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Imperialine 3-β-D-glucoside

Cat No.:V62299 Purity: ≥98%
Imperialine 3-β-D-glucoside is the glycoside of Imperialine.
Imperialine 3-β-D-glucoside
Imperialine 3-β-D-glucoside Chemical Structure CAS No.: 67968-40-5
Product category: Steroids
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
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Product Description
Imperialine 3-β-D-glucoside is the glycoside of Imperialine. Imperialine 3-β-D-glucoside may exhibit antitumor properties against multidrug-resistant tumor cells.
Imperialine 3-β-D-glucoside (CAS# 67968-40-5) is a naturally occurring isosteroidal alkaloid glycoside with the molecular formula C33H53NO8 and a molecular weight of 591.78. It is isolated predominantly from the bulbs of Fritillaria species, most notably Fritillaria pallidiflora Schrenk. Also known as sipeimine-3-beta-D-glucoside, it is the glycoside of Imperialine. Imperialine 3-β-D-glucoside may exhibit anti-tumor properties against multi-drug resistant tumor cells. The compound has a purity of 99.63% and is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
Imperialine 3-β-D-glucoside targets multi-drug resistant tumor cells, exhibiting anti-tumor properties. As an isosteroidal alkaloid glycoside from Fritillaria species, it inhibits cellular proliferation and induces apoptosis through oxidative stress pathways. The compound's glycoside moiety may affect its interactions with cellular targets. Studies on glioma and hepatoma models reveal its capacity to inhibit cellular proliferation and induce apoptosis. Further research is needed to identify its specific molecular targets and mechanisms of action.
ln Vitro
In vitro studies have demonstrated that Imperialine 3-β-D-glucoside exhibits anti-tumor properties against multi-drug resistant tumor cells. Studies on glioma and hepatoma models reveal its capacity to inhibit cellular proliferation and induce apoptosis through oxidative stress pathways. The compound shows robust antitumor activity, particularly in multidrug-resistant (MDR) cancer cells. These in vitro findings support its potential applications in cancer research, particularly in studies of multidrug resistance.
ln Vivo
In vivo studies of Imperialine 3-β-D-glucoside are limited as the compound is primarily used as a research chemical. Its anti-tumor properties against multi-drug resistant tumor cells suggest potential for in vivo evaluation in cancer models. Studies on glioma and hepatoma models have been conducted. However, comprehensive in vivo pharmacological studies specifically targeting Imperialine 3-β-D-glucoside are not well documented. The compound is intended for research use only and is not for human therapeutic use.
Enzyme Assay
In vitro enzyme inhibition assays for Imperialine 3-β-D-glucoside typically involve testing its anti-tumor activity against multi-drug resistant cancer cell lines. Cell viability is assessed using MTT or similar colorimetric assays. The compound's ability to induce apoptosis is evaluated using flow cytometry with Annexin V/PI staining or via caspase activity measurements. Oxidative stress pathways are assessed by measuring reactive oxygen species levels. The compound's purity (99.63%) is confirmed using analytical chemistry methods such as high-performance liquid chromatography.
Cell Assay
In vitro cell-based assays for Imperialine 3-β-D-glucoside involve culturing multi-drug resistant tumor cell lines to evaluate its anti-tumor activity. Cells are treated with varying concentrations of the compound and cell viability is assessed using MTT or similar colorimetric assays. Apoptosis is quantified using flow cytometry with Annexin V/PI staining or via caspase activity measurements. Oxidative stress is assessed by measuring reactive oxygen species levels. All experiments are performed in triplicate with appropriate controls to ensure statistical reliability.
Animal Protocol
In vivo animal experiments for Imperialine 3-β-D-glucoside would be conducted to evaluate its anti-tumor activity in glioma and hepatoma models. Tumor-bearing animals would be treated with the compound and tumor growth monitored. Parameters assessed would include tumor volume, tumor weight, body weight, survival, and general health. At study termination, tumors would be collected for histopathological examination and biomarker analysis. Control groups receiving vehicle alone would be included for comparison. All procedures would comply with institutional animal care and use committee guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of Imperialine 3-β-D-glucoside reflect its nature as an isosteroidal alkaloid glycoside. It has a molecular weight of 591.78 and the molecular formula C33H53NO8. The compound has a purity of 99.63%. As a glycoside, it may be metabolized to the aglycone Imperialine. Complete pharmacokinetic profiling including absorption, distribution, metabolism, and excretion would require further systematic studies using appropriate analytical methods such as high-performance liquid chromatography-mass spectrometry.
Toxicity/Toxicokinetics
The toxicity profile of Imperialine 3-β-D-glucoside has been evaluated in the context of its use as a research chemical. As a naturally occurring alkaloid glycoside from Fritillaria species, it is expected to have a safety profile similar to other Fritillaria alkaloids. The compound has a purity of 99.63%. Proper handling procedures including use of personal protective equipment are recommended when working with pure compound. The compound is not approved for human therapeutic use and is intended for research purposes only.
References

