| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| 25mg |
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| 100mg |
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| Enzyme Assay |
The recombinant IpeGlu1 enzyme was expressed in E. coli and purified via metal chelation chromatography. The enzymatic activity toward ipecoside was assayed in a reaction mixture (100 μL) containing 0.1 M citrate/0.2 M phosphate buffer (pH 5.0), 1 mM substrate (ipecoside), and 2 μg of purified IpeGlu1 enzyme. The reaction was incubated at 30 °C for 1 h, then terminated by adding 20 μL of 1 N HCl. After centrifugation, the supernatant was analyzed by HPLC using an ODS column with a gradient elution of 12–80% acetonitrile in 0.1% trifluoroacetic acid over 30 min, and detection at 230 nm. The decrease in substrate was monitored to calculate enzyme activity. [1]
For kinetic parameter determination, the enzyme assay was performed in 0.1 M citrate/0.2 M phosphate buffer (pH 5.0) at 30 °C. The amount of enzyme and reaction time were adjusted to ensure linear progression. The reaction was terminated and analyzed by HPLC under the same gradient conditions (12–80% acetonitrile in 30 min, detection at 230 nm). The kinetic parameters for ipecoside were determined from three replicates by plotting [s] versus [s]/v. The obtained values were: Km = 0.1 mM, kcat = 51.6 s−1, and catalytic efficiency (kcat/Km) = 516 mM−1 s−1. [1] For identification of deglucosylation products of ipecoside, the reaction mixture (100 μL) containing 0.1 M citrate/0.2 M phosphate buffer (pH 5.0), 1 mM ipecoside, and 2 μg of IpeGlu1 was incubated at 30 °C for 1 h. The reaction was terminated by adding 20 μL of 1 N HCl and subjected to LC‑MS/MS analysis. HPLC separation was performed with a gradient of 12–80% acetonitrile in 0.1% trifluoroacetic acid over 30 min at a flow rate of 0.8 mL/min. Mass spectrometry was conducted in positive ion mode using a triple quadrupole instrument. The molecular ion of the main product was m/z 404, corresponding to the immediate deglucosylation product of ipecoside. No further conversion products (e.g., m/z 344 or 362) were detected, indicating the aglycon of ipecoside is stable and does not undergo spontaneous rearrangements. [1] |
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| References | |
| Additional Infomation |
Ipecoside is a terpene glycoside, β-D-glucoside, methyl ester, isoquinoline alkaloid, isoquinoline alcohol, and olefin compound, belonging to the acetamide class. It is a plant metabolite functionally related to the Ipecoside aglycone. Ipecoside has been reported to exist in ipecac (Carapichea ipecacuanha), and relevant data are available.
ipecoside is accumulated as the main alkaloidal glucoside in Psychotria ipecacuanha, and its aglycon is not further converted by spontaneous reactions, suggesting it may serve a defensive role rather than being an intermediate in alkaloid biosynthesis. The deglucosylation of ipecoside by IpeGlu1 is highly efficient (kcat/Km = 516 mM−1 s−1), yet ipecoside is stored in the plant without being hydrolyzed, indicating that IpeGlu1 and ipecoside are localized in distinct subcellular compartments (vacuole for the glucoside, cytosol for the enzyme). This compartmentalization prevents premature deglucosylation and allows ipecoside to function as a stable defense-related glucoside that releases a potentially toxic aglycon only upon cell disruption. No non-glucosidic Ipecac alkaloid with β-configuration has been found in nature, supporting the idea that the 1β(R)-epimer is acetylated to ipecoside and metabolically inactivated. [1] |
| Molecular Formula |
C27H35NO12
|
|---|---|
| Molecular Weight |
565.5663
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| Exact Mass |
565.216
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| CAS # |
15401-60-2
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| PubChem CID |
442249
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| Appearance |
Off-white to light yellow solid
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| Density |
1.5g/cm3
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| Boiling Point |
821.6ºC at 760 mmHg
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| Melting Point |
177-180 ºC
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| Flash Point |
450.7ºC
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| Vapour Pressure |
1.42E-28mmHg at 25°C
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| Index of Refraction |
1.65
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| LogP |
-0.3
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
40
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| Complexity |
960
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O([C@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H])[C@]1([H])[C@@]([H])(C([H])=C([H])[H])[C@]([H])(C(C(=O)OC([H])([H])[H])=C([H])O1)C([H])([H])[C@@]1([H])C2=C([H])C(=C(C([H])=C2C([H])([H])C([H])([H])N1C(C([H])([H])[H])=O)O[H])O[H]
|
| InChi Key |
QISXROCIXKXUPS-OWVLCBNUSA-N
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| InChi Code |
InChI=1S/C27H35NO12/c1-4-14-16(8-18-15-9-20(32)19(31)7-13(15)5-6-28(18)12(2)30)17(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)21(10-29)39-27/h4,7,9,11,14,16,18,21-24,26-27,29,31-35H,1,5-6,8,10H2,2-3H3/t14-,16+,18-,21-,22-,23+,24-,26+,27+/m1/s1
|
| Chemical Name |
methyl (2S,3R,4S)-4-[[(1R)-2-acetyl-6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-1-yl]methyl]-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-5-carboxylate
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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 (~176.81 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 | 1.7681 mL | 8.8406 mL | 17.6813 mL | |
| 5 mM | 0.3536 mL | 1.7681 mL | 3.5363 mL | |
| 10 mM | 0.1768 mL | 0.8841 mL | 1.7681 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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