α-Glucosidase and Pancreatic Lipase Inhibitory Activities of Diterpenes from Indian Mango Ginger (Curcuma amada Roxb.) and Its Derivatives

Abstract

Enzymatic inhibitions of crude extracts and their constituents from Zingiberaceae against both rat intestinal α-glucosidase and porcine pancreatic lipase were investigated. Structure–activity relationships using their derivatives were also investigated. The rhizomes extract of mango ginger, Curcuma amada showed remarkable inhibitory activity in the screening test. Two natural labdane diterpenes 1 and 2 and a drimane sesquiterpene 3 were major constituents isolated from this hexane extract. Among them, (E)-labda-8(17),12-diene-15,16-dial (1) was the most prominent compound and showed inhibitory activity against both α-glucosidase and lipase. Derivatives 4–10 from compound 1 were prepared and evaluated using inhibitory assays with these enzymes. The reduced derivative 4 maintained α-glucosidase inhibitory activity, but had decreased pancreatic lipase inhibitory activity compared with parent compound 1. Other tested derivatives of compound 1, including acetates 5–7 and oxidative derivatives 8–10, had very weak α-glucosidase inhibitory activity. Most of these compounds showed moderate pancreatic lipase inhibitory activity. However, only sesquiterpene albicanal (3) showed drastically decreased pancreatic lipase activity compared with 1. These findings suggested that molecular size was essential for enzymatic inhibitory activities of these compounds. These results demonstrated that mango ginger may be useful for the prevention of obesity and being overweight.