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

• Published in: Talanta (Oxford) Vol. 135; pp. 50 - 57
• Main Authors: Carlotto, Juliane, da Silva, Luisa M., Dartora, Nessana, Maria-Ferreira, Daniele, Sabry, Diego de A., Filho, Arquimedes P.S., de Paula Werner, Maria F., Sassaki, Guilherme L., Gorin, Philip A.J., Iacomini, Marcello, Cipriani, Thales R., de Souza, Lauro M.
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 01-04-2015
• Subjects: 1,3-O-dicaffeoylquinic acid; Animals; Anti-ulcer activity; Anti-Ulcer Agents - chemistry; Anti-Ulcer Agents - isolation & purification; Anti-Ulcer Agents - therapeutic use; Arctium; Arctium lappa; Ethanol; Ethyl alcohol; Fractionation; Isomerism; Isomers; Isopropylidene derivative; Liquids; NMR; Plant Extracts - chemistry; Plant Leaves; Quinic Acid - analogs & derivatives; Quinic Acid - chemistry; Quinic Acid - isolation & purification; Quinic Acid - therapeutic use; Rats; Rats, Wistar; Spectrometry; Stomach Ulcer - chemically induced; Stomach Ulcer - drug therapy; Ulcers; NMR; 1,3-O-dicaffeoylquinic acid; MS; Arctium lappa; Anti-ulcer activity; Isopropylidene derivative
• ISSN: 0039-9140; 1873-3573
• DOI: 10.1016/j.talanta.2014.11.068

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 57µgkg−1 on gastric protection, lesser than the therapeutic concentration of omeprazole (40mgkg−1).
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•Leaf extract from Arctium lappa was active against ethanol-induced ulcers;•The active compound was isolated and characterized as 1,3-O-dicaffeoylquinc acid;•The isomer 1,5-O-dicaffeoylquinic acid was not effective;•NMR and MS fingerprints analysis of native and modified structure were developed.