Tirucalla-5,24-dien-3β-ol ((13α,14β,17α,20S)- Lanosta-5,24-dien-3β-ol) and Three Other δ5-Unsaturated Tirucallanes from the Roots of Bryonia dioica Jacq.: The First Naturally Occurring C-10 Methylated Tetracyclic Triterpene Alcohols w

Four novel triterpene alcohols with a Δ5-unsaturated tirucallane-type skeleton, i.e. tirucall-5-en-3β-ol, tirucalla-5,24-dien-3β-ol, 24-methyltirucalla-5,24(241)-dien-3β-ol and (24S)-24-methyltirucalla-5,25-dien-3β-ol, have been isolated from the roots of Bryonia dioica Jacq. (Cucurbitaceae). The structures have been determined by spectroscopic and chromatographic methods. These compounds are the first examples of naturally occurring C-10 methylated triterpenes with a Δ5-monounsaturated skeleton.