24-Epibrassinolide

24-Epibrassinolide is a type of brassinosteroid, a natural occurring plant hormone.[1][2] It was first discovered 1979 as a growth promoting substance in rape pollen,[3] and was subsequently discovered in many other plant organs.[4] 24-Epibrassinolide is essential for proper plant development growth and development,[5][6][7][8] is involved in the regulation of cell elongation and division,[9] and has been shown to improve plant functions in salt- and nickel-stressed environments,[10] as well as increasing enzyme activity.[11] It is sold commercially as a white powder for use in plant culture.

24-Epibrassinolide
Names
IUPAC name
(22R,23R)-2α,3α,22,23-Tetrahydroxy-6,7-epoxy-6,7-seco-5α-ergostan-6-one
Systematic IUPAC name
(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(2S,3R,4R,5R)-3,4-Dihydroxy-5,6-dimethylheptan-2-yl]-8,9-dihydroxy-10a,12a-dimethylhexadecahydro-6H-indeno[4,5-d][2]benzoxepin-6-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.167.027
KEGG
  • InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16+,17+,18-,19+,20+,21-,22+,23-,24-,25-,27-,28-/m1/s1
    Key: IXVMHGVQKLDRKH-QHBHMFGVSA-N
  • C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2COC(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)[C@H]([C@@H]([C@H](C)C(C)C)O)O
Properties
C28H48O6
Molar mass 480.686 g·mol−1
Appearance White powder
Melting point 274 °C (525 °F; 547 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Pubchem. "24-Epibrassinolide". pubchem.ncbi.nlm.nih.gov. US: National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 2019-02-26.
  2. Tanveer, Mohsin; Shahzad, Babar; Sharma, Anket; Biju, Sajitha; Bhardwaj, Renu (2018). "24-Epibrassinolide; an active brassinolide and its role in salt stress tolerance in plants: A review". Plant Physiology and Biochemistry. 130: 69–79. doi:10.1016/j.plaphy.2018.06.035. PMID 29966934. S2CID 49644350.
  3. Grove, Michael D.; Spencer, Gayland F.; Rohwedder, William K.; Mandava, Nagabhushanam; Worley, Joseph F.; Warthen, J. David; Steffens, George L.; Flippen-Anderson, Judith L.; Cook, J. Carter (1979). "Brassinolide, a plant growth-promoting steroid isolated from Brassica napus pollen". Nature. Springer Science and Business Media LLC. 281 (5728): 216–217. Bibcode:1979Natur.281..216G. doi:10.1038/281216a0. ISSN 0028-0836. S2CID 4335601.
  4. Kim, Seong-Ki (1991-11-04). "Natural Occurrences of Brassinosteroids". ACS Symposium Series. Vol. 474. Washington, DC: American Chemical Society. pp. 26–35. doi:10.1021/bk-1991-0474.ch003. ISBN 0-8412-2126-X. ISSN 1947-5918.
  5. Staswick, Paul E.; Raskin, Ilya; Arteca, Richard N. (1995). "Jasmonates, Salicylic acid and Brassinosteroids". Plant Hormones. Dordrecht: Springer Netherlands. pp. 179–213. doi:10.1007/978-94-011-0473-9_9. ISBN 978-0-7923-2985-5.
  6. Yokota, Takao (1997). "The structure, biosynthesis and function of brassinosteroids". Trends in Plant Science. Elsevier BV. 2 (4): 137–143. doi:10.1016/s1360-1385(97)01017-0. ISSN 1360-1385.
  7. Sasse, Jenneth M. (1997). "Recent progress in brassinosteroid research". Physiologia Plantarum. Wiley. 100 (3): 696–701. doi:10.1111/j.1399-3054.1997.tb03076.x. ISSN 0031-9317.
  8. Clouse, Steven D.; Sasse, Jenneth M. (1998). "BRASSINOSTEROIDS: Essential Regulators of Plant Growth and Development". Annual Review of Plant Physiology and Plant Molecular Biology. Annual Reviews. 49 (1): 427–451. doi:10.1146/annurev.arplant.49.1.427. ISSN 1040-2519. PMID 15012241.
  9. MITCHELL, J. W.; MANDAVA, N.; WORLEY, J. F.; PLIMMER, J. R.; SMITH, M. V. (1970). "Brassins—a New Family of Plant Hormones from Rape Pollen". Nature. Springer Science and Business Media LLC. 225 (5237): 1065–1066. Bibcode:1970Natur.225.1065M. doi:10.1038/2251065a0. ISSN 0028-0836. PMID 16056912. S2CID 4116426.
  10. Ali, B.; Hayat, S.; Fariduddin, Q.; Ahmad, A. (2008). "24-Epibrassinolide protects against the stress generated by salinity and nickel in Brassica juncea". Chemosphere. 72 (9): 1387–1392. Bibcode:2008Chmsp..72.1387A. doi:10.1016/j.chemosphere.2008.04.012. PMID 18499221.
  11. Yuan, Lingyun; Yuan, Yinghui; Du, Jing; Sun, Jin; Guo, Shirong (2012). "Effects of 24-epibrassinolide on nitrogen metabolism in cucumber seedlings under Ca(NO3)2 stress". Plant Physiology and Biochemistry. 61: 29–35. doi:10.1016/j.plaphy.2012.09.004. PMID 23031845.
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