Brassinosteroids - Structures, analysis and synthesis

Recent Advances in Phytochemistry

Volumn 34C, Issue , 2000, Pages 385-407

  Schmidt, Jürgen ^a   Spengler, Barbara ^a   Voigt, Brunhilde ^a   Adam, Günter ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0009979003     PISSN: 00799920     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0079-9920(00)80013-1     Document Type: Chapter

References (74)

1. Grove M.D., Spencer G.F., Rowedder W.K., Mandava N., Worley J.F., Warthen Jr. J.D., Steffens G.L., Flippen-anderson J.L., and Cook Jr. J.K. Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen. Nature 281 (1979) 216-217
2. Sakurai A., and Fujioka S. The current status of physiology and biochemistry of brassinosteroids. Plant Growth Regul. 13 (1993) 147-159
3. Adam G., Porzel A., Schmidt J., Schneider B., and Voigt B. New developments in brassinosteroid research. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry (1996), Elsevier Science, Amsterdam 495-549
4. Yokota T. Structure, biosynthesis and function of brassinosteroids. Trends Plant Sci. 2 (1997) 137-143
5. Sasse J.M. Recent progress in brassinosteroid research. Physiol. Plant 100 (1997) 696-701
6. Fujioka S., and Sakurai A. Brassinosteroids. Nat. Prod. Rep. 14 (1997) 1-10
7. Clouse S.D., and Sasse J.M. Brassinosteroids: Essential regulators of plant growth and development. Annu. Rev. Plant Physiol. Plant Mol. Biol. 49 (1998) 427-451
8. In: Cutler H.G., Yokota T., and Adam G. (Eds). Brassinosteroids-Chemistry, Bioactivity, and Applications (1991), American Chemical Society, Washington, DC
9. Khripach V.A., Zhabinskii V.N., and De Groot A.E. Brassinosteroids-A New Class of Plant Hormones (1999), Academic Press, San Diego
10. In: Sakurai A., Yokota T., and Clouse S.D. (Eds). Brassinosteroids, Steroidal Plant Hormones (1999), Springer-edition, Tokyo
11. Adam G., Schmidt J., and Schneider B. Brassinosteroids. Progress in the Chemistry of Natural Products 78 (1999), Springer-edition, Wien-New York 1-46
12. Clouse S.D., and Feldmann K.A. Molecular genetics of brassinosteroid action. Brassinosteroids, Steroidal Plant Hormones (1999), Springer-edition, Tokyo 163-189
13. Szekeres M., and Koncz C. Biochemical and genetic analysis of brassinosteroid metabolism and function in Arabidopsis. Plant Physiol. Biochem. 36 (1998) 145-155
14. Fujioka S. Natural occurrence of brassinosteroids in the plant kingdom. Brassinosteroids, Steroidal Plant Hormones (1999), Springer-edition, Tokyo 21-45
15. Schmidt J., Voigt B., and Adam G. 2-Deoxybrassinolide-a naturally occurring brassinosteroid from Apium graveolens. Phytochemistry 40 (1995) 1041-1043
16. Fujioka S., Choi Y.-H., Takatsuto S., Yokota T., Li J., Chory J., and Sakurai A. Identification of castasterone, 6-deoxocastasterone, typhasterol and 6-deoxotyphasterol from shoots of Arabidopsis thaliana. Plant Cell Physiol. 37 (1996) 1201-1203
17. Fujioka S., Noguchi T., Yokota T., Takatsuto S., and Yoshida S. Brassinosteroids in Arabidopsis thaliana. Phytochemistry 48 (1998) 595-599
18. Fujioka S., Inoue T., Takatsuto S., Yanagisawa T., Yokota T., and Sakurai A. Identification of a new brassinosteroid, cathasterone, in cultured cells of Catharanthus roseus as a biosynthetic precursor of teasterone. Biosci. Biotechnol. Biochem. 59 (1995) 1543-1547
19. Choi Y.-H., Fujioka S., Nomura T., Harada A., Yokota T., Takatsuto S., and Sakurai A. An alternative brassinolide biosynthetic pathway via late C-6 oxidation. Phytochemistry 44 (1997) 609-613
