Identification and characterization of UDP-glucose:Phloretin 4′-O-glycosyltransferase from Malus x domestica Borkh

Phytochemistry

Volumn 130, Issue , 2016, Pages 47-55

  Yahyaa, Mosaab ^a   Davidovich Rikanati, Rachel ^a   Eyal, Yoram ^a   Sheachter, Alona ^a   Marzouk, Sally ^a   Lewinsohn, Efraim ^a   Ibdah, Mwafaq ^a  

^a VOLCANI CENTER   (Israel)

Author keywords

Apple; Dihydrochalcone; Glycosyltransferase; Malus x domestica; Phloretin; Rosaceae; Trilobatin

Indexed keywords

GLUCOSE; GLYCOSYLTRANSFERASE; PHLORETIN; POLYPHENOL; URIDINE DIPHOSPHATE GLUCOSE;

CHEMISTRY; FRUIT; GENE EXPRESSION REGULATION; GLYCOSYLATION; ISOLATION AND PURIFICATION; MALUS; METABOLISM;

FRUIT; GENE EXPRESSION REGULATION, PLANT; GLUCOSE; GLYCOSYLATION; GLYCOSYLTRANSFERASES; MALUS; PHLORETIN; POLYPHENOLS; URIDINE DIPHOSPHATE GLUCOSE;

EID: 84995684238     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2016.06.004     Document Type: Article

References (46)

