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| Targets |
Brassicasterol targets sterol Δ24-reductase (also known as DHCR24), an enzyme involved in the mammalian cholesterol biosynthesis pathway. It inhibits this enzyme with a Ki value of 42.7 μM in vitro. By inhibiting sterol Δ24-reductase, brassicasterol increases accumulation of desmosterol, a cholesterol precursor and substrate of sterol Δ24-reductase, and inhibits cholesterol formation. The compound also serves as a plant sterol analog for studying sterol-lipid interactions, membrane fluidity control, and sterol-mediated protein function.
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| ln Vitro |
Brassicasterol demonstrates inhibition of recombinant sterol Δ24-reductase with a Ki value of 42.7 μM in vitro. It increases accumulation of desmosterol, a cholesterol precursor and substrate of sterol Δ24-reductase, and inhibits cholesterol formation in HL-60 cells in a dose-dependent manner. The compound also inhibits the hemolytic activity of pneumolysin. As a phytosterol structurally similar to cholesterol, brassicasterol modulates bilayer order and permeability. It is used as a biomarker for the presence of certain algae and phytoplankton.
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| ln Vivo |
In vivo activity data for brassicasterol are limited but suggest potential biological effects. The compound has been shown to inhibit sterol Δ24-reductase, an enzyme involved in the cholesterol biosynthesis pathway, which could affect cholesterol metabolism in vivo. Brassicasterol plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling. It shows dual anti-infective properties. As a phytosterol, it may also have effects on lipid metabolism and membrane properties when administered in vivo.
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| Enzyme Assay |
The in vitro enzyme assay for brassicasterol typically involves measuring the inhibition of recombinant sterol Δ24-reductase (DHCR24). The enzyme is incubated with varying concentrations of brassicasterol (typically 0.1-100 μM) in the presence of substrate (desmosterol) and cofactors (NADPH). The enzymatic activity is monitored by measuring the conversion of desmosterol to cholesterol using HPLC or GC-MS. The Ki value is determined by fitting the inhibition data to appropriate kinetic models. Brassicasterol is dissolved in ethanol or DMSO and diluted in assay buffer.
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| Cell Assay |
In vitro cellular assays for brassicasterol typically involve treating cultured cells (such as HL-60 cells or other cell lines) with the compound at concentrations ranging from 0.1 to 50 μM for 24-72 hours. Cellular cholesterol and desmosterol levels are measured by HPLC or GC-MS to assess the compound's effects on cholesterol biosynthesis. Cell viability is assessed using MTT or trypan blue exclusion assays. The compound is dissolved in ethanol or DMSO as a stock solution and diluted in cell culture medium, with appropriate vehicle controls.
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| Animal Protocol |
In vivo animal studies for brassicasterol are not extensively documented. For potential in vivo applications, the compound could be administered to mice or rats via oral gavage or intraperitoneal injection at doses determined from preliminary studies. Blood and tissue samples would be collected to measure cholesterol and desmosterol levels. Efficacy studies might involve models of cholesterol metabolism disorders, cancer, or infection. The compound's ability to inhibit sterol Δ24-reductase could be evaluated by measuring the accumulation of desmosterol in tissues.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of brassicasterol are similar to other phytosterols. The compound has a molecular weight of 398.66 g/mol and formula C28H46O. It is soluble in ethanol (20 mg/mL), DMF (1 mg/mL), and DMSO (0.1 mg/mL), and has limited solubility in aqueous buffers. Recommended storage is at -20°C. Detailed PK parameters such as half-life, Cmax, AUC, and bioavailability would require experimental determination. As a phytosterol, it is expected to have limited oral bioavailability and to be metabolized in the liver.
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| Toxicity/Toxicokinetics |
Toxicity data for brassicasterol are not extensively reported. As a naturally occurring phytosterol found in foods such as canola and rapeseed oils, it is generally considered to have low toxicity. The compound is intended for research use only and is not approved for human therapeutic applications. Standard toxicity assessments would include acute toxicity, genotoxicity, and repeated-dose toxicity studies. Its structural similarity to cholesterol suggests it may be well-tolerated at moderate doses. However, appropriate safety precautions should be taken when handling.
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| References |
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| Additional Infomation |
Brassicasterol is a 3β-sterol, a compound in which (22E)-ergosterol-5,22-diene is substituted with a hydroxyl group at the 3β position. It is a phytosterol found in marine algae, fish, and rapeseed oil. Brassicasterol has multiple functions, including as an EC 1.3.1.72 (Δ(24)-sterol reductase) inhibitor, a biomarker, a human metabolite, a plant metabolite, an animal metabolite, an algal metabolite, a sterol biosynthesis inhibitor, and a marine metabolite. It is an ergosterane compound, belonging to the 3β-sterol class, a member of the phytosterol family, and is also a 3β-hydroxy-Δ5-steroid. Brassicasterol has been reported to be found in tubers (Tuber indicum), Cyttaria johowii, and other organisms with relevant data.
Rapeseed sterol is a steroid derivative characterized by the elimination of the hydroxyl group at the C-3 position of the steroid skeleton, the elimination of the carbon atom at the 24th and 2nd positions of the alkyl substituent, and the unsaturated bonds at the 5th and 6th positions of the B ring and the 22nd and 23rd positions of the alkyl substituent. It is synthesized by various unicellular algae and some terrestrial plants. Brassicasterol (CAS 474-67-9) is a phytosterol found in rapeseed and canola oils, marine algae, and shellfish. It has a molecular weight of 398.66 g/mol and formula C28H46O. The compound inhibits sterol Δ24-reductase with a Ki value of 42.7 μM in vitro. It increases accumulation of desmosterol and inhibits cholesterol formation in HL-60 cells. Brassicasterol is used as a biomarker for certain algae and phytoplankton. It is also known as ergosta-5,22-dien-3β-ol. The compound is not approved for clinical use. |
| Molecular Formula |
C28H46O
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| Molecular Weight |
398.6642
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| Exact Mass |
398.354
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| CAS # |
474-67-9
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| PubChem CID |
5281327
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| Appearance |
White to light yellow solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
488.7±14.0 °C at 760 mmHg
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| Melting Point |
150 - 151 °C
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| Flash Point |
213.3±12.4 °C
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| Vapour Pressure |
0.0±2.8 mmHg at 25°C
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| Index of Refraction |
1.532
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| LogP |
9.68
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
1
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
29
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| Complexity |
659
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| Defined Atom Stereocenter Count |
9
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| SMILES |
C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
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| InChi Key |
OILXMJHPFNGGTO-ZAUYPBDWSA-N
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| InChi Code |
InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-9,18-20,22-26,29H,10-17H2,1-6H3/b8-7+/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
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| Chemical Name |
(3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Ethanol : ~4.76 mg/mL (~11.94 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.5084 mL | 12.5420 mL | 25.0840 mL | |
| 5 mM | 0.5017 mL | 2.5084 mL | 5.0168 mL | |
| 10 mM | 0.2508 mL | 1.2542 mL | 2.5084 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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