20. Yokota T., Higuchi K., Takahashi N., Kamuro Y., Watanabe T., and Takatsuto S. Identification of brassinosteroids with epimeric substituents and/or the 23-oxo group in pollen and anthers of Japanese cedar. Biosci. Biotechnol. Biochem. 62 (1998) 526-531
21. Griffiths P.G., Sasse J.M., Yokota T., and Cameron D.W. 6-Deoxotyphasterol and 3-dehydro-6-deoxoteasterone, possible precursors to brassinosteroids in the pollen of Cupressus arizonica. Biosci. Biotechnol. Biochem. 59 (1995) 956-959
22. Abe H., Honjo C., Kyokawa Y., Asakawa S., Natsume M., and Narushima M. 3-Oxoteasterone and the epimerization of teasterone: identification in lily anthers and Distylium racemosum leaves and its biotransformation into typhasterol. Biosci. Biotechnol. Biochem. 58 (1994) 986-989
23. Yasuta E., Terahata T., Nakayama M., Abe H., Takatsuto S., and Yokota T. Free and conjugated brassinosteroids in the pollen and anthers of Erythronium japonicum Decne. Biosci. Biotechnol. Biochem. 59 (1995) 2156-2158
24. Asakawa S., Abe H., Kyokawa Y., Nakamura S., and Natsume M. Teasterone 3-myristate: a new type of brassinosteroid derivative in Lilium longiflorum anthers. Biosci. Biotechnol. Biochem. 58 (1994) 219-220
25. Asakawa S., Abe H., Nishikawa N., Natsume M., and Koshioka M. Purification and identification of new acyl-conjugated teasterones in lily pollen. Biosci. Biotechnol. Biochem. 60 (1996) 1416-1420
26. Friebe A., Volz A., Schmidt J., Voigt B., Adam G., and Schnabl H. 24-Epi-secasterone and 24-epi-castasterone from Lychnis viscaria seeds. Phytochemistry 52 (1999) 1607-1610
27. Spengler B., Schmidt J., Voigt B., and Adam G. 6-Deoxo-28-norcastasterone and 6-deoxo-24-epicastasterone-two new brassinosteroids from Ornithopus sativus. Phytochemistry 40 (1995) 907-910
28. Abe H., Takatsuto S., Nakayama M., and Yokota T. Homotyphasterol, a new natural brassinosteroid from rice (Oryza sativa L.) bran. Biosci. Biotechnol. Biochem. 59 (1995) 176-178
29. Yokota T., Matsuoka T., Koarai T., and Nakayama M. 2-Deoxybrassinolide, a brassinosteroid from Pisum sativum seed. Phytochemistry 42 (1996) 509-511
30. Schmidt J., Yokota T., Spengler B., and Adam G. 28-Homoteasterone-a new naturally occurring brassinosteroid from seeds of Raphanus sativus. Phytochemistry 34 (1993) 391-392
31. Schmidt J., Spengler B., Yokota T., Nakayama M., Takatsuto S., Voigt B., and Adam G. Secasterone, the first naturally occurring 2,3-epoxybrassinosteroid from Secale cereale. Phytochemistry 38 (1995) 1095-1097
32. Yokota T., Nakayama M., Wakisaki T., Schmidt J., and Adam G. 3-Dehydroteasterone, a 3,6-diketobrassinosteroid as a possible biosynthetic intermediate of brassinolide from wheat grain. Biosci. Biotechnol. Biochem. 58 (1994) 1183-1186
33. Suzuki H., Inoue T., Fujioka S., Takatsuto S., Yanagisawa T., Yokota T., Murofushi N., and Sakurai A. Possible involvement of 3-dehydroteasterone in the conversion of teasterone to typhasterol in cultured cells of Catharanthus roseus. Biosci. Biotech. Biochem. 58 (1994) 1186-1188
34. Fujioka S., and Sakurai A. Biosynthesis and metabolism of brassinosteroids. Physiol. Plant. 100 (1997) 710-715
35. Sakurai A. Brassinosteroids, Steroidal Plant Hormones. Biosynthesis (1999), Springer-edition, Tokyo 91-111
