Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

Bildziukevich, Uladzimir; Özdemir, Zülal; Wimmer, Zdeněk

doi:10.3390/molecules24193546

Cited by 49 publications

(29 citation statements)

References 72 publications

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“…The treatment of malignant melanoma usually includes surgery, radiotherapy, and chemotherapy, all of which show a limited selectivity for tumor cells at the same time causing adverse effects to other living cells in the body [14], [16]. For that reason, many studies have focused on using natural products to prevent and/ or treat cancer [8], [16], [17], [18], [19], [20]. Herbs and plants have been a source of prophylaxis and medicinal treatments for thousands of years, although their use was diminished when synthetic drugs were introduced.…”

Section: Discussionmentioning

confidence: 99%

“…Previous results indicate that BA, UA, and OA have pleiotropic biologic activities such as antiinflammatory, cytotoxic, and antiproliferative activities on cancer cells [8], [16]. BA and its derivatives have been extensively researched for their strong cytotoxic properties against melanoma [16], [17]. Recently, OA has attracted more attention due to its marked antitumor effects and pharmacological safety [18].…”

Section: Introductionmentioning

confidence: 99%

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Antiproliferative Activity of Selected Triterpene Acids from Rosemary on Metastatic Melanoma Cell Line WM-266-4

Isaković-Vidović

Dariš

Knez

et al. 2021

Open Access Maced J Med Sci

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BACKGROUND: Natural products and their derivatives, particularly secondary metabolites, have been recognized for many years as an important source of therapeutic agents. In this context, pentacyclic triterpene acids including betulinic acid (BA), oleanolic acid (OA), and ursolic acid (UA) are highly valuable triterpenic acids because of their wide range of biological activities. AIM: Therefore, the aim of our study was to investigate any potential effect of BA, UA, and OA on human melanoma WM-266-4 cells’ proliferation activity. METHODS: BA, UA, and OA have been prepared in dimethyl sulfoxide in concentration range from 0.002 to 200 μM separately or in selected combination (UA+OA ratio 1:1 or 3.5:1), while cells in cell culture medium served as controls. The rapid colorimetric MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay was used to measure proliferation activity of the metastatic melanoma cell line WM-266-4 after being exposed to selected concentrations of BA, UA, OA, or UA+OA and during different time periods. Student’s t-test was used for single statistical comparisons. Data were analyzed using IBM SPSS 25.0 (IBM Corp., Armonk, NY). To account for multiple comparisons bias, p < 0.001 was considered statistically significant. RESULTS: Our results showed decreased cell proliferation activity after 4 h of incubation of WM-266-4 cells with BA, UA, OA, and UA+OA. The highest inhibitory effect was noted when cells were incubated with selected triterpenic acids and both combinations of UA+OA during the incubation period of 48 h. When compared to control cells, concentration of 2 μM was the lowest concentration of BA that showed a significant decrease of the cells’ proliferation activity regardless the incubation period (4 h, 24 h, and 48 h) (p < 0.001). CONCLUSION: Our encouraging results could be a good starting point for further studies on possible use of BA, UA, and OA in prevention and treatment of metastatic melanoma.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Antiproliferative Activity of Selected Triterpene Acids from Rosemary on Metastatic Melanoma Cell Line WM-266-4

Isaković-Vidović

Dariš

Knez

et al. 2021

Open Access Maced J Med Sci

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“…The promising antiviral activity of betulin and betulinic acid was reported by several workers ( Fujioka et al, 1994 ; Pavlova et al, 2003 ). Further studies indicated that betulinic acid acts in the early phase of HIV infection by preventing cleavage of Gag protein, thereby hindering maturation of the virus ( Bildziukevich et al, 2019 ). Again, Navid et al, 2014 demonstrated effective inhibition of herpes virus by analogues of betulin against acyclovir-resistant clinical isolates of HSV-1; also, hepatitis B virus has been found to be susceptible to betulin analogues ( Yao et al, 2009 ; Navid et al, 2014 ).…”

Section: Future Prospectmentioning

confidence: 99%

Plant Products as Inhibitors of Coronavirus 3CL Protease

Mandal¹,

Jha

Hazra

2021

Front. Pharmacol.

