Esters of Ferula akitschkensis

Abstract

The NMR spectrum of (I) (Jeol 60 MHz, CDC13, 0 - HMDS) contains the following signals: doublets at 0.78 and 0.85 ppm (J =6.5 Hz, 3 H each), singlets at 1.05 and 1.70 ppm (3 H each ), 3.40 and 3.42 ppm (3 H each), sextet at 5,02 ppm (Jl=10 Hz, J2 =2.5 Hz, 1 H), multiplet at 5.32 ppm (1 H), doublet at 6.74 ppm (J =10 Hz, 1 H), quartet at 7.5 ppm (J1 =10 Hz, J2 =2.5 Hz, 1 H), and doublet at 7.4 ppm (J =2.5 Hz, 1 H). A comparison of the NMR spectra of (I) with those of ferutin, ferutinin [1], and teferin [2] showed that substance (I) is also an ester of ferutinol. When (I) was hydrolyzed with 5% aqueous methanolic caustic potash with heating for 4 h, the neutral fraction of the hydrolyzate yielded an alcohol C15H2~O z [2] with mp 89-90°C, [~]~ + 38 ° (c 1.0, chloroform), identical with ferutinol [1], and the acid fraction yielded an acid CsHsQ (IID with mp 193°C. By a comparison of IR spectra and a mixed melting point with an authentic sample, the acid (III) was identified as veratric acid. The position of the acid residue in substance (I) follows from the value of the signal of its hemiacyl proton (5.05 ppm) in the NMR spectrum, and by analogy with ferutin and ferutinin, it is attached to the secondary hydroxy group at C 6. Thus, substance (I), which we have called akiferia, isa new ester and has the structure of 6-O-veratroglyferutinol