Brassinolide, a plant growth modulator and a plant hormone, is a sterol compound first isolated from pollen of rape (Brassica napus L.). It might facilitate cell division and stem cell elongation. Brassinolide may also have anticancer properties. It might cause PC-3 cells to exhibit a time- and concentration-dependent cytotoxicity. The predominant mode of cell death seemed to be apoptosis. Treatment with brassinolide may boost Caspase-3 activity. According to Western blot analyses, treatment with brassinolide led to a time-dependent reduction in the expression of the anti-apoptotic protein Bcl-2. Therefore, brassinolide might cause cytotoxicity in PC-3 cells by inducing apoptosis. Therefore, brassinolide may be a promising candidate for the treatment of prostate cancer.
Physicochemical Properties
| Molecular Formula | C28H48O6 |
| Molecular Weight | 480.68 |
| Exact Mass | 480.345 |
| CAS # | 72962-43-7 |
| Related CAS # | Epibrassinolide;78821-43-9 |
| PubChem CID | 443055 |
| Appearance | White to off-white solid |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 633.7±55.0 °C at 760 mmHg |
| Melting Point | 200-204ºC |
| Flash Point | 202.3±25.0 °C |
| Vapour Pressure | 0.0±4.2 mmHg at 25°C |
| Index of Refraction | 1.536 |
| LogP | 3.12 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 34 |
| Complexity | 755 |
| Defined Atom Stereocenter Count | 13 |
| SMILES | O1C(C2([H])C([H])([H])C([H])(C([H])(C([H])([H])C2(C([H])([H])[H])C2([H])C([H])([H])C([H])([H])C3(C([H])([H])[H])C([H])(C([H])(C([H])([H])[H])C([H])(C([H])(C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])[H])O[H])O[H])C([H])([H])C([H])([H])C3([H])C2([H])C1([H])[H])O[H])O[H])=O |
| InChi Key | IXVMHGVQKLDRKH-KNBKMWSGSA-N |
| InChi Code | 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 |
| Chemical Name | (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R,5S)-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 |
| Synonyms | Brassinolide; 72962-43-7; 24-Epibrassinolide; Brassinolide >90%; Y9IQ1L53OX; Brassin lactone; 2alpha,3alpha,22alpha,23alpha-Tetrahydroxy-24alpha-methyl-B-homo-7-oxa-5alpha-cholestan-6-one; 6H-Benz(c)indeno(5,4-e)oxepin-6-one, 1-((1S,2R,3R,4S)-2,3-dihydroxy-1,4,5-trimethylhexyl)hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-, (1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-; Brassinolide |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Plant growth modulator | ||
| ln Vitro | A naturally occurring plant hormone called brassinolide encourages growth, boosts crop yields for grains and fruits, and makes plants more resilient to drought and cold temperatures. In PC-3 cells, brassinolide may cause a cytotoxicity that is dependent on both time and concentration. A time-dependent reduction in the expression of the anti-apoptotic protein Bcl-2 and a significant accumulation in the G2/M phase of the cell cycle are brought on by brassinolide treatment[1]. The level of protein expression of p53 in resistant cells is higher than that of sensitive cells. After Brassinolide treatment, the expression of p53 in CCRF-VCR cells restored to the level of sensitive cells. Brassinolide can effectively reverse the resistance of CCRF-VCR cells by inhibiting the effusion of drug transported by P-glucoprotein. To down regulate the abnormal expression of p53 maybe one of the mechanisms of reversing MDR for Brassinolide. MTT method is used to detect the resistant factor of resistant cell line and the reversing fold after addition of Brassinolide. The intracellular accumulation of rhodamine 123, a fluorescent dye transported by P-glycoprotein is detected by flow cytometry, the catalytic activity of topoisomerase II is assessed by Sulliven method to find the effect of Brassinolide on resistance. The protein expression of p53 is measured using Western blotting in the sensitive cells and resistant cells to explore the effect of Brassinolide. | ||
| ln Vivo |
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| Enzyme Assay | Brassinolide is a plant sterol first isolated from pollen of rape (Brassica napus L.). The present study was carried out to investigate the effect of brassinolide on androgen-independent human prostate cancer PC-3 cell viability. Results showed that brassinolide could induce a time and concentration-dependent cytotoxicity in PC-3 cells. The mode of cell death appeared to be predominately apoptosis, as shown by flow-cytometric analysis, fluorescence and transmission electron microscopes. Caspase-3 activity was obviously increased after brassinolide treatment. Western blot studies indicated that treatment with brassinolide triggered a time-dependent decrease in the expression of anti-apoptotic protein Bcl-2. We suggest that brassinolide could induce cytotoxicity in PC-3 cells by triggering apoptosis. Brassinolide might therefore be a promising candidate for the treatment of prostate cancer[1]. | ||
| Cell Assay | MTT method is used to detect the resistant factor of resistant cell line and the reversing fold after addition of Brassinolide. The effect of Brassinolide on resistance is determined by flow cytometry, which measures the intracellular accumulation of rhodamine 123, a fluorescent dye transported by P-glycoprotein. To investigate the impact of brassinolide, Western blotting is used to quantify the protein expression of p53 in both resistant and sensitive cells. | ||
| Animal Protocol |
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| References |
[1]. Brassinolide, a plant sterol from pollen of Brassica napus L., induces apoptosis in human prostate cancer PC-3 cells. Pharmazie. 2007 May;62(5):392-5. [2]. Reversing effect of brassinolide on multidrug resistance of-CCRF-VCR1000 cells and a preliminary investigation on its mechanisms. Yao Xue Xue Bao. 2005 Feb;40(2):117-21. |
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| Additional Infomation |
24-epi-brassinolide is a 2alpha-hydroxy steroid, a 3alpha-hydroxy steroid, a 22-hydroxy steroid, a 23-hydroxy steroid and a brassinosteroid. 24-epi-Brassinolide has been reported in Vicia faba, Gypsophila perfoliata, and other organisms with data available. See also: Brassinolide (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO: ≥ 5 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (5.20 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0804 mL | 10.4019 mL | 20.8039 mL | |
| 5 mM | 0.4161 mL | 2.0804 mL | 4.1608 mL | |
| 10 mM | 0.2080 mL | 1.0402 mL | 2.0804 mL |