36. Taylor P.E., Spuck K., Smith P.M., Sasse J.M., Yokota T., Griffiths P.G., and Cameron D.W. Detection of brassinosteroids in pollen of Lolium perenne by immunocytochemistry. Planta 189 (1993) 91-100
37. Takatsuto S. Brassinosteroids: Distribution in plants, bioassay and microanalysis by gas chromatography-mass spectrometry. J. Chromatogr. A 658 (1994) 3-15
38. Takatsuto S., Abe H., and Gamoh K. Evidence for brassinosteroids in strobilus of Equisetum arvense L. Agric. Biol. Chem. 54 (1990) 1057-1059
39. Yokota T., Kim S.-K., Fukui Y., Takahashi N., Takeuchi Y., and Takematsu T. Brassinosteroids and sterols from a green alga, Hydrodictyon reticulatum: Configuration at C-24. Phytochemistry 26 (1987) 503-506
40. Yokota T., Arima M., and Takahashi N. Castasterone, a new phytosterol with plant-hormone potency, from chestnut insect gall. Tetrahedron Letters 23 (1982) 1275-1278
41. Yokota T., Arima M., Takahashi N., Takatsuto S., Ikekawa N., and Takematsu T. 2-Deoxycastasterone, a new brassinolide-related bioactive steroid from pinus pollen. Agric. Biol. Chem. 47 (1983) 2419-2420
42. Schneider J.A., Yoshihara K., Nakanishi K., and Kato N. Typhasterol (2-deoxycastasterone): A new plant growth regulator from cat-tail pollen. Tetrahedron Letters 24 (1983) 3859-3860
43. Abe H., Morishita T., Uchiyama M., Takatsuto S., and Ikekawa N. A new brassinolide-related steroid in leaves of Thea sinensis. Agric. Biol. Chem. 48 (1984) 2171-2172
44. Ikekawa N., Nishiyama F., and Fujimoto Y. Identification of 24-epibrassinolide in bee pollen of the broad bean, Vicia faba L. Chem. Pharm. Bull. 36 (1988) 405-407
45. Takatsuto S., and Yokota T. Biochemical analysis of natural brassinosteroids. Brassinosteroids, Steroidal Plant Hormones (1999), Springer-edition, Tokyo 47-68
46. Wada K., Marumo S., Abe H., Morishita T., Nakamura K., Uchiyama M., and Mori K. A rice lamina inclination test-a microquantitative bioassay for brassinosteroids. Agric. Biol. Chem. 48 (1984) 719-726
47. Ikekawa N., Takatsuto S., Kitsuwa T., Saito H., Morishita T., and Abe H. Analysis of natural brassinosteroids by gas chromatography and gas chromatography-mass spectrometry. J. Chromatogr. 290 (1984) 289-302
48. Takatsuto S., Ying B., Morisaki M., and Ikekawa N. Microanalysis of brassinolide and its analogues by gas chromatography and gas chromatography-mass spectrometry. J. Chromatogr. 239 (1982) 233-241
49. Ikekawa N., and Takatsuto S. Microanalysis of brassinosteroids in plants by gas chromatography/mass spectrometry. Mass Spectroscopy (Japan) 32 (1984) 55-70
50. Takatsuto S., and Ikekawa N. Analysis of 2-deoxybrassinosteroids by gas chromatography-mass spectrometry. Chem. Pharm. Bull. 34 (1986) 3435-3439
51. Abe H., Morishita T., Uchiyama M., Takatsuto S., Ikekawa N., Ikeda M., Sassa T., Kitsuwa T., and Marumo S. Occurrence of three new brassinosteroids: Brassinone, (24S)-24-ethylbrassinone and 28-norbrassinone, in higher plants. Experientia 39 (1983) 351-353
52. Abe H., Nakamura K., Morishita T., Uchiyama M., Takatsuto S., and Ikekawa N. Endogenous brassinosteroids of the rice plant: Castasterone and dolichosterone. Agric. Biol. Chem. 48 (1984) 1103-1104
53. Schmidt J., Spengler B., Voigt B., and Adam G. New brassinosteroids from european cultivated plants. Proceedings 23rd Annual Meeting Plant Growth Regulator Society of America. Calgary (1996) 61
54. Gamoh K., Kitsuwa T., Takatsuto S., Fujimoto Y., and Ikekawa N. Determination of trace brassinosteroids by high performance liquid chromatography. Anal. Sci. 4 (1988) 533-535
