Bergamotane-type sesquiterpenes from the leaves and twigs of Illicium oligandrum and their anti-inflammatory activities

Abstract

Eight undescribed β-bergamotene-type sesquiterpene oliganins A-H (1-8) and one known α-bergamotene-type sesquiterpene (9) were isolated from the leaves and twigs of Illicium oligandrum Merr. & Chun. The structures of compounds 1-8 were elucidated by extensive spectroscopic data, and the absolute configurations were determined by using a modified Mosher's method and electronic circular dichroism calculations. The isolates were further evaluated in terms of their anti-inflammatory potential on nitric oxide (NO) generation in lipopolysaccharide-stimulated RAW264.7 and BV2 cells. Compounds 2 and 8 exhibited potent inhibitory effects on the production of NO with IC₅₀ values ranging from 21.65 to 49.28 μM, which were greater than or comparable to those of dexamethasone (positive control).

Keywords: Anti-inflammatory activity; Bergamotane-type sesquiterpene derivatives; ECD calculation; Illiciaceae; Illicium oligandrum; Oliganin a.