| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Chalcone synthase (CHS); flavonoid O-methyltransferase. Isovitexin 2''-O-arabinoside is a chalcone synthase (CHS) inhibitor with an IC₅₀ of 62 μM. CHS is the key enzyme in the flavonoid biosynthesis pathway, catalyzing the condensation of p-coumaroyl-CoA with malonyl-CoA. The compound is confirmed as a non-substrate for Avena sativa methyltransferase (EC 2.1.1.153), making it a critical tool for probing flavonoid O-methyltransferase substrate specificity. Its immunoregulatory activity suggests interactions with immune cell signaling pathways.
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| ln Vitro |
Isovitexin 2''-O-arabinoside inhibits chalcone synthase with an IC₅₀ of 62 μM. For comparison, apigenin has an IC₅₀ of 9 μM and luteolin has an IC₅₀ of 13 μM. The compound (62 μM) reduced enzyme activity by 50%. It is confirmed as a non-substrate for Avena sativa methyltransferase (EC 2.1.1.153). The compound exhibits significant antioxidant, anti-inflammatory, and neuroprotective properties by scavenging free radicals and modulating cellular signaling pathways. It has demonstrated immunoregulatory activity in keratinocyte and T-cell research models.
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| ln Vivo |
In vivo studies of isovitexin 2''-O-arabinoside are limited. As a flavonoid with antioxidant, anti-inflammatory, and neuroprotective properties, it has potential for evaluation in animal models of oxidative stress, inflammation, and neurodegenerative diseases. The compound’s immunoregulatory activity suggests potential benefits in inflammatory and dermatological conditions. Further in vivo studies are needed to characterize its pharmacokinetic and pharmacodynamic properties.
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| Enzyme Assay |
Non-cell-based assays for isovitexin 2''-O-arabinoside include chalcone synthase (CHS) inhibition assays using purified enzyme. The enzyme is incubated with p-coumaroyl-CoA and malonyl-CoA in the presence of various concentrations of the compound. The formation of naringenin chalcone is measured spectrophotometrically, and the IC₅₀ value of 62 μM is calculated. Flavonoid O-methyltransferase assays confirm the compound as a non-substrate. Standard analytical methods including HPLC and NMR are used for compound characterization.
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| Cell Assay |
Cell-based assays for isovitexin 2''-O-arabinoside use various cell lines to assess its immunoregulatory and anti-inflammatory activities. Keratinocyte and T-cell research models are used to study its immunoregulatory effects. For antioxidant studies, cells are exposed to oxidative stress inducers and treated with the compound, and intracellular ROS levels are measured. For anti-inflammatory studies, macrophage cell lines are stimulated with LPS and treated with the compound, and inflammatory mediators are measured.
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| Animal Protocol |
In vivo studies of isovitexin 2''-O-arabinoside are limited. Based on its biological activities, potential animal models include: models of inflammation for anti-inflammatory evaluation; models of oxidative stress for antioxidant evaluation; and models of neurodegenerative diseases for neuroprotective evaluation. Standard protocols for these models involve administration of the compound followed by measurement of relevant endpoints.
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| ADME/Pharmacokinetics |
Isovitexin 2''-O-arabinoside has a molecular formula of C₂₆H₂₈O₁₄ and a molecular weight of 564.5 g/mol. The SMILES and InChI keys are available. Purity is ≥98% HPLC. The compound is a naturally occurring C-glycosyl flavonoid isolated from oat and rye. It is used as a reference standard for C-glycosyl flavone identification and quantification. Storage: powder at -20°C.
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| Toxicity/Toxicokinetics |
Specific toxicity data for isovitexin 2''-O-arabinoside are limited. As a natural flavonoid, it is generally considered to have low toxicity. The compound’s immunoregulatory activity suggests biological activity at certain concentrations. Standard laboratory safety practices should be followed when handling this compound. It is intended for research use only.
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| References | |
| Additional Infomation |
Isorhizonine 2''-O-arabinoside is an arabinoside, C-glycoside compound, disaccharide derivative, and trihydroxyflavonoid. It is a metabolite functionally related to isorhizonine.
Isovitexin 2''-O-arabinoside is a naturally occurring C-glycosyl flavonoid isolated from oat and rye. It consists of an apigenin-6-C-glucoside core with an α-L-arabinopyranosyl residue at the 2''-position. The compound inhibits chalcone synthase (IC₅₀ = 62 μM) and is a non-substrate for flavonoid O-methyltransferase. It exhibits antioxidant, anti-inflammatory, neuroprotective, and immunoregulatory properties. It is used as a reference standard for flavonoid pathway research and is for research use only. |
| Molecular Formula |
C26H28O14
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|---|---|
| Molecular Weight |
564.49
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| Exact Mass |
564.147
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| CAS # |
53382-71-1
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| PubChem CID |
44468060
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| Appearance |
Light yellow to yellow solid
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| Density |
1.79±0.1 g/cm3(Predicted)
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| Boiling Point |
941.5±65.0 °C(Predicted)
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| Source |
Originated from plants: Gramineae Avena sativa Linn.
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| LogP |
-1.3
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
14
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
40
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| Complexity |
923
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| Defined Atom Stereocenter Count |
9
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| SMILES |
O1[C@H](CO)[C@H]([C@@H]([C@H]([C@@H]1C1C(=CC2=C(C(C=C(C3C=CC(=CC=3)O)O2)=O)C=1O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)O)O
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| InChi Key |
ACRIYYKEWCXQOS-XAYOXWHSSA-N
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| InChi Code |
InChI=1S/C26H28O14/c27-7-16-20(33)22(35)25(40-26-23(36)19(32)13(31)8-37-26)24(39-16)18-12(30)6-15-17(21(18)34)11(29)5-14(38-15)9-1-3-10(28)4-2-9/h1-6,13,16,19-20,22-28,30-36H,7-8H2/t13-,16+,19-,20+,22-,23+,24-,25+,26-/m0/s1
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| Chemical Name |
6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
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| Synonyms |
Isovitexin 2''-O-arabinoside
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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: 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)
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| Solubility (In Vitro) |
DMSO: 100 mg/mL (177.15 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1.25 mg/mL (2.21 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 1.25 mg/mL (2.21 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of DMSO stock solution (12.5 mg/mL) to 900 μL of 20% SBE-β-CD saline and mix well. 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.7715 mL | 8.8576 mL | 17.7151 mL | |
| 5 mM | 0.3543 mL | 1.7715 mL | 3.5430 mL | |
| 10 mM | 0.1772 mL | 0.8858 mL | 1.7715 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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