Coumarins from the roots of Ferula pseudooreoselinum

By chromatography on A1203, from an acetone extract of the roots of Ferula pseudooreoselinum (Rgl. et Schrnalh.) K. Pol., in addition to samarcandin acetate and isosarnarcandin angelate [1], we have isolated three umbellfferone derivatives with a bicyclic terpenoid side chain: (I) C24H3004 {M + 382), mp 116.5117.5°C, [ol]~ -98.5 ° (c 0.22; ethanol), which has been called feselol [additional purification of the coumarin was performed by preparing the acetate C~.sHs20~_ (M+424), mp 163-165°C, [~]~ -119.1 ° (c 0.9; ethanol) and its subsequent saponification]; (II)C241{3004 ~I 382), mp 136.5-137.5°C, [c~] ~ -82.8 ° (c 5.2; ethanol) a stereoisomer of feselol; and (HI) C24H2sO 4 (M + 380), mp 141-142°C, [c~]~-49.8 ° (c 0.23; ethanol). Compounds (1), (If), and (III) have UV and IR spectra typical for derivatives of 7-hydroxycournarin. The IR spectra of (I) and (II) have the absorption bands of OH groups at v3350 and 3620 cm -I, respectively. The oxidation of these compounds with chromium trioxide in acetone forms the same product, a ketone C24H2sO 4, mp 141-142°C, which was identical in melting point and IR spectrum with the coumarin (HI). The NMR spectra of (I) and (II) have the signals of protons geminal to hydroxy groups with 5, ppm, 3.20 (1H}, a triplet ~J= 15 Hz), and 3.41 (1H) (half-width of the signal ~ 8 Hz), respectively. It follows from this that the hydroxy group has the equatorial orientation in feselol and the axial orientation in its stereoisomer. In the NMR