Triterpene alcohols from camellia and sasanqua oils and their anti-inflammatory effects

The nonsaponifiable lipids of camellia and sasanqua oils from the seeds of Camellia japonica L. and C. sasanqua THUNB., respectively, were investigated for their triterpene alcohol constituents. This led to the isolation of twenty-seven triterpene alcohols of which seven were novel naturally occurring compounds, tirucalla-5,7,24-trien-3 beta-ol (1), lemmaphylla-7,21-dien-3 beta-ol (2), isoeuphol (3), isotirucallol (4), (24R)-24,25-epoxybutyrospermol (5) and its 24S-epimer (6), and isoaglaiol (7). The structures were determined by spectroscopic and chemical methods. The inhibitory effects of 3, 4 a mixture of 5 and 6, a mixture of 7 and its 24S-epimer (aglaiol), and eight known triterpene alcohols isolated in this study were evaluated in ear inflammation in mice induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 microgram per ear) was 0.2-0.9 mg/ear.