ABSTRACT
A new natural Diels-Alder adduct (3) was isolated from the leaves and stem bark of Artocarpus integer, along with seventeen known compounds (1, 2, and 4-18). Structural elucidation was conducted using NMR and HR-ESI-MS data, and comparisons were made with previous studies. Deoxyartoninâ I (3) exhibited the most potent α-glucosidase inhibition (IC50 7.80±0.1â µM), outperforming the acarbose positive control. This was mixed-mode inhibition, as indicated by the intersect in the second quadrant of each respective plot. An inâ silico molecular docking model and the pharmacokinetic features of 3 suggest that it is a potential inhibitor of enzyme α-glucosidase, and is therefore a lead candidate as a drug against diabetes mellitus.
Subject(s)
Artocarpus/chemistry , Glycoside Hydrolase Inhibitors/pharmacology , Molecular Docking Simulation , Plant Extracts/pharmacology , alpha-Glucosidases/metabolism , Dose-Response Relationship, Drug , Glycoside Hydrolase Inhibitors/chemistry , Glycoside Hydrolase Inhibitors/isolation & purification , Humans , Plant Components, Aerial/chemistry , Plant Extracts/chemistry , Plant Extracts/isolation & purificationABSTRACT
A novel dimeric alkylresorcinol derivative, manilkzapotane (1), along with seven known compounds, lupeol acetate (2), lupeol (3), arjunolic acid (4), ergosterol peroxide (5), taraxerol (6), hederagonic acid (7), and glochidiol (8) were isolated from the stem bark of Manilkara zapota. Their structures were determined on the basis of spectroscopic data. DFT-NMR chemical shift calculations and a modified probability (DP4+) method were applied to define the relative configuration of 1. To the best of our knowledge, this represents the first isolation of a dimeric alkylresorcinol derivative from the Sapotaceae family.