1. Bar, A., Borrego, F., Benavente, O., Castillo, J., Delrio, J.A., Neohesperidin dihydrochalcone – properties and applications. Food Sci. Technol-Leb 23 (1990), 371–376.
2. Boyer, J., Liu, R., Apple phytochemicals and their health benefits. Nutr. J., 3, 2004, 5.
3. Brazier, M., Cole, D.J., Edwards, R., Partial purification and characterisation of a 2, 4, 5-trichlorophenol detoxifying O-glucosyltransferase from wheat. Phytochemistry 64 (2003), 419–424.
4. Chizzali, C., Gaid, M.M., Belkheir, A.K., Beuerle, T., Hansch, R., Richter, K., Flachowsky, H., Peil, A., Hanke, M.V., Liu, B.Y., Beerhues, L., Phytoalexin formation in fire blight-infected apple. Trees Struct. Funct. 27 (2013), 477–484.
5. Costa, F., Peace, C.P., Stella, S., Serra, S., Musacchi, S., Bazzani, M., Sansavini, S., Van de Weg, W.E., QTL dynamics for fruit firmness and softening around an ethylene-dependent polygalacturonase gene in apple (Malus×domestica Borkh.). J. Exp. Bot. 61 (2010), 3029–3039.
6. Dugé de Bernonville, T., Guyot, S., Paulin, J.-P., Gaucher, M., Loufrani, L., Henrion, D., Derbré, S., Guilet, D., Richomme, P., Dat, J.F., Brisset, M.-N., Dihydrochalcones: implication in resistance to oxidative stress and bioactivities against advanced glycation end-products and vasoconstriction. Phytochemistry 71 (2010), 443–452.
7. Dugé de Bernonville, T.D., Gaucher, M., Guyot, S., Durel, C.E., Dat, J.F., Brisset, M.N., The constitutive phenolic composition of two Malus x domestica genotypes is not responsible for their contrasted susceptibilities to fire blight. Environ. Exp. Bot. 74 (2011), 65–73.
8. Ehrenkranz, J.R.L., Lewis, N.G., Ronald Kahn, C., Roth, J., Phlorizin: a review. Diabetes Metab. Res. 21 (2005), 31–38.
9. Figtree, G.A., Griffiths, H., Liu, Y.Q., Webb, C.M., MacLeod, K., Collins, P., Plant-derived estrogens relax coronary arteries in vitro by a calcium antagonistic mechanism. J. Am. Coll. Cardiol. 35 (2000), 1977–1985.
10. Ford, C.M., Boss, P.K., Hoj, 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. Franceschi, P., Dong, Y.H., Strupat, K., Vrhovsek, U., Mattivi, F., Combining intensity correlation analysis and MALDI imaging to study the distribution of flavonols and dihydrochalcones in golden delicious apples. J. Exp. Bot. 63 (2012), 1123–1133.
12. Gosch, C., Flachowsky, H., Halbwirth, H., Thill, J., Mjka-Wittmann, R., Treutter, D., Richter, K., Hanke, M.-V., Stich, K., Substrate specificity and contribution of the glycosyltransferase UGT71A15 to phloridzin biosynthesis. Trees 26 (2012), 259–271.
13. Gosch, C., Halbwirth, H., Kuhn, J., Miosic, S., Stich, K., Biosynthesis of phloridzin in apple (Malus domestica Borkh.). Plant Sci. 176 (2009), 223–231.
14. Gosch, C., Halbwirth, H., Schneider, B., Hölscher, D., Stich, K., Cloning and heterologous expression of glycosyltransferases from Malus x domestica and Pyrus communis, which convert phloretin to phloretin 2′-O-glucoside (phloridzin). Plant Sci. 178 (2010), 299–306.
15. Gosch, C., Halbwirth, H., Stich, K., Phloridzin: biosynthesis, distribution and physiological relevance in plants. Phytochemistry 71 (2010), 838–843.
16. Griesser, M., Vitzthum, F., Fink, B., Bellido, M.L., Raasch, C., Munoz-Blanco, J., Schwab, W., Multi-substrate flavonol O-glucosyltransferases from strawberry (Fragaria×ananassa) achene and receptacle. J. Exp. Bot. 59 (2008), 2611–2625.
17. Hansen, S.F., Harholt, J., Oikawa, A., Scheller, H.V., Plant glycosyltransferases beyond CAZy: a perspective on DUF families. Front. Plant Sci., 3, 2012, 59.
18. Hunter, L.D., Phloridzin and apple scab. Phytochemistry 14 (1975), 1519–1522.
19. Ibdah, M., Berim, A., Martens, S., Valderrama, A.L.H., Palmieri, L., Lewinsohn, E., Gang, D.R., Identification and cloning of an NADPH-dependent hydroxycinnamoyl-CoA double bond reductase involved in dihydrochalcone formation in Malus x domestica Borkh. Phytochemistry 107 (2014), 24–31.
20. Isayenkova, J., Wray, V., Nimtz, M., Strack, D., Vogt, T., Cloning and functional characterisation of two regioselective flavonoid glucosyltransferases from Beta vulgaris. Phytochemistry 67 (2006), 1598–1612.
21. Ishikura, N., Mato, M., Partial purification and some properties of flavonol 3-O-glycosyltransferases from seedlings of Vigna mungo, with special reference to the formation of kaempferol 3-O-galactoside and 3-O-glucoside. Plant Cell Physiol. 34 (1993), 329–335.
22. Jugde, H., Nguy, D., Moller, I., Cooney, J.M., Atkinson, R.G., Isolation and characterization of a novel glycosyltransferase that converts phloretin to phlorizin, a potent antioxidant in apple. FEBS J. 275 (2008), 3804–3814.
