A germacranolide and three hydroxybenzyl alcohol derivatives from Hieracium murorum and Crepis bocconi

The methanol extract of sub-aerial parts of Hieracium murorum L. gave germacra-7 alpha H-1(10)E,4Z,11 (13)-trien-12,8 alpha-olide-15-oic acid (15-->1)-beta-D-glucopyranosyl ester (1), a new sesquiterpenoid of the germacrane-type, and two new 4-hydroxybenzyl alcohol derivatives, 4-hydroxy-cinnamomic acid 4-beta-D-glucopyranosyloxybenzyl ester (2) and 3-hydroxy-2-[(4-hydroxy-phenyl)-acetoxy]-3-methyl-butyric 4-beta-D-glucopyranosyloxybenzyl ester (3). The methanol extract of sub-aerial parts of Crepis bocconi P. D. Sell gave 4-hydroxybenzoic acid 4-beta-D-glucopyranosyloxybenzyl ester (4), another new 4-hydroxybenzyl alcohol derivative. The structures of these compounds were established by means of MS and one- and two dimensional-NMR experiments.