Analysis of Brassinosteroids in Plants

Journal of Plant Growth Regulation

Volumn 36, Issue 4, 2017, Pages 1002-1030

  Kanwar, Mukesh Kumar ^a,b   Bajguz, Andrzej ^c   Zhou, Jie ^a   Bhardwaj, Renu ^d  

^a ZHEJIANG UNIVERSITY   (China)

^b SRI GURU GRANTH SAHIB WORLD UNIVERSITY   (India)

^c UNIVERSITY OF BIALYSTOK   (Poland)

^d GURU NANAK DEV UNIVERSITY   (India)

Author keywords

Analytical techniques; Brassinosteroids; Isolation; Plant hormones

Indexed keywords

EID: 85027964480     PISSN: 07217595     EISSN: 14358107     Source Type: Journal    
DOI: 10.1007/s00344-017-9732-4     Document Type: Article

References (123)

1. Abe H, Marumo S (1991) Brassinosteroids in leaves of Distylium racemosum Sieb. et Zucc.: the beginning of brassinosteroid research study in Japan. In: Cutler HG, Yokota T, Adam G (eds) Brassinsoteroids: chemistry, bioactivity and applications. American Chemical Society, Washington, DC, pp 18–24
2. Abe H, Morishita T, Uchiyama M, Takatsuto S, Ikekawa N, Ikeda M, Sassa T, Kitsuwa T, Marumo S (1983) Occurrence of three new brassinosteroids: brassinone, 24(S)-24-ethylbrassione and 28-norbrassinolide in higher plants. Experientia 39:351–353
3. Abe H, Morishita T, Uchiyama M, Takatsuto S, Ikekawa N (1984a) A new brassinolide-related steroid in the leaves of Thea sinensis. Agric Biol Chem 48:1271–1273
4. Abe H, Hongo C, Kyokawa Y, Asakawa S, Natsume M, Narushima M (1994) 3-Oxoteasterone and the epimerization of teasterone: Identification: in lily anthers and Distylium racemosum leaves and its biotransformation into typhasterol. Biosci Biotechnol Biochem 58:986–989
5. Abe H, Takatsuto S, Nakayama M, Yokota T (1995) 28-homotyphasterol, a new natural brassinosteroid from rice (Oryza sativa L.) bran. Biosci Biotechnol. Biochem 59:176–178
6. Abe H, Soeno K, Koseki N-N, Natsume M (2001) Conjugated and unconjugated brassinosteroids. In: Baker DR, Umetsu NK (eds) Agrochemical discovery. Insect, weed, and fungal control. American Chemical Society, Washington, DC, pp 91–101
7. Adam G, Porzel A, Schmidt J, Schneider B, Voigt B (1996) New developments in brassinosteroid research. In: Atta-ur-Rahman (ed) Studies in natural product chemistry, vol 18. Elsevier Science B.V, Amsterdam, pp 495–549
8. Adam G, Schmidt J, Schneider B (1999) Brassinosteroids in progress. In: Herz W, Falk H, Kirby GW, Moore RE, Tamm C (eds) The chemistry of organic natural products. Springer, New York, pp 1–46
9. Ahammed GJ, Gao CJ, Ogweno JO, Zhou Yh, Xia XJ, Mao WH, Shi K, Yu JQ (2012) Brassinosteroids induce plant tolerance against phenanthrene by enhancing degradation and detoxification in Solanum lycopersicon L. Ecotox Environ Safe 80:28–36
10. Antonchick AP, Schneider B, Zhabinskii VN, Konstantinova OV, Khripach VA (2003) Biosynthesis of 2,3-epoxybrassinosteroids in seedlings of Secale cereale. Phytochemistry 63:771–776
11. Antonchick A, Svatoš A, Schneider B, Konstantinova OV, Zhabinskii VZ, Khripach VA (2005) 2,3-Epoxybrassinosteroids are intermediates in the biosynthesis of castasterone in seedlings of Secale cereale. Phytochemistry 66:65–72
12. Asakawa S, Abe H, Kyokawa Y, Nakamura S, Natsume M (1994) Teasterone 3-myristate: a new type of brassinosteroids derivative in Lilium longiflorium anthers. Biosci Biotechnol Biochem 58:219–220
13. Asakawa S, Abe H, Nishikawa N, Natsume M, Koshioka M (1996) Purification and identification of new acyl-conjugated teasterone in lily pollen. Biosci Biotechnol Biochem 60:1416–1420
14. Baba J, Yokota T, Takahashi N (1983) Brassinolide-related new bioactive steroids for Dolichos lablab seed. Agric Biol Chem 47:659–661
