Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives

Yang, Yang; Zhu, Qi; Zhong, Yingying; Cui, Xiping; Jiang, Zhengyun; Wu, Panpan; Zheng, Xi; Zhang, Kun; Zhao, Suqing

doi:10.1016/j.bioorg.2020.103985

Cited by 39 publications

(21 citation statements)

References 38 publications

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“…However, GA is poorly soluble in water with low bioavailability, and long-term use can cause hyperaldosteronism: these factors limit its application greatly. To improve the activity of GA, the structure has been modified, and good results have been achieved [ 21 , 22 , 23 , 24 , 25 ]. Simultaneously, it has been found that GA can target hepatocyte membranes [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Grafting of 18β-Glycyrrhetinic Acid and Sialic Acid onto Chitosan to Produce a New Amphipathic Chitosan Derivative: Synthesis, Characterization, and Cytotoxicity

Quan

Kong

et al. 2021

Molecules

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Chitosan is the only cationic polysaccharide found in nature. It has broad application prospects in biomaterials, but its application is limited due to its poor solubility in water. A novel chitosan derivative was synthesized by amidation of chitosan with 18β-glycyrrhetinic acid and sialic acid. The chitosan derivatives were characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, and measurement of the zeta potential. We also investigated the solubility, cytotoxicity, and blood compatibility of chitosan derivatives. 18β-glycyrrhetinic acid and sialic acid could be grafted onto chitosan molecular chains. The thermal stability of the synthesized chitosan derivatives was decreased and the surface was positively charged in water and phosphate-buffered saline. After chitosan had been modified by 18 β-glycyrrhetinic acid and sialic acid, the solubility of chitosan was improved greatly in water and phosphate-buffered saline, and percent hemolysis was <5%. Novel amphiphilic chitosan derivatives could be suitable polymers for biomedical purposes.

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Section: Introductionmentioning

confidence: 99%

Grafting of 18β-Glycyrrhetinic Acid and Sialic Acid onto Chitosan to Produce a New Amphipathic Chitosan Derivative: Synthesis, Characterization, and Cytotoxicity

Quan

Kong

et al. 2021

Molecules

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“…Recently, C2-chalcones of 18β-glycyrrhetinic acid were described as promising bio-functional agents with anti-inflammatory and antimicrobial activities. [16] C2-benzylidene derivatives of ursolic acid, obtained by three component reaction with indole and substituted benzaldehydes, are new hybrid compounds against glioma cell proliferation. [17] Other ursolic acid derivatives were synthesized by introducing benzylidene moiety at C2 accompining with an aminoguanidine moiety at C3 and exhibited high levels of antibacterial activity against Gram-positive and Gram-negative bacterial strains.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and alpha ‐ inhibitory activity of lupane type С2‐benzylidene‐ triterpenoids

Khusnutdinova

Hà

Giniyatullina

et al. 2021

Vietnam Journal of Chemistry

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A series of novel and previously synthesized lupane type С2‐benzylidene derivatives was evaluated on α‐glucosidase enzyme inhibition. Most of the tested compounds exhibited significantly better activity (1.8‐700 times higher) than the standard drug acarbose. The structure‐activity relationship indicated that the type of benzylidene moiety and C28‐substituent of lupane core plays an important influence on the activity. Methyl 2‐furfurylidene betulonate, m‐iodo‐benzylidene betulonic acid and 3‐pyridinylideno‐betulonic acid hydrazide have been founded as effective α‐glucosidase inhibitors and deserve further attention.

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“…The hydroxy group at position C-3 and the carboxyl group at position C-30 are the main functional groups. Currently, chemical strategies are mainly used for modification of GA (Yang et al, 2020). Introduction of protected or de-protected amino acids have been shown to increase GA activity (Schwarz et al, 2014).…”

Section: Chemical Structure Of Gamentioning

confidence: 99%

“…Introduction of protected or de-protected amino acids have been shown to increase GA activity (Schwarz et al, 2014). By esterification of the C-3 and C-30 positions in GA, different GA groups can be introduced and other derivatives can be formed, and these derivatives have been shown to improve the activities of the GA-derived components (Maitraie et al, 2009;Schwarz and Csuk, 2010;Yang et al, 2020). Nowadays, the cost of chemical synthesis of GA is high, while the yield is low (Wang C. et al, 2019).…”

Section: Chemical Structure Of Gamentioning

confidence: 99%

Metabolic Engineering for Glycyrrhetinic Acid Production in Saccharomyces cerevisiae

Guan

Wang

Guan

et al. 2020

Front. Bioeng. Biotechnol.

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Glycyrrhetinic acid (GA) is one of the main bioactive components of licorice, and it is widely used in traditional Chinese medicine due to its hepatoprotective, immunomodulatory, anti-inflammatory and anti-viral functions. Currently, GA is mainly extracted from the roots of cultivated licorice. However, licorice only contains low amounts of GA, and the amount of licorice that can be planted is limited. GA supplies are therefore limited and cannot meet the demands of growing markets. GA has a complex chemical structure, and its chemical synthesis is difficult, therefore, new strategies to produce large amounts of GA are needed. The development of metabolic engineering and emerging synthetic biology provide the opportunity to produce GA using microbial cell factories. In this review, current advances in the metabolic engineering of Saccharomyces cerevisiae for GA biosynthesis and various metabolic engineering strategies that can improve GA production are summarized. Furthermore, the advances and challenges of yeast GA production are also discussed. In summary, GA biosynthesis using metabolically engineered S. cerevisiae serves as one possible strategy for sustainable GA supply and reasonable use of traditional Chinese medical plants.

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Synthesis, anti-microbial and anti-inflammatory activities of 18β-glycyrrhetinic acid derivatives

Cited by 39 publications

References 38 publications

Grafting of 18β-Glycyrrhetinic Acid and Sialic Acid onto Chitosan to Produce a New Amphipathic Chitosan Derivative: Synthesis, Characterization, and Cytotoxicity

Grafting of 18β-Glycyrrhetinic Acid and Sialic Acid onto Chitosan to Produce a New Amphipathic Chitosan Derivative: Synthesis, Characterization, and Cytotoxicity

Synthesis and alpha ‐ inhibitory activity of lupane type С2‐benzylidene‐ triterpenoids

Metabolic Engineering for Glycyrrhetinic Acid Production in Saccharomyces cerevisiae

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