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Leptophylloside

Alias: Isorutarin; Leptophylloside
Cat No.:V23910 Purity: ≥98%
Isorutarin is a naturally occurring compound extracted from the seeds of Apium graueolens.
Leptophylloside
Leptophylloside Chemical Structure CAS No.: 53846-51-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Isorutarin is a naturally occurring compound extracted from the seeds of Apium graueolens.
Leptophylloside (CAS#: 53846-51-8), also known as Isorutarin, is a naturally occurring linear-type furanocoumarin glycoside that is isolated from various plant sources, including Apium graveolens (celery) seeds, Peucedanum praeruptorum (Bai-Hua Qian-Hu) roots, and Ruta graveolens (common rue). It belongs to the class of organic compounds known as psoralens, which are characterized by a furan ring fused to a chromenone moiety. Leptophylloside is a glycosylated derivative of psoralen, with a glucose moiety attached to the aglycone. Psoralens are known for their phototoxic and photosensitizing properties and have been used in the treatment of skin disorders such as psoriasis and vitiligo (PUVA therapy). Leptophylloside has been reported in various plant species and is a subject of research for its potential biological activities, although its specific pharmacological properties have not been extensively characterized.
Biological Activity I Assay Protocols (From Reference)
Targets
The specific molecular targets of Leptophylloside have not been well-characterized in the published literature. As a psoralen derivative, it may interact with DNA through intercalation and, upon ultraviolet (UVA) irradiation, form covalent adducts with pyrimidine bases, leading to DNA cross-linking and inhibition of DNA synthesis. This mechanism is responsible for the phototoxic and photosensitizing effects of psoralens and is the basis for their use in PUVA therapy for skin disorders. In addition to its DNA interactions, Leptophylloside may have antioxidant or anti-inflammatory activities, as other psoralen derivatives have been reported to possess these properties. However, the specific targets and mechanisms of action of Leptophylloside require further investigation.
ln Vitro
In vitro, Leptophylloside has been studied for its potential cytotoxic activity against cancer cell lines. However, specific data on its in vitro potency and activity are limited. As a psoralen glycoside, it may exhibit phototoxicity in cell culture when exposed to UVA light. In the absence of UVA irradiation, the compound may have minimal cytotoxic effects. Its antioxidant activity, if any, would be assessed using standard cell-free or cell-based antioxidant assays. The compound's glycosidic moiety may affect its cellular uptake and activity compared to the aglycone psoralen. Further studies are needed to fully characterize the in vitro biological activities of Leptophylloside.
ln Vivo
In vivo, the biological activities of Leptophylloside have not been extensively studied. As a naturally occurring psoralen glycoside, it may be metabolized to the aglycone psoralen, which could then exert phototoxic or other effects. However, the compound's in vivo pharmacokinetics, metabolism, and pharmacological effects have not been well-documented in the available literature. Leptophylloside has been reported in various plant species, suggesting that it may contribute to the biological properties of these plants, but its specific role and efficacy in vivo remain to be determined.
Enzyme Assay
The non-cellular assay for Leptophylloside, if performed, would likely involve the measurement of its phototoxic activity or its ability to interact with DNA. In a typical psoralen-DNA interaction assay, the compound is incubated with calf thymus DNA in the presence or absence of UVA irradiation. The formation of DNA adducts is monitored by changes in UV absorbance, fluorescence, or by gel electrophoresis. The compound's ability to inhibit DNA synthesis or to cross-link DNA can be assessed. In addition, the compound's antioxidant activity can be measured using cell-free assays such as DPPH radical scavenging or ABTS assays. However, specific experimental protocols for Leptophylloside have not been published.
Cell Assay
The cellular assay for Leptophylloside would involve testing its phototoxicity or cytotoxicity in cultured cells. Cells are treated with Leptophylloside at various concentrations, either in the dark or with exposure to UVA light. Cell viability is assessed using standard assays such as MTT or trypan blue exclusion. The phototoxic index (the ratio of cytotoxicity with UVA exposure to cytotoxicity without UVA exposure) is calculated to quantify the compound's phototoxic potential. In addition, the effects of Leptophylloside on cell cycle progression, apoptosis, and DNA damage (as assessed by comet assay or γ-H2AX staining) can be studied. These assays are standard for evaluating psoralen derivatives.
Animal Protocol
In vivo animal studies for Leptophylloside have not been well-documented in the available literature. As a naturally occurring compound, it may be studied in models of photodermatology or in models of the conditions for which psoralens are used, such as psoriasis or vitiligo. However, specific protocols and findings have not been reported.
ADME/Pharmacokinetics
Leptophylloside has a molecular weight of 424.40 g/mol and a molecular formula of C₂₀H₂₄O₁₀. It is a solid compound that is soluble in organic solvents. The compound is a glycosylated psoralen, which may affect its solubility, stability, and bioavailability compared to the aglycone. Its pharmacokinetic properties have not been characterized. Leptophylloside should be stored in a cool, dry place, protected from light, as psoralens are light-sensitive compounds.
Toxicity/Toxicokinetics
The toxicological profile of Leptophylloside has not been extensively characterized. As a psoralen derivative, it is expected to have phototoxic potential, meaning that it can cause skin irritation and damage upon exposure to UVA light. This is a well-known property of psoralens and is the basis for their therapeutic use in PUVA therapy, but also for their side effects, including phototoxicity and an increased risk of skin cancer with long-term use. The compound should be handled with care, avoiding exposure to UV light, and appropriate personal protective equipment should be used.
References

