Synthesis of new curcumin derivatives as influential antidiabetic α-glucosidase and α-amylase inhibitors with anti-oxidant activity

Tavaf, Zohreh; Dangolani, Soheila Khajeh; Yousefi, Reza; Panahi, Farhad; Shahsavani, Mohammad Bagher; Khalafi‐Nezhad, Ali

doi:10.1016/j.carres.2020.108069

Cited by 22 publications

(11 citation statements)

References 25 publications

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“…When natural organic molecules to be used in MCR, it is possible to synthesize complex natural-like products which are very useful in drug design and synthesis. Along this line, we have disclosed some MCRs including small natural organic molecules such as carbohydrates and nucleosides for the synthesis of diverse biologically active compounds [26,27]. We have also synthesized an interesting class of natural product-like compounds using curcumin as starting material.…”

Section: Resultsmentioning

confidence: 99%

The assessment of antidiabetic properties of novel synthetic curcumin analogues: α-amylase and α-glucosidase as the target enzymes

Hasaninezhad

Tavaf

Panahi

et al. 2020

J Diabetes Metab Disord

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Diabetes mellitus is a metabolic disorder characterized by high blood glucose levels and instability in carbohydrate metabolism. For treating diabetes, one important therapeutic approach is reducing the postprandial hyperglycemia which can be managed by delaying the absorption of glucose through inhibition of the carbohydrate-hydrolyzing enzymes, α-amylase (α-Amy) and αglucosidase (α-Gls) in the digestive tract. In this work, a new class of curcumin derivatives incorporating pyrano[2,3-d]pyrimidine heterocycles was synthesized using a multicomponent reaction between curcumin, aldehydes, and barbituric acid. Using UV-Vis spectroscopic method, the synthetic compounds were assessed for their inhibitory properties against α-Amy and α-Gls enzymes. Also, the antioxidant potential of these compounds was measured spectroscopically and compared with Trolox which is known as a gold standard to measure antioxidant capacity. The results of present study suggest that the curcumin derivatives were able to efficiently inhibit both yeast and mammalian α-Gls. In comparison with the antidiabetic medicine acarbose, the synthetic curcumin derivatives were also capable to inhibit more effectively the yeast α-Gls. The partial inhibitory effects of these compounds against pancreatic α-Amy were also important in the terms of avoiding development of the possible gastrointestinal side effects. Moreover, some of the curcumin derivatives indicated stronger antioxidant activity than Trolox. Overall, these synthetic curcumin analogues might be considered as novel molecular templates for development of efficient antidiabetic compounds with promising inhibitory activities against α-Amy and α-Gls enzymes.

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Section: Resultsmentioning

confidence: 99%

The assessment of antidiabetic properties of novel synthetic curcumin analogues: α-amylase and α-glucosidase as the target enzymes

Hasaninezhad

Tavaf

Panahi

et al. 2020

J Diabetes Metab Disord

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“…Zohreh et al . reported the synthesis of a new class of curcumin derivatives using a multicomponent reaction containing curcumin, aldehydes, and malononitrile and conducted antidiabetic α‐glucosidase and α‐amylase inhibitors with antioxidant activity [84] . The findings reveal that four out of five synthetic compounds indicated an improved inhibition activity against both enzymes.…”

Section: Miscellaneous Agentsmentioning

confidence: 99%

The Multi‐Biological Targeted Role of Dehydrozingerone and its Analogues

et al. 2022

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Curcumin (Cur) has shown its potential in the treatment of a wide variety of ailments. As a result, several investigations on curcumin have been conducted in vitro, in vivo, and in clinical trials. Regrettably, researchers have largely lost interest in this excellent scaffold due to its chemical instability, poor solubility, and rapid metabolism, which directly affect its pharmacological properties. Alternatively, the researchers are working on it to improve the solubility and biological half-life, it is one of the most researched natural phytochemical to date. Among these, Dehydrozingerone (DZG), a curcumin half structure has garnered considerable research interest due to a wide spectrum of its biological activities. Thus, this study offers insight into the pharmacological activity of modified DZG conjugates (incorporate multiple effective modifications to the various positions), which have been developed since 2016. Additionally, the structure-activity relationship (SAR) of DZG hybrids was illustrated for their specific pharmacological properties. This review presents an update for the scientific community, which could assist in addressing the gaps, challenges and pharmacological aspects of DZG.

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“…New curcuminoids incorporating 4 H -pyran heterocycles were prepared by one-pot condensation of curcumin with propanodinitrile and a substituted benzenecarbaldehyde ( Scheme 48 ) [ 443 ]. The consequent modification of β -dicarbonyl moiety improved inhibition of the α-glucosidase, one of the enzymes responsible for carbohydrate hydrolyses and therefore for postprandial hyperglycemia.…”

Section: Curcumin and Curcuminoidsmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored.

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Synthesis of new curcumin derivatives as influential antidiabetic α-glucosidase and α-amylase inhibitors with anti-oxidant activity

Cited by 22 publications

References 25 publications

The assessment of antidiabetic properties of novel synthetic curcumin analogues: α-amylase and α-glucosidase as the target enzymes

The assessment of antidiabetic properties of novel synthetic curcumin analogues: α-amylase and α-glucosidase as the target enzymes

The Multi‐Biological Targeted Role of Dehydrozingerone and its Analogues

Tailored Functionalization of Natural Phenols to Improve Biological Activity

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