Diterpenoid constituents of Euphorbia macrorrhiza

Abstract

Ten diterpenoids, named macrorilone A-B, macroripremyrsinone A, macrorilathyrone A-B, macrorieuphorone A-B and macroricasbalone A-C, together with ten known diterpenoids, jatrophalone, sikkimenoids A-D, jatrophodione A, latilagascenes F, jolkinol B, 15β-O-benzoyl-5α-hydroxyisolathyrol and jatrophalactone were isolated from the whole plant of Euphorbia macrorrhiza C.A. Mey. These diterpenoids belong to six skeleton-types, including jatropholane, premyrsinane, lathyrane, euphoractin, casbene and rhamnofolane diterpenoids. Their structures were elucidated by extensive analysis of 1D, 2D NMR and HRESIMS spectroscopic data. The absolute configurations of macrorilone B, macroripremyrsinone A and macrorilathyrone A were established by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. Several of the isolated compounds exhibited weak cytotoxicity against the KB and KBv200 cell lines with IC50 values ranging from 21.19 to 47.87μM. Some also showed multidrug resistance (MDR) reversal activity, among which macrorilathyrone B exhibited a remarkable inhibitory effect on P-gp-mediated drug exclusion.

In vitro and in silico studies on clinically important enzymes inhibitory activities of flavonoids isolated from Euphorbia pulcherrima

“…According to the interaction study, compound 1 forms one hydrogen bond at the binding site of urease enzyme. This hydrogen bond of 3.32 Å length was found in His541 with the –OH group of compound 1 ( Figures 1(a,b ) and 2 ). Additionally, the surrounding residues Cys442, His408, Ile517, His491, Leu488, and Tyr543 were examined for the six hydrophobic interactions.…”

“…However, all of these species contain latex as an abundant source of secondary metabolites [ 1 ]. Furthermore, the genus Euphorbia is known to contain diterpenoids, and several isolated compounds exhibited biological activities including significant multidrug resistance reversal effects [ 2 ]. For instance, the essential oil from E. hirta L., which is also called ‘asthma plant’ has been traditionally used to cure asthma.…”

Research Progress on Natural Diterpenoids in Reversing Multidrug Resistance

“…The IC 50 values for navelbine in combination with compound 77 decreased (from 2.14 to 0.48 μM), suggesting that compound 77 had MDR reversal potential. However, compound 77 was much less active in the MDR reversal assay (RF = 4.47 at 10 μM), compared to that of the positive control (RF = 43.63 at 10 μM) ( Gao et al, 2016 ).…”

“…Among them, compound 43 showed significant inhibitory activity on ABCB1-mediated drug efflux in KBv200 cell line (RF = 43.63) The inhibitory effect of compound 43 on ABCB1-mediated drug efflux was further tested at several concentrations by Rh123 accumulation assay. Compound 43 exhibited significant effect in increasing the intracellular accumulation of Rh123 (FAR = 2.12 at 30 μM) when compared with the postive control verapamil (FAR = 1.63 at 10 μM) ( Gao et al, 2016 ).…”

In Vivo Anti-Inflammatory, Analgesic, Sedative, Muscle Relaxant Activities and Molecular Docking Analysis of Phytochemicals from Euphorbia pulcherrima

“…ese species contain latex which is a rich source of bioactive secondary metabolites [6]. is genus comprises diterpenoids and other compounds which his documented for excellent anticancer and other properties [7]. For example, the essential oil isolated from E. hirta is used for the treatment of asthma and is also used as a mosquito repellent.…”