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Peonidin 3-O-glucoside (chloride) (Synonyms: Peonidin 3-β-D-glucopyranoside)

Catalog No.GC45777 Copy One-Click Copy Product Info

Peonidin 3-O-glucoside (chloride) is an anthocyanin compound with anti-inflammatory effects, widely found in Oryza sativa L, red wine, and various fruits and vegetables.

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Peonidin 3-O-glucoside (chloride) Chemical Structure

Cas No.: 6906-39-4

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1mg
$94.00
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5mg
$288.00
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Sample solution is provided at 25 µL, 10mM.



Description of Peonidin 3-O-glucoside (chloride)

Peonidin 3-O-glucoside (chloride) is an anthocyanin compound with anti-inflammatory effects, widely found in Oryza sativa L, red wine, and various fruits and vegetables. Peonidin 3-O-glucoside exerts anti-inflammatory effects by inhibiting the phosphorylation of IKKα, IκBα, and ERK. Peonidin 3-O-glucoside promotes insulin secretion and increasing glucose uptake in hepatocytes through the activation of FFAR1 and glucokinase. Peonidin 3-O-glucoside can be used in research related to cancer, diabetes, and inflammatory diseases[1-4].

In vitro, Peonidin 3-O-glucoside (100–300μM) was used to pretreat L02 cells for 24 hours, followed by stimulation with 0.5mM free fatty acids for 24 hours. Peonidin 3-O-glucoside significantly inhibited the expression of pro-inflammatory factors such as IL-1β, IL-6, and TNF-α, thereby reducing the inflammatory response[5]. Peonidin-3-O-glucoside (1μg/ml) was used to treat hFOB 1.19 human osteoblast cells for 72 hours. Peonidin-3-O-glucoside significantly increased cell proliferation and differentiation and reduced apoptosis[6].

In vivo, Peonidin 3-O-glucoside (6mg/kg; once daily) was administered via oral gavage to female nude mice subcutaneously implanted with MDA-MB-453 cells for 25 days. Peonidin 3-O-glucoside significantly inhibited tumor growth and reduced tumor volume and weight[7]. Peonidin 3-O-glucoside (6mg/kg; twice weekly) was administered via intraperitoneal injection to female nude mice implanted with BT474R cells for 3 weeks. Peonidin 3-O-glucoside significantly inhibited tumor growth[8].

References:
[1] Semmarath W, Mapoung S, Umsumarng S, et al. Cyanidin-3-O-glucoside and Peonidin-3-O-glucoside-Rich Fraction of Black Rice Germ and Bran Suppresses Inflammatory Responses from SARS-CoV-2 Spike Glycoprotein S1-Induction In Vitro in A549 Lung Cells and THP-1 Macrophages via Inhibition of the NLRP3 Inflammasome Pathway. Nutrients. 2022 Jun 30;14(13):2738.
[2] Olivas-Aguirre FJ, Rodrigo-García J, Martínez-Ruiz ND, et al. Cyanidin-3-O-glucoside: Physical-Chemistry, Foodomics and Health Effects. Molecules. 2016 Sep 21;21(9):1264.
[3] Wu G, Zhao Z, Hu J, et al. Optimized Synthesis and Antioxidant Activity of Anthocyanins Delphinidin-3-O-glucoside and Petunidin-3-O-glucoside. J Agric Food Chem. 2024 Jul 3;72(26):15005-15012.
[4] Luna-Vital DA, Gonzalez de Mejia E. Anthocyanins from purple corn activate free fatty acid-receptor 1 and glucokinase enhancing in vitro insulin secretion and hepatic glucose uptake. PLoS One. 2018 Jul 11;13(7):e0200449.
[5] Hao R, Shan S, Yang D, et al. Peonidin-3-O-Glucoside from Purple Corncob Ameliorates Nonalcoholic Fatty Liver Disease by Regulating Mitochondrial and Lysosome Functions to Reduce Oxidative Stress and Inflammation. Nutrients. 2023 Jan 11;15(2):372.
[6] Ren Z, Raut NA, Lawal TO, et al. Peonidin-3-O-glucoside and cyanidin increase osteoblast differentiation and reduce RANKL-induced bone resorption in transgenic medaka. Phytother Res. 2021 Nov;35(11):6255-6269.
[7] Liu W, Xu J, Wu S, et al. Selective anti-proliferation of HER2-positive breast cancer cells by anthocyanins identified by high-throughput screening. PLoS One. 2013 Dec 3;8(12):e81586.
[8] Chen PN, Chu SC, Chiou HL, et al. Cyanidin 3-glucoside and peonidin 3-glucoside inhibit tumor cell growth and induce apoptosis in vitro and suppress tumor growth in vivo. Nutr Cancer. 2005;53(2):232-43.

