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Leucanthoside

Cat No.:V23934 Purity: ≥98%
Swertiajaponin is a tyrosinase inhibitor that forms multiple hydrogen bonds and hydrophobic interactions with the tyrosinase binding pocket, with IC50 of 43.47 μM.
Leucanthoside
Leucanthoside Chemical Structure CAS No.: 6980-25-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Swertiajaponin is a tyrosinase inhibitor that forms multiple hydrogen bonds and hydrophobic interactions with the tyrosinase binding pocket, with IC50 of 43.47 μM. Swertiajaponin can also cause a decrease in tyrosinase protein levels by inhibiting oxidative stress-mediated MAPK/MITF signaling. Swertiajaponin can inhibit the accumulation of melanin and has strong anti-oxidant effect.
Leucanthoside, also known as Swertiajaponin, is a flavone C-glycoside, structurally defined as 6-β-D-glucopyranosyl-3′,4′,5-trihydroxy-7-methoxyflavone—the 7-O-methyl ether of isoorientin. It has a molecular weight of 462.12 g/mol and a molecular formula of C₂₂H₂₂O₁₁. Leucanthoside is a defined oleanane-type triterpenoid saponin, a class of natural glycosides known for a wide range of biological activities, including cytotoxic and immunomodulatory properties. It is a tyrosinase inhibitor that forms multiple hydrogen bonds and hydrophobic interactions with the tyrosinase binding pocket, with an IC₅₀ of 43.47 μM. The compound also shows antimicrobial and antioxidative activities.
Biological Activity I Assay Protocols (From Reference)
Targets
Leucanthoside targets tyrosinase, the key enzyme in melanin biosynthesis. It inhibits tyrosinase activity by forming multiple hydrogen bonds and hydrophobic interactions with the tyrosinase binding pocket, with an IC₅₀ of 43.47 μM. The compound also exhibits antimicrobial and antioxidative activities, suggesting additional mechanisms of action. As a triterpenoid saponin, it may also interact with cell membranes and modulate immune responses.
ln Vitro
In vitro, leucanthoside inhibits tyrosinase with an IC₅₀ of 43.47 μM. It shows antimicrobial and antioxidative activities. The compound's cytotoxic and immunomodulatory properties suggest potential activity against cancer cells and immune modulation. Detailed IC₅₀ values for antimicrobial and cytotoxic activities are not extensively reported in the available literature.
ln Vivo
Detailed in vivo activity data for leucanthoside are not extensively reported in the available literature. As a natural product with tyrosinase inhibitory, antimicrobial, and antioxidative activities, it is expected to have potential for in vivo efficacy in skin pigmentation disorders, infections, and oxidative stress-related conditions. However, specific in vivo efficacy data from animal studies are not provided in the available sources.
Enzyme Assay
Non-cell-based enzyme assays for leucanthoside typically involve tyrosinase inhibition assays using purified mushroom tyrosinase. The enzyme is incubated with a substrate (e.g., L-DOPA or tyrosine) and varying concentrations of leucanthoside. Tyrosinase activity is measured by monitoring the oxidation of the substrate spectrophotometrically at 475 nm. IC₅₀ values are determined from dose-response curves. Antioxidant activity can be assessed using DPPH or ABTS radical scavenging assays.
Cell Assay
Cellular assays for leucanthoside are performed using melanocytes to assess inhibition of melanin production. Cells are treated with the compound at various concentrations, and melanin content is measured spectrophotometrically. Tyrosinase activity in cell lysates is assessed by measuring the oxidation of L-DOPA. Cell viability is assessed to distinguish anti-melanogenic effects from cytotoxicity. Antimicrobial activity is assessed using standard broth microdilution methods.
Animal Protocol
In vivo animal models for leucanthoside would be required to assess its therapeutic potential. Based on its mechanism as a tyrosinase inhibitor, relevant models could include mouse models of skin pigmentation, such as UV-induced pigmentation or melanin deposition models. The compound would be administered topically or systemically, and pigmentation changes would be assessed visually or by measuring melanin content in skin biopsies.
ADME/Pharmacokinetics
Leucanthoside has a molecular weight of 462.12 g/mol and a molecular formula of C₂₂H₂₂O₁₁. CAS number is 6980-25-2. The compound is soluble in DMSO. Appearance is a light yellow to yellow solid powder. Purity is >98%. Storage conditions: powder at -20°C. Detailed PK parameters such as half-life and bioavailability are not extensively reported.
Toxicity/Toxicokinetics
Detailed toxicological data for leucanthoside are not extensively reported in the available literature. As a naturally occurring compound, it is generally considered to have a good safety profile, but thorough toxicological studies would be required for therapeutic development. The compound is intended for research use only and is not for human consumption. Standard laboratory safety precautions should be followed.
References

[1]. Swertiajaponin inhibits skin pigmentation by dual mechanisms to suppress tyrosinase. Oncotarget. 2017 Sep 15;8(56):95530-95541.

Additional Infomation
According to reports, swertiamarin is found in Japanese swertiamarin, pseudo-Chinese swertiamarin, and other organisms with available data.
Leucanthoside is also known as Swertiajaponin. It is a flavone C-glycoside, structurally defined as 6-β-D-glucopyranosyl-3′,4′,5-trihydroxy-7-methoxyflavone—the 7-O-methyl ether of isoorientin. The compound inhibits tyrosinase with an IC₅₀ of 43.47 μM and shows antimicrobial and antioxidative activities. It is a triterpenoid saponin with cytotoxic and immunomodulatory properties. Leucanthoside is used in research applications studying melanogenesis, antimicrobial activity, and oxidative stress. It is for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C22H22O11
Molecular Weight
462.4035
Exact Mass
462.116
CAS #
6980-25-2
PubChem CID
442659
Appearance
Light yellow to yellow solid powder
Density
1.6±0.1 g/cm3
Boiling Point
761.3±60.0 °C at 760 mmHg
Flash Point
266.6±26.4 °C
Vapour Pressure
0.0±2.7 mmHg at 25°C
Index of Refraction
1.717
LogP
1.83
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
33
Complexity
744
Defined Atom Stereocenter Count
5
SMILES
COC1=C(C(=C2C(=C1)OC(=CC2=O)C3=CC(=C(C=C3)O)O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
InChi Key
DLVLXOYLQKCAME-DGHBBABESA-N
InChi Code
InChI=1S/C22H22O11/c1-31-13-6-14-16(11(26)5-12(32-14)8-2-3-9(24)10(25)4-8)19(28)17(13)22-21(30)20(29)18(27)15(7-23)33-22/h2-6,15,18,20-25,27-30H,7H2,1H3/t15-,18-,20+,21-,22+/m1/s1
Chemical Name
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-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: 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)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~540.66 mM)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.1626 mL 10.8131 mL 21.6263 mL
5 mM 0.4325 mL 2.1626 mL 4.3253 mL
10 mM 0.2163 mL 1.0813 mL 2.1626 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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