GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea

Elhady, Sameh S.; Goda, Marwa S.; Nafie, Mohamed S.; Ibrahim, El-Nobi A.; Diri, Reem; Alahdal, Abdulrahman M.; Thomford, Ama Kyeraa; Gindy, Alaa El; Hadad, Ghada M.; Badr, Jihan M.; Abdelhameed, Reda F. A.

doi:10.3390/molecules27134109

Cited by 6 publications

(4 citation statements)

References 34 publications

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“…The binding score for BCL-2 was near that of icterogenin, an oleanan-type triterpene inhibitor of BCL-2 ( Table 2 , Figure 6 ) [ 33 ], and that for EGFR was close to that of betulinic acid, which affects the EFGR protein ( Figure 7 ) [ 34 ]. For the anti-apoptotic protein BCL-2, T1m produced lower binding energies than its source triterpene ( T1 ).…”

Section: Resultsmentioning

confidence: 99%

Lupane Triterpene Derivatives Improve Antiproliferative Effect on Leukemia Cells through Apoptosis Induction

et al. 2022

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Leukemia is one of the most frequent types of cancer. No effective treatment currently exists, driving a search for new compounds. Simple structural modifications were made to novel triterpenes isolated from Phoradendron wattii. Of the three resulting derivatives, 3α-methoxy-24-hydroxylup-20(29)-en-28-oic acid (T1m) caused a decrease in the median inhibitory concentration (IC50) on the K562 cell line. Its mode of action was apparently apoptosis, ROS generation, and loss of mitochondrial membrane potential (MMP). Molecular docking analysis showed T1m to produce lower binding energies than its precursor for the Bcl-2 and EGFR proteins. Small, simple, and viable modifications to triterpenes can improve their activity against leukemia cell lines. T1m is a potentially promising element for future research. Clarifying the targets in its mode of action will improve its applicability.

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Section: Resultsmentioning

confidence: 99%

Lupane Triterpene Derivatives Improve Antiproliferative Effect on Leukemia Cells through Apoptosis Induction

et al. 2022

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“…Compound 5 is a commonly occurring phytosterol called β-sitosterol, which is a key component present in plants. Out of the many pharmacological and biological effects that have been reported for this compound over the past decades, anti-inflammatory, angiogenic, antiadipogenic, anti-diabetic, anti-oxidant, anti-cancer, immunomodulatory activities and a role in cardiovascular diseases prevention can be mentioned, reported from recent findings that can be beneficial in drug developments and other therapeutic applications [45][46][47][48][49][50][51]. The hypocholesterolemic effects of E. hirta and its role in curing obesity have been linked to this natural compound [22], as well as the larvicidal activity of E. thymifolia [21].…”

Section: Discussionmentioning

confidence: 99%

“…13 C NMR data (CDCl 3 , 100 MHz): 33.5 (C-1), 25.4 (C-2), 76.0 (C-3), 37.5 (C-4),48.8 (C-5), 18.2 (C-6), 35.2 (C-7), 43.5 (C-8), 55.8 (C-9), 38.2 (C-10), 68.4 (C-11), 128.7 (C-12), 142.9 (C-13), 42.2 (C-14), 27.9 (C-15), 27.7 (C-16), 33.6 (C-17), 58.1 (C-18), 39.4 (C-19), 39.3 (C-20), 31.1 (C-21), 41.3 (C-22), 28.7 (C-23), 22.4 (C-24), 16.6 (C-25), 18.0 (C-26), 23.3 (C-27), 28.6 (C-28), 17.5 (C-29), 21.3 (C-30). 8.…”

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confidence: 99%

Phytochemical Study of Euphorbia turcomanica Boiss.