15. Bajguz A (2009) Isolation and characterization of brassinosteroids from algal cultures of Chlorella vulgaris Beijerinck (Trebouxiophycaea). J Plant Physiol 166:1946–1949
16. Bajguz A (2011) Brassinosteroids – occurrence and chemical structures in plants. In: Hayat S, Ahmad A (eds) Brassinosteroids: a class of plant hormone. Springer, Dordrecht, pp 1–27
17. Bajguz A, Hayat S (2009) Effects of brassinosteroids on the plant responses to environmental stresses. Plant Physiol Biochem 47:1–8
18. Bajguz A, Tretyn A (2003) The chemical characteristic and distribution of brassinosteroids in plants. Phytochemistry 62:1027–1046
19. Bajguz A, Bajguz AJ, Tryniszewska EA (2013) Recent advanced in medicinal applications of brassinosteroids, a group of plant hormones. In: Atta-ur-Rahman (ed) Studies in natural products chemistry, vol 40. Elsevier Science Publishers, Amsterdam, pp 33–49
20. Bhardwaj R, Kaur S, Nagar PK, Arora HK (2007) Isolation and characterization of brassinosteroids from immature seeds of Camellia sinensis (O) Kuntze. Plant Growth Regul 53:1–5
21. Bishop GT, Nomuma T, Yokota T, Harrison K, Noguchi T, Fujioka S, Takatsuto S, Jones JDG, Kamiya Y (1999) The tomato DWARF enzyme catalyses C-6-oxidation in brassinosteroids biosynthesis. Proc Natl Acad Sci USA 96:1761–1766
22. Borisevich NA, Skornyakov IV, Khripach VA, Tolstorozhev GB, Zhabinskii VN (2007) Manifestation of structure and intermolecular interactions of biologically active brassinosteroids in infrared spectra. J Appl Spectrosc 74:673–680
23. Borisevich NA, Buslov DK, Khripach VA, Zhabinskii VN (2008) Infrared spectra of S- and R-isomers of biologically active brassinosteroids. J Appl Spectrosc 75:637–643
24. Cao L, Yang J, Zheng L, Wang D, Huang Q (2014) Quantitative determination of 24-epibrassinolide by high-performance liquid chromatography with evaporative light scattering detector. Chin J Pestic Sci 16:72–77
25. Cao L, Yang J, Li X, Wang D, Huang Q (2015) Determination of brassinolide analogs by high-performance liquid chromatography with evaporative light scattering detection. Anal Lett 48:575–585
26. Carbonell ML, Javegui O (2005) A rapid method for analysis of abscisic acid (ABA) in crude extracts of water stressed Arabidopsis thaliana plants by liquid chromatography-mass spectrometry in tandem mode. Plant Physiol Biochem 43:11–40
27. Cui JX, Zhou YH, Ding JG, Xia XJ, Shi K, Chen SC, Asami T, Chen Z, Yu JQ (2011) Role of nitric oxide in hydrogen peroxide-dependent induction of abiotic stress tolerance by brassinosteroids in cucumber. Plant Cell Environ 34:347–358
28. Deng T, Wua D, Duana C, Guana Y (2016) Ultrasensitive quantification of endogenous brassinosteroids in milligram fresh plant with a quaternary ammonium derivatization reagent by pipette-tip solid-phase extraction coupled with ultra-high-performance liquid chromatography tandem mass spectrometry. J Chromatogr A 1456:105–112
29. Dinan L, Bourne PC, Meng Y, Sarker SD, Toletino R, Whiting P (2001) Assessment of natural products in the Drosophila melanogaster BII cell bioassay for ecdysteroid agonist and antagonist activities. Cell Mol Life Sci 58:321–342
30. Ding J, Mao LJ, Wang ST, Yuan BF, Feng YQ (2013) Determination of endogenous brassinosteroids in plant tissues using solid-phase extraction with double layered cartridge followed by high-performance liquid chromatography-tandem mass spectrometry. Phytochem Anal 24:386–394
