An anthocyanin with diverse biological activities
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Parent Compound(s)
16406Cyanidin 3-O-glucoside (chloride)
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Peonidin 3-O-glucoside (chloride)

Item No. 28743

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-1-benzopyrylium, monochloride
CAS Number
6906-39-4
Synonyms
  • Peonidin 3-β-D-glucopyranoside
Molecular Formula
C22H23O11 • Cl
Formula Weight
498.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
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-]
InChi Code
InChI=1S/C22H22O11.ClH/c1-30-15-4-9(2-3-12(15)25)21-16(7-11-13(26)5-10(24)6-14(11)31-21)32-22-20(29)19(28)18(27)17(8-23)33-22;/h2-7,17-20,22-23,27-29H,8H2,1H3,(H2-,24,25,26);1H/t17-,18-,19+,20-,22-;/m1./s1
InChi Key
VDTNZDSOEFSAIZ-VXZFYHBOSA-N
Origin
Plant/Elymus
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $222

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    5 mg

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    Product Description

    Peonidin 3-O-glucoside is a metabolite of cyanidin 3-glucoside (Item No. 16406) and an anthocyanin that has been found in red wine extracts and has diverse biological activities, including antioxidant, anti-inflammatory, antiproliferative, and anti-metastatic properties.1,2,3,4,5 Peonidin 3-O-glucoside scavenges 2,2-diphenyl 1-picylhydrazyl (DPPH; Item No. 14805) and ABTS (Item No. 27317) radicals in cell-free assays (EC50s = 757 and 98 μM, respectively).2 It inhibits IL-1β-induced phosphorylation of IKKα, IκBα, and ERK in human articular chondrocytes when used at a concentration of 2.5 μM.3 Peonidin 3-O-glucoside inhibits the growth of Hs578T human breast cancer cells in vitro in a concentration-dependent manner and decreases pulmonary metastasis in a mouse model of Lewis lung carcinoma when administered at a dose of 20 mg/kg.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vanzo, A., Vrhovsek, U., Tramer, F., et al. Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver. J. Nat. Prod. 74(5), 1049-1054 (2011).

    2. Li, Y., Li, L., Cui, Y., et al. Separation and purification of polyphenols from red wine extracts using high speed counter current chromatography. J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1054, 105-113 (2017).

    3. Wongwichai, T., Teeyakasem, P., Pruksakorn, D., et al. Anthocyanins and metabolites from purple rice inhibit IL-1β-induced matrix metalloproteinases expression in human articular chondrocytes through the NF-κB and ERK/MAPK pathway. Biomed. Pharmacother. 112:108610, (2019).

    4. Chen, P.-N., Chu, S.-C., Chiou, H.-L., 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 53(2), 232-243 (2005).

    5. Ho, M.-L., Chen, P.-N., Chu, S.-C., et al. Peonidin 3-glucoside inhibits lung cancer metastasis by downregulation of proteinases activities and MAPK pathway. Nutr. Cancer 62(4), 505-516 (2010).