[1]. Furanocoumarin glucosides from the seeds of Apium graveolens. Phytochemistry, 1988.

Additional Infomation
Psoralen compounds contain folioside. Reports have indicated that rue and Corsican rue contain folioside, and relevant data are available for reference.
Leptophylloside (Isorutarin) is a naturally occurring furanocoumarin glycoside that belongs to the psoralen class of compounds. It is found in various plant sources, including celery, Peucedanum praeruptorum, and Ruta graveolens. As a psoralen derivative, it is of interest for its potential phototoxic and photosensitizing properties, which are the basis for the therapeutic use of psoralens in skin disorders. However, the specific biological activities and pharmacological potential of Leptophylloside have not been extensively characterized, and further research is needed to fully understand its properties and potential applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H24O10
Molecular Weight
424.4
Exact Mass
275.152
CAS #
53846-51-8
PubChem CID
185756
Appearance
Typically exists as solid at room temperature
Density
1.59g/cm3
Boiling Point
690.7ºC at 760mmHg
Flash Point
245.1ºC
Index of Refraction
1.673
LogP
2.348
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
4
Heavy Atom Count
30
Complexity
681
Defined Atom Stereocenter Count
6
SMILES
CC(C)(C1CC2=C(O1)C(=C3C(=C2)C=CC(=O)O3)O)OC4C(C(C(C(O4)CO)O)O)O
InChi Key
QZUDEXAHKXCIDG-NUUDRHLNSA-N
InChi Code
InChI=1S/C20H24O10/c1-20(2,30-19-15(25)14(24)13(23)10(7-21)27-19)11-6-9-5-8-3-4-12(22)29-17(8)16(26)18(9)28-11/h3-5,10-11,13-15,19,21,23-26H,6-7H2,1-2H3/t10-,11-,13-,14+,15-,19+/m1/s1
Chemical Name
(2R)-9-hydroxy-2-[2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-2,3-dihydrofuro[3,2-g]chromen-7-one
Synonyms
Isorutarin; Leptophylloside
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 2.3563 mL 11.7813 mL 23.5627 mL
5 mM 0.4713 mL 2.3563 mL 4.7125 mL
10 mM 0.2356 mL 1.1781 mL 2.3563 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

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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?
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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • 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:
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  • 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)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • 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.

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  • 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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