Lycoperosides A-C, three stereoisomeric 23-acetoxyspirosolan-3 beta-ol beta-lycotetraosides from Lycopersicon esculentum

Three new steroidal alkaloid glycosides, lycoperosides A-C, were isolated from leaves and fruits of tomato, Lycopersicon esculentum, and structurally elucidated as the 3-O-beta-lycotetraosides of (23R)-23-acetoxytomatidine, (23S)-23-acetoxysoladulcidine and (23S,25S)-23-acetoxy-5 alpha,22 alpha N-spirosolan-3 beta-ol. In addition to these glycosides, leaves and fruits were found to contain the known major alkaloid tomatine (tomatidine 3-O-beta-lycotetraoside) and leaves a small amount of gamma-tomatine (tomatidine 3-O-[beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside], lycoperoside D).