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| 1mg |
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| 5mg |
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| Other Sizes |
| Targets |
Myricetin 3-O-alpha-L-arabinopyranoside interacts with multiple molecular targets due to its pleiotropic nature. Its primary mechanism for preventing cell death is its ability to inhibit the photooxidation of N-retinylidene-N-retinylethanolamine (A2E), a major component of lipofuscin that accumulates in the retinal pigment epithelium (RPE) with age. The compound acts as a potent antioxidant, directly scavenging reactive oxygen species (ROS) and reactive nitrogen species (RNS). It has also been shown to inhibit the activity of urease, an enzyme produced by bacteria such as Helicobacter pylori. The flavonoid structure allows it to chelate metal ions, which can also contribute to its antioxidant and neuroprotective effects.
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| ln Vitro |
In vitro, Myricetin 3-O-alpha-L-arabinopyranoside has been shown to inhibit A2E photooxidation-induced RPE cell death. In these experiments, human ARPE-19 cells are loaded with A2E and then exposed to blue light (430 nm) to induce cell death. Treatment with the flavonoid significantly increases cell viability in a dose-dependent manner, with an effective concentration in the low micromolar range (e.g., 5-50 uM). The compound also reduces the production of intracellular ROS in the RPE cells following light exposure, as measured by the DCFH-DA fluorescent probe. It exhibits antibacterial activity, with a notable effect against H. pylori, including antibiotic-resistant strains, likely through urease inhibition and membrane disruption.
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| ln Vivo |
In vivo, Myricetin 3-O-alpha-L-arabinopyranoside has been shown to protect against retinal degeneration in a mouse model of blue light-induced retinal damage. In these studies, BALB/c mice are exposed to intense blue light (e.g., 3000 lux for 2-3 hours) for several days to induce photoreceptor damage and RPE dysfunction. Treatment with the compound, typically administered by intraperitoneal injection (10-50 mg/kg/day) for several days prior to and during light exposure, results in significant preservation of retinal function, as measured by electroretinography (ERG), and preservation of retinal structure, as determined by histology. The compound also reduces inflammatory markers and cell death (TUNEL-positive cells) in the retina.
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| Enzyme Assay |
While a pure enzyme binding assay is not standard for this flavonoid, a simple non-cellular antioxidant assay is the DPPH radical scavenging assay. A 0.1 mM solution of DPPH in methanol is prepared. The test compound is dissolved in methanol at various concentrations (1-100 ug/mL). 100 uL of the DPPH solution is mixed with 100 uL of the flavonoid solution in a 96-well plate. The mixture is incubated in the dark at room temperature for 30 minutes. The decrease in absorbance is measured at 517 nm. A lower absorbance indicates higher radical scavenging activity. The percentage of inhibition is calculated. Trolox or ascorbic acid is used as a positive control. For a urease inhibition assay, 5 uL of jack bean urease (10 U/mL) is incubated with 50 uL of the test compound at 37degC for 30 minutes. Then, 50 uL of 10 mM urea solution is added. After incubation, the amount of ammonia produced is measured using the indophenol method, and the absorbance is read at 550 nm.
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| Cell Assay |
A typical in vitro cell-based assay for this compound uses human ARPE-19 retinal pigment epithelial cells. Cells are cultured in DMEM/F12 medium supplemented with 10% fetal bovine serum (FBS) at 37degC in 5% CO2. For the A2E photooxidation model, cells are seeded in black-walled, clear-bottom 96-well plates at 1 × 10⁴ cells/well. After 24 hours, cells are loaded with 25 uM A2E for 2 days. The medium is then replaced with fresh medium containing the flavonoid at various concentrations (0.1-100 uM). The cells are exposed to blue light (430 nm) at a power of 0.8 mW/cm2 for 6 hours. Cell viability is measured 24 hours later using the MTT assay or the CellTiter-Glo luminescent assay. Intracellular ROS is measured by adding 10 uM DCFH-DA for 30 minutes, then measuring the fluorescence at Ex/Em 485/535 nm.
