Identification of three (Iso)flavonoid glucosyltransferases from Pueraria lobata

Frontiers in Plant Science

Volumn 10, Issue , 2019, Pages

  Wang, Xin ^a   Li, Changfu ^a,b   Zhou, Zilin ^a,c   Zhang, Yansheng ^a,b  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b SHANGHAI UNIVERSITY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Daidzin; Flavonoids; Glucosyltransferase; Isoflavonoids; Pueraria lobata

Indexed keywords

EID: 85062447563     PISSN: None     EISSN: 1664462X     Source Type: Journal    
DOI: 10.3389/fpls.2019.00028     Document Type: Article

References (44)

1. Dai, X., Zhuang, J., Wu, Y., Wang, P., Zhao, G., Liu, Y., et al. (2017). Identification of a flavonoid glucosyltransferase involved in 7-OH site glycosylation in tea plants (Camellia sinensis). Sci. Rep. 7:5926. doi: 10.1038/s41598-017-06453-z
2. Dixon, R. A., and Pasinetti, G. M. (2010). Flavonoids and isoflavonoids: from plant biology to agriculture and neuroscience. Plant Physiol. 154, 453–457. doi: 10.1104/pp.110.161430
3. Egorova, K. S., and Toukach, P. V. (2017). CSDB_GT: a new curated database on glycosyltransferases. Glycobiology 27, 285–290. doi: 10.1093/glycob/cww137
4. Farag, M. A., Huhman, D. V., Dixon, R. A., and Sumner, L. W. (2008). Metabolomics reveals novel pathways and differential mechanistic and elicitor-specific responses in phenylpropanoid and isoflavonoid biosynthesis in Medicago truncatula cell cultures. Plant Physiol. 146, 387–402. doi: 10.1104/pp. 107.108431
5. Funaki, A., Waki, T., Noguchi, A., Kawai, Y., Yamashita, S., Takahashi, S., et al. (2015). Identification of a highly specific isoflavone 7-O-glucosyltransferase in the soybean (Glycine max (L.) Merr.). Plant Cell Physiol. 56, 1512–1520. doi: 10.1093/pcp/pcv072
6. Goyal, S., and Ramawat, K. G. (2008). Increased isoflavonoids accumulation in cell suspension culture of Pueraria tuberosa by elicitors. Indian J. Biotechnol. 7, 378–382.
7. He, X., Blount, J. W., Ge, S., Tang, Y., and Dixon, R. A. (2011). A genomic approach to isoflavone biosynthesis in kudzu (Pueraria lobata). Planta 233, 843–855. doi:10.1007/s00425-010-1344-1
8. Heim, K. E., Tagliaferro, A. R., and Bobilya, D. J. (2002). Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships. J. Nutr. Biochem. 13, 572–584. doi: 10.1016/S0955-2863(02)00208-5
9. Keung, W. M., Lazo, O., Kunze, L., and Vallee, B. L. (1996). Potentiation of the bioavailability of daidzin by an extract of Radix puerariae. Proc. Natl. Acad. Sci. U.S.A. 93, 4284–4288. doi: 10.1073/pnas.93.9.4284
10. Keung, W. M., and Vallee, B. L. (1993). Daidzin and daidzein suppress free-choice ethanol intake by Syrian golden hamsters. Proc. Natl. Acad. Sci. U.S.A. 90, 10008–10012. doi: 10.1073/pnas.90.21.10008
11. Keung, W. M., and Vallee, B. L. (1998). Kudzu root: an ancient Chinese source of modern antidipsotropic agents. Phytochemistry 47, 499–506. doi: 10.1016/S0031-9422(97)00723-1
12. Korsangruang, S., Soonthornchareonnon, N., Chintapakorn, Y., Saralamp, P., and Prathanturarug, S. (2010). Effects of abiotic and biotic elicitors on growth and isoflavonoid accumulation in Pueraria candollei var. candollei and P. candollei var. mirifica cell suspension cultures. Plant Cell Tissue Organ. Cult. 103, 333–342. doi: 10.1007/s11240-010-9785-6
13. Kovinich, N., Saleem, A., Arnason, J. T., and 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. doi: 10.1016/j.phytochem.2010.05.009
