| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| 100mg |
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| Targets |
Hupehenine has multiple targets. This compound acts by inhibiting acetylcholine (ACh) and antagonizing muscarinic acetylcholine receptors (mAChR), and possesses cholinesterase inhibitory activity. In anti-leishmanial studies, hupehenine targets dephospho-coenzyme A kinase (DPCK) of the parasite. Additionally, this compound inhibits α-synuclein-induced fibril formation, suggesting potential applications in Parkinson‘s disease research.
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| ln Vitro |
In vitro studies demonstrate that hupehenine and its derivatives exhibit anti-tumor activity. Hupehenine and its three related alkaloid derivatives (o-caproyl-hupehenenine, o-(2-furanoyl)-hupehenenine, and Δ5(6)-isopeimine) show inhibitory proliferation effects on human lung cancer cell lines, human chronic myeloid leukemia cell lines, and human thyroid duct cancer cell lines. In anti-leishmanial studies, hupehenine induces autophagy-mediated cell death in the parasite rather than typical apoptosis. This compound also inhibits α-synuclein-induced fibril formation.
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| ln Vivo |
In vivo studies demonstrate that hupehenine exhibits antitussive and expectorant activities, consistent with its traditional use as an antitussive component of Fritillaria Hupehensis. This compound has good affinity for multiple tissues but is unable to cross the blood-brain barrier. In pharmacokinetic studies, the maximum plasma concentration of hupehenine exhibits gender differences.
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| Enzyme Assay |
For in vitro receptor binding studies of hupehenine, reference protocols are as follows:
Cholinesterase Inhibition Assay: Use the Ellman colorimetric method. Pre-incubate varying concentrations of hupehenine (0.1-100 μM) with acetylcholinesterase or butyrylcholinesterase in phosphate buffer (pH 8.0), add substrates acetylthiocholine and DTNB, monitor absorbance changes at 412 nm, and calculate enzyme inhibition rates and IC₅₀ values.
Muscarinic Receptor Binding Assay: Use cell membranes expressing muscarinic receptors, incubate with [³H]-QNB and varying concentrations of hupehenine, separate bound and unbound ligands by rapid filtration, and detect radioactivity by liquid scintillation counting.
Data Analysis: Calculate IC₅₀ and Ki values.
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| Cell Assay |
Cell Culture: Culture human lung cancer cell lines, human chronic myeloid leukemia cell lines, or human thyroid duct cancer cell lines in RPMI-1640/DMEM medium containing 10% fetal bovine serum at 37°C in a 5% CO₂ incubator.
Drug Treatment: Dissolve hupehenine in DMSO to prepare stock solution, dilute to working concentrations (e.g., 0.1-100 μM) with culture medium, and treat cells for 24-72 hours.
Cell Proliferation Assay: Measure cell viability using MTT or CCK-8 assays to calculate IC₅₀ values.
Anti-leishmanial Activity Assay: Culture Leishmania donovani promastigotes, treat with varying concentrations of hupehenine, and detect acidic organelle formation and autophagy-related markers by flow cytometry.
Data Analysis: Compare cell viability and related marker differences between treatment and control groups.
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| Animal Protocol |
Animal Models: Use Sprague-Dawley rats for pharmacokinetic and tissue distribution studies.
Dosing Regimen: Administer hupehenine via oral gavage or intravenous injection. Oral doses should be determined based on study design; common intravenous doses are 2-5 mg/kg.
Sample Collection: Collect blood samples at specified time points (0.083, 0.25, 0.5, 1, 2, 4, 6, 8, 12, 24 hours) after administration. Euthanize some animals and collect tissues including liver, kidney, heart, spleen, lung, and brain for tissue distribution analysis.
Sample Analysis: Process plasma and tissue homogenate samples by protein precipitation, and detect hupehenine concentrations by UPLC-MS/MS or HPLC-MS/MS. Chromatographic conditions: C18 column (e.g., 2.1×100 mm, 1.7 μm), mobile phase of 0.1% formic acid in water and acetonitrile with gradient elution. Mass spectrometry detection uses ESI positive ion mode with MRM monitoring of ion transition m/z 416.3→98.0 for hupehenine.
Data Analysis: Calculate pharmacokinetic parameters (Cmax, Tmax, t₁/₂, AUC, bioavailability, etc.). The oral bioavailability of hupehenine in rats is 13.4%.
