Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H48O6 |
Molecular Weight | 480.6771 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])COC(=O)[C@@]4([H])C[C@H](O)[C@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
InChI
InChIKey=IXVMHGVQKLDRKH-KNBKMWSGSA-N
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+/m0/s1
Molecular Formula | C28H48O6 |
Molecular Weight | 480.6771 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26987039Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28847728 | https://www.ncbi.nlm.nih.gov/pubmed/24769247 | https://www.ncbi.nlm.nih.gov/pubmed/26318418
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26987039
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28847728 | https://www.ncbi.nlm.nih.gov/pubmed/24769247 | https://www.ncbi.nlm.nih.gov/pubmed/26318418
Brassinolide ((22R,23R,24S)-2a,3a,22,23-tetrahydroxy- 24-methyl-B-homo-7-oxa-5a-cholestan-6-one) is a plant growth hormone that has been implicated in Auxin Signaling. In vitro and field experiments have shown that application of Brassinolide and Brassinolide analogs produces protection against phytopathogens and stress conditions, as well as higher production of biomass, which resulted in an increase in the quality and yield of different crops, such as legumes, cereals, and fruits. Since Brassinolide and its congeners are natural products, and abundant in the vegetable kingdom, they are not excluded from the usual diet of all living organisms, and therefore do not constitute an 'unnatural' additive. These facts make this family of compounds a potential environmental friendly helper to agricultural production. In preclinical experiments, Brassinolide shows marked cytotoxicity to cancer cells via Wnt pathway inhibition. Brassinolide induced a concentration-dependent increase in the apoptotic rate and marked accumulation in the G2/M phase of cell cycle. PC-3 cells treated with brassinolide showed characteristic apoptotic alterations: shrinking cellular figure, decreasing cell surface microvilli, cytoplasmic vacuoles, chromatin condensation. Oral administration of Brassinolide decreased the levels of blood glucose. The levels of blood glucose displayed significant differences after treatment with a different dose of brassinolide. Brassinolide can still reduce the blood glucose levels without toxicity effect even at a lower dose.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0016055 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28847728 |
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Target ID: map04068 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26318418 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Brassinosteroids. Plant counterparts to animal steroid hormones? | 2002 |
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Cloning the tomato curl3 gene highlights the putative dual role of the leucine-rich repeat receptor kinase tBRI1/SR160 in plant steroid hormone and peptide hormone signaling. | 2002 Dec |
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Acceleration of ripening of tomato pericarp discs by brassinosteroids. | 2002 Dec |
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Synthesis of hexadeuterated 23-dehydroxybrassinosteroids. | 2002 Dec |
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Androgen physiology: unsolved problems at the millennium. | 2002 Dec 30 |
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[NOR (nucleolar organizer region) activity in wheat species with different ploidy levels treated with phytohormones]. | 2002 Nov |
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Three redundant brassinosteroid early response genes encode putative bHLH transcription factors required for normal growth. | 2002 Nov |
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Loss-of-function of a rice brassinosteroid biosynthetic enzyme, C-6 oxidase, prevents the organized arrangement and polar elongation of cells in the leaves and stem. | 2002 Nov |
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Arabidopsis brassinosteroid-insensitive dwarf12 mutants are semidominant and defective in a glycogen synthase kinase 3beta-like kinase. | 2002 Nov |
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Microarray analysis of brassinosteroid-regulated genes in Arabidopsis. | 2002 Nov |
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Two putative BIN2 substrates are nuclear components of brassinosteroid signaling. | 2002 Nov |
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Isolation and characterization of a rice dwarf mutant with a defect in brassinosteroid biosynthesis. | 2002 Nov |
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Interaction of wheat lectin with 24-epibrassinolide in the regulation of cell division in wheat roots. | 2002 Nov-Dec |
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Aquaporin isoforms responsive to salt and water stresses and phytohormones in radish seedlings. | 2002 Oct |
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Promotion of transcript accumulation of novel Zinnia immature xylem-specific HD-Zip III homeobox genes by brassinosteroids. | 2002 Oct |
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Biosynthesis and metabolism of brassinosteroids. | 2003 |
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A window on the world of plants. | 2003 |
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Genome organization in Arabidopsis thaliana: a survey for genes involved in isoprenoid and chlorophyll metabolism. | 2003 Apr |
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A proteomics approach to investigating promotive effects of brassinolide on lamina inclination and root growth in rice seedlings. | 2003 Apr |
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Acceleration of Aux/IAA proteolysis is specific for auxin and independent of AXR1. | 2003 Aug |
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Activation of cell proliferation by brassinolide application in tobacco BY-2 cells: effects of brassinolide on cell multiplication, cell-cycle-related gene expression, and organellar DNA contents. | 2003 Dec |
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A rice brassinosteroid-deficient mutant, ebisu dwarf (d2), is caused by a loss of function of a new member of cytochrome P450. | 2003 Dec |
