Some notes on the terminology of brassinosteroids

Plant Growth Regulation

Volumn 39, Issue 1, 2003, Pages 1-11

  Zullo, Marco António Teixeira ^a   Kohout, Ladislav ^b   De Azevedo, Mariangela De Burgos Martins ^a  

^a INSTITUTO AGRONÔMICO   (Brazil)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Brassin; Brassinolide; Brassinolide activity; Brassinosteroid analogues; Brassins; Natural brassinosteroids

Indexed keywords

BIOSYNTHESIS; ORGANIC COMPOUNDS; TERMINOLOGY;

BRASSIN;

PLANTS (BOTANY);

EID: 0345829923     PISSN: 01676903     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1021802910454     Document Type: Article

References (58)

1. Abe H., Morishita T., Uchiyama M., Marumo S., Munakata K., Takatsuto S. et al. 1982. Identification of brassinolide-like substances in Chinese cabbage. Agric. Biol. Chem. 46: 2609-2611.
2. Adam G. and Marquardt V. 1986. Brassinosteroids. Phytochemistry 25: 1787-1799.
3. Adam G., Schmidt J. and Schneider B. 1999. Brassinosteroids. In: Herz W., Falk H., Kirby G.W., Moore R.E. and Tamm C. (eds), Progress in the Chemistry of Organic Natural Products. Spinger Verlag, Wien, pp. 1-46.
4. Aiello A., Fattorusso E. and Menna M. 1999. Steroids from sponges: recent reports. Steroids 64: 687-714.
5. Anastasia M., Allevi P., Ciuffreda P., Fiecchi A. and Oleotti A. 1985. Synthesis of (2R,3S,22R,23R)- and (2R,3S,22S,23S)-2,3,22,23-tetrahydroxy-B-homo-7a-oxa-5α-ergostan-7- ones, two new brassinolide analogues. J. Org. Chem. 50: 321-325.
6. Andersen D.L., Back T.G., Jansen L., Michalak K., Pharis R.P. and Sung G.C.I. 2001. Design, synthesis, and bioactivity of the first nonsteroidal mimetics of brassinolide. J. Org. Chem. 66: 7129-7141.
7. Arsenault G.P., Biemann K., Barksdale A.W. and McMorris T.C. 1968. Structure of antheridiol a sex hormone in Achlya bisexualis. J. Amer. Chem Soc. 90: 5635.
8. Asami T. and Yoshida S. 1999. Brassinosteroid biosynthesis inhibitors. Trends Plant Sci. 4: 348-353.
9. Baron D.L., Back T.G., Luo W., Janzen L. and Pharis R.P. 1998. Structure-activity studies of brassinolide B-ring analogues. Phytochemistry 49: 1849-1858.
10. Brosa C., Capdevila J.M. and Zamora I. 1996. Brassinosteroids: a new way to define the structural requirements. Tetrahedron 52: 2435-2448.
11. Brosa C., Soca L., Terricabras E., Ferrer J.C. and Alsina A. 1998. New synthetic brassinosteroids: a 5α-hydroxy-6-ketone analog with strong plant growth promoting activity. Tetrahedron 54: 12337-12348.
12. Butenandt A. and Karlson P. 1954. Über die isolierung eines metamorphose-hormons der insekten in kristallisierter form. Z. Naturforsch. (B) 9: 389-391.
13. Canonica L., Weisz-Vincze I. and Danieli B. 1972. Structure of muristerone A, a new phytoecdysone. J. Chem. Soc. Chem. Commun.: 1060-1061.
14. Clouse S.D. and Feldmann K.A. 1999. Molecular genetics of brassinosteroid action. In: Sakurai A., Yokota T. and Clouse S.D. (eds), Brassinosteroids: Steroidal Plant Hormones. Springer Verlag, Tokyo, pp. 163-190.
15. Clouse S.D. and Sasse J.M. 1998. Brassinosteroids: essential regulators of plant growth and development. Ann. Rev. Plant Physiol. Plant Mol. Biol. 49: 427-451.
16. De Azevedo M.B.M., Zullo M.A.T., Queiroz H.M., Salva T.J.G., Duran N. and Alderete J.B. 2001. Epibrassinolide/β-cyclodextrin inclusion complex: physico-chemical characterization and rice lamina inclination assay. In: Abstracts 17th International Conference on Plant Growth Substances. July 1-6, 2001, Brno, Czech Republic. Mendel University of Agriculture and Forestry, Brno, Czech Republic, p. 181.
17. De Marino S., Palagiano E., Zollo F., Minale L. and Iorizzi M. 1997. A novel sulfated steroid with a 7-membered 5-oxalactone B-ring from an Antarctic starfish of the family Asteriidae. Tetrahedron 53: 8625-8628.
