18β-Glycyrrhetinic Acid Derivatives Possessing a Trihydroxylated A Ring Are Potent Gram-Positive Antibacterial Agents

Huang, Lirong; Hao, Xiao‐Jiang; Li, Qiji; Wang, Dao-Ping; Zhang, Jianxin; Luo, Heng; Xiao-sheng, Yang

doi:10.1021/acs.jnatprod.5b00641

Cited by 35 publications

(31 citation statements)

References 40 publications

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“…The substitution of 18β‐glycyrrhetinic acid with hydroxyl groups in the C‐1 and C‐2 positions enhanced inhibitory activity against Gram–positive bacterial strains ( S. scabies , B. subtilis , S. aureus, MRSA). These derivatives are believed to influence the regulation of the expression of the genes associated with peptidoglycan production, the respiratory metabolism and the inherent virulence factors found in bacteria .…”

Section: Antimicrobial Activity Of Gamentioning

confidence: 99%

“…From a biological perspective, the pentacyclic triterpenoids (PTs), bearing a basic molecular structure with five rings, have attracted much attention due to their pharmacological properties. So, 18β‐glycyrrhetinic acid (GA) and its derivatives exhibit a remarkable broad spectrum of biological and pharmacological activities, including antitumor , anti‐inflammatory , antioxidant , antiviral , antimicrobial , antiulcer , antidiabetic, hepatoprotective , cardioprotective and neuroprotective effects .…”

Section: Introductionmentioning

confidence: 99%

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18β‐Glycyrrhetinic acid: its core biological properties and dermatological applications

Kowalska

Kalinowska-Lis

2019

Intern J of Cosmetic Sci

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Recently, attention has been focused on identifying natural herbal compounds with high biological activity, especially antioxidative, anti‐inflammatory and antimicrobial properties, for preventing and controlling various skin conditions, including inflammation‐related diseases such as atopic dermatitis and UV‐induced skin photoaging. One key active plant ingredient is 18β‐glycyrrhetinic acid (GA), the main metabolite of glycyrrhizin (GL), obtained from licorice root. The review examines the valuable biological properties of GA, particularly those playing key roles in the treatment of various dermatological disorders in humans. The review highlights the key anti‐inflammatory, antioxidant and antimicrobial properties of GA and its toxicity towards normal cells lines. It also examines the physicochemical properties of GA and presents methods of increasing its penetration through the stratum corneum and bioaccumulation with the use of modern delivery systems such as liposomes and nanoemulsions.

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Section: Antimicrobial Activity Of Gamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

18β‐Glycyrrhetinic acid: its core biological properties and dermatological applications

Kowalska

Kalinowska-Lis

2019

Intern J of Cosmetic Sci

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“…Other studies have further shown that the activities of hydroxylated pentacyclic triterpenoids are significantly affected by the number of hydroxyl groups contained in ring A. This was observed on chemically modified 18β-Glycyrrhetinic acid, an oleanane-type triterpene [ 6 ]. Furthermore, a highly hydroxylated and bioactive pentacyclic triterpenoid named 1β, 2α, 3β, 16β, 19β,)-1, 2, 3, 16, 19,pentahydroxyolean-12-en-28-oic acid from E. sieboldiana exhibited modest anticancer activities against human liver carcinoma (HepG2) cells, human cervical cancer cells (HT-3), and normal human carcinoma (HeLa) cells [ 7 ].…”

Section: Introductionmentioning

confidence: 97%

A Review of the Ethnomedicinal Uses, Biological Activities, and Triterpenoids of Euphorbia Species

et al. 2020

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The genus Euphorbia is one of the largest genera in the spurge family, with diversity in range, distribution, and morphology. The plant species in this genus are widely used in traditional medicine for the treatment of diseases, ranging from respirational infections, body and skin irritations, digestion complaints, inflammatory infections, body pain, microbial illness, snake or scorpion bites, pregnancy, as well as sensory disorders. Their successes have been attributed to the presence of diverse phytochemicals like polycyclic and macrocyclic diterpenes with various pharmacological properties. As a result, Euphorbia diterpenes are of interest to chemists and biochemists with regard to drug discovery from natural products due to their diverse therapeutic applications as well as their great structural diversity. Other chemical constituents such as triterpenoids have also been reported to possess various pharmacological properties, thus supporting the traditional uses of the Euphorbia species. These triterpenoids can provide potential leads that can be developed into pharmaceutical compounds for a wide range of medicinal applications. However, there are scattered scientific reports about the anticancer activities of these constituents. Harnessing such information could provide a database of bioactive pharmacopeia or targeted scaffolds for drug discovery. Therefore, this review presents an updated and comprehensive summary of the ethnomedicinal uses, phytochemistry, and the anticancer activities of the triterpenoids of Euphorbia species. Most of the reported triterpenoids in this review belong to tirucallane, cycloartanes, lupane, oleanane, ursane, and taraxane subclass. Their anticancer activities varied distinctly with the majority of them exhibiting significant cytotoxic and anticancer activities in vitro. It is, therefore, envisaged that the report on Euphorbia triterpenoids with interesting anticancer activities will form a database of potential leads or scaffolds that could be advanced into the clinical trials with regard to drug discovery.

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“…The minimum inhibitory concentration (MIC) value was determined with broth microdilution method [21]. …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Evaluation of In Vitro Antibacterial and Antitumor Activities of Novel N,N-Disubstituted Schiff Bases

Luo

Xia

Sun

et al. 2017

Biochemistry Research International

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To get inside the properties of N,N-disubstituted Schiff bases, we synthesized three high-yielding benzaldehyde Schiff bases. We used the reaction between salicylaldehyde and different diamine compounds, including diamine, ethanediamine, and o-phenylenediamine, determining the structure of obtained molecules by nuclear magnetic resonance spectroscopy and electrospray ionization mass spectroscopy. We thus evaluated the microbicidal and antitumor activity of these compounds, showing that salicylaldehyde-hydrazine hydrate Schiff base (compound 1a) significantly inhibited the growth of S. aureus; salicylaldehyde-o-phenylenediamine Schiff base (compound 1c) displayed a strong capability to inhibit the proliferation of leukemia cell lines K562 and HEL. Moreover, we observed that the antibacterial action of 1a might be associated with the regulation of the expression of key virulence genes in S. aureus. Compound 1c resulted in a strong apoptotic activity against leukemia cells, also affecting the cell cycle distribution. Overall, our novel N,N-disubstituted Schiff bases possess unique antibacterial or antitumor activities that exhibit the potent application prospect in prophylactic or therapeutic interventions, providing new insights for developing new antibacterial and anticancer chemical agents.

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18β-Glycyrrhetinic Acid Derivatives Possessing a Trihydroxylated A Ring Are Potent Gram-Positive Antibacterial Agents

Cited by 35 publications

References 40 publications

18β‐Glycyrrhetinic acid: its core biological properties and dermatological applications

18β‐Glycyrrhetinic acid: its core biological properties and dermatological applications

A Review of the Ethnomedicinal Uses, Biological Activities, and Triterpenoids of Euphorbia Species

Synthesis and Evaluation of In Vitro Antibacterial and Antitumor Activities of Novel N,N-Disubstituted Schiff Bases

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