WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 465311

CAS#: 529-55-5

Description: Prunin is a polyketide synthase-derived flavonoid glycoside that has been found in G. glabra and has diverse biological activities. It inhibits neuraminidase (NA) activity in oseltamivir-sensitive and -resistant H1N1 influenza strains (IC50s = 3 and 4.53 µM, respectively). Prunin (2 µM) scavenges DPPH radicals in a cell-free assay. 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. Prunin inhibits the proliferation of, and induces apoptosis in, HL-60 leukemia cells.

Chemical Structure

CAS# 529-55-5

Theoretical Analysis

MedKoo Cat#: 465311
Name: Prunin
CAS#: 529-55-5
Chemical Formula: C21H22O10
Exact Mass: 434.12
Molecular Weight: 434.397
Elemental Analysis: C, 58.06; H, 5.11; O, 36.83

Price and Availability

Size Price Availability Quantity
1mg USD 450 2 Weeks
5mg USD 1550 2 Weeks
10mg USD 2850 2 Weeks
Bulk inquiry

Synonym: Prunin; Naringenin 7-O-β-D-glucopyranoside; Naringenin 7-O-glucoside; NSC 135064; NSC-135064; NSC135064;

IUPAC/Chemical Name: (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one


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

SMILES Code: OC1=C2C(O[C@H](C3=CC=C(C=C3)O)CC2=O)=CC(O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H]([C@H]4O)O)=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
DMSO 20.0 46.04
DMF 30.0 69.06
DMF:PBS (pH 7.2) (1:2) 0.3 0.69

Preparing Stock Solutions

The following data is based on the product molecular weight 434.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.


Dilution Calculator

Calculate the dilution required to prepare a stock solution.

1: Budny M, Zalewski K, Stolarski MJ, Wiczkowski W, Okorski A, Stryiński R. The Phenolic Compounds in the Young Shoots of Selected Willow Cultivars as a Determinant of the Plants' Attractiveness to Cervids (Cervidae, Mammalia). Biology (Basel). 2021 Jul 2;10(7):612. doi: 10.3390/biology10070612. PMID: 34356467; PMCID: PMC8301130.

2: Albohy A, Zahran EM, Abdelmohsen UR, Salem MA, Al-Warhi T, Al-Sanea MM, Abelyan N, Khalil HE, Desoukey SY, Fouad MA, Kamel MS. Multitarget in silico studies of Ocimum menthiifolium, family Lamiaceae against SARS-CoV-2 supported by molecular dynamics simulation. J Biomol Struct Dyn. 2020 Dec 15:1-11. doi: 10.1080/07391102.2020.1852964. Epub ahead of print. PMID: 33317409; PMCID: PMC7784784.

3: Trombetta D, Smeriglio A, Denaro M, Zagami R, Tomassetti M, Pilolli R, De Angelis E, Monaci L, Mandalari G. Understanding the Fate of Almond (Prunus dulcis (Mill.) D.A. Webb) Oleosomes during Simulated Digestion. Nutrients. 2020 Nov 5;12(11):3397. doi: 10.3390/nu12113397. PMID: 33167391; PMCID: PMC7694400.

4: Lalani S, Poh CL. Correction: Lalani, S. and Poh, C.L. Flavonoids as Antiviral Agents for Enterovirus A71 (EV-A71). Viruses 2020, 12, 184. Viruses. 2020 Jun 30;12(7):712. doi: 10.3390/v12070712. Erratum for: Viruses. 2020 Feb 06;12(2): PMID: 32630136; PMCID: PMC7412425.

5: Xu J, Shi X, Zhang X, Wang Z, Xiao W, Zhao L. Immobilization of GH78 α-L- Rhamnosidase from Thermotoga petrophilea with High-Temperature-Resistant Magnetic Particles Fe3O4-SiO2-NH2-Cellu-ZIF8 and Its Application in the Production of Prunin Form Naringin. J Microbiol Biotechnol. 2021 Mar 28;31(3):419-428. doi: 10.4014/jmb.2004.04055. PMID: 32627762.

6: Kim DS, Lim SB. Semi-Continuous Subcritical Water Extraction of Flavonoids from Citrus unshiu Peel: Their Antioxidant and Enzyme Inhibitory Activities. Antioxidants (Basel). 2020 Apr 25;9(5):360. doi: 10.3390/antiox9050360. PMID: 32344942; PMCID: PMC7278842.

7: Zhang Y, Jin T. Almond allergens: update and perspective on identification and characterization. J Sci Food Agric. 2020 Oct;100(13):4657-4663. doi: 10.1002/jsfa.10417. Epub 2020 Apr 29. PMID: 32270879.

8: Gürağaç Dereli FT, Khan H, Sobarzo-Sánchez E, Akkol EK. Antidepressant Potential of Lotus corniculatus L. subsp. corniculatus: An Ethnobotany Based Approach. Molecules. 2020 Mar 12;25(6):1299. doi: 10.3390/molecules25061299. PMID: 32178424; PMCID: PMC7144109.

