24-Epibrassinolide

Last updated
24-Epibrassinolide
24-Epibrassinolide.svg
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
  • 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
AppearanceWhite powder
Melting point 274 °C (525 °F; 547 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
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).

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.

Related Research Articles

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<span class="mw-page-title-main">Brassinolide</span> Chemical compound

Brassinolide is a plant hormone. The first isolated brassinosteroid, it was discovered when it was shown that pollen from rapeseed could promote stem elongation and cell division. The biologically active component was isolated and named brassinolide.

Expansins are a family of closely related nonenzymatic proteins found in the plant cell wall, with important roles in plant cell growth, fruit softening, abscission, emergence of root hairs, pollen tube invasion of the stigma and style, meristem function, and other developmental processes where cell wall loosening occurs. Expansins were originally discovered as mediators of acid growth, which refers to the widespread characteristic of growing plant cell walls to expand faster at low (acidic) pH than at neutral pH. Expansins are thus linked to auxin action. They are also linked to cell enlargement and cell wall changes induced by other plant hormones such as gibberellin, cytokinin, ethylene and brassinosteroids.

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Brassinosteroid insensitive 1 (BRI1) is the major receptor of the plant hormone brassinosteroid. It plays very important roles in plant development, especially in the control of cell elongation and for the tolerance of environmental stresses. BRI1 enhances cell elongation, promotes pollen development, controls vasculature development and promotes chilling and freezing tolerance. BRI1 is one of the most well studied hormone receptors and it acts a model for the study of membrane-bound receptors in plants.

June Nasrallah is Barbara McClintock Professor in the Plant Biology Section of the School of Integrative Plant Science at Cornell University. Her research focuses on plant reproductive biology and the cell-cell interactions that underlie self-incompatibility in plants belonging to the mustard (Brassicaceae) family. She was elected to the US National Academy of Sciences in 2003 for this work and her contributions generally to our understanding of receptor-based signalling in plants.

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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.