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Meloside A (NSC-287464)

Alias: Isovitexin 2''-O-β-glucoside Meloside A GLUCOISOVITEXIN 2''-Glucoisovitexin NSC 287464 NSC-287464 NSC287464
Cat No.:V37643 Purity: ≥98%
Meloside A (Isovitexin 2''-O-glucoside) is a phenylpropanoid with anti-oxidant effect extracted from barley.
Meloside A (NSC-287464)
Meloside A (NSC-287464) Chemical Structure CAS No.: 60767-80-8
Product category: Disease Research Fields
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Meloside A (Isovitexin 2''-O-glucoside) is a phenylpropanoid with anti-oxidant effect extracted from barley. In barley, phenylpropanoids have been described as having a protective effect against excess UV-B radiation and are associated with resistance to pathogens.
Meloside A (NSC-287464) (CAS#: 60767-80-8), also known as isovitexin 2''-O-β-D-glucoside or glucoisovitexin, is a phenylpropanoid and C-glycosyl flavone disaccharide extracted from barley (Hordeum vulgare). This compound has a molecular weight of 594.52 and the molecular formula C27H30O15. Meloside A exhibits antioxidant activity and protective properties against excess UV-B radiation, and has been linked to resistance to pathogens in plants. The compound also demonstrates antidiabetic, antioxidant, and anti-inflammatory effects by modulating glucose metabolism and inhibiting pro-inflammatory pathways, making it of interest for managing metabolic disorders such as diabetes and obesity.
Biological Activity I Assay Protocols (From Reference)
Targets
Multiple targets involved in glucose metabolism, inflammatory pathways, and oxidative stress responses.
ln Vitro
In vitro studies demonstrate that Meloside A exhibits antioxidant activity through scavenging of free radicals and protection against oxidative stress. The compound has been shown to modulate glucose metabolism and inhibit pro-inflammatory pathways, suggesting potential antidiabetic and anti-inflammatory effects. As a phenylpropanoid isolated from barley, Meloside A has been described as having protective properties against excess UV-B radiation and has been linked to resistance to pathogens in plants. These activities are attributed to the compound's ability to modulate cellular signaling pathways involved in stress responses and metabolism.
ln Vivo
In vivo studies on Meloside A are limited, as the compound is primarily used as a research tool for studying plant secondary metabolites and their biological activities. The compound's antioxidant and anti-inflammatory properties have been demonstrated in various in vitro models, and its potential for managing metabolic disorders such as diabetes and obesity has been suggested based on its ability to modulate glucose metabolism. Further studies are needed to assess the compound's pharmacokinetic properties, oral bioavailability, and efficacy in animal models of metabolic diseases. The compound's natural origin and presence in barley make it a candidate for functional food development and phytopharmaceutical research.
Enzyme Assay
For antioxidant activity assessment, in vitro assays such as DPPH radical scavenging, ABTS radical scavenging, and ferric reducing antioxidant power (FRAP) assays are performed. The compound is incubated with the radical-generating system, and the decrease in absorbance is measured spectrophotometrically. IC50 or EC50 values for radical scavenging are calculated. For anti-inflammatory activity, enzyme inhibition assays (e.g., COX-1, COX-2, or LOX inhibition) or cell-based assays measuring inhibition of pro-inflammatory cytokine production are used. Glucose metabolism modulation is assessed using enzymatic assays measuring alpha-glucosidase or alpha-amylase inhibition.
Cell Assay
Cellular assays for Meloside A typically involve culturing cell lines relevant to metabolic and inflammatory diseases, such as adipocytes (3T3-L1), hepatocytes (HepG2), or macrophages (RAW 264.7). Cells are treated with Meloside A at various concentrations, and glucose uptake, lipid accumulation, or cytokine production is measured. For anti-inflammatory activity, macrophages are stimulated with LPS and the production of pro-inflammatory cytokines (TNF-α, IL-1β, IL-6) is measured by ELISA. Antioxidant activity is assessed by measuring intracellular reactive oxygen species (ROS) levels using fluorescent probes such as DCFH-DA. Cytotoxicity against mammalian cells is assessed in parallel to evaluate selectivity.
Animal Protocol
In vivo efficacy of Meloside A is evaluated in animal models of metabolic diseases such as diabetes and obesity. Mice are fed a high-fat diet to induce obesity and insulin resistance, and then treated with Meloside A via oral or intraperitoneal administration. Parameters assessed include blood glucose levels, insulin sensitivity (by glucose tolerance test or insulin tolerance test), body weight, adipose tissue mass, and serum lipid profiles. For anti-inflammatory studies, animal models of inflammation such as carrageenan-induced paw edema are used. Histopathological examination of tissues such as liver, adipose tissue, and pancreas is performed to assess treatment effects.
ADME/Pharmacokinetics
Pharmacokinetic properties of Meloside A have been characterized to support its use as a research compound and potential therapeutic agent. The compound's high molecular weight of 594.52 and polar nature (due to multiple hydroxyl and sugar groups) influence its absorption, distribution, metabolism, and excretion (ADME) characteristics. As a glycosylated flavonoid, Meloside A is likely metabolized in the gastrointestinal tract by gut microbiota or intestinal enzymes, which may affect its bioavailability. Key PK parameters including half-life, clearance, and bioavailability are determined using LC-MS/MS analysis of plasma and tissue samples following administration.
Toxicity/Toxicokinetics
Toxicological evaluation of Meloside A is typically conducted in parallel with efficacy studies in cell-based and animal models. Standard toxicology assessments include in vitro cytotoxicity assays against a panel of normal and cancer cell lines to determine the compound's selectivity index. In vivo toxicity studies in rodents include acute toxicity testing to determine the maximum tolerated dose, observation of clinical signs and body weight changes, and histopathological examination of major organs following repeated dosing. As a natural compound found in barley, Meloside A is generally considered to have a favorable safety profile for food and supplement applications, though comprehensive toxicology data may be limited.
References

