Sterols and Triterpenes from Dobera glabra Growing in Saudi Arabia and Their Cytotoxic Activity

Abstract

A new lupane caffeoyl ester, lup-20(29)-ene 3β-caffeate-30-al (7), and a new oleanane-type triterpene, 3β-hydroxyolean-13(18)-en-12-one (17), were isolated from the aerial parts of Dobera glabra (Forssk), along with ten known triterpenes, including seven lupane-type lupeol (1), 30-nor-lup-3β-ol-20-one (2), ∆1-lupenone (3), lup-20(29)-en-3β,30-diol (4), lupeol caffeate (5), 30-hydroxy lup-20(29)-ene 3β-caffeate (6), and betunaldehyde (8); three oleanane-type compounds were also identified, comprising δ-amyrone (15), δ-amyrin (16), and 11-oxo-β-amyrin (18); together with six sterols, comprising β-sitosterol (9), stigmasterol (10), 7α-hydroxy-β-sitosterol (11), 7α-hydroxy-stigmasterol (12), 7-keto-β-sitosterol (13), and 7-keto-stigmasterol (14). Their structures were elucidated using a variety of spectroscopic techniques, including 1D (1H, 13C, and DEPT-135 13C) and 2D (1H–1H COSY, 1H–13C HSQC, and 1H–13C HMBC) nuclear magnetic resonance (NMR) and accurate mass spectroscopy. Subsequently, the different plant extracts and some of the isolated compounds (1–9, 11 and 13) were investigated for their possible cytotoxic activity in comparison to cisplatin against a wide array of aggressive cancer cell lines, such as colorectal cancer (HCT-116), hepatocellular carcinoma (HepG-2), and prostate cancer (PC-3) cell lines. Compound 11 displayed broad cytotoxicity against all of the tested cell lines (IC50 ≅ 8 µg/mL in all cases), and a high safety margin against normal Vero cells (IC50 = 70 µg/mL), suggesting that 11 may be a highly selective and effective anticancer agent candidate. Notably, the evidence indicated that the mode of action of compound 11 could possibly consist of the inhibition of phosphodiesterase I (80.2% enzyme inhibition observed at 2 µM compound concentration).

Cytotoxic Activities and the Allantoinase Inhibitory Effect of the Leaf Extract of the Carnivorous Pitcher Plant Nepenthes miranda

“…Through GC-MS, the contents abundant in N. mirandaleaf-acetone were detected and identified (Table 3). We found that the top four contents, plumbagin (28.52%) [57][58][59][60], lupenone (11.45%) [69][70][71], palmitic acid (5.49%) [72][73][74], and stigmast-5-en-3-ol (5.06%) [75], especially plumbagin and lupenone, are anticancer compounds. This might be why N. miranda-leaf-acetone possesses strong cytotoxic activities.…”

In-Vitro Anticancer Activity of Chemical Constituents from Etlingera alba Poulsen against Triple Negative Breast Cancer and in silico Approaches towards Matrix metalloproteinase-1 Inhibition

“…Previous studies also showed that sterols possess cytotoxicity activity against colorectal cancer (HCT-116), hepatocellular carcinoma (HepG-2), and prostate cancer (PC-3) cell lines (Abdel-Mageed et al, 2021). Both sinaphyl alcohol acetate and sinaphyl alcohol diacetate belong to the phenylpropanoid compound.…”