Synthesis and evaluation of ent-Conduramine C-1 derivatives as α-glucosidase inhibitors via CSI-mediated amination reaction

Park, Gi Min; Kong, Sun Ju; Park, Jae Hyeon; Kang, Ji Eun; An, Sung Hwan; Kim, Hyung Sik; Kim, In Su; Boggu, Pulla Reddy; Jung, Young Hoon

doi:10.1016/j.carres.2023.108746

Cited by 1 publication

(3 citation statements)

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“…Sweeteners are a ubiquitous component of the human diets . Previous studies have indicated that they may have an impact on enzymes located in the lumen of the gut, as well as the downstream glycemic response . The α-glucosidase enzyme is located in the small intestinal brush border, where it is key for food digestion and plays a significant role in regulating the quantity of glucose released, thereby influencing glycemic variability .…”

Section: Resultsmentioning

confidence: 99%

“…29 Previous studies have indicated that they may have an impact on enzymes located in the lumen of the gut, as well as the downstream glycemic response. 30 The α-glucosidase enzyme is located in the small intestinal brush border, where it is key for food digestion and plays a significant role in regulating the quantity of glucose released, thereby influencing glycemic variability. 30 This study determined the inhibitory rates of the commonly used sweetener candidates with different degrees of sweetness against αglucosidase using acarbose as the positive reference.…”

Section: Discovery Of a Potential α-Glucosidasementioning

confidence: 99%

“…30 The α-glucosidase enzyme is located in the small intestinal brush border, where it is key for food digestion and plays a significant role in regulating the quantity of glucose released, thereby influencing glycemic variability. 30 This study determined the inhibitory rates of the commonly used sweetener candidates with different degrees of sweetness against αglucosidase using acarbose as the positive reference. The results indicate that the natural sweetener GAMG is a novel and remarkably potent α-glucosidase inhibitor, outperforming other potentially beneficial natural and artificial sweeteners in terms of its α-glucosidase inhibitory activity (Figure 1a,b).…”

Section: Discovery Of a Potential α-Glucosidasementioning

confidence: 99%

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Natural Sweetener, Glycyrrhetinic Acid 3-O-Mono-beta-d-glucuronide, for Postprandial Hyperglycemia Management

Guo,

Zhang,

Fei

et al. 2024

J. Agric. Food Chem.

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This study examines the inhibitory effects of a range of sweeteners on α-glucosidase. Our findings revealed that only one natural sweetener, namely, glycyrrhetinic acid 3-O-mono-beta-d-glucuronide (GAMG), derived from licorice, exhibited a mixed-type inhibition against α-glucosidase with a IC50 value of 0.73 ± 0.05 mg/mL. The fluorescence intensity of α-glucosidase was quenched by GAMG in the formation of an α-glucosidase–GAMG complex. GAMG has been shown to induce conformational changes in α-glucosidase, likely through hydrogen bonding, van der Waals force, and alkyl–alkyl interactions with amino acid residues, including Arg 281, Leu 283, Trp 376, Asp 404, Asp 443, Trp 481, Asp 518, Phe 525, Ala 555, and Asp 616. Additional animal validation experiments demonstrated that GAMG slowed starch digestion, thereby attenuating the postprandial glycemic response. Taken together, these findings provide evidence that GAMG is a natural sweetener with potent inhibitory activity that selectively targets α-glucosidase. This study supports the use of GAMG as a natural sweetener, which holds a high biological value and may be beneficial for managing postprandial hyperglycemia.

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Section: Resultsmentioning

confidence: 99%