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| ADME/Pharmacokinetics |
The pharmacokinetic profile of hupehenine in rats has been systematically studied. It is well absorbed after oral administration, with an oral bioavailability of 13.4% in rats. This compound has good affinity for various tissues but cannot cross the blood-brain barrier. The area under the plasma concentration-time curve and maximum plasma concentration exhibit gender differences. The UPLC-MS/MS method has a linear detection range of 2-2000 ng/mL (plasma) with a lower limit of quantification of 1 ng/mL (plasma and liver homogenate). Hupehenine has good stability in solution, but long-term storage at -20°C is recommended.
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| Toxicity/Toxicokinetics |
As a natural isosteroidal alkaloid extracted from Fritillaria hupehensis, hupehenine is used in traditional applications as an antitussive and expectorant component, suggesting good safety at conventional doses. In in vitro experiments, hupehenine exhibits inhibitory proliferation effects on various tumor cell lines, though its toxicity to normal cells requires further investigation. This compound is for research use only and is not intended for human therapeutic applications. Standard laboratory safety practices and appropriate personal protective equipment should be used when handling.
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| References | |
| Additional Infomation |
Delavine is an alkaloid. It has been reported to be found in Fritillaria monoflora, Fritillaria delavica, and other organisms with relevant data.
Hupehenine is a Type A 5α-cevanine isosteroidal alkaloid (trans-D/E ring configuration). It was quantified in 23 Fritillaria species using gas chromatography. Among the tested species, Hupehenine was detected only in Fritillaria hupehensis (Hubei-Beimu) at a concentration of 152.79 ± 15.27 μg/g in the bulb powder. In crude alkaloid extract of Hubei-Beimu, Hupehenine content was 5.78 ± 0.16%; in crude water extract, it was present only in trace amounts (Tr.). The study did not evaluate the pharmacological activity of Hupehenine in isolation. [1] |
| Molecular Formula |
C27H45NO2
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|---|---|
| Molecular Weight |
415.6517
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| Exact Mass |
415.345
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| CAS # |
98243-57-3
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| PubChem CID |
14240934
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| Appearance |
White to off-white solid
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
538.0±35.0 °C at 760 mmHg
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| Flash Point |
250.4±24.6 °C
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| Vapour Pressure |
0.0±3.2 mmHg at 25°C
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| Index of Refraction |
1.577
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| LogP |
5.85
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
30
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| Complexity |
667
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| Defined Atom Stereocenter Count |
13
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| SMILES |
O([H])[C@]1([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@@]4([H])[C@@]([H])(C([H])([H])[H])[C@]5([H])C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])C([H])([H])N5C([H])([H])[C@@]4([H])[C@]3([H])C([H])([H])[C@]2([H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[C@@]21[H])O[H]
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| InChi Key |
NEMWYOKGHGSVSC-MSSYMPDSSA-N
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| InChi Code |
InChI=1S/C27H45NO2/c1-15-4-7-25-16(2)18-5-6-19-20(22(18)14-28(25)13-15)11-23-21(19)12-26(30)24-10-17(29)8-9-27(23,24)3/h15-26,29-30H,4-14H2,1-3H3/t15-,16+,17-,18-,19+,20+,21-,22+,23-,24+,25-,26+,27+/m0/s1
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| Chemical Name |
(1R,2S,6S,9S,10R,11R,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosane-17,20-diol
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| Synonyms |
Hupehenine; 98243-57-3; (1R,2S,6S,9S,10R,11R,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo[12.11.0.02,11.04,9.015,24.018,23]pentacosane-17,20-diol; (1R,2S,6S,9S,10R,11R,14S,15S,17R,18S,20S,23R,24S)-6,10,23-trimethyl-4-azahexacyclo(12.11.0.02,11.04,9.015,24.018,23)pentacosane-17,20-diol; RefChem:146911;
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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) |
DMSO : ~100 mg/mL (~240.59 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.01 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL 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: ≥ 2.5 mg/mL (6.01 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.01 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4059 mL | 12.0294 mL | 24.0587 mL | |
| 5 mM | 0.4812 mL | 2.4059 mL | 4.8117 mL | |
| 10 mM | 0.2406 mL | 1.2029 mL | 2.4059 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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