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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
Structure of BRASSINOLIDE

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

HIDE SMILES / InChI

Molecular Formula C28H48O6
Molecular Weight 480.6771
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 13 / 13
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rat 200,100,and 50 mg/kg/day for 7 days
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
Y9IQ1L53OX
Record Status Validated (UNII)
Record Version