9: Gunaseelan S, Wong KZ, Min N, Sun J, Ismail NKBM, Tan YJ, Lee RCH, Chu JJH. Prunin suppresses viral IRES activity and is a potential candidate for treating enterovirus A71 infection. Sci Transl Med. 2019 Oct 30;11(516):eaar5759. doi: 10.1126/scitranslmed.aar5759. PMID: 31666401.

10: Ali MY, Jannat S, Edraki N, Das S, Chang WK, Kim HC, Park SK, Chang MS. Flavanone glycosides inhibit β-site amyloid precursor protein cleaving enzyme 1 and cholinesterase and reduce Aβ aggregation in the amyloidogenic pathway. Chem Biol Interact. 2019 Aug 25;309:108707. doi: 10.1016/j.cbi.2019.06.020. Epub 2019 Jun 11. PMID: 31194956.

11: Wang D, Zheng P, Chen P. Production of a Recombinant α-L-Rhamnosidase from Aspergillus niger CCTCC M 2018240 in Pichia pastoris. Appl Biochem Biotechnol. 2019 Nov;189(3):1020-1037. doi: 10.1007/s12010-019-03020-2. Epub 2019 Jun 3. PMID: 31161379.

12: Sarwar MW, Riaz A, Nahid N, Al Qahtani A, Ahmed N, Nawaz-Ul-Rehman MS, Younus A, Mubin M. Homology modeling and docking analysis of ßC1 protein encoded by Cotton leaf curl Multan betasatellite with different plant flavonoids. Heliyon. 2019 Mar 7;5(3):e01303. doi: 10.1016/j.heliyon.2019.e01303. PMID: 30899831; PMCID: PMC6407081.

13: Perner SP, Heupel L, Zimmermann L, Peters Y, Vongehr KU, El-Bedewy H, Siebeneicher S, Weiß T, Hektor T, Lindemann B, Loos-Theisen S, Schneider K. Investigation of Reduced ELISA Recovery of Almond and Hazelnut Traces from Roasted Nut Samples by SDS-PAGE and Mass Spectrometry. J AOAC Int. 2019 Sep 1;102(5):1271-1279. doi: 10.5740/jaoacint.19-0055. Epub 2019 Mar 19. PMID: 30890205.

14: Thiébaut G, Thouvenot L, Rodríguez-Pérez H. Allelopathic Effect of the Invasive Ludwigia hexapetala on Growth of Three Macrophyte Species. Front Plant Sci. 2018 Dec 18;9:1835. doi: 10.3389/fpls.2018.01835. PMID: 30631329; PMCID: PMC6315127.

15: Kumar D, Yadav S, Yadava S, Yadav KDS. An alkali tolerant α-l-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides. Bioorg Chem. 2019 Mar;84:24-31. doi: 10.1016/j.bioorg.2018.11.027. Epub 2018 Nov 20. PMID: 30476650.

16: Hernández-García E, García A, Garza-González E, Avalos-Alanís FG, Rivas- Galindo VM, Rodríguez-Rodríguez J, Alcantar-Rosales VM, Delgadillo-Puga C, Del Rayo Camacho-Corona M. Chemical composition of Acacia farnesiana (L) wild fruits and its activity against Mycobacterium tuberculosis and dysentery bacteria. J Ethnopharmacol. 2019 Feb 10;230:74-80. doi: 10.1016/j.jep.2018.10.031. Epub 2018 Oct 25. PMID: 30367988.

17: Aguilar-Guadarrama AB, Rios MY. Flavonoids, Sterols and Lignans from Cochlospermum vitifolium and Their Relationship with Its Liver Activity. Molecules. 2018 Aug 5;23(8):1952. doi: 10.3390/molecules23081952. PMID: 30081608; PMCID: PMC6222972.

18: Kurahayashi K, Hanaya K, Higashibayashi S, Sugai T. Synthesis of trilobatin from naringin via prunin as the key intermediate: acidic hydrolysis of the α-rhamnosidic linkage in naringin under improved conditions. Biosci Biotechnol Biochem. 2018 Sep;82(9):1463-1467. doi: 10.1080/09168451.2018.1482455. Epub 2018 Jun 4. PMID: 29865928.

19: Li LJ, Wu ZY, Yu Y, Zhang LJ, Zhu YB, Ni H, Chen F. Development and characterization of an α-l-rhamnosidase mutant with improved thermostability and a higher efficiency for debittering orange juice. Food Chem. 2018 Apr 15;245:1070-1078. doi: 10.1016/j.foodchem.2017.11.064. Epub 2017 Nov 16. PMID: 29287324.

20: Ghorab H, Lammi C, Arnoldi A, Kabouche Z, Aiello G. Proteomic analysis of sweet algerian apricot kernels (Prunus armeniaca L.) by combinatorial peptide ligand libraries and LC-MS/MS. Food Chem. 2018 Jan 15;239:935-945. doi: 10.1016/j.foodchem.2017.07.054. Epub 2017 Jul 12. PMID: 28873655.