Abstract
Burdock roots are healthy dietary supplements and a kind of famous traditional Chinese medicine, which contains large amounts of caffeoylquinic acid derivatives. However, little research has been reported on the preparative separation of these compounds from burdock roots. In the present study, a combinative method of HSCCC and semi-preparative HPLC was developed for the semi-preparative separation of caffeoylquinic acid derivatives from the burdock roots. The ethyl acetate extract of burdock roots was first fractionated by MCI macroporous resin chromatography and give three fractions (Fr. 1–3) from the elution of 40% methanol. Then, these three fractions (120 mg) were separately subjected to HSCCC for purification with the solvent system composed of petroleum ether-ethyl acetate-methanol-water at different volume ratios, and the mixtures were further purified by semi-preparative HPLC. As a result, a total of eight known caffeoylquinic acid derivatives including 3-O-caffeoylquinic acid (32.7 mg, 95.7%), 1,5-O- dicaffeoylquinic acid (4.3 mg, 97.2%), 3-O-caffeoylquinic acid methyl ester (12.1 mg, 93.2%), 1,3-O-dicaffeoylquinic acid (42.9 mg, 91.1%), 1,5-O-dicaffeoyl-3-O-(4-maloyl)-quinic acid (4.3 mg, 84.5%), 4,5-O-dicaffeoylquinic acid (5.3 mg, 95.5%), 1,5-O-dicaffeoyl-3-O-succinylquinic acid (8.7 mg, 93.4%), and 1,5-O-dicaffeoyl-4-O-succinylquinic acid (1.7 mg, 91.8%), and two new compounds were obtained. The new compounds were 1,4-O-dicaffeoyl-3-succinyl methyl ester quinic acid (14.6 mg, 96.1%) and 1,5-O-dicaffeoyl-3-O-succinyl methyl ester quinic acid (3.1 mg, 92.6%), respectively. The research indicated that the combination of HSCCC and semi-preparative HPLC is a highly efficient approach for preparative separation of the instability and bioactive caffeoylquinic acid derivatives from natural products.
Highlights
Burdock (Arctium lappa L.) is a biennial plant of the Asteraceae family and its root has been consumed as a tonic vegetable in Asia
The search of appropriate solvent system plays an important role in separation of High-speed counter-current chromatography (HSCCC)
Due to the similarity of these compounds in chemical structure, repeat and multiple chromatography has often been adopted for their purification, which leads to the degrade and loss of these compounds
Summary
Burdock (Arctium lappa L.) is a biennial plant of the Asteraceae family and its root has been consumed as a tonic vegetable in Asia. Pharmacological studies indicated that burdock root has antioxidant [2], antiallergic [3], anti-inflammatory [4] and hepatoprotective activities [5]. Caffeoyl quinic acid derivatives are considered to be one of the main active ingredients, such as 1,3-, 1,4-, 1,5-dicaffeoylquinic acids, which were all positional isomers in chemical structure [6,7]. Molecules 2018, 23, 429 to be one of the main active ingredients, such as 1,3-, 1,4-, 1,5-dicaffeoylquinic acids, which were all positional isomers in chemical structure [6,7].
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