Effect-Directed Isolation and Identification of Antibacterial Chelidonium majus L. Alkaloids

• Published in: Chromatographia 2015-05, Vol.78 (9-10), p.707-716
• Main Authors: Móricz, Ágnes M, Fornal, Emilia, Jesionek, Wioleta, Majer-Dziedzic, Barbara, Choma, Irena M
• Format: Article
• Language: English
• Subjects: Analytical Chemistry; antibacterial properties; Bacillus subtilis; berberine; Chelidonium majus; Chemistry; Chemistry and Materials Science; Chromatography; Escherichia coli; ethyl acetate; Laboratory Medicine; leaves; methanol; Original; Pharmacy; Proteomics; sanguinarine; silica; thin layer chromatography
• ISSN: 0009-5893; 1612-1112
• DOI: 10.1007/s10337-015-2870-6

The components of alkaloid, methanol and ethyl acetate extracts of Chelidonium majus L. root, leaf and stem were tested for antibacterial activity against Bacillus subtilis and Escherichia coli by thin-layer chromatography coupled with direct bioautography (TLC-DB). Effect-directed analyses were performed to obtain the active compounds as follows: separation with preparative layer chromatography (PLC, 0.5-mm-thick silica layer, 20 × 10 cm); a part of the preparative layer (3 cm wide) was used for PLC-DB to detect the antibacterial components against B. subtilis; elution of the appropriate lanes as indicated by PLC-DB from the remaining 17-cm-wide layer; verification of the bioactivity of the eluted compounds by TLC-DB; further purification of the fractions was carried out with TLC, when it was necessary. The eluates of interest were analysed by LC-HRMS and LC-Q/TOF. The antibacterial effect against B. subtilis was mainly attributed to the isoquinoline alkaloid components, which were identified as chelidonine, sanguinarine, chelerythrine, berberine, coptisine, corydine, dihydrosanguinarine, dihydrochelerythrine, 6-acetonyl-dihydrosanguinarine, 6-acetonyl-dihydrochelerythrine and stylopine. Only chelidonine, sanguinarine and chelerythrine possessed inhibiting effect against E. coli.