55. Gamoh K., Omote N., Okamoto N., and Takatsuto S. High-performance liquid chromatography of brassinosteroids in plants with derivatization using 9-phenanthreneboronic acid. J. Chromatogr. 469 (1989) 424-428
56. Gamoh K., Okamoto N., Takatsuto S., and Teijima I. Determination of traces of natural brassinosteroids as dansylaminophenylboronates by liquid chromatography with fluorimetric detection. Anal. Chim. Acta 228 (1990) 101-105
57. Gamoh K., and Takatsuto S. A boronic acid derivative as a highly sensitive fluorescence derivatization reagent for brassinosteroids in liquid chromatography. Anal. Chim. Acta 222 (1989) 201-204
58. Gamoh K., Takatsuto S., and Ikekawa N. Effective separation of C-24 epimeric brassinosteroids by liquid chromatography. Anal. Chim. Acta 256 (1992) 319-322
59. Gamoh K., Abe H., Shimada K., and Takatsuto S. Liquid chromatography/mass spectrometry with atmospheric pressure chemical ionization of free brassinosteroids. Rap. Commun. Mass Spectrom. 10 (1996) 903-906
60. Gamoh K., Prescott M.C., Goad L.J., and Takatsuto S. Analysis of brassinosteroids by liquid chromatography-mass spectrometry. Bunseki Kagaku 45 (1996) 523-527
61. Fung S., and Siddall J.B. Stereoselective synthesis of brassinolide: A plant promoting steroidal lactone. J. Amer. Chem. Soc. 102 (1980) 6581-6582
62. Ishiguro M., Takatsuto S., Morisaki M., and Ikekawa N. Synthesis of brassinolide, a steroidal lactone with plant growth promoting activity. Chem. Comm. 20 (1980) 962-964
63. Thompson M.J., Mandava N.B., Meudt W.J., Lusby W.R., and Spaulding D.W. Synthesis and biological activity of brassinolide and its 22β,23β-isomer: Novel plant growth steroids. Steroids 38 (1981) 567-580
64. Back T.G., Blazecka P.G., and Krishna M.V. A new synthesis of castasterone and brassinolide from stigmasterol: A concise and stereoselective elaboration of the side chain from a C-22 aldehyde. Can. J. Chem. 71 (1993) 156-163
65. McMorris T.C., Chavez R.G., and Patil P.A. Improved synthesis of brassinolide. J. Chem. Soc. Perkin Trans 1 (1996) 295-302
66. Watanabe T., Takatsuto S., Fujioka S., and Sakurai A. Improved synthesis of castasterone and brassinolide. J. Chem. Research (S) (1997) 360-361
67. Back T.G. Stereoselective synthesis of brassinosteroids. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry (1995), Elsevier Science, Amsterdam 321-364
68. Kovganko N.V., and Ananich S.K. Advances in the chemical synthesis of brassinosteroids. Chem. Nat. Comp. 33 (1997) 389-416
69. McMorris T.C. Chemical synthesis of brassinosteroids. Brassinosteroids, Steroidal Plant Hormones (1999), Springer-edition, Tokyo 69-90
70. McMorris T.C., and Patil P.A. Improved synthesis of 24-epibrassinolide from ergosterol. J. Org. Chem. 58 (1993) 2338-2339
71. Schmidt J., Spengler B., Yokota T., and Adam G. The cooccurrence of castasterone and 24-epicastasterone in seeds of Ornithopus sativus. Phytochemistry 32 (1993) 1614-1615
72. Voigt B., Takatsuto S., Yokota T., and Adam G. Synthesis of secasterone and further epimeric 2,3-epoxybrassinosteroids. J. Chem. Soc. Perkin Trans 1 (1995) 1495-1498
73. Voigt B., Schmidt J., and Adam G. Synthesis of 24-epiteasterone, 24-epityphasterol and their B-homo-6a-oxalactones from ergosterol. Tetrahedron 52 (1996) 1997-2004
74. Gamoh K., and Takatsuto S. Liquid chromatographic assay of brassinosteroids in plants. J. Chromatogr. A 658 (1994) 17-25