| Stereochemistry | ABSOLUTE |
| Molecular Formula | C25H24O12 |
| Molecular Weight | 516.4509 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1C[C@@](O)(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@H]1OC(=O)\C=C\C3=CC(O)=C(O)C=C3)C(O)=O
InChI
InChIKey=UFCLZKMFXSILNL-RVXRWRFUSA-N
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
3,4-Dicaffeoylquinic acid is a component of Brazilian green propolis water extract, green coffee beans and other plants. It was reported to have antivirus activity against Influenza A Virus. The compound was also shown to inhibit AngII-induced rVSMC proliferation and migration, probably through downregulating the Akt, JNK and part of the ERK1/2 pathways, in which the anti-oxidant property plays an important role. 3,4-Dicaffeoylquinic acid possesses a high binding affinity to plasma proteins, making it less preferable as a drug candidate as this characteristic would affect diffusion or transport across cell membranes, limiting pharmacological actions. 3,4-Dicaffeoylquinic acid is also a selective inhibitor of human immunodeficiency virus type 1 integrase.
CNS Activity
Originator
Approval Year
PubMed
Patents
Sample Use Guides
In a preclinical study, mice infected with influenza A virus were given 3,4-dicaffeoylquinic acid at a dose of 50 mg twice/kg/day. In a model of liver disease, mice received 5 and 10 mg/kg orally.
Route of Administration:
Oral
In an anti-influenza virus assay, MDCK cells (2*10(5)/well) were cultured in MEM that contained 10% fetal bovine serum, 60 U/mL of penicillin, and 60 ug/mL of streptomycin for 24 hrs on 96-well plates, washed with PBS, and infected with 20 to 200 TCID50 A/WSN/33 virus in the presence of 0, 10, 30, 100, 300 ug/ml of 3,4-dicaffeoylquinic acid. The compound was added almost simultaneously in an assay medium, MEM that was supplemented with 1% BSA, 1% DMSO, and 6.25 ug/mL trypsin. Cell cultures were maintained without medium exchange at 37 degrees Celsius, 5% CO2 for 48 hrs.
SUBSTANCE RECORD
