Abstract
In this study, we report on an orthogonal strategy for the precise synthesis of 3,3′-, 3,4′-, and 3,6′-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3′-, 4′- and 6′-positions of PSEs.
Highlights
Phenylpropanoid sucrose esters (PSEs, Figure 1) are plant-derived compounds and possess many biological activities, including inhibitory activities against both α-glucosidases and α-amylase [1]
Based on a preliminary structure–activity relationship (SAR) study [6,9,10], we demonstrated that their in vitro inhibition of α-glucosidase and α-amylase depended on the type, number, and position of the phenylpropanoid moieties on the sucrose core and the presence/absence of the di-isopropylidene bridges (Figure 1)
We demonstrated the efficacy of a tetrafeuloyl phenylpropanoid sucrose esters (PSEs) in a mouse model and found it to be as effective as acarbose in controlling the rise in post-prandial blood glucose levels
Summary
Phenylpropanoid sucrose esters (PSEs, Figure 1) are plant-derived compounds and possess many biological activities, including inhibitory activities against both α-glucosidases and α-amylase [1]. AGIs possess an excellent efficacy and safety record, and are represented by the commercial drugs acarbose (the gold standard), voglibose, and miglitol. They function by inhibiting the α-glucosidase enzymes responsible for hydrolyzing carbohydrates in the small intestine, thereby restricting its absorption into the bloodstream [11]. There is a lack of comprehensive and systematic SAR studies identifying the contribution of the type, number, and position of the phenylpropanoid moiety to the inhibition activity. This can be attributed to difficulties in synthesizing PSEs. Molecules 2022, 27, 535 position of the phenylpropanoid moiety to the inhibition activity. Tcohmispplricoacteesds tchaennpoutribfiecuatsieodntporsoycnetshse[s1i6z,e17th].eTphriescpisreolcyessus bcsatnitnuottebdePuSsEesdretoqusyirnetdhefosirzceotmhepprreechiesnelsyivseuSbAstRitustteuddiPeSsE. s required for comprehensive SAR studies
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