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Luteolin-4'-O-glucoside

Cat No.:V45636 Purity: ≥98%
Luteolin-4'-O-glucoside is an IL-5 inhibitor (antagonist) with IC50 of 3.7 μM.
Luteolin-4'-O-glucoside
Luteolin-4'-O-glucoside Chemical Structure CAS No.: 6920-38-3
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
Other Sizes
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Product Description
Luteolin-4'-O-glucoside is an IL-5 inhibitor (antagonist) with IC50 of 3.7 μM. Luteolin-4'-O-glucoside counteracts hyperuricemic and acute gouty arthritis activity. Luteolin-4'-O-glucoside has anti-cancer effect.
Luteolin-4'-O-glucoside is a naturally occurring flavonoid glycoside, consisting of the flavonoid aglycone luteolin with a glucose moiety attached at the 4'-position. It has the molecular formula C₂₁H₂₀O₁₁ and a molecular weight of 448.38. Luteolin-4'-O-glucoside is found in various plant sources and exhibits antioxidant, anti-inflammatory, and anti-cancer activities. The compound is used in natural product research to study the biological activities of flavonoid glycosides and to explore their potential therapeutic applications.
Biological Activity I Assay Protocols (From Reference)
Targets
Luteolin-4'-O-glucoside targets multiple cellular pathways involved in oxidative stress, inflammation, and cancer. As a flavonoid, it acts as a potent antioxidant by scavenging free radicals and chelating metal ions. It may modulate the activity of enzymes such as cyclooxygenases (COX) and lipoxygenases (LOX), reducing the production of pro-inflammatory mediators. Luteolin-4'-O-glucoside also influences signaling pathways such as NF-κB, MAPK, and PI3K/Akt, contributing to its anti-inflammatory and anti-cancer effects. The glycosylation at the 4'-position affects its bioactivity and bioavailability compared to the luteolin aglycone.
ln Vitro
NCI-H929, U266, and OPM2 cell lines are all susceptible to the cytotoxic effects of luteolin-4'-O-glucoside [3].
Luteolin-4'-O-glucoside exhibits antioxidant activity through DPPH, ABTS, and FRAP radical scavenging assays. It shows anti-inflammatory activity by inhibiting the production of nitric oxide, prostaglandins, and pro-inflammatory cytokines in LPS-stimulated macrophages. Luteolin-4'-O-glucoside also exhibits anti-cancer activity, including inhibition of cancer cell proliferation and induction of apoptosis. The compound's activities are generally lower than those of the luteolin aglycone due to the glycosylation. Specific IC₅₀ values for various activities depend on the assay system.
ln Vivo
In vivo activity data for luteolin-4'-O-glucoside are limited in the available literature. Based on its in vitro antioxidant, anti-inflammatory, and anti-cancer activities, it is anticipated to have potential in vivo efficacy in models of oxidative stress, inflammation, and cancer. However, as a glycosylated flavonoid, it may have limited oral bioavailability due to poor absorption and extensive metabolism. Specific animal studies are not extensively documented.
Enzyme Assay
Non-cellular assays for luteolin-4'-O-glucoside typically involve measuring its antioxidant activity using chemical assays such as DPPH, ABTS, and FRAP. The compound's ability to scavenge free radicals is measured spectrophotometrically. Anti-inflammatory activity can be assessed using enzyme inhibition assays for COX-1, COX-2, and LOX. The compound is incubated with the enzyme and substrate, and the inhibition of product formation is measured. IC₅₀ values are calculated from dose-response curves.
Cell Assay
In vitro cellular assays for luteolin-4'-O-glucoside typically use macrophage cell lines such as RAW 264.7 to evaluate anti-inflammatory activity. Cells are treated with various concentrations of the compound, followed by stimulation with lipopolysaccharide (LPS) to induce inflammation. Nitric oxide production is measured using the Griess assay. Pro-inflammatory cytokine levels (TNF-α, IL-1β, IL-6) are quantified by ELISA. Cell viability is assessed using MTT assays to ensure that observed effects are not due to cytotoxicity. For anti-cancer activity, cancer cell lines are treated with the compound, and cell proliferation and apoptosis are assessed.
Animal Protocol
In vivo animal studies for luteolin-4'-O-glucoside are not extensively documented in the available literature. Based on its potential anti-inflammatory and anti-cancer activities, typical study designs would involve rodent models of inflammation or cancer. The compound would be administered orally or intraperitoneally. Inflammatory markers, tumor growth, and histopathological changes would be evaluated.
ADME/Pharmacokinetics
Pharmacokinetic properties of luteolin-4'-O-glucoside are not characterized in the available literature. As a flavonoid glycoside with a molecular weight of 448.38, it is expected to have limited oral bioavailability due to poor membrane permeability and extensive first-pass metabolism. The glucose moiety may be hydrolyzed by intestinal glucosidases, releasing the luteolin aglycone. Metabolic pathways likely involve phase II conjugation (glucuronidation and sulfation) of the phenolic hydroxyl groups. Specific PK parameters such as half-life, Cmax, and bioavailability are not documented.
Toxicity/Toxicokinetics
Toxicological data for luteolin-4'-O-glucoside are limited in the available literature. As a naturally occurring flavonoid glycoside, it is generally considered to have low toxicity. However, comprehensive toxicology studies are not available. The compound may cause skin and eye irritation upon contact. Standard laboratory safety precautions should be observed when handling this compound.
References

