Chem. Pharm. Bull., 47(12),1749-1752, December 1999

Regular Articles

Structures of Novel Sesquiterpenes from the Pericarps of Illicium merrillianum

Jian-mei HUANG,^a Chun-shu YANG,^b Hai WANG,^b Qiu-ming WU,^b Jia-ling WANG,^b and Yoshiyasu FUKUYAMA^*,a

Institute of Pharmacognosy, Faculty of Pharmaceutical Sciences, Tokushima Bunri University,^a Yamashiro-cho, Tokushima 770-8514, Japan and Faculty of Pharmaceutical Sciences, Beijing University of Chinese Medicine,^b Beijing 100029, China.

Five new sesquiterpenes, named merrillianone (1), cyclomerrillianolide (2), merrillianolide (3), 1a-hydroxy-3-deoxypseudoanisatin (4) and 7-O-acetylanislactone B (5), were isolated from the pericarps of Illicium merrillianum, a species indigenous to southwestern China and Burma. Their structures were elucidated based on spectroscopic and chemical data. The structure of 1 was confirmed by X-ray crystallographic analysis of its acetylated derivative 1a to consist of a novel cagelike acetal and hemiacetal structure. The NMR data for compounds 2 and 3, which could not be separated due to an equilibrium mixture of keto and hemiacetal forms, were unambiguously assigned, respectively.

Key words Illicium merrillianum; merrillianone; cyclomerrillianolide; merrillianolide; 1a-hydroxy-3- deoxypseudoanisatin; 7-O-acetylanislactone B