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Cat. No.: HY-N11608

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3,5-Di-O-galloylshikimic acid

3,5-Di-O-galloylshikimic acid is a naturally derived phenolic acid compound with potential antiviral and hepatoprotective activities. 3,5-Di-O-galloylshikimic acid inhibits HIV replication, inactivates HIV viral particles and blocks virus-cell interactions. 3,5-Di-O-galloylshikimic acid has the potential to bind simultaneously to SARS-CoV-2 main protease (Mpro) and human ACE2 receptor. 3,5-Di-O-galloylshikimic acid can be used in studies related to coronavirus disease 2019 (COVID-19), acquired immunodeficiency syndrome (AIDS) and acute liver injury.

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

CAS No.: 95753-52-9
Formula: C₂₁H₁₈O₁₃
Molecular Weight:478.36

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

3,5-Di-O-galloylshikimic acid Chemical Structure

CAS No.: 95753-52-9

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- Cellular Effect
- In Vitro
- In Vivo
Chemical Information
Purity & Documentation
References
Calculators
Help & FAQs
Classifications
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Biological Activity

Description

All Endogenous Metabolite Isoforms :

All HIV Isoforms :

Cellular Effect

Cell Line	Type	Value	Description	References
A549	ED₅₀	>10 μg/mL Compound: 18	Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay	[PMID: 1431932]
HCT-8	ED₅₀	>10 μg/mL Compound: 18	Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay	[PMID: 1431932]
KB	ED₅₀	>10 μg/mL Compound: 18	Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay	[PMID: 1431932]
TE-671	ED₅₀	>10 μg/mL Compound: 18	Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay	[PMID: 1431932]

In Vitro

3,5-Di-O-galloylshikimic acid binds to human ACE2 (docking score = -11.16 kcal/mol, MM-GBSA binding free energy = -51.7 kcal/mol) and SARS-CoV-2 main protease (M_pro) (docking score = -10.3 kcal/mol, MM-GBSA binding free energy = -35.09 kcal/mol) according to molecular docking results^[1].
3,5-Di-O-galloylshikimic acid (compound 2) (10-200 μM; 3 days) inhibits HIV replication in infected H9 lymphocytes with an inhibition rate of 97%, and exhibits only extremely low cytotoxicity at concentrations up to 50 μM^[2].
3,5-Di-O-galloylshikimic acid exerts the strongest inhibitory effect on HIV replication in H9 lymphocytes when present during the virus-cell infection stage, and its activity is enhanced when pre-incubated with virions compared to post-infection treatment^[2].
3,5-di-O-galloylshikimic acid (DGSA) is the primary metabolite synthesized in calli of Opuntia ficus-indica, Opuntia grandiflora and Opuntia streptacantha^[3].

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

In Vivo

3,5-di-O-galloylshikimic acid (DGSA) acts as the major active component in ethanolic extracts of Opuntia callus (100 mg/kg; oral gavage twice before model establishment), which exert remarkable hepatoprotective activity against acute CCl₄-induced liver injury in male Wistar rats, and the O. ficus indica-PEG callus extract with doubled DGSA content possesses the optimal protective effect^[1].

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

Chemical Information

CAS No. 95753-52-9
Molecular Weight 478.36
Formula C₂₁H₁₈O₁₃
SMILES

O(C(=O)C1=CC(O)=C(O)C(O)=C1)[C@H]2[C@H](O)[C@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)C=C(C(O)=O)C2
Structure Classification
- Phenols
- Polyphenols
Initial Source
- Plants
- Fagaceae
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Handling Instructions (2659 KB)

References

[1]. Sharma P. Natural derivatives with dual binding potential against SARS-CoV-2 main protease and human ACE2 possess low oral bioavailability: a brief computational analysis. Journal of Biomolecular Structure and Dynamics, 2020.

[2]. Nonaka G, et al. Anti-AIDS agents, 2: Inhibitory effects of tannins on HIV reverse transcriptase and HIV replication in H9 lymphocyte cells. Journal of natural products. 1990;53(3):587-95. [Content Brief]

[3]. Camarena-Rangel N G, et al. Identification of metabolites present in Opuntia callus and study of their antioxidant, anti-inflammatory and anti-adipogenic properties. Plant Cell, Tissue and Organ Culture, 2020, 143: 31-43.

[4]. Hernández-Martínez J G, et al. The hepatoprotective effect of Opuntia callus metabolites on acute CCl4-induced intoxication in Wistar rats. SSRN, 2026.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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