18. Freire R., González A.G. and Suárez E. 1970. New sources of steroid sapogenins. 8. Sceptrumgenin and isoplexigenin A, B, C and D from Isoplexis sceptrum. Tetrahedron 26: 3233-3244.
19. Fu X., Ferreira M.L.G., Schmitz F.J. and Kelly M. 1999. Tamosterone sulfates: a C-14 epimeric pair of polyhydroxylated sterols from a new Oceanapiid sponge genus. J. Org. Chem. 64: 6706-6709.
20. Fujioka S. 1999. Natural occurrence of brassinosteroids in the plant kingdom. In: Sakurai A., Yokota T. and Clouse S.D. (eds), Brassinosteroids: Steroidal Plant Hormones. Springer Verlag, Tokyo, pp. 21-45.
21. Fujioka S., Noguchi T., Watanabe T., Takatsuto S. and Yoshida S. 2000. Biosynthesis of brassinosteroids in cultured cells of Catharanthus roseus. Phytochemistry 53: 549-553.
22. Fung S. and Siddall J.B. 1980. Stereoselective synthesis of brassinolide: a plant growth promoting steroidal lactone. J. Amer. Chem Soc. 102: 6580-6581.
23. Grove M.D., Spencer F.G., Rohwededer W.K., Mandava N.B., 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.
24. Hayashi S., Hohjoh T., Shida A. and Ikekawa N. 1989. 23-Phenylbrassinosteroids. US Patent 4,767,442.
25. Ikekawa N., Nishiyama F. and Fujimoto Y. 1988. Identification of 24-epibrassinolide in bee pollen of the broad bean Vicia faba L. Chem. Pharm. Bull. 36: 405-407.
26. Ishiguro M., Takatsuto S., Morisaki M. and Ikekawa N. 1980. Synthesis of brassinolide, a steroidal lactone with plant growth promoting activity. J. Chem. Soc. Chem. Commun.: 962-964.
27. Kametani T., Katoh T., Fujio J., Nogiwa I., Tsubuki M. and Honda T. 1988. An improved synthesis of plant-growth regulating steroid brassinolide and its congeners. J. Org. Chem. 53: 1982-1991.
28. Kamuro Y. and Takatsuto S. 1999. Practical application of brassinosteroids in agricultural fields. In: Sakurai A., Yokota T. and Clouse S.D. (eds), Brassinosteroids: Steroidal Plant Hormones. Springer Verlag, Tokyo, pp. 223-241.
29. Khripach V.A., Zhabinskii V.N. and De Groot A.E. 1999. Brassinosteroids, a new class of plant hormones. Academic Press, San Diego, 286pp.
30. Kim S.-K. 1991. Natural occurrences of brassinosteroids. In: Cutler H.G., Yokota T. and Adam G. (eds), Brassinosteroids - Chemistry, Bioactivity and Applications. American Chemical Society, Washington, pp. 26-35.
31. Kirson I., Cohen A., Greenberg M., Gottlieb H.E., Glotter E., Varenne P. et al. 1979. Ixocarpalactones A and B, two unusual naturally occurring steroids of the ergostane type. J. Chem. Res.: 103.
32. Kishi T., Wada K., Marumo S. and Mori K. 1986. Synthesis of brassinolide analogs with a modified ring B and their plant growth-promoting activity. Agric. Biol. Chem. 50: 1821-1830.
33. Kohout L., Brosa C., Holá D., Hradecká D., Koncz C. and Strnad M. 2001. Bioactivity comparison of 24-epibrassinolide and androstane analogue of castasterone. In: Book of Abstracts. 19th Conference on Isoprenoids, September 8-14 2001, Jurata, Poland., p. 92.
34. Kohout L., Strnad M. and Kamínek M. 1991. Types of brassinosteroids and their bioassays. In: Cutler H.G., Yokota T. and Adam G. (eds), Brassinosteroids - Chemistry, Bioactivity and Applications. American Chemical Society, Washington, pp. 56-73.
35. Kushiro M., Nakano T., Sato K., Yamagishi K., Asami T., Nakano A. et al. 2001. Obtusifoliol 14α-demethylase (CYP51) antisense Arabidopsis shows slow growth and long life. Biochem. Biophys. Res. Commun. 285: 98-104.
36. Lichtblau D., Porzel A., Schmidt J., Voigt B. and Adam G. 1999. Synthesis of a novel brassinosteroid type with an annelated dioxonane side chain. J. Chem. Soc. Perkin Trans. I: 53-58.
37. Luo W., Janzen L., Pharis R.P. and Back T.G. 1998. Bioactivity of brassinolide methyl ethers. Phytochemistry 49: 637-642.
38. Mandava N.B. 1988. Plant growth-promoting brassinosteroids. Annu. Rev. Plant Physiol. Plant Mol. Biol. 39: 23-52.
