLUCOSYLTRANSFERASES; KINETICS; MAGNESIUM; MOLECULAR SEQUENCE DATA; PLANT PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; XENOBIOTICS;

FRAGARIA; FRAGARIA X ANANASSA;

EID: 34250028213     PISSN: 00320935     EISSN: 14322048     Source Type: Journal    
DOI: 10.1007/s00425-007-0492-4     Document Type: Article

References (38)

1. Aharoni A, Keizer LCP, Van den Broeck HC, Blanco-Portales R, oz-Blanco J, Bois G, Smit P, De Vos RCH, O'Connell AP (2002) Novel insight into vascular, stress, and auxin-dependent and -independent gene expression programs in strawberry, a non-climacteric fruit. Plant Physiol 129:1019-1031
2. Aubert C, Baumann S, Arguel H (2005) Optimization of the analysis of flavor volatile compounds by liquid-liquid microextraction (LLME). Application to the aroma analysis of melons, peaches, grapes, strawberries, and tomatoes. J Agric Food Chem 53:8881-8895
3. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein dye binding. Anal Biochem 72:248-254
4. Brazier-Hicks M, Edwards R (2005) Functional importance of the family 1 glucosyltransferase UGT72B1 in the metabolism of xenobiotics in Arabidopsis thaliana. Plant J 42:556-566
5. Ford CM, Boss PK, Hmj PB (1998) 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 273:9224-9233
6. Fraissinet-Tachet L, Baltz R, Chong J, Kauffmann S, Fritig B, Saindrenan P (1998) Two tobacco genes induced by infection, elicitor and salicylic acid encode glucosyltransferases acting on phenylpropanoids and benzoic acid derivatives, including salicylic acid. FEBS Lett 437:319-323
7. Gomes Da Silva MDR, Chaves Das Neves HJ (1999) Complementary use of hyphenated purge-and-trap gas chromatography techniques and sensory analysis in the aroma profiling of strawberries (Fragaria ananassa). J Agric Food Chem 47:4568-4573
8. Groyne J, Lognay G, Marlier M (1999) Accumulation of glycosidically bound compounds in Fragaria × ananassa cv. Elsanta fruits at various developmental stages. Biotechnol Agron Soc Environ 3:5-9
9. Hefner T, Arend J, Warzecha H, Siems K, Stöckigt J (2002) Arbutin synthase, a novel member of the NRD1β-glycosyltransferase family, is a unique multifunctional enzyme converting various natural products and xenobiotics. Bioorgan Med Chem 10:1731-1741
10. Jackson RG, Lim EK, Li Y, Kowalczyk M, Sandberg G, Hogget J, Ashford DA, Bowles DJ (2001) Identification and biochemical characterization of an Arabidopsis indole-3-acetic acid glucosyltransferase. J Biol Chem 276:4350-4356
11. Jones P, Vogt T (2001) Glycosyltransferases in secondary plant metabolism: Tranquilizers and stimulant controllers. Planta 213:164-174
12. Jones PR, Møller BL, Hoj PB (1999) The UDP-glucose:p- hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity. J Biol Chem 274:35483-35491
13. Lamb C, Dixon RA (1997) The oxidative burst in plant disease resistance. Annu Rev Plant Physiol Plant Mol Biol 48:251-275
14. Langlois-Meurinne M, Gachon CMM, Saindrenan P (2005) Pathogen-responsive expression of glycosyltransferase genes UGT73B3 and UGT73B5 is necessary for resistance to Pseudomonas syringae pv tomato in Arabidopsis. Plant Physiol 139:1890-1901
15. Latza S, Berger RG (1997) 1-O-trans-cinnamoyl-β-d-glucopyranose: alcohol cinnamoyltransferase activity in fruits of cape gooseberry (Physalis peruviana L.). Z Naturforsch C 52:747-755
16. Lee HI, Raskin I (1999) Purification, cloning, and expression of a pathogen inducible UDP-glucose:salicylic acid glucosyltransferase from tobacco. J Biol Chem 274:36637-36642
17. Lehfeldt C, Shirley AM, Meyer K, Ruegger MO, Cusumano JC, Viitanen PV, Strack D, Chapple C (2000) Cloning of the SNG1 gene of Arabidopsis reveals a role for a serine carboxypeptidase-like protein as an acyltransferase in secondary metabolism. Plant Cell 12:1295-1306
18. Lim EK, Li Y, Parr A, Jackson R, Ashford DA, Bowles DJ (2001) Identification of glucosyltransferase genes involved in sinapate metabolism and lignin synthesis in Arabidopsis. J Biol Chem 276:4344-4349
