A comprehensive and effective mass spectrometry-based screening strategy for discovery and identification of new brassinosteroids from rice tissues

Frontiers in Plant Science

Volumn 7, Issue NOVEMBER2016, 2016, Pages

  Xin, Peiyong ^a   Yan, Jijun ^a,b   Li, Bingbing ^a   Fang, Shuang ^a   Fan, Jinshi ^b   Tian, Hailong ^c   Shi, Yong ^c   Tian, Weisheng ^c   Yan, Cunyu ^a,d   Chu, Jinfang ^a  

^a INSTITUTE OF GENETICS AND DEVELOPMENTAL BIOLOGY   (China)

^b QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^d UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

Biosynthetic intermediates; Brassinosteroids; Discovery; Identification; Rice; Screening; UPLC MS

Indexed keywords

EID: 85003454604     PISSN: None     EISSN: 1664462X     Source Type: Journal    
DOI: 10.3389/fpls.2016.01786     Document Type: Article

References (30)

1. Al-Babili, S., and Bouwmeester, H. J. (2015). Strigolactones, a novel carotenoidderived plant hormone. Annu. Rev. Plant Biol. 66, 161-186. doi: 10.1146/ annurev-arplant-043014-114759
2. Bajguz, A. (2009). Isolation and characterization of brassinosteroids from algal cultures of Chlorella vulgaris Beijerinck (Trebouxiophyceae). J. Plant Physiol. 166, 1946-1949. doi: 10.1016/j.jplph.2009.05.003
3. Fujioka, S., Inoue, T., Takatsuto, S., Yanagisawa, T., Yokota, T., and Sakurai, A. (1995). Identification of a new brassinosteroid, cathasterone, in cultured cells of Catharanthus roseus as a biosynthetic precursor of teasterone. Biosci. Biotechnol. Biochem. 59, 1543-1547. doi: 10.1271/bbb.59.1543
4. Fujioka, S., Noguchi, T., Takatsuto, S., Sakurai, A., Yoshida, S., Li, J. M., et al. (1999). Arabidopsis det2 is defective in the conversion of (24R)-24-methylcholest-4-en-3-one to (24R)-24-methyl-5α-cholestan-3-one in brassinosteroid biosynthesis. Plant Physiol. 120, 833-839. doi: 10.1104/pp.120.3.833
5. Fujioka, S., and Yokota, T. (2003). Biosynthesis and metabolism of brassinosteroids. Annu. Rev. Plant Biol. 54, 137-164. doi: 10.1146/annurev. arplant.54.031902.134921
6. 29 sterols. Plant J. 45, 765-774. doi: 10.1111/j.1365-313X.2005.02639.x
7. Grove, M. D., Spencer, G. F., Rohwedder, W. K., Mandava, N., Worley, J. F., Warthen, J. D. Jr., et al. (1979). Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen. Nature 281, 216-217.
8. Hayat, S. (2011). Brassinosteroids: A Class of Plant Hormone. Dordrecht: Springer Science+Business Media.
9. Hoff, R. B., Meneghini, L., Pizzolato, T. N. M., Peralba, M. D. C. R., Díaz-Cruz, M. S., and Barceló, D. (2014). Structural elucidation of sulfaquinoxaline metabolism products and their occurrence in biological samples using highresolution orbitrap mass spectrometry. Anal. Chem. 86, 5579-5586. doi: 10.1021/ac501132r
10. Hong, Z., Ueguchi-Tanaka, M., Umemura, K., Uozu, S., Fujioka, S., Takatsuto, S., et al. (2003). A rice brassinosteroid-deficient mutant, ebisu dwarf (d2), is caused by a loss of function of a new member of cytochrome P450. Plant Cell 15, 2900-2910. doi: 10.1105/tpc.014712
11. Hostettmann, K., Wolfender, J. L., and Terreaux, C. (2001). Modern screening techniques for plant extracts. Pharm. Biol. 39, 18-32. doi: 10.1076/phbi.39.s1.18.0008
12. Hwang, J. Y., Park, C. H., Namgung, H., and Kim, S. K. (2006). Identification of a new brassinosteroid, 23-dehydro-2-epicastasterone, from immature seeds of Phaseolus vulgaris. J. Plant Biol. 49, 409-412. doi: 10.1007/BF03178820
13. Joo, S.-H., Jang, M.-S., Kim, M. K., Lee, J.-E., and Kim, S.-K. (2015). Biosynthetic relationship between C28-brassinosteroids and C29-brassinosteroids in rice (Oryza sativa) seedlings. Phytochemistry 111, 84-90. doi: 10.1016/j.phytochem.2014.11.006
14. Kim, B. K., Fujioka, S., Takatsuto, S., Tsujimoto, M., and Choe, S. (2008). Castasterone is a likely end product of brassinosteroid biosynthetic pathway in rice. Biochem. Biophys. Res. Commun. 374, 614-619. doi: 10.1016/j.bbrc.2008.07.073
