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Diabetes mellitus is a chronic disease and one of the fastest-growing health challenges of the last decades. Studies have shown that chronic low-grade inflammation and activation of the innate immune system are intimately involved in type 2 diabetes pathogenesis. Momordica charantia L. fruits are used in traditional medicine to manage diabetes. Herein, we report the purification of a new 23- O -β-d-allopyranosyl-5β,19-epoxycucurbitane-6,24-diene triterpene (charantoside XV, 6 ) along with 25ξ-isopropenylchole-5(6)-ene-3- O -β-d-glucopyranoside ( 1 ), karaviloside VI ( 2 ), karaviloside VIII ( 3 ), momordicoside L ( 4 ), momordicoside A ( 5 ) and kuguaglycoside C ( 7 ) from an Indian cultivar of Momordica charantia . At 50 µM compounds, 2 - 6 differentially affected the expression of pro-inflammatory markers IL-6 , TNF-α , and iNOS , and mitochondrial marker COX-2 . Compounds tested for the inhibition of α-amylase and α-glucosidase enzymes at 0.87 mM and 1.33 mM, respectively. Compounds showed similar α-amylase inhibitory activity than acarbose (0.13 mM) of control (68.0-76.6%). Karaviloside VIII (56.5%) was the most active compound in the α-glucosidase assay, followed by karaviloside VI (40.3%), while momordicoside L (23.7%), A (33.5%), and charantoside XV (23.9%) were the least active compounds. To better understand the mode of binding of cucurbitane-triterpenes to these enzymes, in silico docking of the isolated compounds was evaluated with α-amylase and α-glucosidase.

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Anti-Inflammatory, Antidiabetic Properties and In Silico Modeling of Cucurbitane-Type Triterpene Glycosides from Fruits of an Indian Cultivar of Momordica charantia L.