Disease relevance of Dicaffeoyl-L-tartaric acid

• Three compounds, 3,5-dicaffeoylquinic acid, 1-methoxyoxalyl-3,5-dicaffeoylquinic acid, and L-chicoric acid, inhibit HIV-1 integrase in biochemical assays at concentrations ranging from 0.06-0.66 microgram/ml; furthermore, these compounds inhibit HIV-1 replication in tissue culture at 1-4 microgram/ml [1].
• In this study, 17 analogues of L-chicoric acid, a potent inhibitor of HIV integrase, were studied [2].

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

• Catechol-substituted L-chicoric acid analogues as HIV integrase inhibitors [7].
• To determine whether HIV integrase is a suitable target for combination therapy, the ability of an HIV integrase inhibitor, L-chicoric acid, to work in combination with a protease inhibitor and Zidovudine was tested in vitro [8].

Biological context of Dicaffeoyl-L-tartaric acid

• ECHINACEA plants grown in the controlled environment systems had higher or similar amounts of cynarin, caftaric acid, echinacoside and cichoric acid as previously reported in the literature for both field-cultivated and wild-harvested ECHINACEA plants [9].
• Among them, four dicaffeoylglucosides (IC50 = 29.1+/-35.1 microM), 6a, 6b, 9b and 10b, showed HIV-1 integrase inhibitory activity as potent as L-chicoric acid [10].

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

• The most potent inhibitors of HSV were E. pallida var. sanguinea crude (70 % ethanol) inflorescence extract (MIC = 0.026 mg/mL), cichoric acid (MIC = 0.045 mg/mL) and Echinacea purpurea n-hexane root extract (MIC = 0.12 mg/mL) [11].
• A reversed-phase high-performance liquid chromatography (HPLC) method has been developed to determine caffeic acid derivatives, for example, cichoric acid, and alkamides in plant parts and herbal products of Echinacea purpurea [12].
• In temporary immersion bioreactors, exogenous application of the auxin indolebutyric acid significantly increased the cichoric acid and caftaric acid concentration in the root tissues [13].
• A fast and reliable HPLC method for the determination of caffeic acid derivatives (caftaric acid, chlorogenic acid, caffeic acid, cynarin, echinacoside and cichoric acid) in various species of the genus Echinacea has been developed [14].

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].

References