19. Lim EK, Doucet CJ, Li Y, Elias L, Worrall D, Spencer SP, Ross J, Bowles DJ (2002) The activity of Arabidopsis glycosyltransferases toward salicylic acid, 4-hydroxybenzoic acid, and other benzoates. J Biol Chem 277:586-592
20. Loutre C, Dixon DP, Brazier M, Slater M, Cole DJ, Edwards R (2003) Isolation of a glucosyltransferase from Arabidopsis thaliana active in the metabolism of the persistent pollutant 3,4-dichloroaniline. Plant J 34:485-493
21. Lunkenbein S, Bellido M, Aharoni A, Salentijn EMJ, Kaldenhoff R, Coiner HA, Munoz-Blanco J, Schwab W (2006a) Cinnamate metabolism in ripening fruit. Characterization of a UDP-glucose:cinnamate glucosyltransferase from strawberry. Plant Physiol 140:1047-1058
22. Lunkenbein S, Coiner H, de Vos CHR, Schaart JG, Boone MJ, Krens FA, Schwab W, Salentijn EMJ (2006b) Molecular characterization of a stable antisense chalcone synthase phenotype in strawberry (Fragaria × ananassa). J Agric Food Chem 54:2145-2153
23. Marrs KA (1996) The functions and regulation of glutathione S-transferases in plants. Annu Rev Plant Physiol Plant Mol Biol 47:127-158
24. Meßner B, Thulke O, Schäffner AR (2003) Arabidopsis glucosyltransferases with activities toward both endogenous and xenobiotic substrates. Planta 217:138-146
25. Milkowski C, Baumert A, Schmidt D, Nehlin L, Strack D (2004) Molecular regulation of sinapate ester metabolism in Brassica napus: expression of genes, properties of the encoded proteins and correlation of enzyme activities with metabolite accumulation. Plant J 38:80-92
26. Pflugmacher S, Sandermann J (1998) Taxonomic distribution of plant glucosyltransferases acting on xenobiotics. Phytochemistry 49:507-511
27. Poppenberger B, Berthiller F, Lucyshyn D, Sieberer T, Schuhmacher R, Krska R, Kuchler K, Glössl J, Luschnig C, Adam G (2003) Detoxification of the Fusarium Mycotoxin Deoxynivalenol by a UDP-glucosyltransferase from Arabidopsis thaliana. J Biol Chem 278:47905-47914
28. Poppenberger B, Fujioka S, Soeno K, George GL, Vaistij FE, Hiranuma S, Seto H, Takatsuto S, Adam G, Yoshida S, Bowles D (2005) The UGT73C5 of Arabidopsis thaliana glucosylates brassinosteroids. Proc Natl Acad Sci USA 102:15253-15258
29. Quiel JA, Bender J (2003) Glucose conjugation of anthranilate by the Arabidopsis UGT74F2 glucosyltransferase is required for tryptophan mutant blue fluorescence. J Biol Chem 278:6275-6281
30. Roscher R, Herderich M, Steffen JP, Schreier P, Schwab W (1996) 2,5-dimethyl-4-hydroxy-3[2H]-furanone 6'O-malonyl-β-d-glucopyranoside in strawberry fruits. Phytochemistry 43:155-159
31. Schaller B, Schneider B, Schütte HR (1992) Metabolism of the herbicide bromoxynil in Hordeum vulgare and Stellaria media. Z Naturforsch C 47:126-131
32. Taguchi G, Imura H, Maeda Y, Kodaira R, Hayashida N, Shimosaka M, Okazaki M (2000) Purification and characterization of UDP-glucose:hydroxycoumarin 7-O-glucosyltransferase, with broad substrate specificity from tobacco cultured cells. Plant Sci 157:105-112
33. Taguchi G, Yazawa T, Hayashida N, Okazaki M (2001) Molecular cloning and heterologous expression of novel glucosyltransferases from tobacco cultured cells that have broad substrate specificity and are induced by salicylic acid and auxin. Eur J Biochem 268:4086-4094
34. Ulrich D, Hoberg E, Rapp A, Kecke S (1997) Analysis of strawberry flavor. Discrimination of aroma types by quantification of volatile compounds. Z Lebensm Unters Forsch A 205:218-223
35. Villegas RJA, Kojima M (1986) Purification and characterization of hydroxycinnamoyl d-glucose:Quinate hydroxycinnamoyl transferase in the root of the sweet potato, Ipomoea batatas Lam. J Biol Chem 261:8729-8733
36. Vogt T, Jones P (2000) Glycosyltransferases in plant-natural product synthesis: characterization of a supergene family. Trends Plant Sci 5:380-386
37. Wang J, De Luca V (2005) The biosynthesis and regulation of biosynthesis of Concord grape fruit esters, including 'foxy' methylanthranilate. Plant J 44:606-619
38. Wintoch H, Krammer G, Schreier P (1991) Glycosidically bound aroma compounds from two strawberry fruit species, Fragaria vesca f. semperflorens and Fragaria × ananassa, cv. Korona. Flavour Frag J 6:209-215