Coumarin derivatives from the roots of Heptaptera cilicica

Abstract

The genus Heptaptera (Apiaceae) has four species growing in Turkey. Heptaptera cilicica (Syn. Meliocarpus cilicicus, Colladonia cilicica, Prangos cilicica) is an endemic species growing only in Adana-Mersin area of South Anatolia in Turkey [1]. Heptaptera species are known to be rich in coumarin derivatives [2 – 4] and have antioxidant and acetylcholinesterase inhibitory activities [5]. In this study, air-dried and powdered roots of Heptaptera cilicica (Boiss. & Bal.) Tutin were extracted with CHCl3. The CHCl3 extract was subjected to column chromatography on silica gel with a solvent gradient of n-hexane-EtOAc (100:0 → 0:100, v/v) to give four main fractions. These main fractions were separately subjected to silica gel column using n-hexane with increasing amounts of EtOAc. Then, the subfractions were crystallized with the same solvent system to yield a new furocoumarin: trichoclin angelate with five known coumarin derivatives: umbelliprenin, badrakemone, badrakemin, badrakemin acetate and prunate. Their structures were identified by means of spectroscopic methods (1D and 2D-NMR, HRESIMS, ESI-MS). Trichoclin angelate was new for the literature and the known compounds, badrakemin and badrakemin acetate, were isolated from Heptaptera species for the first time.