4,5-Dicaffeoylquinic acid (Isochlorogenic acid C)

4,5-Dicaffeoylquinic acid (4,5-DCQA) is a polyphenol originally isolated from G. fagetorum and G. pseudomollugo that has diverse biological activities, including anti-HIV replication, antioxidative, anti-inflammatory, and anti-melanogenic properties.^1,2,3,4,5 It inhibits HIV-1 integrase 3' end processing, 3’ end joining, and disintegration with IC₅₀ values of 0.13, 0.24, and 0.3 μg/ml, respectively.³ It also inhibits HIV-1 replication in MT-2 T lymphoblastoid cells with an EC₅₀ value of 2 μg/ml. 4,5-DCQA scavenges 2,2-diphenyl-1-picrylhydrazyl radicals in a cell-free assay (IC₅₀ = 19.8 μM) and inhibits superoxide production in human neutrophils activated by N-formyl-Met-Leu-Phe and cytochalasin B .² It decreases prostaglandin E₂ production in LPS-stimulated U937 cells when used at concentrations of 5 and 10 ?g/ml but increases it when used at 200 ?g/ml and increases production of TNF-α at concentrations ranging from 5 to 200 ?g/ml.⁴ It inhibits the synthesis of MCP3 in U937 cells. 4,5-DCQA (25 ?M) inhibits melanogenesis by 84% and decreases the levels of proteins involved in melanin biosynthesis, including tyrosinase, TRP-1, DCT, and MITF in B16F1 murine melanocytes.⁵

1.Bogaevskii, A.K., Dranik, L.I., and Borisov, M.I.The hydroxycinnamic acids of Galium fagetorum and G. pseudomollugoChem. Nat. Compd.6(6)761-762(1970) 2.Chen, Y.-L., Hwang, T.-L., Yu, H.-P., et al.Ilex kaushue and its bioactive component 3,5-dicaffeoylquinic acid protected mice from lipopolysaccharide-induced acute lung injurySci. Rep.634243(2016) 3.Robinson, W.E., Jr., Cordeiro, M., Abdel-Malek, S., et al.Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: Inhibition of the core catalytic domain of human immunodeficiency virus integraseMol. Pharmacol.50(4)846-855(1996) 4.dos Santos, M.D., Chen, G., Almeida, M.C., et al.Effects of caffeoylquinic acid derivatives and C-flavonoid from Lychnophora ericoides on in vitro inflammatory mediator productionNat. Prod. Commun.5(5)733-740(2010) 5.Ha, J.H., and Park, S.N.Mechanism underlying inhibitory effect of six dicaffeoylquinic acid isomers on melanogenesis and the computational molecular modeling studiesBioorg. Med. Chem.26(14)4201-4208(2018)