Dereplication of bioactive constituents of the genus hypericum using LC-(+,-)-ESI-MS and LC-PDA techniques: Hypericum triquterifolium as a case study

Utilizing liquid chromatography–electro spray ionization-mass spectrometry (LC– (+, -)-ESI-MS) and liquid chromatography-photodiode array detection (LC-PDA) techniques, a dereplication strategy for the analysis of the secondary metabolites constituents of the genus Hyper- icum has been developed. From the crude methanolic extract of the aerial parts of H. triquetrifolium (leaves, stems, and flowers) and on the basis of their UV-profiles, chromatographic retention times and (+, -)-ESI-MS (TIC and SIM) mass spectral data, seven known (1–7) compounds were dereplicated fairly rapidly. The compounds were classified into three structural classes: phloroglucinols: hyperfirin and adhyperfirin; naphthodianthrones: hypericin, pseudo-hypericin, proto-hypericin, and protopseudo-hypericin; and the flavonoid rutin.