14. Kumar, S., Stecher, G., and Tamura, K. (2016). MEGA7: molecular evolutionary genetics analysis version 7.0 for bigger datasets. Mol. Biol. Evol. 33, 1870–1874. doi: 10.1093/molbev/msw054
15. Le Roy, J., Huss, B., Creach, A., Hawkins, S., and Neutelings, G. (2016). Glycosylation is a major regulator of phenylpropanoid availability and biological activity in plants. Front. Plant Sci. 7:735. doi: 10.3389/fpls.2016.00735
16. Li, J., Li, C. F., Gou, J. B., Wang, X., Fan, R. Y., and Zhang, Y. S. (2016). An alternative pathway for formononetin biosynthesis in Pueraria lobata. Front. Plant Sci. 7:861. doi: 10.3389/fpls.2016.00867
17. Li, J., Li, Z., Li, C., Gou, J., and Zhang, Y. (2014). Molecular cloning and characterization of an isoflavone 7-O-glucosyltransferase from Pueraria lobata. Plant Cell Rep. 33, 1173–1185. doi: 10.1007/s00299-014-1606-7
18. Lichtenstein, A. H. (1998). Soy protein, isoflavones and cardiovascular disease risk. J. Nutr. 128, 1589–1592. doi: 10.1093/jn/128.10.1589
19. Liu, X., Lin, C., Ma, X., Tan, Y., Wang, J., and Zeng, M. (2018). Functional characterization of a flavonoid glycosyltransferase in sweet orange (Citrus sinensis). Front. Plant Sci. 9:166. doi: 10.3389/fpls.2018.00166
20. Modolo, L. V., Blount, J. W., Achnine, L., Naoumkina, M. A., Wang, X., and Dixon, R. A. (2007). A functional genomics approach to (iso)flavonoid glycosylation in the model legume Medicago truncatula. Plant Mol. Biol. 64, 499–518. doi: 10.1007/s11103-007-9167-6
21. Naoumkina, M., Farag, M. A., Sumner, L. W., Tang, Y., Liu, C. J., and Dixon, R. A. (2007). Different mechanisms for phytoalexin induction by pathogen and wound signals in Medicago truncatula. Proc. Natl. Acad. Sci. U.S.A. 104, 17909–17915. doi: 10.1073/pnas.0708697104
22. Noguchi, A., Saito, A., Homma, Y., Nakao, M., Sasaki, N., Nishino, T., et al. (2007). A UDP-glucose:isoflavone 7-O-glucosyltransferase from the roots of soybean (Glycine max) seedlings. Purification, gene cloning, phylogenetics, and an implication for an alternative strategy of enzyme catalysis. J. Biol. Chem. 282, 23581–23590. doi: 10.1074/jbc.M702651200
23. Panche, A. N., Diwan, A. D., and Chandra, S. R. (2016). Flavonoids: an overview. J. Nutr. Sci. 5:e47. doi: 10.1017/jns.2016.41
24. Peng, M., Shahzad, R., Gul, A., Subthain, H., Shen, S., Lei, L., et al. (2017). Differentially evolved glucosyltransferases determine natural variation of rice flavone accumulation and UV-tolerance. Nat. Commun. 8:1975. doi: 10.1038/s41467-017-02168-x
25. Rong, H., Stevens, J. F., Deinzer, M. L., Cooman, L. D., and Keukeleire, D. D. (1998). Identification of isoflavones in the roots of Pueraria lobata. Planta Med. 64, 620–627. doi: 10.1055/s-2006-957534
26. Ruiz-Larrea, M. B., Mohan, A. R., Paganga, G., Miller, N. J., Bolwell, G. P., and Rice-Evans, C. A. (1997). Antioxidant activity of phytoestrogenic isoflavones. Free Radic. Res. 26, 63–70. doi:10.3109/1071576970909 7785
27. Sharma, R., Rawat, V., and Suresh, C. G. (2014). Genome-wide identification and tissue-specific expression analysis of UDP-glycosyltransferases genes confirm their abundance in Cicer arietinum (Chickpea) genome. PLoS One 9:e109715. doi: 10.1371/journal.pone.0109715
28. Szeja, W., Grynkiewicz, G., and Rusin, A. (2017). Isoflavones, their glycosides and glycoconjugates. Synthesis and biological activity. Curr. Org. Chem. 21, 218–235. doi:10.2174/1385272820666160928120822