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Background: The ongoing COVID-19 pandemic has created an alarming situation due to extensive loss of human lives and economy, posing enormous threat to global health security. Till date, no antiviral drug or vaccine against SARS-CoV-2 has reached the market, although a number of clinical trials are under way. The viral 3-chymotrypsin-like cysteine protease (3CLpro), playing pivotal roles in coronavirus replication and polyprotein processing, is essential for its life cycle. In fact, 3CLpro is already a proven drug discovery target for SARS- and MERS-CoVs. This underlines the importance of 3CL protease in the design of potent drugs against COVID-19.Methods: We have collected one hundred twenty-seven relevant literatures to prepare the review article. PubMed, Google Scholar and other scientific search engines were used to collect the literature based on keywords, like “SARS-CoVs-3CL protease,” “medicinal plant and anti-SARS-CoVs-3CL protease” published during 2003–2020. However, earlier publications related to this topic are also cited for necessary illustration and discussion. Repetitive articles and non-English studies were excluded.Results: From the literature search, we have enlisted medicinal plants reported to inhibit coronavirus 3CL protease. Some of the plants like Isatis tinctoria L. (syn. Isatis indigotica Fort.), Torreya nucifera (L.) Siebold and Zucc., Psoralea corylifolia L., and Rheum palmatum L. have exhibited strong anti-3CLpro activity. We have also discussed about the phytochemicals with encouraging antiviral activity, such as, bavachinin, psoralidin, betulinic acid, curcumin and hinokinin, isolated from traditional medicinal plants.Conclusion: Currently, searching for a plant-derived novel drug with better therapeutic index is highly desirable due to lack of specific treatment for SARS-CoV-2. It is expected that in-depth evaluation of medicinally important plants would reveal new molecules with significant potential to inhibit coronavirus 3CL protease for development into approved antiviral drug against COVID-19 in future.

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“…In the present study, 9 compounds in S. officinalis were screened by ADME criteria, of which Mairin, beta-sitosterol, kaempferol, methyl-2,3,6-tri-O-galloyl-beta-D-glucopyranoside, 3,7,8- Tri-O-methylellagic acid, methyl-6-O-galloyl-beta-D-glucopyranoside, quercetin, and ellagic acid were 8 compounds that shared common targets with H. pylori infection. Mairin was a phytogenic antineoplastic agent, which was also named Betulinic acid, besides anti-tumor, it also had anti-HIV, antimalarial, anti-inflammatory pharmacological activity [ 40 ]. Its anti-tumor activity was related to the regulation of protein kinase B/Akt signaling pathway [ 41 ] and targeted mitochondria to promote apoptosis [ 42 ].…”

Section: Discussionmentioning

confidence: 99%

In vitro anti‐bacterial activity and network pharmacology analysis of Sanguisorba officinalis L. against Helicobacter pylori infection

et al. 2021

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Background Helicobacter pylori (H. pylori) infection has become an international public health problem, and antibiotic-based triple or quadruple therapy is currently the mainstay of treatment. However, the effectiveness of these therapies decreases due to resistance to multiple commonly used antibiotics. Sanguisorba officinalis L. (S. officinalis), a traditional Chinese medicine clinically used for hemostasis and treatment of diarrhea, has various pharmacological activities. In this study, in vitro antimicrobial activity was used for the preliminary evaluation of S. officinalis against H. pylori. And a pharmacology analysis approach was also utilized to elucidate its underlying mechanisms against H. pylori infection. Methods Micro-broth dilution method, agar dilution method, checkerboard assay, scanning electron microscopy (SEM), and transmission electron microscopy (TEM) were used for the assessment of anti-bacterial activity. Active ingredients screening, GO analysis, KEGG analysis, construction of PPI network, molecular docking, and RT-qPCR were used to elucidate the underlying pharmacological mechanisms of S. officinalis against H. pylori infection. Results The minimum inhibitory concentration (MIC) values of S. officinalis against multiple H. pylori strains including clinically isolated multi-drug resistant (MDR) strains were ranging from 160 to 320 µg/ml. These results showed that S. officinalis had additive interaction with four commonly used antibiotics and could exert antibacterial effect by changing the morphology of bacteria without developing drug resistance. Through network pharmacology analysis, 8 active ingredients in S. officinalis were screened out for subsequent studies. Among 222 putative targets of S. officinalis, 49 targets were identified as potential targets for treatment of H. pylori infection. And these 49 targets were significantly enriched in GO processes such as protein kinase B signaling, protein kinase activity, protein kinase binding, and KEGG pathways such as Pathways in cancer, MicroRNAs in cancer, and TNF signaling pathway. Protein-protein interaction analysis yielded 5 core targets (AKT1, VEGFA, EGFR, SRC, CCND1), which were validated by molecular docking and RT-qPCR. Conclusions Overall, this study confirmed the in vitro inhibitory activity of S. officinalis against H. pylori and explored the possible pharmacological mechanisms, laying the foundation for further research and clinical application.

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Recent Achievements in Medicinal and Supramolecular Chemistry of Betulinic Acid and Its Derivatives ‡

Cited by 49 publications

References 72 publications

Antiproliferative Activity of Selected Triterpene Acids from Rosemary on Metastatic Melanoma Cell Line WM-266-4

Antiproliferative Activity of Selected Triterpene Acids from Rosemary on Metastatic Melanoma Cell Line WM-266-4

Plant Products as Inhibitors of Coronavirus 3CL Protease

In vitro anti‐bacterial activity and network pharmacology analysis of Sanguisorba officinalis L. against Helicobacter pylori infection

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