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Chemical Compound Review

L-DCTA     (2R,3R)-2,3-bis[[(E)-3-(3,4...

Synonyms: L-CA, Chicoric acid, Cichoric Acid, Cichoric?Acid, CHEMBL282731, ...
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Disease relevance of Dicaffeoyl-L-tartaric acid


High impact information on Dicaffeoyl-L-tartaric acid

  • All mutant HIVs were resistant to l-chicoric acid, a dicaffeoyltartaric acid IN inhibitor, both in tissue culture and in biochemical assays, yet remained susceptible to the reverse transcriptase inhibitors zidovudine and nevirapine [3].
  • A number of compounds (i.e. zintevir and L-chicoric acid, on the one hand; and CGP64222 on the other hand) have recently been found to interact with virus-cell binding and viral entry in contrast to their proposed modes of action targeted at the integrase and transactivation process, respectively [4].
  • These results confirm through natural selection previous biochemical studies showing that L-chicoric acid inhibits integrase and that the drug is likely to interact at residues near the catalytic triad in the integrase active site [5].
  • Two amino acid derivates and one digalloylderivative of L-chicoric acid (L-CA) showed improved selectivity over L-CA against integration in cell culture [2].
  • The human immunodeficiency virus (HIV) integrase (IN) must covalently join the viral cDNA into a host chromosome for productive HIV infection. l-Chicoric acid (l-CA) enters cells poorly but is a potent inhibitor of IN in vitro [6].

Chemical compound and disease context of Dicaffeoyl-L-tartaric acid


Biological context of Dicaffeoyl-L-tartaric acid


Associations of Dicaffeoyl-L-tartaric acid with other chemical compounds


Analytical, diagnostic and therapeutic context of Dicaffeoyl-L-tartaric acid

  • A micellar electrokinetic chromatographic (MEKC) method was developed for the separation of ten phenolic acids including cichoric acid and caftaric acids, specific marker phytochemicals of Echinacea purpurea [15].
  • Over 50 accessions grown under greenhouse conditions were subjected to AFLP analysis and the same assessed for content of tetraene and cichoric acid by high pressure liquid chromatography [16].
  • HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products [12].


  1. Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. Robinson, W.E., Reinecke, M.G., Abdel-Malek, S., Jia, Q., Chow, S.A. Proc. Natl. Acad. Sci. U.S.A. (1996) [Pubmed]
  2. Dicaffeoyltartaric acid analogues inhibit human immunodeficiency virus type 1 (HIV-1) integrase and HIV-1 replication at nontoxic concentrations. Reinke, R.A., King, P.J., Victoria, J.G., McDougall, B.R., Ma, G., Mao, Y., Reinecke, M.G., Robinson, W.E. J. Med. Chem. (2002) [Pubmed]
  3. Human immunodeficiency virus type 1 (HIV-1) integrase: resistance to diketo acid integrase inhibitors impairs HIV-1 replication and integration and confers cross-resistance to L-chicoric acid. Lee, D.J., Robinson, W.E. J. Virol. (2004) [Pubmed]
  4. New developments in anti-HIV chemotherapy. De Clercq, E. Current medicinal chemistry. (2001) [Pubmed]
  5. Resistance to the anti-human immunodeficiency virus type 1 compound L-chicoric acid results from a single mutation at amino acid 140 of integrase. King, P.J., Robinson, W.E. J. Virol. (1998) [Pubmed]
  6. L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Reinke, R.A., Lee, D.J., McDougall, B.R., King, P.J., Victoria, J., Mao, Y., Lei, X., Reinecke, M.G., Robinson, W.E. Virology (2004) [Pubmed]
  7. Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors. Lee, J.Y., Yoon, K.J., Lee, Y.S. Bioorg. Med. Chem. Lett. (2003) [Pubmed]
  8. L-chicoric acid, an inhibitor of human immunodeficiency virus type 1 (HIV-1) integrase, improves on the in vitro anti-HIV-1 effect of Zidovudine plus a protease inhibitor (AG1350). Robinson, W.E. Antiviral Res. (1998) [Pubmed]
  9. Growing Environment and Nutrient Availability Affect the Content of Some Phenolic Compounds in Echinacea purpurea and Echinacea angustifolia. Zheng, Y., Dixon, M., Saxena, P.K. Planta Med. (2006) [Pubmed]
  10. Synthesis and HIV-1 integrase inhibitory activities of caffeoylglucosides. Kim, S.N., Lee, J.Y., Kim, H.J., Shin, C.G., Park, H., Lee, Y.S. Bioorg. Med. Chem. Lett. (2000) [Pubmed]
  11. Antiviral activity of characterized extracts from echinacea spp. (Heliantheae: Asteraceae) against herpes simplex virus (HSV-I). Binns, S.E., Hudson, J., Merali, S., Arnason, J.T. Planta Med. (2002) [Pubmed]
  12. HPLC method validated for the simultaneous analysis of cichoric acid and alkamides in Echinacea purpurea plants and products. Mølgaard, P., Johnsen, S., Christensen, P., Cornett, C. J. Agric. Food Chem. (2003) [Pubmed]
  13. Genetic diversity in seed populations of Echinacea purpurea controls the capacity for regeneration, route of morphogenesis and phytochemical composition. Murch, S.J., Peiris, S.E., Shi, W.L., Zobayed, S.M., Saxena, P.K. Plant Cell Rep. (2006) [Pubmed]
  14. Variability in the composition of anti-oxidant compounds in Echinacea species by HPLC. Pellati, F., Benvenuti, S., Melegari, M., Lasseigne, T. Phytochemical analysis : PCA. (2005) [Pubmed]
  15. Analysis of phenolic acids by micellar electrokinetic chromatography: application to Echinacea purpurea plant extracts. Pomponio, R., Gotti, R., Hudaib, M., Cavrini, V. Journal of chromatography. A. (2002) [Pubmed]
  16. Predicting quantitative phytochemical markers in single Echinacea plants or clones from their DNA fingerprints. Baum, B.R., Mechanda, S., Livesey, J.F., Binns, S.E., Arnason, J.T. Phytochemistry (2001) [Pubmed]
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