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Brassinolide induces IAA5, IAA19, and DR5, a synthetic auxin response element in Arabidopsis, implying a cross talk point of brassinosteroid and auxin signaling. | 2003 Dec |
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CYP72B1 inactivates brassinosteroid hormones: an intersection between photomorphogenesis and plant steroid signal transduction. | 2003 Dec |
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Light-dependent induction of proline biosynthesis by abscisic acid and salt stress is inhibited by brassinosteroid in Arabidopsis. | 2003 Feb |
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Organ-specific expression of brassinosteroid-biosynthetic genes and distribution of endogenous brassinosteroids in Arabidopsis. | 2003 Jan |
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Hormone levels and response during de-etiolation in pea. | 2003 Jan |
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Modulation of vacuolar H+ -pumps and aquaporin by phytohormones in rice seedling leaf sheaths. | 2003 Jan |
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Crystal structure of a hypoallergenic isoform of the major birch pollen allergen Bet v 1 and its likely biological function as a plant steroid carrier. | 2003 Jan 3 |
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[Role of trophic and hormonal factors in exogenous regulation of the formation of reproductive organs in yellow lupine (Lupinus luteus L.)]. | 2003 Jan-Feb |
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The unusual Arabidopsis extensin gene atExt1 is expressed throughout plant development and is induced by a variety of biotic and abiotic stresses. | 2003 Jul |
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A novel brassinolide-enhanced gene identified by cDNA microarray is involved in the growth of rice. | 2003 Jul |
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Mutations in the huge Arabidopsis gene BIG affect a range of hormone and light responses. | 2003 Jul |
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Effect of brassinosteroids on the hormonal balance in wheat seedlings. | 2003 Jul-Aug |
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The auxin-induced maize gene ZmSAUR2 encodes a short-lived nuclear protein expressed in elongating tissues. | 2003 Jun 27 |
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Brassinosteroid and systemin: two hormones perceived by the same receptor. | 2003 Mar |
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Sterols regulate development and gene expression in Arabidopsis. | 2003 Mar |
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Brassinosteroid functions in a broad range of disease resistance in tobacco and rice. | 2003 Mar |
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Uzu mutation in barley (Hordeum vulgare L.) reduces the leaf unrolling response to brassinolide. | 2003 May |
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A dwarf mutant strain of Pharbitis nil, Uzukobito (kobito), has defective brassinosteroid biosynthesis. | 2003 Nov |
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A semidwarf phenotype of barley uzu results from a nucleotide substitution in the gene encoding a putative brassinosteroid receptor. | 2003 Nov |
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Brassinosteroids promote root growth in Arabidopsis. | 2003 Nov |
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The growth movement in the peduncle of Eichhornia crassipes II. | 2003 Oct |
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Brassinosteroids signal through two receptor-like kinases. | 2003 Oct |
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AXR1 is involved in BR-mediated elongation and SAUR-AC1 gene expression in Arabidopsis. | 2003 Oct 9 |
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Brassinolide improves embryogenic tissue initiation in conifers and rice. | 2003 Sep |
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Nuclear protein phosphatases with Kelch-repeat domains modulate the response to brassinosteroids in Arabidopsis. | 2004 Feb 15 |
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Cytochrome P450-catalyzed brassinosteroid pathway activation through synthesis of castasterone and brassinolide in Phaseolus vulgaris. | 2004 Mar |
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Loss of function of 3-hydroxy-3-methylglutaryl coenzyme A reductase 1 (HMG1) in Arabidopsis leads to dwarfing, early senescence and male sterility, and reduced sterol levels. | 2004 Mar |
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Effects of brassinazole, an inhibitor of brassinosteroid biosynthesis, on light- and dark-grown Chlorella vulgaris. | 2004 Mar |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28847728
NCI-H69 SCLC cells were used for activity evaluation. Epibrassinolide (EB), etoposide, and the Wnt signaling inhibitor WIKI4 were obtained from Sigma-Aldrich (St. Louis, MO) and dissolved at 10mM in DMSO. The drugs were stored at 4 C for up to 1 month prior to use. The concentration of DMSO in experiments on cells did not exceed 2%. Drugs were added to logarithmically growing cells in 0.2x1.0 ml AIM-V medium containing 1-2 x 10^4 cells/ml. After 5 d of incubation, cell counts were made using a TC-20 counter (BioRad, Hercules, CA). Counts of live cells were validated microscopically by hemocytometer after trypan blue staining.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:22:14 GMT 2023
by
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on
Fri Dec 15 19:22:14 GMT 2023
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Record UNII |
Y9IQ1L53OX
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Record Status |
Validated (UNII)
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Record Version |
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m2640
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brassinolide
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BRASSINOLIDE
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DTXSID0039699
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