31. Ding J, Hong J, Wu JH, Liu JF, Yuan BF, Feng YQ (2014) Improved methodology for assaying brassinosteroids in plant tissues using magnetic hydrophilic material for both extraction and derivatization. Plant Methods 10:1–11
32. Friebe A, Volz A, Schmidt J, Voigt B, Adam G, Schnabl H (1999) 24-epi-secasterone and 24-epi-castasterone from Lychnis viscaria seeds. Phytochemistry 52:1607–1610
33. Fujioka S, Inoue T, Takatsuto S, Yanagisawa T, Yokota T, 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
34. Fujioka S, Noguchi T, Sekimoto M, Takatsuto S, Yoshida S (2000a) 28-Norcastasterone is biosynthesized from castasterone. Phytochemistry 55:97–101
35. Fujioka S, Noguchi T, Watanabe T, Takatsuto S, Yoshida S (2000b) Biosynthesis of brassinosteroids in cultured cells of Catharanthus roseus. Phytochemistry 53:549–553
36. Fujioka S, Takatsuo S, Yoshida S (2002) An early C-22 oxidation branch in the brassinosteroid biosynthetic pathway. Plant Physiol 130:930–939
37. Gamoh K (1994) Liquid chromatographic assay of brassinosteroids in plants. J Chromatogr A 658:17–25
38. Gamoh K, Takatsuto S (1989) A boronic acid derivative as a highly sensitive fluorescence derivatization reagent for brassinosteroids in liquid chromatography. Anal Chim Acta 222:201–204
39. Gamoh K, Kitsuwa T, Takatsuto S, Fujimoto Y, Ikekawa N (1988) Determination of trace brassinosteroids by HPLC. Anal Sci 4:533–535
40. Gamoh K, Omote K, Okamoto N, Takatsuto S (1989) High-performance liquid chromatography of brassinosteroids in plants with derivatization using 9-phenanthreneboronic acids. J Chromatogr 469:424–428
41. Gamoh K, Okamoto N, Takatsuto S, Tejima I (1990a) Determination of natural brassinosteroids as dansyl-amino phenylboronates by liquid chromatography with fluorimetric detection. Anal Chim Acta 228:101–105
42. Gamoh K, Sawamoto H, Takatsuto S, Watabe Y, Arimoto H (1990b) Ferroceneboronic acid as a derivatization reagent for the determination of brassinosteroids by high-performance liquid chromatography with electrochemical detection. J Chromatogr 515:227–231
43. Gamoh K, Takatsuto S, Ikekawa N (1992) Effect of separation of C-24 epimeric brassinosteroids by liquid chromatography. Anal Chim Acta 256:319–322
44. Gamoh K, Abe H, Shimada K, Takatsuto S (1996) Liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization of free brassinosteroids. Rapid Commun Mass Spectrom 10:903–906
45. Gonzalez SM, Bustos DA, Zudenigo ME, Ruveda EA (1986) Configurational assignment of epimeric 22,23-epoxides of steroids by carbon-13 NMR spectroscopy. Tetrahedron 42:755–758
46. Griffiths PG, Sasse JM, Yokota T, Cameron DW (1995) 6-Deoxotyphasterol and 3-dehydro-6-deoxoteasterone, possible precursors to brassinosteroids in the pollen of Cupressus arizonica. Biosci Biotechnol Biochem 59:956–959
47. Grove MD, Spencer GF, Rohwedder WK, Mandava N, Worley JF, Warthen JD, Steffens GL, Flipper-Anderson JL, Cook JC (1979) Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen. Nature 281:216–217
48. Horgen PA, Nakagawa CH, Irvin RT (1984) Production of monoclonal-antibodies to a steroid plant-growth regulator. Can J Biochem Cell B 62:715–721
49. Huo F, Wang X, Han Y, Bai Y, Zhang W, Yuan H, Liu H (2012) A new derivatization approach for the rapid and sensitive analysis of brassinosteroids by using ultra high performance liquid chromatography-electrospray ionization triple quadrupole mass spectrometry. Talanta 99:420–425
50. Ikekawa N, Takatsuto S (1984) Microanalysis of brassinosteroids in plants by gas chromatography/mass spectroscopy. Mass Spectrosc Jpn 32:55–70
