Chem. Pharm. Bull.

Chem. Pharm. Bull., 50(1),133-136, 2002

Notes

Brine Shrimp Lethality Test Active Constituents and New Highly Oxygenated Seco-prezizaane-Type Sesquiterpenes from Illicium merrillianum

Jian-Mei HUANG,^a Kousuke NAKADE,^a Mamiko KONDO,^a Chun-Shu YANG,^b and Yoshiyasu FUKUYAMA^*,a

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

In the study of bioactive substances in Illicium plants, the methanol extract of I. merrillianum showed brine shrimp lethality test (BST) activity at 200 mg/ ml. Bioassay-guided fractionation of the BST active fractions resulted in the isolation of 4-O-methyleudesm-11-en-4 a-ol, eudesmol-11-en-4 a-ol and (-)-hinokinin as potent BST active compounds. On the other hand, four new highly oxygenated seco-prezizaane-type sesquiterpenes, merrilliortholactone (1), 2 a-hydroxycycloparvifloralone (2), 2 a-hydroxycycloparviflorolide (3), and 2 a-hydroxyanisatin (4) were isolated from the BST-inactive polar fractions. The structures of new compounds were elucidated by extensive analyses of spectral data. Furthermore, the absolute configuration of 3 was established by the modified Mosher's method. Compounds 1—4 showed neither BST activity at 100 mg/ ml nor neurite outgrowth-promoting activity.

Key words Illicium merrillianum; seco-prezizaane-type sesquiterpene; brine shrimp lethality

Notes

Brine Shrimp Lethality Test Active Constituents and New Highly Oxygenated Seco-prezizaane-Type Sesquiterpenes from Illicium merrillianum

Jian-Mei HUANG,a Kousuke NAKADE,a Mamiko KONDO,a Chun-Shu YANG,b and Yoshiyasu FUKUYAMA*,a

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

Jian-Mei HUANG,^a Kousuke NAKADE,^a Mamiko KONDO,^a Chun-Shu YANG,^b and Yoshiyasu FUKUYAMA^*,a

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