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  • Title: High-performance countercurrent chromatography separation of Peucedanum cervaria fruit extract for the isolation of rare coumarin derivatives.
    Author: Skalicka-Woźniak K, Mroczek T, Kozioł E.
    Journal: J Sep Sci; 2015 Jan; 38(2):179-86. PubMed ID: 25380281.
    Abstract:
    For the first time, rare major and minor compounds from fruits of Peucedanum cervaria were isolated. High-performance countercurrent chromatography with two different solvent systems, heptane/ethyl acetate/methanol/water (3:2:3:2 and 2:1:2:1, v/v), was successfully used in the reversed-phase mode. A scale-up process from analytical to semipreparative in a very short time was developed. The structures of isolated compounds were evaluated by high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry, gas chromatography with mass spectrometry, and one- and two-dimensional NMR spectroscopy. (8S,9R)-9-(3-Methylbutenoyloxy)-O-acetyl-8,9-dihydrooroselol (compound B), (8S,9R)-9-(2-methyl-Z-butenoyloxy)-O-acetyl-8,9-dihydrooroselol (edultin, compound C), and (8S,9R)-9-acetoxy-O-(2α-methylbutyryl)-8,9-dihydrooroselol (compound D) were obtained using heptane/ethyl acetate/methanol/water (2:1:2:1, v/v) in <40 min. The method yielded 4.6 mg of a mixture of compounds B and C (11:89) and 3.7 mg of compound D. These amounts were obtained from the crude extract (0.5 g) in a single run. Although the compounds are known, their isolation by countercurrent chromatography and the analysis of their relative stereochemistry by two-dimensional NMR spectroscopy have been performed for the first time. Additionally, heptane/ethyl acetate/methanol/water (3:2:3:2, v/v) led to the isolation of oxypeucedanin (1.2 mg; compound A). This is the first time that angular dihydrofuranocoumarin was isolated from plant extract by countercurrent chromatography.
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