[1]. Metabolite profiling of the short-term responses of rice leaves (Oryza sativa cv. Ilmi) cultivated under different LED lights and its correlations with antioxidant activities. Plant Sci. 2013;210:61-69.

[2]. Changes in isovitexin-O-glycosylation during the development of young barley plants. Phytochemistry. 2018;148:11-20.

Additional Infomation
2''-O-(β-D-glucosyl)isopurin is a disaccharide derivative with the β-D-glucosyl group replacing isopurin at the 2'' position of the glucose ring. It is a metabolite. It is a C-glycoside, a disaccharide derivative, and a trihydroxyflavon. Its function is related to isopurin. It has been reported that jujube (Ziziphus jujuba) contains melanoside A, and relevant data are available.
Meloside A is a naturally occurring phenylpropanoid and C-glycosyl flavone disaccharide found in barley with antioxidant, anti-inflammatory, and potential antidiabetic activities. The compound is studied for its role in plant stress responses, specifically protection against UV-B radiation and pathogen resistance, as well as for its potential applications in functional food development and phytopharmaceutical research. Its mechanism of action involves modulation of glucose metabolism, inhibition of pro-inflammatory pathways, and scavenging of free radicals. The compound is not approved as a drug but is used as a research chemical for studying plant secondary metabolites and their biological activities.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H30O15
Molecular Weight
594.522
Exact Mass
594.158
Elemental Analysis
C, 54.55 H, 5.09 O, 40.37
CAS #
60767-80-8
PubChem CID
185995
Appearance
Light yellow to yellow solid powder
LogP
-1.4
Hydrogen Bond Donor Count
10
Hydrogen Bond Acceptor Count
15
Rotatable Bond Count
6
Heavy Atom Count
42
Complexity
971
Defined Atom Stereocenter Count
10
SMILES
C1=CC(=CC=C1C2=CC(=O)C3=C(O2)C=C(C(=C3O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O)O
InChi Key
RQTTXGQDIROLTQ-FASGCTRLSA-N
InChi Code
InChI=1S/C27H30O15/c28-7-15-20(34)23(37)26(42-27-24(38)22(36)19(33)16(8-29)41-27)25(40-15)18-12(32)6-14-17(21(18)35)11(31)5-13(39-14)9-1-3-10(30)4-2-9/h1-6,15-16,19-20,22-30,32-38H,7-8H2/t15-,16-,19-,20-,22+,23+,24-,25+,26-,27+/m1/s1
Chemical Name
4H-1-Benzopyran-4-one, 6-(2-O-beta-D-glucopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-2-(4-hydroxyphenyl)- InChi Key
Synonyms
Isovitexin 2''-O-β-glucoside Meloside A GLUCOISOVITEXIN 2''-Glucoisovitexin NSC 287464 NSC-287464 NSC287464
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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 : ~100 mg/mL (~168.20 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 1.6820 mL 8.4101 mL 16.8203 mL
5 mM 0.3364 mL 1.6820 mL 3.3641 mL
10 mM 0.1682 mL 0.8410 mL 1.6820 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.

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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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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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