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Isoquercetin (Synonyms: NSC 115918, Quercetin 3-β-D-glucoside, Quercetin 3-O-glucoside)

Catalog No.GC41273 Copy One-Click Copy Product Info

Isoquercetin is a flavonoid with diverse biological activities, including antioxidant, antiproliferative, and anti-inflammatory properties.

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Isoquercetin Chemical Structure

Cas No.: 482-35-9

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10mM (in 1mL DMSO)
$39.00
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1mg
$18.00
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5mg
$35.00
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10mg
$49.00
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25mg
$84.00
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50mg
$126.00
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100mg
$189.00
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Sample solution is provided at 25 µL, 10mM.



Description of Isoquercetin

Isoquercetin is a flavonoid with diverse biological activities, including antioxidant, antiproliferative, and anti-inflammatory properties[1, 2]. Due to its high bioavailability and low toxicity, Isoquercetin is a promising candidate for preventing congenital defects in diabetic pregnancy[3].

In vitro, pretreatment of primary cultured rat cortical neurons with Isoquercetin (20, 40, 80µg/mL) for 24h reduced the increase in intracellular calcium concentration and lactate dehydrogenase (LDH) release induced by oxygen-glucose deprivation/reperfusion (OGD/R) injury, and prevented the decrease in cell viability[4]. Pretreatment of HepG2 cells with Isoquercetin (10μM) for 1h significantly downregulated ethanol-induced iNOS protein expression levels in the cells[5].

In vivo, intravenous administration of Isoquercetin (50mg/kg) for 7 days to rats subjected to middle cerebral artery occlusion (MCAO) injury reduced the cerebral infarct volume and mitigated the decrease in Nrf2 expression levels in hippocampal tissue[6]. Oral administration of Isoquercetin (20mg/kg) for 3 days to rats subjected to middle cerebral artery occlusion/reperfusion (MCAO/R) injury reduced the cerebral infarct volume, improved neurological deficits, and decreased the production of reactive oxygen species (ROS) and malondialdehyde (MDA) in brain tissue[7].

References:
[1] Mbikay M, Chrétien M. Isoquercetin as an anti-COVID-19 medication: A potential to realize[J]. Frontiers in Pharmacology, 2022, 13: 830205.
[2] Azeem M, Hanif M, Mahmood K, et al. An insight into anticancer, antioxidant, antimicrobial, antidiabetic and anti-inflammatory effects of quercetin: A review[J]. Polymer Bulletin, 2023, 80(1): 241-262.
[3] Cao L, Tan C, Meng F, et al. Amelioration of intracellular stress and reduction of neural tube defects in embryos of diabetic mice by phytochemical quercetin[J]. Scientific Reports, 2016, 6(1): 21491.
[4] Wang C P, Li J L, Zhang L Z, et al. Isoquercetin protects cortical neurons from oxygen–glucose deprivation–reperfusion induced injury via suppression of TLR4–NF-кB signal pathway[J]. Neurochemistry international, 2013, 63(8): 741-749.
[5] Lee S, Lee J, Lee H, et al. Relative protective activities of quercetin, quercetin‐3‐glucoside, and rutin in alcohol‐induced liver injury[J]. Journal of food biochemistry, 2019, 43(11): e13002.
[6] Chen M, Dai L H, Fei A, et al. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro[J]. Experimental and Therapeutic Medicine, 2017, 13(4): 1353-1359.
[7] Dai Y, Zhang H, Zhang J, et al. Isoquercetin attenuates oxidative stress and neuronal apoptosis after ischemia/reperfusion injury via Nrf2-mediated inhibition of the NOX4/ROS/NF-κB pathway[J]. Chemico-biological interactions, 2018, 284: 32-40.

Protocol of Isoquercetin

Cell experiment [1]:

Cell lines

Primary culture of rat cortical neurons

Preparation Method

The primary culture of rat cortical neurons were pretreated with 20, 40 and 80µg/mL Isoquercetin and 2.5, 5µg/mL nimodipine, respectively, for 24h, followed by exposure to oxygen-glucose deprivation (OGD) for 6h, then reperfusion for 24h. The cortical neurons cultured in plain medium served as control.

Reaction Conditions

20, 40, 80µg/mL; 24h

Applications

Isoquercetin administered prior to the insult could prevent OGD/R-induced intracellular calcium concentrations ([Ca2+]i) increase, lactate dehydrogenase (LDH) release and cell viability decrease.
Animal experiment [2]:

Animal models

Sprague-Dawley (SD) rats

Preparation Method

The rats were randomly allocated to one of four groups: Control, sham, model and Isoquercetin. In the model group, rats were anesthetized via the intraperitoneal injection of 10% chloral hydrate. The rectal temperature was monitored and maintained at 37.0±0.5˚C by the use of a feedback‑regulated heating system during surgery. Permanent focal ischemia was induced by occluding the right middle cerebral artery (MCA) via an intraluminal technique. Briefly, a 4‑0 nylon monofilament suture with a slightly enlarged rounded tip was inserted into the stump of the external carotid artery and advanced into the lumen of the internal carotid artery until it reached and occluded the MCA. The distance from the bifurcation of the common carotid artery (CCA) to the tip of the inserted suture averaged 18‑20mm. Sham operated animals were subjected to the aforementioned procedures, with the exception of suture insertion. Rats in the Isoquercetin group were subjected to MCAO surgery and treated with intravenous 50mg/kg Isoquercetin once a day for 7 days. Rats that did not undergo any surgery served as the control group.

Dosage form

50mg/kg; 7 days; i.v.

Applications

The rats treated with Isoquercetin exhibited a lower degree of neurological dysfunction and smaller infarct volume than the vehicle‑treated rats. In the hippocampal tissue, the expression of Nrf2 at the mRNA and protein levels was decreased in the model group 7 days after ischemia, and the reduction in expression levels was significantly attenuated in the Isoquercetin treated-group.

References:
[1] Wang C P, Li J L, Zhang L Z, et al. Isoquercetin protects cortical neurons from oxygen–glucose deprivation–reperfusion induced injury via suppression of TLR4–NF-кB signal pathway[J]. Neurochemistry international, 2013, 63(8): 741-749.
[2]Chen M, Dai L H, Fei A, et al. Isoquercetin activates the ERK1/2-Nrf2 pathway and protects against cerebral ischemia-reperfusion injury in vivo and in vitro[J]. Experimental and Therapeutic Medicine, 2017, 13(4): 1353-1359.

Chemical Properties of Isoquercetin

Cas No. 482-35-9 SDF
Synonyms NSC 115918, Quercetin 3-β-D-glucoside, Quercetin 3-O-glucoside
Canonical SMILES OC1=CC(O)=C(C(C(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)=C(C3=CC=C(O)C(O)=C3)O4)=O)C4=C1
Formula C21H20O12 M.Wt 464.4
Solubility DMF: 10 mg/ml,DMSO: 10 mg/ml,PBS (pH 7.2): 0.3 mg/ml Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Isoquercetin

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1 mg 5 mg 10 mg
1 mM 2.1533 mL 10.7666 mL 21.5332 mL
5 mM 430.7 μL 2.1533 mL 4.3066 mL
10 mM 215.3 μL 1.0767 mL 2.1533 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 20 reference(s) in Google Scholar.)

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