Chem. Pharm. Bull., 52(1),104-107, January 2004

Regular Articles

Seven Novel seco-Prezizaane-Type Sesquiterpenes from the Pericarps of Illicium merrillianum

Jian-Mei HUANG,^a Chun-Shu YANG,^a Ren ZHAO,^b Hironobu TAKAHASHI,^c and Yoshiyasu FUKUYAMA^*,c

^a Faculty of Pharmaceutical Sciences, Beijing University of Chinese Medicine; No. 6 Wangjing Zhonghuannanlu, Chaoyang District, Beijing 100102, China: ^b Yunnan Chinese Medicine Corporation; Kunming 650031, China: and ^c Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University; Yamashiro-cho, Tokushima 770-8514, Japan. * To whom correspondence should be addressed. e-mail: fukuyama@ph.bunri-u.ac.jp

Seven new seco-prezizaane-type sesquiterpenes were isolated from the methanol extract of the pericarps of Illicium merrillianum. Their structures were elucidated as 3-deoxypseudoanisatin (1), 2β-hydroxy-3,6-dedioxypseudoanisatin (2), 8α-hydroxy-10-deoxycyclomerrillianolide (3), 10β-hydroxypseudoanisatin (4), 10β-hydroxycyclopseudoanisatin (5), 1,6-dihydroxy-3-deoxyminwanensin (6), and 8-deoxymerrilliortholactone (7) by analyses of their spectroscopic data and chemical transformation. Compounds 4 and 5 as well as 6 and 7 coexist as a keto/acetal equilibrated mixture in methanol solution.

Key words Illicium; Illicium merrillianum; seco-prezizaane-type sesquiterpene