Spirostanol glycosides with hemostatic and antimicrobial activities from Trillium kamtschaticum

Ten spirostanol glycosides, trillikamtosides A–J, together with eleven known analogues, were isolated from the hemostatic fraction of the 75% aqueous EtOH extract of the whole herbs of Trillium kamtschaticum. Their structures were established by extensive spectroscopic data analysis and chemical methods. The aglycones of three of these compounds had unique 3β,17α-dihydroxy-spirostanes featuring a double bond between C-4 and C-5, while two others represent a rare class of spirostanol glycosides which possess a 5(6 → 7) abeo-steroidal aglycone. All the compounds were evaluated for their hemostatic and antimicrobial activities. Three of the spirostanol glycosides exhibited induced-platelet aggregation at a concentration of 300 μg/mL with maximal induced-platelet aggregation rates of 72%, 71%, and 62% in rabbits, respectively, and their EC50 values were 492.7, 203.3, and 109.8 μM. Five of the spirostanol glycosides showed an anti-Candida albicans effect with MIC values of 21.1, 10.6, 8.8, 21.6, and 11.0 μM, respectively. Ten spirostanol glycosides, together with eleven known analogues, were isolated from Trillium kamtschaticum. Three aglycones had unique 3β,17α-dihydroxy-spirostanes featuring a double bond between C-4 and C-5, while two others possess a rare 5(6 → 7) abeo-steroidal aglycone. Some of the tested compounds showed induced-platelet aggregation activities, and some others showed significant anti-Candida albicans effects. [Display omitted] •Twenty-one spirostanol glycosides were isolated from the hemostatic fraction of the extract of Trillium kamtschaticum.•Ten previously undescribed spirostanol glycosides were characterized.•Three spirostanol aglycones were previously unknown.•All compounds were evaluated for hemostatic and antimicrobial activities.