39. Mandava N.B., Sasse J.M. and Yopp J.H. 1981. Brassinolide, a growth-promoting steroidal lactone. II. Activity in selected gibberellin and cytokinin bioassays. Physiol. Plant. 53: 453-461.
40. Marquardt V., Coll Manchado F. and Alonso Becerra E.M. 1988. Preparation of brassinosteroid analogs of spirostans as plant growth regulators. Ger. (East) DD: 273,638.
41. Mitchell J.W., Mandava N.B., 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.
42. Quyen L.T., Adam G. and Schreiber K. 1994. Partial synthesis of nitrogenous brassinosteroids with solanidane skeleton. Tetrahedron 50: 10923-10932.
43. Ramirez J.A., Gros E.G. and Galagovsky L.R. 2000. Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs. Tetrahedron 56: 6171-6180.
44. Sakurai A. 1999. Biosynthesis. In: Sakurai A., Yokota T. and Clouse S.D. (eds), Brassinosteroids: Steroidal Plant Hormones. Springer Verlag, Tokyo, pp. 91-111.
45. Schrick K., Mayer U., Horrichs A., Kuhnt C., Bellini C., Dangl J. et al. 2000. FACKEL is a sterol C-14 reductase required for organized cell division and expansion in Arabidopsis embryogenesis. Genes Dev. 14: 1471-1484.
46. Soeno K., Kyokawa Y., Natsume M. and Abe H. 2000. Teasterone-3-O-β-D-glucopyranoside, a new conjugated brassinosteroid metabolite from lily cell suspension cultures and its identification in lily anthers. Biosc. Biotechnol. Biochem. 64: 702-709.
47. Steffens G.L. 1991. U.S. Department of Agriculture Brassins Project: 1970-1980. In: Cutler H.G., Yokota T. and Adam G. (eds), Brassinosteroids - Chemistry, Bioactivity and Applications. American Chemical Society, Washington, pp. 2-17.
48. Suzuki H., Inoue T., Fujioka S., Saito T., Takatsuto S., Yokota T. et al. 1995. Conversion of 24-methylcholesterol to 6-oxo-24-methylcholestanol, a putative intermediate of the biosynthesis of brassinosteroids in cultured cells of Catharantus roseus. Phytochemistry 40: 1391-1397.
49. Takatsuto S., Ikekawa N., Morishita T. and Abe H. 1987. Structure-activity relationship of brassinosteroids with respect to the A/B-ring functional groups. Chem. Pharm. Bull. 35: 211-216.
50. Takatsuto S., Yazawa N. and Ikekawa N. 1984. Synthesis and biological activity of brassinolide analogues, 26,27-bisnorbrassinolide and its 6-oxo analogue. Phytochemistry 23: 525-528.
51. Thompson M.J., Mandava N.B., Flippen-Anderson J.L., Worley J.F., Dutky S.R., Robbins W.E. et al. 1979. Synthesis of brassino steroids: new plant growth-promoting regulators. J. Org. Chem. 44: 5002-5004.
52. Thompson M.J., Meudt W.J., Mandava N.B., Dutky S.R., Lusby W.R. and Spaulding D.W. 1982. Synthesis of brassinosteroids and relationship of structure to plant growth-promoting effect. Steroids 39: 89-105.
53. Voigt B., Porzel A., Undisz K., Hoerholde-Schubert C. and Adam G. 1993. Microbial hydroxylation of 24-epicastasterone by the fungus Cochliobolus lunatus. Nat. Prod. Lett. 3: 123-129.
54. Voigt B., Takatsuto S., Yokota T. and Adam G. 1995. Synthesis of secasterone and further epimeric 2,3-epoxybrassinosteroids. J. Chem. Soc. Perkin Trans.: 1495-1498.
55. Wada K., Kondo H. and Marumo S. 1985. A simple bioassay for brassinosteroids: a wheat leaf-unrolling test. Agric. Biol. Chem. 49: 2249-2251.
56. Wada K., Marumo S., Ikekawa N., Morisaki M. and Mori K. 1981. Brassinolide and homobrassinolide promotion of lamina inclination of rice seedlings. Plant Cell Physiol. 22: 323-326.
57. Watanabe T., Yokota T., Shibata K., Nomura T., Seto H. and Takatsuto S. 2000. Cryptolide, a new brassinolide catabolite with a 23-oxo group from Japanese cedar pollen/anther and its synthesis. J. Chem. Res.: 18-19.
58. Yopp J.H., Mandava N.B. and Sasse J.M. 1981. Brassinolide, a growth-promoting steroidal lactone. I. Activity in selected auxin bioassays. Physiol. Plant. 53: 445-452.