51. Ikekawa N, Takatsuto S, Marumo S, Abe H, Morishita T, Uchiyama M, Ikeda M, Sasa T, Kisuwa T (1983) Identification of brassinolide and its 6-oxo analog in the plant kingdom by selected ion monitoring. Proc Jpn Acad Ser B, Phys Biol Sci 59:9–12
52. Ikekawa N, Takatsuto S, Kitsuwa T, Saito H, Morishita T, Abe H (1984) Analysis of natural brassinosteroids by gas chromatography and gas chromatography-mass spectroscopy. J Chromatogr 290:289–302
53. Ikekawa N, Nishiyama F, Fujimoto Y (1988) Identification of 24-epibrassinolide in bee pollen of the broad bean Vicia faba L. Chem Pharm Bull 36:405–407
54. Joo SH, Kim TW, Son SH, Lee WS, Yokota T, Kim SK (2012) Biosynthesis of a cholesterol-derived brassinosteroid, 28-norcastasterone, in Arabidopsis thaliana. J Exp Bot 63:1823–1833
55. Kanwar MK, Bhardwaj R (2015) Arsenic induced modulation of antioxidative defense system and brassinosteroids in Brassica juncea L. Ecotox Environ Safe 115:119–125
56. Kanwar MK, Bhardwaj R, Arora P, Chowdhary SP, Sharma P, Kumar S (2012) Plant steroid hormones produced under Ni stress are involved in the regulation of metal uptake and oxidative stress in Brassica juncea L. Chemosphere 86:41–49
57. Kanwar MK, Bhardwaj R, Chowdhary SP, Arora P, Sharma P, Kumar S (2013) Isolation and characterization of 24-epibrassinolide from Brassica juncea L. and its effects on growth, Ni ion uptake, antioxidant defense of Brassica plants and in vitro cytotoxicity. Acta Physiol Plant 35:1351–1362
58. Khripach VA, Zhabinskii VN, de Groot AE (1999) Brassinosteroids: a new class of plant hormones. Academic Press, San Diego
59. Khripach VA, Zhabinskii VN, Litvinovskaya RP (2011) Immunoassays of brassinosteroids. In: Hayat S, Ahmad A (eds) Brassinosteroids: a class of plant hormone. Springer Science + Bussiness Media BV, Dordrecht, pp 375–392
60. Kim SK (1991) Natural occurrences of brassinosteroids. In: Cutler HG, Yokota T, Adam G (eds) Brassinosteroids: chemistry, bioactivity and applications. American Chemical Society, Washington, DC, pp 26–35
61. Kim SK, Yokota T, Takahashi N (1987) 25-methyldolichosterone, a new brassinosetroid with a tertiary butyl group from immature seed of Phaseolus vulgaris. Agric Biol Chem 51:2303–2305
62. Kim MK, Jang MK, Youn JH, Son SH, Lee WS, Yokota T, Kim SK (2015) Occurrence of phosphorylated castasterone in Arabidopsis thaliana and Lycopersicum esculentum. Physiol Plant 153:58–67
63. Kolbe A, Marquardt V, Adam G (1992) Synthesis of tritium labeled 24-epibrassinolide. J Labelled Comp Radiopharm 31:801–805
64. Konstantinova OV, Antonchick AP, Oldham NJ, Zhabinskii VN, Khripach VA, Schneider B (2001) Analysis of underivatized brassinosteroids by HPLC/APCI-MS. Occurrence of 3-epibrassinolide in Arabidopsis thaliana. Collect Czech. Chem Commun 66:1729–1734
65. Litivinovskaya RP, Lyakhov AS, Govorova AA, Drach SV, Khripach VA (1997) X-ray structure of (20R,22 S,5’S)-22-(3′-methylisoxazolin-5′yl)-6,6-ethylenedioxy-3α,5-cyclo-23-nor-5α-cholestan-22-ol. Bioorg Khim 23:147–151
66. Liyan Ma, Zhang H, Wentao Xu, Xiaoyun He, Lili Y, Yunbo L, Huang K (2013) Simultaneous determination of 15 plant growth regulators in bean sprout and tomato with liquid chromatography–triple quadrupole tandem mass spectrometry. Food Anal. Methods 6:941–951
67. Lv T, Zhao XEn, Zhu S, Ji Z, Chen G, Sun Z, Song C, You J, Sou Y (2014) Development of an efficient HPLC fluorescence detection method for brassinolide by ultrasonic-assisted dispersive liquid-liquid micro-extraction coupled with derivatization. Chromatographia 77:1653–1660
68. Malíková J, Swaczynová J, Kolář Z, Strnad M (2008) Anticancer and antiproliferative activity of natural brassinosteroids. Phytochemistry 69:418–426