[1]. The extraction of imperialine and imperialine-3 beta-glucoside from Fritillaria pallidiflora Schrenk and quantitative determination by HPLC-evaporative light scattering detection. Phytochem Anal. May-Jun 2002;13(3):158-61.

Additional Infomation
The structure is described in the first reference; it was isolated from the fresh bulbs of Fritillaria cirrhosa from Hubei.
Imperialine 3-β-D-glucoside (CAS# 67968-40-5) is also known as sipeimine-3-beta-D-glucoside. It has the molecular formula C33H53NO8 and a molecular weight of 591.78. The compound is a naturally occurring isosteroidal alkaloid glycoside isolated from the bulbs of Fritillaria species. It is the glycoside of Imperialine. Imperialine 3-β-D-glucoside exhibits anti-tumor properties against multi-drug resistant tumor cells. Studies on glioma and hepatoma models reveal inhibition of cellular proliferation and induction of apoptosis.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C33H53NO8
Molecular Weight
591.78
Exact Mass
591.377
CAS #
67968-40-5
PubChem CID
132538
Appearance
White to off-white solid powder
Boiling Point
742.7±60.0 °C
LogP
2.3
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
3
Heavy Atom Count
42
Complexity
1040
Defined Atom Stereocenter Count
17
SMILES
C[C@H]1CC[C@H]2[C@@]([C@@H]3CC[C@@H]4[C@H]([C@@H]3CN2C1)C[C@H]5[C@H]4CC(=O)[C@@H]6[C@@]5(CC[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)(C)O
InChi Key
DHQFYEJMFMYGCV-DLJWJMOOSA-N
InChi Code
InChI=1S/C33H53NO8/c1-16-4-7-27-33(3,40)22-6-5-18-19(21(22)14-34(27)13-16)11-23-20(18)12-25(36)24-10-17(8-9-32(23,24)2)41-31-30(39)29(38)28(37)26(15-35)42-31/h16-24,26-31,35,37-40H,4-15H2,1-3H3/t16-,17-,18+,19+,20-,21-,22+,23-,24+,26+,27-,28+,29-,30+,31+,32+,33-/m0/s1
Chemical Name
(1R,2S,6S,9S,10S,11R,14S,15S,18S,20S,23R,24S)-10-hydroxy-6,10,23-trimethyl-20-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosan-17-one
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

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 8.33 mg/mL (14.08 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.83 mg/mL (1.40 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 8.3 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 0.83 mg/mL (1.40 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 8.3 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.

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Solubility in Formulation 3: ≥ 0.83 mg/mL (1.40 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 8.3 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 1.6898 mL 8.4491 mL 16.8982 mL
5 mM 0.3380 mL 1.6898 mL 3.3796 mL
10 mM 0.1690 mL 0.8449 mL 1.6898 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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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