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[CAS NO. 65995-63-3] Punicalagin

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Catalog:	HY-N0063
Brand:	MCE
CAS:	65995-63-3

Overview

MDL	MFCD09838017
Molecular Weight	1084.72
Molecular Formula	C48H28O30
SMILES	O=C1C2=C(C3=C(O)C(O)=C2C4=C(O)C(O)=C(O)C=C4C(OC(C(OC5=O)C(C=O)OC(C6=C(C7=C5C=C(O)C(O)=C7O)C(O)=C(O)C(O)=C6)=O)C8O)=O)C9=C(C(O3)=O)C(C(C(O)=C(O)C(O)=C%10)=C%10C(OC8)=O)=C(O)C(O)=C9O1

For research use only. We do not sell to patients.

3 Publications Citing Use of MCE

[1]Antioxid Redox Signal. 2021 Apr 28.
[2]Antivir Res. 2021, 105075.
[3]J Chromatogr A. 24 December 2021, 462784.

Summary

Punicalagin is a polyphenol ingredient isolated from Pomegranate ( Punica granatum L.) or the leaves of Terminalia catappa L.. Punicalagin is a reversible and non-competitive 3CL ^pro inhibitor and inhibits SARS-CoV-2 replication in vitro. Punicalagin is an anti-hepatitis B virus (HBV) agent and has antioxidant, anti-inflammatory, and anticancer effects. Punicalagin has the potential for the research of COVID-19 ^[1] ^[2] ^[3] .

In Vitro

Punicalagin (100 mg/ml) induces apoptosis in HT-29, HCT116 colon cells ^[1] .
Punicalagin slightly inhibits the PL ^pro activity with an IC ₅₀ of over 50 μM. Punicalagin inhibits the plaque formation of SARS-CoV-2 in a dose-dependent manner, with EC ₅₀ values of 7.20 μM ^[4] .
Punicalagin binds at an allosteric site in the dimer interface. Punicalagin inhibit SARS-CoV-2 replication by a mechanism other than preventing S-mediated viral entry ^[4] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Punicalagin (10 mg/kg) inhibits the edema rate of 58.15% in rats ^[2] .

MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Clinical Trial

NCT Number	Sponsor	Condition	Start Date	Phase
NCT02042742	Instituto de Investigación Hospital Universitario La Paz	Healthy	April 2013	Phase 4

Appearance

Solid

Source

Plants
Punicaceae
Punica granatum L.

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

4°C, protect from light

* In solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Solvent & Solubility

In Vitro:

DMSO : 50 mg/mL ( 46.09 mM ; Need ultrasonic)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	0.9219 mL	4.6095 mL	9.2190 mL
5 mM	0.1844 mL	0.9219 mL	1.8438 mL
10 mM	0.0922 mL	0.4609 mL	0.9219 mL

* Please refer to the solubility information to select the appropriate solvent.

In Vivo:

1.

Add each solvent one by one: 10% DMSO >> 40% PEG300 >> 5% Tween-80 >> 45% saline

Solubility: ≥ 2.17 mg/mL (2.00 mM); Clear solution
2.

Add each solvent one by one: 10% DMSO >> 90% (20% SBE-β-CD in saline)

Solubility: ≥ 2.17 mg/mL (2.00 mM); Clear solution

* All of the co-solvents are available by MCE.

References

[1] Seeram NP, et al. In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagicacid and a total pomegranate tannin extract are enhanced in combination with otherpolyphenols as found in pomegranate juice. J Nutr Biochem. 2005 Jun
[2] Lin CC, et al. Effects of punicalagin and punicalin on carrageenan-induced inflammation in rats. Am J Chin Med. 1999;27(3-4):371-6.
[3] Liu C, et al. Identification of hydrolyzable tannins (punicalagin, punicalin and geraniin) as novel inhibitors of hepatitis B virus covalently closed circular DNA. Antiviral Res. 2016 Oct;134:97-107.
[4] RuikunDu, et al. Discovery of Chebulagic Acid and Punicalagin as Novel Allosteric Inhibitors of SARS-CoV-2 3CLpro. Antivir Res. 2021, 105075.

Synonyms

D-Glucose, cyclic 4,6-[(2S,2′S)-2,2′-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1,6-diyl)bis[3,4,5-trihydroxybenzoate]] cyclic 2,3-[(1S)-4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylate]

D-Glucose, cyclic 4,6-[2,2′-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1,6-diyl)bis[3,4,5-trihydroxybenzoate]] cyclic 2,3-(4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylate), [2(S),4(S,S)]-

2,20,1,23-(Epoxy[2]propene[1,2]diyl[3]ylidene)-11H,15H-tribenzo[g,i,q][1,5,12]trioxacyclononadecin, D-glucose deriv.

Dibenzo[f,h][1,4]dioxecin, D-glucose deriv.

Punicalagin

D-Glucose, cyclic 4,6-[(S,S)-2,2′-(5,10-dihydro-2,3,7,8-tetrahydroxy-5,10-dioxo[1]benzopyrano[5,4,3-cde][1]benzopyran-1,6-diyl)bis[3,4,5-trihydroxybenzoate]] cyclic 2,3-[(S)-4,4′,5,5′,6,6′-hexahydroxy[1,1′-biphenyl]-2,2′-dicarboxylate]

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