69. Marumo S, Hattori H, Nanoyama Y, Munakata K (1968) The presence of novel plant growth regulators in leaves of Distylium racemosum Sieb. et. Zucc. Agric Biol Chem 32:528–529
70. Michelini FM, Ramirez JA, Berra A, Galagovsky LR, Alché LE (2004) In vitro and in vivo antiherpetic activity of three new synthetic brassinosteroids analogues. Steroids 69:713–720
71. Michelini FM, Berra A, Alche LE (2008) The in vitro immunomodulatory activity of a synthetic brassinosteroid analogue would account for the improvement of herpetic stromal keratitis in mice. J Steroid Biochem Mol Biol 108:164–170
72. Michelini FM, Zorrilla P, Robello C, Alche AE (2013) Immunomodulatory activity of an anti-HSV-1 synthetic stigmastane analog. Bioorg Med Chem 21:560–568
73. Mitchell JD, Mandava NB, Worley JF, Plimmer JR, Smith MV (1970) Brassins: a new family of plant hormones from rape pollen. Nature 225:1065–1066
74. Mori K, Sakakibara M, Ichikawa Y, Ueda H, Okada K, Umemora T, Yabuta G, Kuwahara S, Kondo M, Minobe M, Sogabe A (1982) Synthesis of (22 S,23 S)-homobrassinolide and brassinolide from stigmasterol. Tetrahedron 38:2099–2109
75. Mori K, Sakakibara M, Okada K (1984) Synthesis of naturally occurring brassinosteroids employing cleavage of 23,24-epoxides as key reactions. Synthesis of brassinolide, castasterone, dolicholide, dolichosterone, homodolicholide, homodolichosterone, 6-deoxocastasterone and 6-deoxodolichosterone. Tetrahedron 40:1767–1781
76. Motegi C, Takatsuto S, Gamoh K (1994) Identification of brassinolide and castasterone in the pollen of orange (Citrus sinensis) by high performance liquid chromatography. J Chromatogr 658:27–30
77. Pachthong C, Supyen D, Buddhasukh D, Jatisatienr A (2007) Isolation and characterization of brassinolide and castasterone from mature seeds of smooth loofah (Luffa cylindrical (L.) M.J. Roem). ACGC Chem Res Comm 21:4–8
78. Pan X, Wang X (2009) Profiling of plant hormones by mass spectrometry. J Chromatogr B 877:2806–2813
79. Plattner RD, Taylor SL, Grove MD (1986) Detection of brassinolide and castasterone is Alnus glutinosa (European alder) pollen by gas chromatography/mass spectrometry. J Nat Prod 49:540–545
80. 13C NMR analysis of brassinosteroids. Magn Reson Chem 30:651–657
81. Pradko A, Litvinovskaya RP, Sauchuk AL, Drach SV, Baranovsky AV, Zhabinskii VN, Mirantsova TV, Khripach VA (2015) A new ELISA for quantification of brassinosteroids in plants. Steroids 97:78–86
82. Rajewska I, Talarek M, Bajguz A (2016) Brassinosteroids and response of plants to heavy metals action. Front Plant Sci 7:629
83. Rarova L, Zahler S, Liebl J, Krystof V, Sedlak D, Bartunek P, Strnad M (2012) Brassinosteroids inhibit in vitro angiogenesis in human endothelial cells. Steroids 77:1502–1509
84. Schlagnhaufer CD, Arteca RN, Phillips AT (1991) Induction of anti-brassinosteroid antibodies. J Plant Physiol 138:404–410
85. Schmidt J, Yokota T, Spengler B, Adam G (1993) 28-Homoteasterone, a naturally occurring brassiosteroid from seeds of Raphanus sativus. Phytochemistry 34:391–392
86. Schmidt J, Spengler B, Tokota T, Nakayama M, Takatsuto S, Voigt B, Adam G (1995b) Secasterone, the first naturally occurring 2,3-epoxybrassinosteroid from Secale cereale. Phytochemistry 38:1095–1097
87. Schmidt J, Voigt B, Adam G (1995c) 2-Deoxybrassinolide – a naturally occurring brassinosteroid from Apium graveolens. Phytochemistry 40:1041–1043
88. Schmidt J, Altmann T, Adam G (1997) Brassinosteroids from seeds of Arabidopsis thaliana. Phytochemistry 45:1325–1327
