Mono-n-butyl Malate-Derived Compounds from Camu-camu (Myrciaria dubia) Malic Acid: The Alkyl-Dependent Antihyperglycemic-Related Activity Article Swipe
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· 2022
· Open Access
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· DOI: https://doi.org/10.1021/acsomega.2c05551
· OA: W4306822045
Malic acid derivatives from camu-camu (<i>Myrciaria dubia</i>) fruit exhibited a strong in vitro inhibitory activity toward pancreatic α-amylase and α-glucosidase enzymes. During a bioguided chromatographic fractionation process of the whole fruit (pulp and peelings) polar extract, isomers (<i>S</i>)-4-butoxy-2-hydroxy-4-oxobutanoic acid (<b>1</b>) and (<i>S</i>)-4-butoxy-3-hydroxy-4-oxobutanoic acid (<b>2</b>) (84:16) were isolated and identified as a potent inhibitor of α-amylase (IC<sub>50</sub>= 11.69 ± 1.75 μg/mL) and α-glucosidase (IC<sub>50</sub> = 102.69 ± 4.16 μg/mL). The chemical structures were confirmed by HPLC-ESIMS and <sup>1</sup>H and <sup>13</sup>C NMR (one- and two-dimensional) analyses. The structure-based virtual screening demonstrated that the aliphatic moiety plays a significant role in the binding mode of the test alkyl malate esters. Compound <b>1</b> exhibited the best interaction profile to bind both enzymes, having key structural features to form relevant contacts by involving adequate enzyme-ligand complex stabilization and compactness over time.
