Plant coumarins. IX.* Phenolic compounds of Ferulopsis hystrix growing in Mongolia. Cytotoxic activity of 8,9-dihydrofurocoumarins

Abstract

distributed in South Siberia and in Mongolia, was assigned to the genus Ferulopsis and given the systematic name F. hystrix (Bunge ex Ledeb.) M. Pimen. [2]. F. hystrix previously yielded oroselone (1), oroselol (2), and 8-(S)-O-senecioyl-8,9dihydrooroselol (libanorin) 3 [3]. We studied substances extracted from F. hystrix collected near Batkhaan Uul, Bulgan Aimak, Mongolian Republic. The concentrated EtOH extract of the aerial part and subterranean organs of the plant were worked up successively with hexane, CHCl 3 , Et 2 O, and EtOAc. The yields of extracted substances and total coumarin contents in fractions were determined after evaporation of the hexane, CHCl 3 , and Et 2 O using PMR and GC–MS data of the total fractions. The coumarin content in the EtOAc extracts was determined using spectra of CHCl 3 extracts of alkaline hydrolysis products. Table 1 presents the results. The total coumarin contents in the aerial part and roots of the plants were 3.9 and 4.6%, respectively. The greatest coumarin content was found in the hexane and CHCl 3 extracts of the EtOH extract. The extracted substances were separated by column chromatography over silica gel. 5-Hydroxy-7-methoxy-2-methylchromone (eugenin, 4, 16% of the extract mass) and coumarins umbelliferone (5, 6% of extract mass), oroselone (1, 3%), (8,9)-dihydrooroselol (columbianetin, 6, 3%), 8-O-angeloyl-8,9-dihydrooroselol (zosimin, columbianadin, 7, 7%), (8S,9R)-9-acetoxy-8-O-senecioyl8,9-dihydrooroselol (peucenidin, 8, 6%), and (8S,9R)-8-O-angeloyl-9-acetoxy-8,9-dihydrooroselol (libanotin, edultin, 9, 5%) were isolated from the hexane extract of the EtOH extract of the aerial part. Also, oroselol (1) and (8S)-2-methylbutanoyl-8,9dihydrooroselol (10) were identified using spectral data. Libanorin (3, 8%), columbianetin (6, 11%), columbianadin (7, 9%), peucenidin (8, 9%), and libanotin (9, 7%) were isolated from the hexane extract of the EtOH extract of the subterranean organs of F. hystrix. Also, dihydrooroselol derivatives such as 10 (1.2% of the extract mass) and (8S,9R)-8-O-acetyl-9-isobutyryloxy