89. Schneider JA, Yoshihara K, Nakanishi K, Kato N (1983) Typhasterol (2-deoxycastasterone): a new plant growth regulator from cattail pollen. Tetrahedron Lett 24:3859–3860
90. 14C]-24-epibrassinolide. J Labelled Comp Radiopharm 27:1383–1393
91. Shim JH, Kim IS, Lee KB, Suh YT, Morgan ED (1998) Determination of brassinolide in rice (Oryza sativa L.) by HPLC equipped with a fluorescence detector. Agric Chem Biotechnol 39:84–88
92. Soeno K, Kyokawa Y, Natsume M, Abe H (2000) Teasterone-3-O-D-glucopyranoside, a new conjugated brassinosteroid metabolite from lily cell suspension cultures and its identification in lily anthers. Biosci Biotechnol Biochem 64:702–709
93. Sondhi N, Bhardwaj R, Kaur S, Kumar N, Singh B (2008) Isolation of 24-epibrassinolide from leaves of Aegle marmelos and evaluation of its antigenotoxicity employing Allium cepa chromosomal aberration assay. Plant Growth Regul 54:217–224
94. 2 induced DNA damage in single cell gel electrophoresis assay (Comet assay) by castasterone isolated from leaves of Centella asiatica. Health (London) 2:595–602
95. Spengler B, Schmidt J, Voigt B, Adam G (1995) 6-Deoxo-28-norcastasterone and 6-deoxo-24-epicastasterone - two new brasinosteroids from Ornithopus sativus. Phytochemistry 40:907–910
96. Stirk WA, Bálint P, Tarkowská D, Novák O, Strnad M, Ördög V, van Staden J (2013) Hormone profiles in microalgae: gibberellins and brassinosteroids. Plant Physiol Biochem 70:348–353
97. Stirk WA, Bálint P, Tarkowská D, Novák O, Maróti G, Ljung K, Turečková V, Strnad M, Ördög V, van Staden J (2014) Effect of light on growth and endogenous hormones in Chlorella minutissima (Trebouxiophyceae). Plant Physiol Biochem 79:66–76
98. Svatoš A, Antonchick A, Schneider B (2004) Determination of brassinosteroids in the sub-femtomolar range using dansyl-3-aminophenylboronate derivatization and electrospray mass spectrometry. Rapid Commun Mass Spectrom 18:816–821
99. Swaczynová J, a M, Hniličková J, Kohout L, Strnad M (2006) Synthesis, biological, immumological and anticancer properties of a new brassinosteroid ligand. Pol J Chem 80:629–635
100. Swaczynová J, Novák O, Hauserová E, Fuksová K, a M, Kohout L, Strnad M (2007) New techniques for the estimation of naturally occurring brassinosteroids. J Plant Growth Regul 26:1–14
101. Takatsuto S (1994) Brassinosteroids: distribution in plants, bioassays, and micro-analysis by gas chromatography-mass spectrometry. J Chromatogr A 658:3–15
102. Takatsuto S, Ying B, Morisaki M, Ikekawa N (1982) Microanalysis of brassinolide and its analogues by gas chromatography and gas chromatography-mass spectrometry. J Chromatogr 239:233–241
103. Takatsuto S, Omote K, Gamoh K, Ishibashi M (1990) Identification of brassinolide and castasterone in buckwheat (Fagopyrum esculentum) pollen. Agric Biol Chem 54:757–762
104. Tarkowská D, Novák O, Oklestkova J, Strnad M (2016) The determination of 22 natural brassinosteroids in a minute sample of plant tissue by UHPLC-ESI-MS/MS. Anal Bioanal Chem 408:6799–6812
105. Taylor PE, Spuck K, Smith PM, Sasse JM, Yokota T, Griffiths PG, Cameron DW (1993) Detection of brassinosteroids in pollen of Lolium perenne L. by immunocytochemistry. Planta 189:91–100
106. Thompson MJ, Mandava NB, Flippen-Anderson JL, Worley JF, Dutky SR, Robbins WE, Lusby WR (1979) Synthesis of brassinosteroids: new plant growth-promoting regulators. J Org Chem 44:5002–5004
107. Wachsman MB, Castilla V (2012) Antiviral properties of brassinosteroids. In: Pereira-Netto AB (ed) Brassinosteroids: practical applications in agriculture and human health. Bentham Science Publishers, Sharjah, pp 57–71
