24-Epibrassinolide
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| Category | Others |
| Catalog number | BBF-04043 |
| CAS | 78821-43-9 |
| Molecular Weight | 480.68 |
| Molecular Formula | C28H48O6 |
| Purity | 95% |
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Description
Epibrassinolide is a biologically active compound of the brassinosteroids that can be isolated from various plants. It belongs to steroid-derived plant growth regulator family and has been shown to decrease toxicity and stimulate healthy plant growth in plants under stress. It may be a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth. It has also been shown to protect neuronal PC12 cells from 1-methyl-4-phenylpyridinium-induced oxidative stress and consequent apoptosis in dopaminergic neurons. It induced the decrease of intracellular polyamine levels accompanied by a significant ornithine decarboxylase (ODC) down-regulation in each prostate cancer cell.
Specification
| Synonyms | B1105; BP55; (5S,6R,7aR,9aS)-10-[(2S,3R,4R,5R)-3,4-Dihydroxy-5,6-dimethylheptan-2-yl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one; 6H-Benz[c]indeno[5,4-e]oxepin-6-one,1-[(1S,2R,3R,4R)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-,(1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-; (22R,23R,24R)-2a,3a,22,23-Tetrahydroxy-B-homo-7-oxa-5a-ergostan-6-one; 24(R)-Epibrassinolide; 24-epi-Brassinolide |
| Shelf Life | 2 month in rt, long time |
| Storage | Store at -20°C |
| IUPAC Name | (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R,5R)-3,4-dihydroxy-5,6-dimethylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one |
| Canonical SMILES | CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2COC(=O)C4C3(CC(C(C4)O)O)C)C)O)O |
| InChI | 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 |
| InChI Key | IXVMHGVQKLDRKH-JBIJCCJYSA-N |
Properties
| Appearance | White Crystalline Powder |
| Application | Plant Growth Regulators |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 633.7±55.0°C at 760 mmHg |
| Melting Point | 256°C |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in DMSO (≥ 5 mg/mL) |
Reference Reading
1.Root proteomics reveals cucumber 24-epibrassinolide responses under Ca(NO3)2 stress.
An Y1,2,3, Zhou H1,2,3, Zhong M1,2,3, Sun J1,2,3, Shu S1,2,3, Shao Q1,2,3, Guo S4,5,6. Plant Cell Rep. 2016 May;35(5):1081-101. doi: 10.1007/s00299-016-1940-z. Epub 2016 Mar 1.
KEY MESSAGE: The application of exogenous 24-epibrassinolide promotes Brassinosteroids intracellular signalling in cucumber, which leads to differentially expressed proteins that participate in different life process to relieve Ca(NO 3 ) 2 damage. NO3 (-) and Ca(2+) are the main anion and cation of soil secondary salinization during greenhouse cultivation. Brassinosteroids (BRs), steroidal phytohormones, regulate various important physiological and developmental processes and are used against abiotic stress. A two-dimensional electrophoresis gel coupled with MALDI-TOF/TOF MS was performed to investigate the effects of exogenous 24-epibrassinolide (EBL) on proteomic changes in cucumber seedling roots under Ca(NO3)2 stress. A total of 80 differentially accumulated protein spots in response to stress and/or exogenous EBL were identified and grouped into different categories of biological processes according to Gene Ontology. Under Ca(NO3)2 stress, proteins related to nitrogen metabolism and lignin biosynthesis were induced, while those related to cytoskeleton organization and cell-wall neutral sugar metabolism were inhibited.
2.[Effects of brassinolide on the antioxidant system and photosynthesis of cucumber seedlings under suboptimal temperature, light and salt environment].
Wu X, Lu XM. Ying Yong Sheng Tai Xue Bao. 2015 Sep;26(9):2751-7.
The effects of 24-epibrassinolide (EBR) on antioxidant system and photosynthesis of cucumber seedlings were studied under suboptimal temperature, light and salt environment. Compared with the control, the leaf H2O2 content, lipid peroxidation and cell membrane permeability significantly increased, and the leaf net photosynthetic rate (Pn), stomatal conductance (g(s)), intercellular CO2 concentration (Ci), transpiration rate (Tr) and dry matter accumulation decreased by 39.3%, 40.0%, 21.2%, 47.2% and 35.9% in the suboptimal environment, respectively. Applying EBR could further improve the antioxidant enzyme activity, reduce the H2O2 content and membrane permeability of seedlings, alleviate the drop range of Pn, g(s) and Tr, improve the growth of seedlings and increase the dry matter accumulation by 25.9%. Therefore, EBR treatment could keep higher photosynthetic performance to effectively promote cucumber seedlings growth through adjusting the protective enzyme activity and reducing membrane lipid peroxide level under suboptimal temperature, light and salt environment.
3.GC-MS studies reveal stimulated pesticide detoxification by brassinolide application in Brassica juncea L. plants.
Sharma A1, Bhardwaj R2, Kumar V1, Thukral AK1. Environ Sci Pollut Res Int. 2016 Apr 12. [Epub ahead of print]
Imidacloprid (IMI) is a commonly used pesticide against aphids and accumulates in plant parts, maximum in leaves. Present study was conducted to check the efficiency of seed pre-soaking with 24-epibrassinolide (24-EBL) for reduction of this pesticide in the leaves of Brassica juncea L. plants raised from 24-EBL pre-soaked seeds and grown in soils supplemented with IMI. Leaves were analyzed for IMI residues using gas chromatography-mass spectrometry (GC-MS). Activities of guaiacol peroxidase (POD), glutathione reductase (GR), and glutathione S-transferase (GST), and glutathione (GSH) content were determined by spectrophotometry. Soil containing 350 mg IMI/kilogram soil resulted in 88.66 μg/g fresh weight (FW) of IMI residue in the leaves, which was maximum decrease to 35.31 μg/g FW (60.17 %), when seeds were pre-soaked in 100 nM 24-EBL. In this treatment (350 mg IMI/kilogram soil + 100 nM 24-EBL), GSH content, GR, POD, and GST activities were increased by 42.
4.Interaction of epibrassinolide and selenium ameliorates the excess copper in Brassica juncea through altered proline metabolism and antioxidants.
Yusuf M1, Khan TA2, Fariduddin Q3. Ecotoxicol Environ Saf. 2016 Mar 11;129:25-34. doi: 10.1016/j.ecoenv.2016.03.001. [Epub ahead of print]
24-Epibrassinolide (EBL) and Selenium (Se) individually confer tolerance to various abiotic stresses, but their interactive effect in the regulation of copper (Cu) homeostasis in plants exposed to toxic levels of Cu is poorly investigated. This study provides an insight into the effects of EBL (foliar) and/or Se (through sand) on Brassica juncea plants exposed to toxic levels of Cu. The combined effect of EBL and Se on compartmentalization of Cu, oxidative stress markers, photosynthetic machinery and biochemical traits in B. juncea were analyzed. Application of EBL and Se through different mode modulated the compartmentalization of Cu in different parts of plants, enhanced the photosynthetic traits, and activities of various antioxidant enzymes and proline accumulation in B. juncea under excess copper levels. These enhanced levels of antioxidant enzymes, proline (osmolyte) accumulation triggered by combination of EBL and Se could have conferred tolerance to the B.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
