Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

Hu, Chunmei; Luo, Yong-Xin; Wang, Wenjing; Li, Jianping; Li, Mengyue; Zhang, Yufei; Xiao, Di; Lu, Li; Xiong, Zhuang; Feng, Na; Li, Chen

doi:10.3389/fchem.2022.926543

Cited by 6 publications

(8 citation statements)

References 34 publications

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“…NBF, NBF2, and NBF3 were selected to further study for their inhibitory modes because of their potent α -glucosidase inhibitory activities. As in the previous literature [ 22 ], we analyzed the results by double reciprocal curves. As shown in Figure 2 A,B, the lines in the Lineweaver–Burk plots of NBF and NBF2 intersected at the point in the third quadrant, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…Then we further evaluated the five subfractions of NBF, among which NBF2 and NBF3 showed the strongest inhibitory activities against α -glucosidase. There are four types of inhibitors that inhibit α -glucosidase: competitive inhibition, non-competitive inhibition, mixed inhibition, and anti-competitive inhibition [ 22 ]. NBF and NBF2 inhibit α -glucosidase through a mixed inhibitory mode, and NBF3 inhibits α -glucosidase through a non-competitive inhibitory mode.…”

Section: Discussionmentioning

confidence: 99%

“…The kinetic analysis was performed with reference to previous literature [ 21 , 22 ]. In the test, different concentrations of samples (NBF: 0.0, 0.5, 1.0, and 2.0 µg/mL; NBF2 and NBF3: 0.0, 0.25, 0.5, and 1.0 µg/mL) reacted with five various concentrations of p -NPG (0.25, 0.5, 0.75, 1.0, and 1.25 mM), and then the absorbance value was measured at 405 nm.…”

Section: Methodsmentioning

confidence: 99%

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In Vitro and In Vivo Evaluation of Antidiabetic Properties and Mechanisms of Ficus tikoua Bur.

et al. 2022

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In folk medicine, Ficus tikoua (F. tikoua) has been used to treat diabetes for a long time, but there is a rare modern pharmacological investigation for its antidiabetic effect and mechanisms. Our study aimed to evaluate its hypoglycemic effect using in vitro and in vivo experimental models and then explore the possible mechanisms. In the ethanol extracts and fractions of F. tikoua, n−butanol fraction (NBF) exhibited the most potent effect on inhibiting α-glucosidase activity (IC50 = 0.89 ± 0.04 μg/mL) and promoting glucose uptake in 3T3−L1 adipocytes. Further animal experiments showed that NBF could play an antidiabetic role by ameliorating random blood glucose, fasting blood glucose, oral glucose tolerance, HbA1c level, and islets damage in diabetic mice. Then, the activities of the five subfractions of NBF (NBF1−NBF5) were further evaluated; NBF2 showed stronger α−glucosidase inhibition activities (IC50 = 0.32 ± 0.05 μg/mL) than NBF. Moreover, NBF2 also possessed the ability to promote glucose uptake, which was mediated via P13K/AKT and AMPK pathways. This study demonstrated that F. tikoua possesses antidiabetic efficacy in vitro and in vivo and provided a scientific basis for its folk medicinal use. NBF2 might be potential natural candidate drugs to treat diabetes mellitus. It is the first time the antidiabetic activity and the potential mechanisms of NBF2 were reported.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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In Vitro and In Vivo Evaluation of Antidiabetic Properties and Mechanisms of Ficus tikoua Bur.

et al. 2022

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“…Among the coumarin–chalcone derivatives developed by Hu et al (2022) as α-glucosidase inhibitors, compound 102t ( Scheme 25 , Figure 8 ) displayed the highest IC 50 value of 24.09 ± 2.36 μM [ 92 ].…”

