Caffeoylquinic Acids: Separation Method, Antiradical Properties and Cytotoxicity

Abstract

Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C‐4 position showed higher antiradical activity compared to acylation at C‐3 or C‐5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4‐caffeoylquinic acid. Excepted to 3,4‐dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C‐4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.

Bioaffinity Fishing Procedure Using Secretory Phospholipase A2 for Screening for Bioactive Components: Modulation of Pharmacological Effect Induced by sPLA2 from Crotalus durissus terrificus by Hispidulin from Moquiniastrum floribundum

“…These compounds were identified using NMR ( 1 H, 13 C, and HMBC spectra) as 3-caffeoylquinic acid (1), chlorogenic acid (2), 4-caffeoylquinic acid (3), 3,4-, 3,5-m, and 4,5-dicaffeoylquinic acids (4-6, respectively), 3,4,5-tricaffeoylquinic acid 7, and hispidulin (8). The proposed structures were confirmed by the comparison of the spectroscopic data with those reported in the literature [12,13]. Subsequent component identification was performed using the retention time of each compound.…”

“…As such, His has the ability to pass through the plasma membrane and increase the antioxidant defense of the cell [8]. Numerous articles suggest that His exhibits a moderate antioxidant activity for free radical scavenging and neutralization, determined by 1,1-Diphenyl-2-picrylhydrazyl radical, 2,2-Diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl (DPPH), and 2,2 -Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) antioxidant activity monitoring assays [12]. The presence of a carbonyl functional group at the C4 position plays an essential role in the neutralizing capacity of the hydroxyl radical [25].…”

“…Compounds present in methanol extract were previously isolated from chromatographic procedures and identified using NMR analysis [12,13]. We tested the effects of unretained and retained compounds during the process of ultrafiltration from methanol extract incubated with sPLA2, as described in Section 4.4.…”

“…Asteraceae is a family of eudicots characterized by diverse bioactive metabolites, and the Moquiniastrum genus, which belongs to this family, is found in South America and is used in folk medicine for treating respiratory diseases, such as asthma, bronchitis, coughs, and colds. Studies revealed these plants exhibit anti-trypanosomal, antiradical, anti-inflammatory, antispasmodic, antibacterial, cytotoxic, and antioxidant activities [10][11][12][13]. This genus has already been found to contain compounds such as genkwanin, hispidulin, cirsimaritin, and chlorogenic acid derivatives.…”

“…Overlap of chromatograms from samples of methanol crude extract and MeOH 1C and MeOH 2C fractions obtained through the sPLA2 protein-ligand approach. Compounds were identified through NMR analysis as previously described[12,13]: (1) 3-CQA, 3-caffeoylquinic acid; (2) 5-CQA, 5-caffeoylquinic acid; (3) 4-CQA, 4-caffeoylquinic acid; (4) 3,4-dicaffeoylquinic acid; (5) 3,5-dicaffeoylquinic acid; (6) 4,5-dicaffeoylquinic acid; (7) 3,4,5-triCQA, 3,4,5-tricaffeoylquinic acid; and (8) hispidulin.…”