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Journal ArticleDOI

Synthetic methods and biological applications of retrochalcones isolated from the root of Glycyrrhiza species: A review

01 Jan 2021-Vol. 3, pp 100216
TL;DR: In this article, the authors highlight the different synthetic procedures for retrochalcones and their in vitro, in vivo, ex vivo and in silico studies, along with the underlying molecular mechanisms.
Abstract: In the search for novel drugs for health preservation, the active ingredients of medicinal herbs have been used since time immemorial. Liquorice, a potent medicinal herb derived from the root and rhizomes of Glycyrrhiza species, has been used worldwide for the treatment of various diseases. A number of compounds have been isolated from the liquorice root, including retrochalcones, viz. echinatin, licochalcone A, B, C, D and E, having a diverse range of pharmacological applications such as antioxidant, anti-inflammatory, anti-cancer, anti-bacterial, anti-diabetic, anti-obesity, anti-parasitic, to name a few. This review highlights the different synthetic procedures for retrochalcones and their in vitro, in vivo, ex vivo and in silico studies, along with the underlying molecular mechanisms. In addition, the total syntheses of licochalcone F and H, the regioisomers of licochalcone E and C, respectively, have also been included. Herein, the maximum possible biological applications of retrochalcones cited so far in the literature have been reviewed. The insights from this review will further advance the role and application of retrochalcones in the field of medicinal chemistry.
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Journal ArticleDOI
TL;DR: In this article , the authors have reported the antioxidant mechanisms and structure-antioxidant activity relationship of several chalcone derivatives, investigated in the recent past, based on the density functional theory (DFT) calculations, considering free radical scavenging and metal chelation ability.
Abstract: Abstract In this review, we have reported the antioxidant mechanisms and structure-antioxidant activity relationship of several chalcone derivatives, investigated in the recent past, based on the density functional theory (DFT) calculations, considering free radical scavenging and metal chelation ability. The antioxidant mechanisms include hydrogen atom transfer (HAT), sequential proton loss electron transfer (SPLET), single electron transfer followed by proton transfer (SET-PT), sequential proton loss hydrogen atom transfer (SPLHAT), sequential double proton loss electron transfer (SdPLET), sequential triple proton loss double electron transfer (StPLdET), sequential triple proton loss triple electron transfer (StPLtET), double HAT, double SPLET, double SET-PT, triple HAT, triple SET-PT, triple SPLET, proton-coupled electron transfer (PCET), single electron transfer (SET), radical adduct formation (RAF) and radical adduct formation followed by hydrogen atom abstraction (RAF-HAA). Furthermore, solvent effects have also been considered using different solvation models. The feasibility of scavenging different reactive oxygen and nitrogen species (ROS/RNS) has been discussed considering various factors such as the number and position of hydroxyl as well as methoxy groups present in the antioxidant molecule, stability of the species formed after scavenging reactive species, nature of substituent, steric effects, etc. This review opens new perspectives for designing new compounds with better antioxidant potential. Graphical Abstract

8 citations

Journal ArticleDOI
TL;DR: In this paper , the effect of licorice compounds against P. vivax Duffy binding protein (DBP) was studied and a molecular docking study was performed to analyze the interaction of licore compounds with the DARC binding site of DBP.
Abstract: Plasmodium vivax (P. vivax) is one of the human’s most common malaria parasites. P. vivax is exceedingly difficult to control and eliminate due to the existence of extravascular reservoirs and recurring infections from latent liver stages. Traditionally, licorice compounds have been widely investigated against viral and infectious diseases and exhibit some promising results to combat these diseases. In the present study, computational approaches are utilized to study the effect of licorice compounds against P. vivax Duffy binding protein (DBP) to inhibit the malarial invasion to human red blood cells (RBCs). The main focus is to block the DBP binding site to Duffy antigen receptor chemokines (DARC) of RBC to restrict the formation of the DBP–DARC complex. A molecular docking study was performed to analyze the interaction of licorice compounds with the DARC binding site of DBP. Furthermore, the triplicates of molecular dynamic simulation studies for 100 ns were carried out to study the stability of representative docked complexes. The leading compounds such as licochalcone A, echinatin, and licochalcone B manifest competitive results against DBP. The blockage of the active region of DBP resulting from these compounds was maintained throughout the triplicates of 100 ns molecular dynamic (MD) simulation, maintaining stable hydrogen bond formation with the active site residues of DBP. Therefore, the present study suggests that licorice compounds might be good candidates for novel agents against DBP-mediated RBC invasion of P. vivax.