Section: Bioactivity Of Coumarins Coumarin–chalcones and Coumarin–tri...mentioning

confidence: 99%

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

Rohman,

Ardiansah,

Wukirsari

et al. 2024

Molecules

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Molecular hybridization represents a new approach in drug discovery in which specific chromophores are strategically combined to create novel drugs with enhanced therapeutic effects. This innovative strategy leverages the strengths of individual chromophores to address complex biological challenges, synergize beneficial properties, optimize pharmacokinetics, and overcome limitations associated with single-agent therapies. Coumarins are documented to possess several bioactivities and have therefore been targeted for combination with other active moieties to create molecular hybrids. This review summarizes recent (2013–2023) trends in the synthesis of coumarins, as well as coumarin–chalcone and coumarin–triazole molecular hybrids. To cover the wide aspects of this area, we have included differently substituted coumarins, chalcones, 1,2,3– and 1,2,4–triazoles in this review and considered the point of fusion/attachment with coumarin to show the diversity of these hybrids. The reported syntheses mainly relied on well-established chemistry without the need for strict reaction conditions and usually produced high yields. Additionally, we discussed the bioactivities of the reported compounds, including antioxidative, antimicrobial, anticancer, antidiabetic, and anti-cholinesterase activities and commented on their IC50 where possible. Promising bioactivity results have been obtained so far. It is noted that mechanistic studies are infrequently found in the published work, which was also mentioned in this review to give the reader a better understanding. This review aims to provide valuable information to enable further developments in this field.

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“…Of the 22 coumarin-chalcone derivatives (3a-3v) synthesized by Hu et al (2022), compounds 3j, 3q, and 3t were significant α-glucosidase inhibitors, as their IC 50 values were 30.30 ± 2.53, 29.74 ± 2.68, 24.09 ± 2.36 μM, respectively, which were all stronger than acarbose [ 27 ].…”

Section: Reviewmentioning

confidence: 99%

A Review of the In Vitro Inhibition of α-Amylase and α-Glucosidase by Chalcone Derivatives

Tran¹,

Tu²,

Hoang³

et al. 2023

Cureus

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Diabetes mellitus is a chronic metabolic disease relating to steady hyperglycemia resulting from the impairment of the endocrine and non-endocrine systems. Many new drugs having varied targets were discovered to treat this disease, especially type 2 diabetes. Among those, α-glucosidase inhibitors showed their effects by preventing the digestion of carbohydrates through their inhibition against α-amylase and αglucosidase. Recently, chalcones have attracted considerable attention as they have a simple structure, are easily synthesized as well as have a variety of derivatives. Some reports suggested that chalcone and its derivates could inhibit α-amylase and α-glucosidase. This narrative review provides a comprehensive evaluation of the inhibition of chalcone and its derivatives against α-amylase and α-glucosidase that were reviewed and reported in published scientific articles. Twenty-eight articles were reviewed after screening 207 articles found in four databases, including PubMed, Google Scholar, VHL (Virtual Health Library), and GHL (Global Health Library). This review presented the inhibitory effects of varied chalcones, including chalcones with a basic structural framework, azachalcones, bis-chalcones, chalcone oximes, coumarinchalcones, cyclohexane chalcones, dihydrochalcones, and flavanone-coupled chalcones. Many of these chalcones had significant inhibition against α-amylase as well as α-glucosidase that were comparable to or even stronger than standard inhibitors. This suggested that such compounds could be potential candidates for the discovery of new anti-diabetic remedies in the years to come.

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Synthesis and Evaluation of Coumarin-Chalcone Derivatives as α-Glucosidase Inhibitors

Cited by 6 publications

References 34 publications

In Vitro and In Vivo Evaluation of Antidiabetic Properties and Mechanisms of Ficus tikoua Bur.

In Vitro and In Vivo Evaluation of Antidiabetic Properties and Mechanisms of Ficus tikoua Bur.

Recent Trends in the Synthesis and Bioactivity of Coumarin, Coumarin–Chalcone, and Coumarin–Triazole Molecular Hybrids

A Review of the In Vitro Inhibition of α-Amylase and α-Glucosidase by Chalcone Derivatives

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