Antioxidant and DNA-Protective Activities of Chlorogenic Acid Isomers

Abstract

Chlorogenic acid is a well-known antioxidant and has more isomers according to the difference in binding location and number of caffeic on quinic acid. In this study, we investigated and compared the profiles of antioxidant and DNA-protective activities of chlorogenic acid isomers including three caffeoylquinic acid isomers (3-O-caffeoylquinic acid, 3-CQA; 4-O-caffeoylquinic acid, 4-CQA; and 5-O- caffeoylquinic acid, 5-CQA) and three dicaffeoylquinic acid isomers (3,5-dicaffeoyl-quinic acid, ICAA; 3,4-dicaffeoylquinic acid, ICAB; and 4,5-dicaffeoyl-quinic acid, ICAC). The results showed that each of chlorogenic acid isomers studied exhibited antioxidant activities and DNA damage protective effects to various extents. On the whole, dicaffeoylquinic acids possessed better antioxidant activities, mostly because they have more hydroxyl groups than caffeoylquinic acids. Three caffeoylquinic acid isomers showed quite similar antioxidant activities, indicating that the position of esterification on the quinic moiety of caffeoylquinic acid had no effect on its antioxidant activities. Quite the contrary, a difference among dicaffeoylquinic acid isomers was observed, namely, ICAA and ICAB exhibited the same antioxidant activities, whereas ICAC had higher antioxidant activities than ICAA and ICAB in some assays, which implied that their antioxidant activities were probably influenced by the position of esterification on the quinic moiety. We speculated that this difference might be due to the fact that there may exist a steric hindrance effect in the ICAC. However, this assumption needs to be further confirmed.

Therapeutic efficacy of chlorogenic acid on cadmium-induced oxidative neuropathy in a murine model

“…Treatment with the CD-treated rats with CA profoundly attenuated the toxicity by diminishing the level of DNA fragmentation, possibly by inhibiting the oxidative reactive radicals induced by Cd. These results are consistent with a previous study (77).…”

Antioxidative activity of caffeic acid: Mechanistic DFT study

“…It has been revealed that all four acids are characterized with very similar values of the corresponding reaction enthalpies, thus indicating that antioxidative activity of these acids does not depend on the esterification position. This finding complements the results of different experimental assays (XU et al, 2012). It has been put forward that HAT may be the major mechanism in nonpolar media, while HAT and SPLET are competitive pathways in polar environment .…”

Phytochemical characterization and antioxidant potential of rustyback fern (Asplenium ceterach L.)

“…Antioxidant activity can be ascribed to high phenolics' content (~232 mg GAE g -1 FW), especially to chlorogenic acid, the major compound found in the methanol extracts in sporophytes. Chlorogenic acid is well-known for its high antioxidant potential (Xu et al, 2012;Kamiyama et al, 2015). Gametophytes displayed lower TPC (~51 mg GAE g -1 FW) and thus lower antioxidant activity in DPPH and ABTS assays than sporophytes.…”