| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Source | Plant — Euphorbiaceae Euphorbia milii Des Moul.; Plant — Fagaceae |
| Molecular weight | |
| Molecular formula | C21H18O13 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
3,5-Di-O-galloylshikimic acid is a naturally derived phenolic acid with reported antiviral and hepatoprotective activities. It inhibits HIV replication, inactivates HIV viral particles, and blocks virus-cell interactions, and it can bind simultaneously to the SARS-CoV-2 main protease (Mpro) and the human ACE2 receptor. It has been used in studies of COVID-19, AIDS, and acute liver injury[1][2][3][4]. It has a molecular formula of C21H18O13 and a molecular weight of 478.36 g/mol.
Physical & Chemical Properties
| CAS Number | 95753-52-9 |
|---|---|
| Molecular Formula | C21H18O13 |
| Molecular Weight | 478.36 g/mol |
| Structure Classification | Phenols Polyphenols |
| 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 |
| Signaling Pathway | Metabolic Enzyme/Protease; Anti-infection |
| Initial Source | Plant — Euphorbiaceae Euphorbia milii Des Moul.; Plant — Fagaceae |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
Molecular docking results show binding of 3,5-Di-O-galloylshikimic acid to human ACE2 (docking score of -11.16 kcal/mol and MM-GBSA binding free energy of -51.7 kcal/mol), as well as to SARS-CoV-2 main protease (Mpro), with a docking score of -10.3 kcal/mol and an MM-GBSA binding free energy of -35.09 kcal/mol[1]. In infected H9 lymphocytes, 3,5-Di-O-galloylshikimic acid (10-200 μM; 3 days) inhibits HIV replication by 97% and shows only very low cytotoxicity at concentrations up to 50 μM[2]. The strongest inhibitory effect of 3,5-Di-O-galloylshikimic acid on HIV replication in H9 lymphocytes occurs when it is present during the virus-cell infection stage, and its activity is higher when pre-incubated with virions than when given after infection[2]. 3,5-di-O-galloylshikimic acid (DGSA) is the main metabolite produced in calli of Opuntia ficus-indica, Opuntia grandiflora and Opuntia streptacantha[3].
In Vivo
3,5-di-O-galloylshikimic acid (DGSA) is the major active component of Opuntia callus ethanolic extracts (100 mg/kg; oral gavage twice before model establishment). In male Wistar rats, these extracts show remarkable hepatoprotective activity against acute CCl4-induced liver injury. The O. ficus indica-PEG callus extract, with doubled DGSA content, has the optimal protective effect[1].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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