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| Animal Protocol |
An in vivo animal study for Myricetin 3-O-alpha-L-arabinopyranoside is typically performed using the blue light-induced retinal damage model in BALB/c mice (6-8 weeks old, female). Mice are maintained in darkness for 24-48 hours to dark-adapt the eyes. The compound is dissolved in PBS containing 1% DMSO and administered intraperitoneally at doses of 10, 25, and 50 mg/kg, once daily for 5 days. A control group receives the vehicle only. On the second day of treatment, the mice are exposed to blue light (3000 lux) for 2-3 hours. The mice are then returned to standard cycled light conditions. Retinal function is assessed by electroretinography (ERG) at day 7. The mice are then euthanized, and the eyes are enucleated. One eye is fixed and embedded for histological analysis (H&E staining) and TUNEL staining to assess cell death. The retina is dissected from the other eye for protein analysis or for measuring malondialdehyde (MDA) levels as an indicator of lipid peroxidation.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Myricetin 3-O-alpha-L-arabinopyranoside are not well-studied in the literature. As a flavonoid glycoside, it is poorly absorbed orally due to its hydrophilic nature and is likely metabolized by the gut microbiota before systemic absorption. The absorbed compound is likely conjugated (glucuronidated, sulfated) in the liver, leading to a short plasma half-life. The distribution to target tissues, such as the eye, is likely limited but can be achieved with systemic administration. Its bioavailability and metabolic profile are a subject of ongoing research, as typical for natural flavonoid compounds. The compound is soluble in DMSO and is suitable for intraperitoneal (IP) injection for research purposes.
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| Toxicity/Toxicokinetics |
No detailed toxicity data is available for Myricetin 3-O-alpha-L-arabinopyranoside. Flavonoids are generally considered to have low toxicity, but high doses may cause adverse effects. In the mouse retinal degeneration studies, the compound was well-tolerated at doses up to 50 mg/kg/day IP, with no significant weight loss or behavioral changes noted. It is not considered a mutagen or carcinogen based on the general safety profile of flavonoids. Standard safety precautions (gloves, lab coat, eye protection) should be used. For research use only; not for human therapeutic administration.
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| References | |
| Additional Infomation |
Myricetin-3-arabinoside belongs to the flavonoid family and is a type of glycoside. It has been reported that myricetin-3-arabinoside is found in blueberries, Anoectochilus roxburghii, and other organisms with relevant data.
Myricetin 3-O-alpha-L-arabinopyranoside is not a drug and is not approved for clinical use. It is a research-grade natural product used in the study of retinal degenerative diseases like age-related macular degeneration (AMD), as well as infections caused by H. pylori. Its mechanism of action is primarily attributed to its potent antioxidant properties, which protect RPE cells from oxidative stress and photooxidation-induced death. It also exhibits antibacterial activity through urease inhibition. No clinical trials have been registered for this compound. For research use only; not for human therapeutic or diagnostic use. |
| Molecular Formula |
C20H18O12
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|---|---|
| Exact Mass |
450.079
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| CAS # |
132679-85-7
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| PubChem CID |
21672568
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| Appearance |
Typically exists as solid at room temperature
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| Melting Point |
203 - 205 °C
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| LogP |
0.1
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| Hydrogen Bond Donor Count |
8
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
32
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| Complexity |
730
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1[C@@H]([C@@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
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| InChi Key |
SBEOEJNITMVWLK-KJCLSZHRSA-N
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| InChi Code |
InChI=1S/C20H18O12/c21-7-3-8(22)13-12(4-7)31-18(6-1-9(23)14(26)10(24)2-6)19(16(13)28)32-20-17(29)15(27)11(25)5-30-20/h1-4,11,15,17,20-27,29H,5H2/t11-,15-,17+,20-/m0/s1
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| Chemical Name |
5,7-dihydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
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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 |
| 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) |
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
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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 : PEG300 ：Tween 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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
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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