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Advisor(s)
Abstract(s)
2-Styrylchromones (2-SC) are a small class of naturally-occurring oxygen-containing heterocycles. Although
they are scarce in nature, a large number of 2-SC derivatives has been synthesized and their biological activ ity
evaluated, namely as antiallergic, anti-inflammatory, antimicrobial, antioxidant and antitumor agents [l]. As far
as we know, the antidiabetic activity of 2-SC is still unexplored. With this rational in mind, a series of 12
polyhydroxylated derivatives of 2-SC (1) were synthethized and used as inhibitors of the carbohydrate
hydrolyzing enzyme a-glucosidase. This enzyme catalyzes the final step of the digestive process of starch and
break down oligosaccharides to monosaccharides being one of the most currently used therapeutic approaches to
decrease postprandial hyperglycemia and consequently to control type 2 diabetes mellitus [2].
The synthesis of polyhydroxylated 2-SC involves a multi-step strategy starting with the condensation of the
appropriate 2'-hydroxyacetophenones with cinnamic acid derivatives, base-promoted Baker- Yenkataraman
rearrangement of the esters formed, cyclodehydration and finnaly cleavage of the protecting groups to afford the
desired polyhydroxylated 2-SC (3]. The in vitro assay to evaluate the inhibitory activity of the compounds under
study and the positive control, acarbose, against a-glucosidase was performed by monitoring the hydrolysis of
the substrate p-nitrophenyl glucopyranoside into the product p-nitrophenol at 405 nm. In addition, the study of
the inhibition type was carried out through nonlinear regression Michaelis-Menton enzymatic kinetics and the
corresponding Lineweaver-Burk plot [4].
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Pedagogical Context
Citation
Santos, Clementina; Proença, Carina; Freitas, Marisa; Araújo, A.N.; Silva, Artur; Fernandes, Eduarda (2019). Synthesis and in vitro α-glucosidase inhibitory activity of polyhydroxylated 2-styrylchromones. In Bioheterocycles 2019 – XVIII International Conference on Heterocycles in Bioorganic Chemistry. Ghent, Bélgica