Further terpenoids from Euphorbia tirucalli

Abstract

The phytochemical investigation of Euphorbia tirucalli L. (Euphorbiaceae) yielded four new compounds, including a rare cadalene-type sesquiterpene (tirucadalenone), two tirucallane triterpenoids, euphorol L and euphorol M, with the latter being described as an epimeric mixture, and a euphane triterpene, namely, euphorol N, together with 7 known compounds. Their structures and absolute configurations were elucidated from analysis of 1D (1H, J-modulated 13 C) and 2D NMR (HSQC, HMBC and NOESY), high-resolution mass spectrometry (HRESIMS), optical rotation, and GIAO NMR shift calculation followed by CP3 analysis, along with comparison with literature reports. All these compounds were tested for cytotoxicity against K562, MCF-7 and/or and HepG2 tumor cell lines. Only tirucadalenone displayed a mild cytotoxic activity. Graphical abstractFour previously undescribed terpenoids: a cadalene (1), two tirucallanes (2 and 3a/3b), and a euphane (4) were isolated from Euphorbia tirucalli L. ACCEPTED MANUSCRIPT

Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco

“…Additionally, compound 2 showed − 5.23° ( c 0.9, CHCl 3 ), and negative optical rotation is also associated with tirucallane triterpenes [ 30 ]. Similar optical rotation data for a number of tirucallanes, including related 3 α -tirucallanes, were reported [ 30 , 35 , 37 ]. In this paper, we report for the first time the 13 C NMR and detailed 1 H NMR data of 2 ( Table 1 ).…”

“…In terms of the limited 1 H NMR data and the fact that euphane and tirucallane triterpenes cannot be distinguished based on 13 C NMR data, because of very similar carbon resonances [ 30 ], we proceeded with detailed 1 H NMR assignments of 2 ( Table 1 ), and subsequent interpretation of the data of a NOESY experiment. The latter was recognized as an essential approach for discrimination between tirucallanes and euphanes [ 30 , 31 , 35 , 36 , 37 ]. NOE correlations between H-21 and H-16 were reported as characteristic for euphanes and between H-21 and H-12 α for tirucallanes.…”

Advances in the synthesis of 1,2-dioxolanes and 1,2-dioxanes

“…They are exhibiting a skeleton related to davanone, a sesquiterpenic tetrahydrofuran. A decahydronaphtalene-like structure can be seen in tirucaladerone, 64 a caladenequinone derivative recently isolated from Euphorbia tirucalli, as well as in schisansphene A, 65 an eudesmene peroxy-derivative isolated from Schisandra sphenanthera. Eudesmanolide derivative tehranolide was isolated from Artemisia diffusa, 66 and exhibits an unprecedented cyclooctane along with an endoperoxy hemiketal.…”

Synthesis and Cytotoxic Activity against K562 and MCF7 Cell Lines of SomeN-(5-Arylidene-4-oxo-2-thioxothiazolidin-3-yl)-2-((4-oxo-3-phenyl-3,4-dihydroquinazoline-2-yl)thio)acetamide Compounds

“…Cell Viability Assay. e experimental procedure was followed by the steps presented in the literature [46,47]. In brief, K562 cells and MCF7 cells were cultured in the DMEM medium supplemented with 10% fetal bovine serum (FBS), 100 IU/mL penicillin, and 100 μg/mL streptomycin and maintained at 37°C and 5% CO 2 with 95% humidity.…”