A flavonoid glycoside with diverse biological activities
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Prunin

Item No. 34034

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-7-(β-D-glucopyranosyloxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
529-55-5
Synonyms
  • Naringenin 7-O-β-D-glucopyranoside
  • Naringenin 7-O-glucoside
  • NSC 135064
Molecular Formula
C21H22O10
Formula Weight
434.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 20 mg/ml
λmax
215, 227, 284 nm
SMILES
OC1=C2C(O[C@@H](CC2=O)C3=CC=C(O)C=C3)=CC(O[C@@H]4O[C@@H]([C@H]([C@H](O)[C@H]4O)O)CO)=C1
InChi Code
InChI=1S/C21H22O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-6,14,16,18-24,26-28H,7-8H2/t14-,16+,18+,19-,20+,21+/m0/s1
InChi Key
DLIKSSGEMUFQOK-SFTVRKLSSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $124

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    5 mg

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    10 mg

    $797

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    Cayman Chemical
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    Product Description

    Prunin is a polyketide synthase-derived flavonoid glycoside that has been found in G. glabra and has diverse biological activities.1,2,3,4,5 It inhibits neuraminidase (NA) activity in oseltamivir-sensitive and -resistant H1N1 influenza strains (IC50s = 3 and 4.53 µM, respectively).2 Prunin (2 µM) scavenges DPPH radicals in a cell-free assay.3 It inhibits the activity of protein tyrosine phosphatase 1B (PTP1B; IC50 = 5.5 µM for the human enzyme) and increases insulin-induced glucose uptake in insulin-resistant HepG2 hepatocellular carcinoma cells in a concentration-dependent manner.4 Prunin inhibits the proliferation of, and induces apoptosis in, HL-60 leukemia cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sharma, P., Kumar, V., and Guleria, P. Naringin: Biosynthesis and pharmaceutical applications. Indian J. Pharm. Sci. 81(6), 988-999 (2019).

    2. Grienke, U., Braun, H., Seidel, N., et al. Computer-guided approach to access the anti-influenza activity of licorice constituents. J. Nat. Prod. 77(3), 563-570 (2014).

    3. Sang, S., Lapsley, K., Jeong, W.-S., et al. Antioxidative phenolic compounds isolated from almond skins (Prunus amygdalus Batsch). J. Agric. Food Chem. 50(8), 2459-2463 (2002).

    4. Jung, H.A., Ali, M.Y., Bhakta, K., et al. Prunin is a highly potent flavonoid from Prunus davidiana stems that inhibits protein tyrosine phosphatase 1B and stimulates glucose uptake in insulin-resistant HepG2 cells. Arch. Pharm. Res. 40(1), 37-48 (2017).

    5. Tung, N.H., Son, J.-H., Cho, K., et al. Phenolic components from the leaves of Panax ginseng and their effects on HL-60 human leukemia cells. Food Sci. Biotechnol. 19(1), 271-274 (2010).