2 citations

References
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Journal ArticleDOI
TL;DR: A preliminary biological investigation on the synthesized small series of chloro-1,4-dimethyl-9H-carbazoles shows a nitro-derivative showed the most interesting profile representing a suitable lead for the development of novel anti-HIV drugs.
Abstract: Background: Despite the progress achieved by anti-retroviral drug research in the last decades, the discovery of novel compounds endowed with selective antiviral activity and reduced side effects is still a necessity. At present, the most urgent requirement includes the improvement of HIV (Human Immunodeficiency Virus) prevention and sexual transmission and the development of new drugs to treat the chronic lifelong infection. Methods: Six chloro-1,4-dimethyl-9H-carbazoles (2a,b–4a,b) have been prepared following opportunely modified known chemical procedures and tested in luciferase and Escherichia coli β-galactosidase expressing CD4+, CXCR4+, CCR5+ TZM-bl cells. Results and Conclusion: a preliminary biological investigation on the synthesized small series of chloro-1,4-dimethyl-9H-carbazoles has been carried out. Among all tested compounds, a nitro-derivative (3b) showed the most interesting profile representing a suitable lead for the development of novel anti-HIV drugs.

478 citations

Journal ArticleDOI
TL;DR: This review will be helpful for the further studies of licorice for its potential therapeutic effects as an antiviral or an antimicrobial agent.

357 citations

Journal ArticleDOI
TL;DR: An updated, critical, and extensive overview on the current knowledge of G. glabra composition and biological activities is provided here in order to explore its therapeutic potential and future challenges to be utilized for the formulation of new products that will contribute to human well‐being.
Abstract: In the last years, consumers are paying much more attention to natural medicines and principles, mainly due to the general sense that natural compounds are safe. On the other hand, there is a growing demand by industry for plants used in traditional medicine that could be incorporated in foods, nutraceuticals, cosmetics, or even pharmaceuticals. Glycyrrhiza glabra Linn. belongs to the Fabaceae family and has been recognized since ancient times for its ethnopharmacological values. This plant contains different phytocompounds, such as glycyrrhizin, 18β-glycyrrhetinic acid, glabrin A and B, and isoflavones, that have demonstrated various pharmacological activities. Pharmacological experiments have demonstrated that different extracts and pure compounds from this species exhibit a broad range of biological properties, including antibacterial, anti-inflammatory, antiviral, antioxidant, and antidiabetic activities. A few toxicological studies have reported some concerns. This review addresses all those issues and focuses on the pharmacological activities reported for G. glabra. Therefore, an updated, critical, and extensive overview on the current knowledge of G. glabra composition and biological activities is provided here in order to explore its therapeutic potential and future challenges to be utilized for the formulation of new products that will contribute to human well-being.

356 citations

Journal ArticleDOI
TL;DR: The results suggest that ZNF132 plays an important role in the development of ESCC as a tumor suppressor gene and support the underlying mechanism caused by the DNA hypermethylation-mediated Sp1-binding decay and gene silencing.
Abstract: Epigenetic alteration of tumor suppression gene is one of the most significant indicators in human esophageal squamous cell carcinoma (ESCC). In this study, we identified a novel ESCC hypermethylation biomarker ZNF132 by integrative computational analysis to comprehensive genome-wide DNA methylation microarray dataset. We validated the hypermethylation status of ZNF132 in 91 Chinese Han ESCC patients and adjacent normal tissues with methylation target bisulfite sequencing (MTBS) assay. Meanwhile, ZNF132 gene silencing mediated by hypermethylation was confirmed in both solid tissues and cancer cell lines. What is more, we found that in vitro overexpression of ZNF132 in ESCC cells could significantly reduce the abilities of the cell in growth, migration and invasion, and tumorigenicity of cells in a nude mouse model. We validated the Sp1-binding site in the ZNF132 promoter region with chromatin immunoprecipitation assay and demonstrated that the hypermethylation status could reduce the Sp1 transcript factor activity. Our results suggest that ZNF132 plays an important role in the development of ESCC as a tumor suppressor gene and support the underlying mechanism caused by the DNA hypermethylation-mediated Sp1-binding decay and gene silencing.

339 citations

Journal ArticleDOI
TL;DR: This review summarizes the ever changing information on antibacterial activity of flavonoids since 2005, with a special focus on the structure–activity relationship and mechanisms of actions of this broad class of natural compounds.
Abstract: Based on World Health Organization reports, resistance of bacteria to well-known antibiotics is a major global health challenge now and in the future. Different strategies have been proposed to tackle this problem including inhibition of multidrug resistance pumps and biofilm formation in bacteria and development of new antibiotics with novel mechanism of action. Flavonoids are a large class of natural compounds, have been extensively studied for their antibacterial activity, and more than 150 articles have been published on this topic since 2005. Over the past decade, some promising results were obtained with the antibacterial activity of flavonoids. In some cases, flavonoids (especially chalcones) showed up to sixfold stronger antibacterial activities than standard drugs in the market. Some synthetic derivatives of flavonoids also exhibited remarkable antibacterial activities with 20- to 80-fold more potent activity than the standard drug against multidrug-resistant Gram-negative and Gram-positive bacteria (including Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus). This review summarizes the ever changing information on antibacterial activity of flavonoids since 2005, with a special focus on the structure-activity relationship and mechanisms of actions of this broad class of natural compounds.

309 citations