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 |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 13 / 13 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
PubMed
Patents
Sample Use Guides
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.