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

Abstract

Medicinal plants are widely used in folk medicine to treat various diseases. Thonningia sanguinea Vahl is widespread in African traditional medicine, and exhibits antioxidant, antibacterial, antiviral, and anticancer activities. T. sanguinea is a source of phytomedicinal agents that have previously been isolated and structurally elucidated. Herein, gas chromatography combined with tandem mass spectrometry (GC-MS/MS) was used to quantify epipinoresinol, β-sitosterol, eriodictyol, betulinic acid, and secoisolariciresinol contents in the methanolic crude extract and its ethyl acetate fraction for the first time. The ethyl acetate fraction was rich in epipinoresinol, eriodictyol, and secoisolariciresinol at concentrations of 2.3, 3.9, and 2.4 mg/g of dry extract, respectively. The binding interactions of these compounds with the epidermal growth factor receptor (EGFR) were computed using a molecular docking study. The results revealed that the highest binding affinities for the EGFR signaling pathway were attributed to eriodictyol and secoisolariciresinol, with good binding energies of −19.93 and −16.63 Kcal/mol, respectively. These compounds formed good interactions with the key amino acid Met 769 as the co-crystallized ligand. So, the ethyl acetate fraction of T. sanguinea is a promising adjuvant therapy in cancer treatments.

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

“…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 ).…”

Phytochemical Study of Euphorbia turcomanica Boiss.

“…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].…”

“…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.…”

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

“…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.…”