[1]. Inhibitory effect of luteolin 4'-O-glucoside from Kummerowia striata and other flavonoids on interleukin-5 bioactivity. Planta Med. 1999 Jun;65(5):457-9.

[2]. Luteolin-4'-O-glucoside and its aglycone, two major flavones of Gnaphalium affine D. Don, resist hyperuricemia and acute gouty arthritis activity in animal models. Phytomedicine. 2018 Mar 1;41:54-61.

[3]. Glycosylation of luteolin in hydrophilic organic solvents and structure–antioxidant relationships of luteolin glycosides. RSC Advances, 2022, 12(28): 18232-18237.

Additional Infomation
Luteolin 4'-glucoside has reportedly been found in Disporum cantoniense, Pseudognaphalium affine, and other organisms with available data.
Luteolin-4'-O-glucoside is a research-grade natural product intended for laboratory use only and is not approved for clinical use. Its CAS number is 6920-38-3. The primary applications of luteolin-4'-O-glucoside include studying the antioxidant, anti-inflammatory, and anti-cancer activities of flavonoid glycosides, investigating the effects of glycosylation on flavonoid bioactivity, and exploring the therapeutic potential of natural flavonoid glycosides. The compound is a valuable tool for natural product chemistry and pharmacology research.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H20O11
Molecular Weight
448.3769
Exact Mass
448.101
CAS #
6920-38-3
PubChem CID
12304737
Appearance
Off-white to yellow solid powder
Density
1.713g/cm3
Boiling Point
814.5ºC at 760 mmHg
Melting Point
210ºC (dec.)
Flash Point
288.5ºC
Index of Refraction
1.74
LogP
0.5
Hydrogen Bond Donor Count
7
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
4
Heavy Atom Count
32
Complexity
714
Defined Atom Stereocenter Count
0
InChi Key
UHNXUSWGOJMEFO-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)31-13-2-1-8(3-10(13)24)14-6-12(26)17-11(25)4-9(23)5-15(17)30-14/h1-6,16,18-25,27-29H,7H2
Chemical Name
5,7-dihydroxy-2-[3-hydroxy-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]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)
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 2.2303 mL 11.1513 mL 22.3025 mL
5 mM 0.4461 mL 2.2303 mL 4.4605 mL
10 mM 0.2230 mL 1.1151 mL 2.2303 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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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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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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  • 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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