Protocol of Peonidin 3-O-glucoside (chloride)

Cell experiment [1]:

Cell lines

L02 cells (normal human liver cell line)

Preparation Method

L02 cells were cultivated in a humidified incubator at a constant temperature of 37°C with 5% CO₂. Ten percent fetal bovine serum, 100units/mL penicillin, and 100units/mL streptomycin were added to RPMI 1640 medium. Cells were treated with Peonidin 3-O-glucoside for 24h.

Reaction Conditions

10–300μM; 24h

Applications

Peonidin 3-O-glucoside significantly reduced lipid accumulation in the NAFLD cell model induced by free fatty acids. Peonidin 3-O-glucoside inhibited oxidative stress via inhibiting the excessive production of reactive oxygen species and superoxide anion, increasing glutathione levels, and enhancing the activities of SOD, GPX, and CAT. Peonidin 3-O-glucoside alleviated inflammation and improved the depletion of mitochondrial content and damage of the mitochondrial electron transfer chain. Peonidin 3-O-glucoside upregulated transcription factor EB (TFEB)-mediated lysosomal function and activated the peroxisome proliferator-activated receptor alpha (PPARα)-mediated peroxisomal lipid oxidation.

Animal experiment [2]:

Animal models

Female nude mice

Preparation Method

HER2-positive breast cancer cell line MDA-MB-453 cells were resuspended to 2×10⁶ cells/100μl in PBS and implanted subcutaneously into the flank region of 6-7-week-old female nude mice. When tumors reached 50 to 60mm³ in volume, mice were treated with Peonidin 3-O-glucoside for 25 day.

Dosage form

6mg/kg; oral gavage; daily for 25 days

Applications

Peonidin 3-O-glucoside treatment significantly suppressed tumor growth rates, final tumor volumes and weights compared to the control group. This suppression was accompanied by decreased phospho-HER2 levels and decreased proliferation marker Ki67 levels.

References:
[1] Hao R, Shan S, Yang D, et al. Peonidin-3-O-Glucoside from Purple Corncob Ameliorates Nonalcoholic Fatty Liver Disease by Regulating Mitochondrial and Lysosome Functions to Reduce Oxidative Stress and Inflammation. Nutrients. 2023 Jan 11;15(2):372.
[2] Liu W, Xu J, Wu S, et al. Selective anti-proliferation of HER2-positive breast cancer cells by anthocyanins identified by high-throughput screening. PLoS One. 2013 Dec 3;8(12):e81586.

Chemical Properties of Peonidin 3-O-glucoside (chloride)

Cas No. 6906-39-4 SDF
Synonyms Peonidin 3-β-D-glucopyranoside
Canonical SMILES OC1=CC(O)=C(C=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(C3=CC(OC)=C(O)C=C3)=[O+]4)C4=C1.[Cl-]
Formula C22H23O11.Cl M.Wt 498.9
Solubility Soluble in DMSO Storage Store at 2-8°C
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 Peonidin 3-O-glucoside (chloride)

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.0044 mL 10.022 mL 20.0441 mL
5 mM 400.9 μL 2.0044 mL 4.0088 mL
10 mM 200.4 μL 1.0022 mL 2.0044 mL
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In vivo Formulation Calculator (Clear solution) of Peonidin 3-O-glucoside (chloride)

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid 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 master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
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