29. Thompson, J. D., Gibson, T. J., and Higgins, D. G. (2002). Multiple sequence alignment using ClustalW and ClustalX. Curr. Protoc. Bioinformatics Chapter 2:Unit 2.3. doi: 10.1002/0471250953.bi0203s00
30. Tohge, T., de Souza, L. P., and Fernie, A. R. (2017). Current understanding of the pathways of flavonoid biosynthesis in model and crop plants. J. Exp. Bot. 68, 4013–4028. doi: 10.1093/jxb/erx177
31. Veitch, N. C. (2009). Isoflavonoids of the leguminosae. Nat. Prod. Rep. 26, 776–802. doi: 10.1039/b616809b
32. Veitch, N. C. (2013). Isoflavonoids of the leguminosae. Nat. Prod. Rep. 30, 988–1027. doi: 10.1039/c3np70024k
33. Wang, X., Fan, R. Y., Li, J., Li, C. F., and Zhang, Y. S. (2016). Molecular cloning and functional characterization of a novel (Iso)flavone 4 ’,7-O-diglucoside glucosyltransferase from Pueraria lobata. Front. Plant Sci. 7:387. doi: 10.3389/fpls.2015.00387
34. Wang, X., Li, C. F., Zhou, C., Li, J., and Zhang, Y. S. (2017). Molecular characterization of the C-glucosylation for puerarin biosynthesis in Pueraria lobata. Plant J. 90, 535–546. doi: 10.1111/tpj.13510
35. Wang, X., Li, S. T., Li, J., Li, C. F., and Zhang, Y. S. (2015). De novo transcriptome sequencing in Pueraria lobata to identify putative genes involved in isoflavones biosynthesis. Plant Cell Rep. 34, 733–743. doi:10.1007/s00299-01 4-1733-1
36. Wong, K. H., Li, G. Q., Li, K. M., Razmovski-Naumovski, V., and Chan, K. (2011). Kudzu root: traditional uses and potential medicinal benefits in diabetes and cardiovascular diseases. J. Ethnopharmacol. 134, 584–607. doi: 10.1016/j.jep. 2011.02.001
37. Wu, B. P., Gao, L. X., Gao, J., Xu, Y. Y., Liu, H. R., Cao, X. M., et al. (2017). Genome-wide identification, expression patterns, and functional analysis of UDP glycosyltransferase family in peach (Prunus persica L. Batsch). Front. Plant Sci. 8:389. doi: 10.3389/fpls.2017.00389
38. Yin, Q., Shen, G., Chang, Z., Tang, Y., Gao, H., and Pang, Y. (2017a). Involvement of three putative glucosyltransferases from the UGT72 family in flavonol glucoside/rhamnoside biosynthesis in Lotus japonicus seeds. J. Exp. Bot. 68, 597–612. doi: 10.1093/jxb/erw420
39. Yin, Q., Shen, G., Di, S., Fan, C., Chang, Z., and Pang, Y. (2017b). Genome-wide identification and functional characterization of UDP-glucosyltransferase genes involved in flavonoid biosynthesis in glycine max. Plant Cell Physiol. 58, 1558–1572. doi: 10.1093/pcp/pcx081
40. Yonekura-Sakakibara, K. (2009). Functional genomics of family 1 glycosyltransferases in Arabidopsis. Plant Biotechnol. 26, 267–274. doi: 10.5511/plantbiotechnology.26.267
41. Yonekura-Sakakibara, K., and Hanada, K. (2011). An evolutionary view of functional diversity in family 1 glycosyltransferases. Plant J. 66, 182–193. doi: 10.1111/j.1365-313X.2011.04493.x
42. Zhao, X., Dai, X., Gao, L., Guo, L., Zhuang, J., Liu, Y., et al. (2017a). Function analysis of an UDP-glycosyltransferase involved in the biosynthesis of polyphenolic glucoside in tea (Camellia sinensis). J. Agric. Food Chem. 65, 10993–11001. doi: 10.1021/acs.jafc.7b0 4969
43. Zhao, X., Wang, P., Li, M., Wang, Y., Jiang, X., Cui, L., et al. (2017b). Functional characterization of a new Tea (Camellia sinensis) flavonoid glycosyltransferase. J. Agric. Food Chem. 65, 2074–2083. doi: 10.1021/acs.jafc.6b0 5619
44. Zhou, J., Li, C. L., Gao, F., Luo, X. P., Li, Q. Q., Zhao, H. X., et al. (2016). Characterization of three glucosyltransferase genes in Tartary Buckwheat and their expression after cold stress. J. Agric. Food Chem. 64, 6930–6938. doi: 10.1021/acs.jafc.6b02064