Bioactive triterpenoids from the caffeine-rich plants guayusa and maté

Unlike all other caffeinated plants, guayusa (Ilex guayusa Loes.) and maté (Ilex paraguariensis A. St. Hill) contain high amounts of pentacyclic triterpenoid acids and alcohols. A phytochemical investigation on these plants revealed a similar triterpenoid profile and a content of ursolic acid (0.7–1%) and amyrin esters (up to 0.5%), quite unusual for dietary plants. The major constituent of the amyrin complex from both plants is α-amyrin palmitate (2a), accompanied by lower amounts of its corresponding palmitoleate (2b) and by the corresponding constitutional isomers from the β-series (3a and 3b, respectively). Ursolic acid (1) was identified as the responsible for the activity of maté and guayusa extracts in the activation of TGR5, a nuclear receptor of relevance for the prevention and management of diabetes and metabolic syndrome because of its involvement in the regulation of energy expenditure and insulin sensitivity. [Display omitted] •Guayusa is growingly popular as a caffeinated beverage, similar to maté.•The phytochemistry and bioactivity of guayusa are still substantially unexplored.•Guayusa and maté extracts activate TGR5, a transcription factor involved in diabetes.•Ursolic acid is the active constituent from both plants.•The amyrin complex (α/β-amyrin palmitate and palmitoleate) is inactive on TGR5.