23. Lairson, L., Henrissat, B., Davies, G., Withers, S., Glycosyltransferases: structures, functions, and mechanisms. Biochem. US, 77, 2008, 521.
24. Ling, T.-J., Lin, L.-D., Wu, P., Zhou, W.-H., Ye, H.-G., Liu, M.-F., Wei, X.-Y., Dihydrochalcones from Symplocos vacciniifolia. Chin. Chem. Lett. 15 (2004), 1182–1184.
25. Mikulic-Petkovsek, M., Slatnar, A., Stampar, F., Veberic, R., The influence of organic/integrated production on the content of phenolic compounds in apple leaves and fruits in four different varieties over a 2-year period. J. Sci. Food Agric. 90 (2010), 2366–2378.
26. Ono, E., Fukuchi-Mizutani, M., Nakamura, N., Fukui, Y., Yonekura-Sakakibara, K., Yamaguchi, M., Nakayama, T., Tanaka, T., Kusumi, T., Tanaka, Y., Yellow flowers generated by expression of the aurone biosynthetic pathway. Proc. Natl. Acad. Sci. U. S. A. 103 (2006), 11075–11080.
27. Pandey, R.P., Li, T.F., Kim, E.-H., Yamaguchi, T., Park, Y.I., Kim, J.S., Sohng, J.K., Enzymatic synthesis of novel phloretin glucosides. Appl. Environ. Microb. 79 (2013), 3516–3521.
28. Qin, X.D., Liu, J.K., A new sweet dihydrochalcone-glucoside from leaves of Lithocarpus pachyphyllus (Kurz) Rehd. (Fagaceae). Z. Naturforsch. C 58 (2003), 759–761.
29. Rezk, B.M., Haenen, G., van der Vijgh, W.J.F., Bast, A., The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids. Biochem. Biophys. Res. Commun. 295 (2002), 9–13.
30. Roowi, S., Crozier, A., Flavonoids in tropical citrus species. J. Agric. Food Chem. 59 (2011), 12217–12225.
31. Rui-Lin, N., Tanaka, T., Zhou, J., Tanaka, O., Phlorizin and trilobatin, sweet dihydrochalcone-glucosides from leaves of Lithocarpus litseifolius (Hance) Rehd. (Fagaceae). Agric. Biol. Chem. Tokyo 46 (1982), 1933–1934.
32. Sánchez-Rabaneda, F., Jáuregui, O., Lamuela-Raventós, R.M., Viladomat, F., Bastida, J., Codina, C., Qualitative analysis of phenolic compounds in apple pomace using liquid chromatography coupled to mass spectrometry in tandem mode. Rapid. Commun. Mass. Sp. 18 (2004), 553–563.
33. She, G.M., Wang, S., Liu, B., Dihydrochalcone glycosides from Oxytropis myriophylla. Chem. Cent. J. 5 (2011), 71–73.
34. Shimoda, K., Otsuka, T., Morimoto, Y., Hamada, H., Hamada, H., Glycosylation and malonylation of quercetin, epicatechin, and catechin by cultured plant cells. Chem. Lett. 36 (2007), 1292–1293.
35. Stangl, V., Lorenz, M., Ludwig, A., Grimbo, N., Guether, C., Sanad, W., Ziemer, S., Martus, P., Baumann, G., Stangl, K., The flavonoid phloretin suppresses stimulated expression of endothelial adhesion molecules and reduces activation of human platelets. J. Nutr. 135 (2005), 172–178.
36. Sunagawa, T., Shimizu, T., Kanda, T., Tagashira, M., Sami, M., Shirasawa, T., Procyanidins from apples (Malus pumila Mill.) extend the lifespan of Caenorhabditis elegans. Planta Med. 77 (2011), 122–127.
37. Tamura, K., Stecher, G., Peterson, D., Filipski, A., Kumar, S., MEGA6: molecular evolutionary genetics analysis version 6.0. Mol. Biol. Evol. 30 (2013), 2725–2729.
38. Tomas-Barberan, F., Borrego, F., Ferreres, F., Lindley, M., Stability of the intense sweetener neohesperidine dihydrochalcone in blackcurrant jams. Food Chem. 52 (1995), 263–265.
39. Treutter, D., Biosynthesis of phenolic compounds and its regulation in apple. Plant Growth Regul. 34 (2001), 71–89.
40. Treutter, D., Significance of flavonoids in plant resistance and enhancement of their biosynthesis. Plant Biol. 7 (2005), 581–591.
41. Veitch, N.C., Grayer, R.J., Chalcones, dihydrochalcones and aurones. Andersen, O.M., Markham, K.R., (eds.) Flavonoids: Chemistry, Biochemistry and Applications, 2006, CRC Press, Boca Raton, 1003–1100.
42. Viet, M.H., Chen, C.-Y., Hu, C.-K., Chen, Y.-R., Li, M.S., Discovery of dihydrochalcone as potential lead for Alzheimer's disease: in silico and in vitro study. PLoS One, 8, 2013, e79151.
43. Vogt, T., Grimm, R., Strack, D., Cloning and expression of a cDNA encoding betanidin 5-O-glucosyltransferase, a betanidin-and flavonoid-specific enzyme with high homology to inducible glucosyltransferases from the Solanaceae. Plant J. 19 (1999), 509–519.
44. Vogt, T., Jones, P., Glycosyltransferases in plant natural product synthesis: characterization of a supergene family. Trends Plant Sci. 5 (2000), 380–386.
45. Witte, S., Moco, S., Vervoort, J., Matern, U., Martens, S., Recombinant expression and functional characterisation of regiospecific flavonoid glucosyltransferases from Hieracium pilosella L. Planta 229 (2009), 1135–1146.
46. Yang, C.S., Landau, J.M., Huang, M.T., Newmark, H.L., Inhibition of carcinogenesis by dietary polyphenolic compounds. Annu. Rev. Nutr. 21 (2001), 381–406.