15. Kim, S.-K., Abe, H., Little, C. A., and Pharis, R. P. (1990). Identification of two brassinosteroids from the cambial region of Scots pine (Pinus silverstris) by gas chromatography-mass spectrometry, after detection using a dwarf rice lamina inclination bioassay. Plant physiol. 94, 1709-1713. doi: 10.1104/pp.94.4.1709
16. Mitchell, J. W., Mandava, N., Worley, J. F., Plimmer, J. R., and Smith, M. V. (1970). Brassins-a new family of plant hormones from rape pollen. Nature 225, 1065-1066. doi: 10.1038/2251065a0
17. Ni, S., Qian, D., Duan, J.-A., Guo, J., Shang, E.-X., Shu, Y., et al. (2010). UPLC-QTOF/MS-based screening and identification of the constituents and their metabolites in rat plasma and urine after oral administration of Glechoma longituba extract. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 878, 2741-2750. doi: 10.1016/j.jchromb.2010.08.014
18. Ohnishi, T., Godza, B., Watanabe, B., Fujioka, S., Hategan, L., Ide, K., et al. (2012). CYP90A1/CPD, a brassinosteroid biosynthetic cytochrome P450 of Arabidopsis, catalyzes C-3 oxidation. J. Biol. Chem. 287, 31551-31560. doi: 10.1074/jbc.M112.392720
19. Ohnishi, T., Watanabe, B., Sakata, K., and Mizutani, M. (2006). CYP724B2 and CYP90B3 function in the early c-22 hydroxylation steps of brassinosteroid biosynthetic pathway in tomato. Biosci. Biotechnol. Biochem. 70, 2071-2080. doi: 10.1271/bbb.60034
20. Quadri, S. S., Stratford, R. E., Boué, S. M., and Cole, R. B. (2013). Screening and identification of glyceollins and their metabolites by electrospray ionization tandem mass spectrometry with precursor ion scanning. Anal. Chem. 85, 1727-1733. doi: 10.1021/ac3030398
21. Sakakibara, H. (2006). Cytokinins: activity, biosynthesis, and translocation. Annu. Rev. Plant Biol. 57, 431-449. doi: 10.1146/annurev.arplant.57.032905.105231
22. Sakamoto, T., Morinaka, Y., Ohnishi, T., Sunohara, H., Fujioka, S., Ueguchi-Tanaka, M., et al. (2006). Erect leaves caused by brassinosteroid deficiency increase biomass production and grain yield in rice. Nat. Biotechnol. 24, 105-109. doi: 10.1038/nbt1173
23. Tanabe, S., Ashikari, M., Fujioka, S., Takatsuto, S., Yoshida, S., Yano, M., et al. (2005). A novel cytochrome P450 is implicated in brassinosteroid biosynthesis via the characterization of a rice dwarf mutant, dwarf11, with reduced seed length. Plant Cell 17, 776-790. doi: 10.1105/tpc.104.024950
24. Vriet, C., Russinova, E., and Reuzeau, C. (2012). Boosting crop yields with plant steroids. Plant Cell 24, 842-857. doi: 10.1105/tpc.111.094912
25. Wan, S.,Wu, J., Zhang, Z., Sun, X., Lv, Y., Gao, C., et al. (2009). Activation tagging, an efficient tool for functional analysis of the rice genome. Plant Mol. Biol. 69, 69-80. doi: 10.1007/s11103-008-9406-5
26. Wen, B.,Ma, L., Nelson, S. D., and Zhu, M. (2008). High-throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry. Anal. Chem. 80, 1788-1799. doi: 10.1021/ac702232r
27. Xin, P., Yan, J., Fan, J., Chu, J., and Yan, C. (2013a). A dual role of boronate affinity in high-sensitivity detection of vicinal diol brassinosteroids from subgram plant tissues via UPLC-MS/MS. Analyst 138, 1342-1345. doi: 10.1039/ c3an36533f
28. Xin, P. Y., Yan, J. J., Fan, J. S., Chu, J. F., and Yan, C. Y. (2013b). An improved simplified high-sensitivity quantification method for determining Brassinosteroids in different tissues of rice and Arabidopsis. Plant Physiol. 162, 2056-2066. doi: 10.1104/pp.113.221952
29. Yamamuro, C., Ihara, Y., Wu, X., Noguchi, T., Fujioka, S., Takatsuto, S., et al. (2000). Loss of function of a rice brassinosteroid insensitive1 homolog prevents internode elongation and bending of the lamina joint. Plant Cell 12, 1591-1605. doi: 10.1105/tpc.12.9.1591
30. Yan, Z., Lin, G., Ye, Y., Wang, Y., and Yan, R. (2014). Triterpenoid saponins profiling by adducts-targeted neutral loss triggered enhanced resolution and product ion scanning using triple quadrupole linear ion trap mass spectrometry. Anal. Chim. Acta 819, 56-64. doi: 10.1016/j.aca.2014.02.019