Coumarins isolated from the roots of Seseli resinosum in Turkey

Seseli resinosum Freyn et Sint. (Umbelliferae) is a perennial herb that grows in the northern region of Anatolia, Turkey. The n-hexane extract obtained from the roots of S. resinosum was investigated for the presence of coumarins. Three angular-type pyranocoumarins and two linear-type furo-coumarins were isolated from the roots. The compounds were identified as (+)-samidin [(3'S, 4'S)-3'-senecioyloxy-4'-acetoxy-3', 4'-dihydroseselin] (1), (-)- anomalin [(3'R, 4'R)-3', 4'-diangeloyloxy-3', 4'-dihydroseselin] (2), calipteryxin (3'R, 4'R)- 3'- angeloyloxy- 4'- senecioyloxy- 3', 4'-dihydroseselin (3), isoimperatorin (4), and deltoin (5). The structures were determined using spectroscopic methods (H-1 NMR, C-13 NMR, H-1-H-1 COSY, H-1-C-13 COSY, HMBC, MS), physical methods (melting point and optical rotation), and chemical correlations with known compounds that have been described in the literature. The chemotaxonomic significance of these isolated coumarins is discussed in the genus Seseli L.