108. Wachsman MB, Ramirez JA, Galagovsky LR, Coto CE (2002) Antiviral activity of brassinosteroid derivatives against measles virus in cell cultures. Antivir Chem Chemother 13:61–66
109. Wang L, Duan C, Wu D, Guan Y (2014) Quantification of endogenous brassinosteroids in sub-gram plant issues by in-line matrix solid-phase dispersion-tandem solid phase extraction coupled with high performance liquid chromatography–tandem mass spectrometry. J Chromatogr A 1359:44–51
110. Wu Q, Wu D, Shen Z, Duan C, Guan Y (2013) Quantification of endogenous brassinosteroids in plant by on-line two-dimensional microscale solid phase extraction-on column derivatization coupled with high performance liquid chromatography–tandem mass spectrometry. J Chromatogr A 1297:56–63
111. Xin P, Yan J, Fan J, Chu J, Yan C (2013a) A dual role of boronate affinity in high-sensitivity detection of vicinal diol brassinosteroids from sub-gram plant tissues via UPLC-MS/MS. Analyst 138:1342–1345
112. Xin P, Yan J, Fan J, Chu J, Yan C (2013b) An improved simplified high-sensitivity quantification method for determining brassinosteroids in different tissues of rice and Arabidopsis. Plant Physiol 162:2056–2066
113. Xin P, Yan J, Li B, Fang S, Fan J, Tian H, Shi Y, Tian W, Yan C, Chu J (2016) A comprehensive and effective mass spectrometry-based screening strategy for discovery and identification of new brassinosteroids from rice tissues. Front Plant Sci 7:1786. doi:10.3389/fpls.2016.01786
114. Yokota T, Arima M, Takahashi N (1982a) Castasterone, a new phytosterol with plant-hormone potency from chestnut insect gall. Tetrahedron Lett 23:1275–1278
115. Yokota T, Baba J, Takahashi N (1982b) A new steroidal lactone with plant growth-regulatory activity from Dolichos lablab seed. Tetrahedron Lett 23:4965–4966
116. Yokota T, Baba J, Takahashi N (1983a) Brassinolide related biocative sterols in Dolichos lablab: brassinolide, castasterone and a new analog, homodolicholide. Agric Biol Chem 47:1409–1411
117. Yokota T, Morita M, Takahashi N (1983b) 6-Deoxocastasterone and 6-deoxodolichsterone-putative precursors for brassinolide-related steroids from Phaseolus vulgaris. Agric Biol Chem 47:2149–2151
118. Yokota T, Kim SK, Fukui Y, Takahashi N, Takeuchi Y, Takematsu T (1987a) Brassinosteroids and sterols from a green alga, Hydrodictyon reticulatum: configuration at C-24. Phytochemistry 26:503–506
119. Yokota T, Koba S, Kim SK, Takatsuto S, Ikekawa N, Sakakibara M, Okada K, Mori K, Takahashi N (1987b) Diverse structural variations of the brassinosteroids in Phaseolus vulgaris. Agric Biol Chem 51:1625–1631
120. Yokota T, Watanabe S, Ogino Y, Yamaguchi I, Takahashi N (1990) Radioimmunoassay for brassinosteroids and its use for comparative-analysis of brassinosteroids in stems and seeds of Phaseolus vulgaris. J Plant Growth Regul 9:151–159
121. Yokota T, Nomura T, Nakayama M (1997) Identification of brassinosteroids that appear to be derived from campesterol and cholesterol in tomato shoots. Plant Cell Physiol 38:1291–1294
122. Yokota T, Higuchi K, Takahashi N, Kamuro Y, Watanabe T, Takatsuto S (1998) Identification of brassinosteroids with epimerization substituent and /or the 23-oxo group in pollen and anthers of Japanese cedar. Biosci Biotechnol Biochem 62:526–531
123. Yokota T, Sato T, Takeuchi Y, Nomura T, Uno K, Watanabe T, Takatsuto S (2001) Roots and shoots of tomato produce 6-deoxo-28-norcathasterone, 6-deoxo-28-nortyphasterol and 6-deoxo-28-norcastasterone, possible precursors of 28-norcastasterone. Phytochemistry 58:233–238