et al. 2022

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The attraction to the Euphorbia genus, with its remarkable diversity in species, is due to its variety of chemical compositions. Euphorbia turcomanica is one of the species of the spurge family growing wildly in Iran. This research aims to investigate the presence of secondary metabolites, specially terpenoid compounds, in terms of structural determination. Samples of E. tucomanica were finely powdered and macerated with acetone/dichloromethane 2:1. Repeated column chromatography using silica gel, MPLC, and HPLC methods followed by the analysis of data obtained from spectroscopic means was carried out to purify and identify the terpenoid constituents. The chemical structures of nine known terpenoids were determined for the first time from E. turcomanica during this study. Loliolide (1), a monoterpene, and eight steroids and triterpenes, including simiarenol (2), isomultiflorenol (3), cycloart-25-ene-3β,24-diol (4), β-sitosterol (5), cycloart-23-ene-3β,25-diol (6), 3α, 11α-dihydroxyurs-12-ene (7), 3β, 24β, 25-trihydroxycycloartane (8), and 7α-hydroxystigmasterol (9) were isolated and identified. E. tucomanica, with a rich terpenoid profile, can be one of the valuable and economic sources providing compounds for drug development.

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“…The following calculation was used to compute the autophosphorylation percentage: 100 − [Control/Treated − Control]. [33] Using GraphPad Prism7, the IC 50 was computed using the percentage inhibition curves of four compound concentrations. and propidium iodide (PI)" at a concentration equivalent to 10 g/mL.…”

Section: Vegfr2 and Egfr Protein Kinase Inhibitionmentioning

confidence: 99%

N‐allyl quinoxaline derivative exhibited potent and selective cytotoxicity through EGFR/VEGFR‐mediated apoptosis: In vitro and in vivo studies

Nafie,

Ali,

Youssef

2024

J Biochem & Molecular Tox

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The cytotoxic activity, EGFR/VEGFR2 target inhibition, apoptotic activity, RT‐PCR gene expression, in vivo employing a solid‐Ehrlich carcinoma model, and in silico investigations for highlighting the binding affinity of eight quinoxaline derivatives were tested for anticancer activities. The results showed that compound 8 (N‐allyl quinoxaline) had potent cytotoxicity against A594 and MCF‐7 cancer cells with IC50 values of 0.86 and 1.06 µM, respectively, with noncytotoxic activity against WISH and MCF‐10A cells having IC50 values more than 100 µM. Furthermore, it strongly induced apoptotic cell death in A549 and MCF‐7 cells by 43.13% and 34.07%, respectively, stopping the cell cycle at S and G1‐phases. For the molecular target, the results showed that compound 8 had a promising EGFR inhibition activity with an IC50 value of 0.088 µM compared to Sorafenib (IC50 = 0.056 µM), and it had a promising VEGFR2 inhibition activity with an IC50 value of 0.108 µM compared to Sorafenib (IC50 = 0.049 µM). Treatment with compound 8 ameliorated biochemical and histochemical parameters near normal in the in vivo investigation, with a tumor inhibition ratio of 68.19% compared to 64.8% for 5‐FU treatment. Finally, the molecular docking study demonstrated the binding affinity through binding energy and interactive binding mode inside the EGFR/VEGFR2 proteins. Potent EGFR and VEGFR2 inhibition of compound 8 suggests its potential for development as a selective anticancer drug.

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GC-MS/MS Quantification of EGFR Inhibitors, β-Sitosterol, Betulinic Acid, (+) Eriodictyol, (+) Epipinoresinol, and Secoisolariciresinol, in Crude Extract and Ethyl Acetate Fraction of Thonningia sanguinea

Cited by 6 publications

References 34 publications

Lupane Triterpene Derivatives Improve Antiproliferative Effect on Leukemia Cells through Apoptosis Induction

Lupane Triterpene Derivatives Improve Antiproliferative Effect on Leukemia Cells through Apoptosis Induction

Phytochemical Study of Euphorbia turcomanica Boiss.

N‐allyl quinoxaline derivative exhibited potent and selective cytotoxicity through EGFR/VEGFR‐mediated apoptosis: In vitro and in vivo studies

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