78821-43-9 Usage
Description
Epibrassinolide is a brassinosteroid that can be isolated from various plants and has been shown to decrease toxicity and stimulate healthy plant growth in plants under stress. Epibrassinolide is also reported to 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.
Chemical Properties
Different sources of media describe the Chemical Properties of 78821-43-9 differently. You can refer to the following data:
1. The solubility of epibrassinolide in ethanol and DMSO is approximately 3 mg/ml and approximately 5 mg/ml in DMF.
2. White Solid
Uses
Different sources of media describe the Uses of 78821-43-9 differently. You can refer to the following data:
1. A plant growth stimulant
2. Epibrassinolide has been used:in Murashige and Skoog (MS) medium to study the cotyledon and shoot length response of Cappelle-Desprez (rht8) and RIL6 (Rht8) plants towards itin callus-inducing medium for callus inductionto induce the expression of the gene leaf inclination 2 (LC2) in rice sampling
Metabolic pathway
Two isomeric metabolites, 25-b- and 26-b-D-
glucopyranosyloxy-24-epi-brassinolides, are formed in
tomato cell suspension cultures with endogenously
applied 24-epi-brassinolide. The two-step metabolic
process involves hydroxylation of the side chain at
C25 and C26, respectively, followed by glucosidation
of the newly formed hydroxyl groups. The ratio
between both metabolites is altered by in vivo
treatment of the cell cultures with various cytochrome
P-450-specific inhibitors, indicating the involvement of two different enzyme systems. Biosynthetically
prepared 25-hydroxy-24-epi-brassinolide, reapplied to
the cell cultures, is exclusively glucosylated at the 25-
hydroxyl group, strongly suggesting regiospecificity of
the corresponding glucosyltransferase.
Check Digit Verification of cas no
The CAS Registry Mumber 78821-43-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,8,8,2 and 1 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 78821-43:
(7*7)+(6*8)+(5*8)+(4*2)+(3*1)+(2*4)+(1*3)=159
159 % 10 = 9
So 78821-43-9 is a valid CAS Registry Number.
InChI:InChI=1/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
78821-43-9Relevant articles and documents
Improved Synthesis of 24-Epibrassinolide from Ergosterol
McMorris, Trevor C.,Patil, Prakash A.
, p. 2338 - 2339 (1993)
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NEW METHOD OF PREPARATION OF BRASSINOSTEROIDS
Kohout, Ladislav
, p. 457 - 460 (1994)
Brassinosteroids with lactone B-ring (II and IV) were prepared by oxidation of the corresponding 6-keto derivatives I and III without protection of the hydroxyl groups against the action of the oxidation reagent.
Biological Activity of Brassinosteroids – Direct Comparison of Known and New Analogs in planta
Wendeborn, Sebastian,Lachia, Mathilde,Jung, Pierre M. J.,Leipner, J?rg,Brocklehurst, David,De Mesmaeker, Alain,Gaus, Katharina,Mondière, Régis
, (2017/02/26)
A systematic investigation of structural modifications of brassinosteroids is presented. We describe in detail their synthetic preparation, which includes significant improvements of previously reported protocols as well as access to new analogs with functional modifications of the steroid skeleton and of the C(17)-attached side chain. We report the biological potency of the prepared brassinosteroid analogs as plant hormones, which were carefully established in the French bean second internode elongation assay and discuss our observations in light of the recently reported structural data detailing the molecular interactions between brassinolide in the trimeric complex with the protein receptors kinases BRASSINOSTEROID INSENSITIVE 1 (BRI1) and SOMATIC EMBRYOGENESIS RECEPTOR KINASE 1 (SERK1). In a further part of this work we describe the preparation of H2O-soluble pro-forms of 24-epicastasterone and we discuss their physical properties, hydrolytic stabilities and biological activity.
The development and use of a general route to brassinolide, its biosynthetic precursors, metabolites and analogues
Hurski,Ermolovich,Zhabinskii,Khripach
, p. 1446 - 1452 (2015/01/30)
A new method for the construction of steroid side chains through the addition of lithium salts of dithianes to a C-22 aldehyde was developed. An efficient one-pot procedure for the preparation of a suitable C-22 aldehyde from commercial epibrassinolide in three steps in 86% isolated yield was described. Enantioselective hydroxymethylation of isovaleraldehyde and Kulinkovich cyclopropanation of silylated Roche esters were used as key steps for the dithiane syntheses. The method was applied for the preparation of brassinolide, its biosynthetic precursors and metabolites. In addition, a number of brassinosteroids with a double bond in the side chain were prepared as precursors for tritiated derivatives for biosynthetic studies.
