Cytotoxic Sesquiterpene Lactones from Kauna lasiophthalma Griseb

Abstract

Two new eudesmane derivatives (3 and 8) were isolated from the ethanol extract of the aerial parts of Kaunia lasiophthalma Griseb, together with 14 known eudesmane, germacrane, and guaiane sesquiterpenes, and four flavones. The structures and relative configurations of all the compounds were established by NMR spectroscopy and high-resolution mass spectrometry. The anticancer activity of sesquiterpenes 1, 3, 6–9, 11, 12, 14, and 16 was evaluated in vitro with the breast cancer cell lines HCC1937, JIMT-1, L56Br-C1, MCF-7, and SK-BR-3, and compared with the cytotoxicity in the non-cancerous breast epithelial cell line MCF-10A. All compounds were found to possess anticancer activity, and compound 1 was the most potent in all of the investigated cancer cell lines with IC50 values ranging between 2.0 and 6.2 μM. In order to demonstrate the importance of the α-methylene-γ-lactone/ester moiety present in all compounds for the effects on the cells, the methyl cysteine adduct 21 was prepared from 9 and found to be inactive or considerably less potent.

Anti‑breast cancer potential of frullanolide from Grangea maderaspatana plant by inducing apoptosis

“…However, further experiments are required to confirm any interactions between frullanolide and EGFR. Additionally and C 17 H 22 O 4 ranged between 9.3 and 27.0 µM (L56Br-C1 >SK-BR-3 >JIMT-1>HCC1937>MCF-7) and 3.2-11.0 µM (HCC1937>SK-BR-3>JIMT-1>L56Br-C1>MCF-7) (27). A previous computational structure-based screening method to identify natural compounds that specifically target the mouse double minute 2 homolog protein revealed that, out of the 35 top candidates, 8 eudesmanolide SLs (IJ-1, IJ-3, IJ-5, IJ-6, IJ-9, IJ-11, IH-45 and IH-49) exerted more potent anti-TNBC activity (MDA-MB-231) than anti-non-TNBC (MCF-7) activity at 72 h (39).…”

“…Purified and crude compounds of one of these anticancer agents were reported to possess strong antitumor activity, with IC 50 values of ≤4 and ≤20 µg/ml, respectively (21). Several studies have identified specific SLs and derivatives which exhibit broad-spectrum antitumor activity towards several cancer types, including non-small cell lung cancer, colorectal cancer, leukemia, laryngeal cancer, gynecological cancer and breast cancer (13,(22)(23)(24)(25)(26)(27). The different anticancer abilities of SLs are associated with their carbocyclic skeleton classification (13,28 In the present study, frullanolide (a eudesmanolide) was assessed by MTT assay, and exhibited potent anti-breast cancer activity in breast cancer cell lines, including MCF-7, MDA-MB-468 and MDA-MB-231.…”

Antioxidant, Antimicrobial, and Anticancer Effects of Anacardium Plants: An Ethnopharmacological Perspective

“…Four isolated compounds, zoapatanolide A, agathisflavone, anacardicin, and methyl gallate, were identified, and authors found that these components exhibited HeLa cell viability reduction in dose-dependent manner, although with distinct efficiencies: zoapatanolide A > anacardicin > agathisflavone > methyl gallate. The cytotoxic potential of zoapatanolide A is welldocumented in literature (212). This class of compounds act as Michael acceptor for the cysteines thiol groups, covalently modifying proteins (213,214).…”

Identification of compounds with cytotoxic activity from the leaf of the Nigerian medicinal plant, Anacardium occidentale L. (Anacardiaceae)

“…Representative photomicrographs for the most potent compound identified as zoapatanolide A (1), a sesquiterpene α-methylene-γ-lactone, are shown(Figure 3), compared to and contrasted with those of agathisflavone(2), which is less than half as potent. The cytotoxic potential of sesquiterpene α-methylene-γ-lactones had been well reported in literature [35][36][37]. Concentration-dependent compound-induced reductions in HeLa cell viability (for compounds 1-3).…”