Chem. Pharm. Bull., 50(3),368-371, March 2002

Regular Articles

Seven-Membered Vibsane-Type Diterpenes with a 5,10-cis Relationship from Viburnum awabuki


Yoshiyasu FUKUYAMA,* Hiroyuki MINAMI, Asami MATSUO, Kanako KITAMURA, Mie AKIZUKI, Miwa KUBO, and Mitsuaki KODAMA

Faculty of Pharmaceutical Sciences, Tokushima Bunri University, 180 Yamashiro-cho, Tokushima 770-8514, Japan.

New five seven-membered vibsane-type diterpenes named 5-epi-vibsanin C, 5-epi-vibsanin H, 5-epi-vibsanin K, 18-O-methyl-5-epi-vibsanin K and 5-epi-vibsanin E have been isolated from the leaves of Viburnum awabuki (Caplifoliaceae). Their structures have been elucidated by analyses of spectroscopic data and comparison of their spectral data with those of the previously known seven-membered vibsane-type diterpenes. The occurrence of these seven-membered vibsane-type diterpenes with a cis relationship on the C-5 and C-10 positions in nature have been predicted by conformational analysis of vibsanin B, an eleven-membered vibsane-type diterpene. Vibsanin C, 5-epi-vibsanin C and 5-epi-vibsanin H exhibited moderate cytotoxic activities on KB cells.

Key words Viburnum awabuki; Caplifoliaceae; 5-epi-vibsanin; seven-membered vibsane-type diterpene; cytotoxicity