Identification of a dicaffeoylquinic acid isomer from Arctium lappa with a potent anti-ulcer activity

Abstract

Leaves of Arctium lappa contain several mono- and dicaffeoylquinic acids, as evaluated by liquid chromatography-mass spectrometry. In order to investigate the protection on gastric mucosa against ulcers, rats were treated with fractions from leaf extract prior to ethanol-induced ulcers. The original fraction obtained as ethanol soluble fraction from hot aqueous extract was able to protect de gastric mucosa, and this effect was retained in the ethyl acetate fraction, obtained from liquid/liquid fractionation. The main compound in this fraction was isolated and chemically characterized by nuclear magnetic resonance and mass spectrometry, assisted by isopropylidene derivatization which gave rise a mass increment of 40 units. Therefore, the underivatized compound that had m/z 515.119 [M-H](-) was shifted to m/z 555.151, being confirmed as 1,3-O-dicaffeoylquinic acid, which presented an ED50 of 57 µg kg(-1) on gastric protection, lesser than the therapeutic concentration of omeprazole (40 mg kg(-1)).

Effect of cytokinins on shoots proliferation and rosmarinic and salvianolic acid B production in shoot culture of Dracocephalum forrestii W. W. Smith

“…All analyzed samples of shoot cultures presented a similar qualitative profile comprising nine peaks, four (1, 2, 6, 8) of which were identified by comparing their data (retention times-Rt, UV-Vis absorption spectra, and MS/MS fragmentation patterns) with those of reference standards. Other compounds for which standards were not available were identified by analysis their MS/MS spectral characteristic and confirmed with literature data (Catarino et al 2015;Carlotto et al 2015;Wang et al 2012;Lecompte et al 2010;Liu et al 2007a;Kuo et al 2000). The properties of the examined compounds and representative HPLC-UV chromatograms are presented in Table 2 and Fig.…”

“…salvianolic acid B, (9) methyl rosmarinate literature data suggests that compound 5 is dicaffeoylquinic acid (Catarino et al 2015;Carlotto et al 2015). Similarly, peak 6 was identified as rosmarinic acid by comparisons with standards and literature data (Ncube et al 2014;Nuenchamong et al 2011;Liu et al 2007a, b;Zeng et al 2006 Liu et al 2007a, b;Zeng et al 2006).…”

Roles of Nitric Oxide and Prostaglandins in the Sustained Antihypertensive Effects of Acanthospermum hispidum DC. on Ovariectomized Rats with Renovascular Hypertension

“…In a previous work [ 6 ], the composition of an extract of Acanthospermum hispidum was partially characterized, with identification of the family of monocaffeoylquinic acids (CQAs) and dicaffeoylquinic acids (diCQAs), observed as multiple isomers in the LC-MS analysis. However, these isomers have characteristic fragmentation profile that can be used for their identification [ 13 , 14 ]. To confirm the isomer identity, an extract of Ilex paraguariensis , containing mono- and dicaffeoylquinic acids, previously characterized [ 13 ], was used as a reference sample.…”

Inhibitory Effect of Supercritical Extracts from Arctium lappa L. on the Lectin Pathway of the Complement System

“…Popularly known as Burdock, the plant Arctium lappa L. presents several biological activities including antioxidant, anti‐inflammatory, anti‐allergic, antimicrobial (bacteria and yeasts), antitumor, hypolipidemic, antidiabetic and antiulcer . Recently, Fontana et al .…”