Ferovinolal, a New Humulane from Ferula ovina

The new humulane-type (α-apiene) ester ferovinolal was isolated from Ferula ovina roots. The structure of ferovinolal was elucidated using IR, PMR, ¹³C NMR, DEPT, HSQC, COSY, NOESY, and HMBC spectra and an X-ray structure analysis (XSA). The XSA revealed the three-dimensional structure and absolute configuration of α-apiene, the chiral centers of which had the 6S and 8R configurations. The 11-membered humulane macrocycle in α-apiene adopted the ₁₄U⁷₈-conformation.