1,5-Dicaffeoylquinic Acid

1,5-Dicaffeoylquinic acid (1,5-DCQA) has been found in A. montana and is an HIV-1 integrase inhibitor and free radical scavenger. 1,5-DCQA inhibits HIV-1 integrase 3' end processing, end joining, and disintegration with IC50 values of 0.35, 0.56, and 0.84 µg/ml, respectively. It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an ED50value of 2 µg/ml. 1,5-DCQA (0.25-1 µM) reduces the level of free radicals released from human polymorphonuclear (PMN) cells stimulated by N-formyl-Met-Leu-Phe (fMLP, Cay-21495) in a dose-dependent manner. It also dose-dependently increases cell survival and glutathione (GSH) levels and decreases reactive oxygen species (ROS) production and lactate dehydrogenase (LDH) release in an oxygen-glucose deprivation/reperfusion assay in rat cerebral astrocytes when used at concentrations ranging from 5 to 100 µM.Formal Name: (1S,3R,4R,5R)-1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid. CAS Number: 19870-46-3. Synonyms: 1,5-DCQA, 1,3-Dicaffeoylquinic Acid. Molecular Formula: C25H24O12. Formula Weight: 516.5. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 71 mg/ml, DMSO: 50 mg/ml, Ethanol: 50 mg/ml, PBS (pH 7.2): 25 mg/ml. lambdamax: 220, 330 nm. SMILES: OC1=CC=C(/C=C/C(O[C@H]2[C@H](O)[C@H](O)C[C@](C(O)=O)(OC(/C=C/C3=CC(O)=C(O)C=C3)=O)C2)=O)C=C1O. InChi Code: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1. InChi Key: YDDUMTOHNYZQPO-PSEXTPKNSA-N. Origin: Plant/Inulae Flos.