Identification of α-Amylase and α-Glucosidase Inhibitors and Ligularoside A, a New Triterpenoid Saponin from Passiflora ligularis Juss (Sweet Granadilla) Leaves, by a Nuclear Magnetic Resonance-Based Metabolomic Study

Abstract

[Abstract] The leaves of Passiflora ligularis Juss (known as sweet granadilla for its edible fruits) are a crop byproduct that is discarded. With the aim of contributing to give value-added products from these crop by-side products to farmers of Colombian Andes, we carried out a 1H-NMR-metabolomics analysis of polar extracts from leaves collected in three locations and stored in two conditions in order to identify glucosyl-hydrolase inhibitors. Variations in the metabolic profile and the bioactivity among samples were analyzed by orthogonal partial least square discriminant analysis. Thus, 1H-NMR signals related to polyphenolic compounds, saponins, and amino acids were correlated with higher inhibitory activities. Moreover, a targeted NMR and HPLC–MS/MS analysis allowed the identification of 14 polyphenolic compounds and the structural characterization of a new triterpenoid saponin, ligularoside A. The measurements of IC50 values for α-amylase and α-glycosidase inhibitors allowed the identification of quercetin-3-O-β-glucoside, kaempferol-3-O-β-glucoside, and ligularoside A as the most active compounds. These results suggest that P. ligularis leaves are a source of glucosyl-hydrolase inhibitors and lay the foundation for exploring additional applications.