Synthesis, biological evaluation and structure–activity relationships of glycyrrhetinic acid derivatives as novel anti-hepatitis B virus agents

Wang, Lijun; Geng, Chang‐An; Ma, Yun‐Bao; Huang, Xiaoyan; Luo, Jie; Chen, Hao; Zhang, Xuemei

doi:10.1016/j.bmcl.2012.03.081

Cited by 55 publications

(41 citation statements)

References 38 publications

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“…In this case, the inhibiting effect of HBV DNA replication with IC 50 to 18.37 μM was accompanied by an increase in cytotoxicity, with CC 50 = 35.71 μM. Unfortunately, molecular mechanisms of 5-8 antiviral activities in cells was not completely evaluated [46].…”

Section: Current Issues In Pharmacy and Medical Sciencesmentioning

confidence: 93%

“…Kumada et al [26] and Van Rossum et al [45] reported the potential of GE against Hepatitis C virus (HCV), while Wang et al [46] presented the synthesis, biological evaluation and structure-activity relationships of GE derivatives against Hepatitis B virus (HBV). In such studies, GE derivatives activity against HBV were assessed by measurement of the stage of the viral DNA replication cycle in HepG 2.2.15 cells, and applications of GE analogues were compared with GE as a reference (IC 50 = 39.28 μM) and the nucleoside drug, tenofovir, as a positive control (IC 50 = 0.98 μM).…”

Section: Current Issues In Pharmacy and Medical Sciencesmentioning

confidence: 99%

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Glycyrrhetinic acid and its derivatives in infectious diseases

Langer

Czarczyńska-Goślińska

Gośliński

2016

Current Issues in Pharmacy and Medical Sciences

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Introduction. Licorice or liquorice (Glycyrrhiza glabra, Leguminosae) is a perennial plant naturally occurring or cultivated in Europe and Asia. It was appreciated by many ancient cultures, and was employed within Arabic medicine and (beginning in the Middle Ages) in Europe folk medicine as a remedy for many diseases. Currently, the sweet flavoured root of this plant – Radix Glycyrrhizae (Liquirtiae), is widely taken for the treating of various upper respiratory tract diseases, as well as for gastric ulcer disease. It is also utilized as a sweetening and flavouring agent in the food, tobacco and pharmacy industries. The main active ingredient of liquorice is the triterpenoid saponin, glycyrrhizin, which is a mixture of calcium, magnesium and potassium salts of glycyrrhizic acid (GA). Glycyrrhizic acid is composed of an aglycone, that is 18β-glycyrrhetinic acid (GE), and a D-glucuronic acid dimer. The aim of this review is to discuss some aspects of the activity of glycyrrhetinic acid and its derivatives in infectious diseases.State of knowledge. The pentacyclic system of glycyrrhetinic acid consists of condensed six-membered rings with a hydroxyl group at C-3, a carboxyl moiety at C-30 and a ketone functional group at C-11. Considering the presence of the above mentioned functional groups, many structural transformations have been proposed, including those by way of esterification, alkylation and reduction reactions. The introduction of various chemical residues into its structure, as well as the modification of the glycyrrhetinic acid in its pentacyclic triterpene skeleton, has led to the generation of compounds with many valuable antimicrobial, anti-parasitic, antiviral properties and modified lipophilic parameters.Summary. In summary, glycyrrhetinic acid derivatives appear to have promise as active pharmaceutical ingredients that contain a wide range of biological and pharmacological properties.

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Section: Current Issues In Pharmacy and Medical Sciencesmentioning

confidence: 93%

Section: Current Issues In Pharmacy and Medical Sciencesmentioning

confidence: 99%

Glycyrrhetinic acid and its derivatives in infectious diseases

Langer

Czarczyńska-Goślińska

Gośliński

2016

Current Issues in Pharmacy and Medical Sciences

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“…[16,17] Amongt hese components, the primary active constituent is glycyrrhizic acid (1:( 3 b,20b)-[(2-O-bd-glucopyranuronosyl-a-d-glucopyranuronosyl)oxy]-11-oxo-12oleanen-29-oic acid), which is at riterpene saponin heavily present in the dried roots of G. glabra. [19][20][21][22] Thus, the synthesis of new synthetic derivatives with elevated antitumor activityw as the focus. However,g lycyrrhetic acid has demonstrated poor inhibitory capability when applied to different tumor cell lines in most studies.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of Glycyrrhetic Acid Derivatives as Potential VEGFR2 Inhibitors

et al. 2017

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Vascular endothelial growth factor receptor 2 (VEGFR2) has been proven to play a major role in the regulation of tumor angiogenesis. A series of novel glycyrrhetic acid derivatives were synthesized and evaluated for their VEGFR2 inhibitory activity as well as their antiproliferative properties against four cancer cell lines (MCF-7, HeLa, HepG2, and A549). In vitro biological evaluations against these human tumor cell lines indicate that most of the prepared compounds have antiproliferative activities; compound 3 a (3β-hydroxy-30-(4-phenyl-1-piperazinyl)olean-12-ene-11,30-dione) exhibited the best inhibitory activity against MCF-7 cells, with an IC value of 1.08 μm. Compound 3 a also showed the most potent inhibitory activity against VEGFR2 tyrosine kinase, with an IC value of 0.35 μm. Docking simulations were performed with the aim of discovering the binding mode of compound 3 a, and the results indicate that 3 a could bind at the VEGFR2 active site.

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“…GA has also been reported to exhibit antiviral activity against a variety of viruses, including herpes simplex virus and varicella zoster virus. [48][49][50][51][52][53][54][55][56] Recent evidence is that GA can delay the development of the autoimmune disease [57] and decrease body fat. [58] Because it is a potent inducer of mitochondrial permeability transition, it can also trigger the pro-apoptotic pathway.…”

Section: Introductionmentioning

confidence: 99%