Biological Evaluation and Docking Studies of Synthetic Oleananetype Triterpenoids Ortega Muñoz, Mariano Rodríguez Serrano, Fernando Reyes Berbel, Eduardo de los Mut Salud, Nuria Hernández Mateo, Fernando Rodríguez López, Andrea Garrido, José M. López Jaramillo, Francisco Javier Santoyo González, Francisco Saponins are potential wide-spectrum antitumor drugs, and copper(I) catalyzed azide−alkyne 1,3-dipolar cycloaddition is a suitable approach to synthesizing saponinlike compounds by regioselective glycosylation of the C2/C3 hydroxyl and C28 carboxylic groups of triterpene aglycones maslinic acid (MA) and oleanolic acid (OA). Biological studies on the T-84 human colon carcinoma cell line support the role of the hydroxyl groups at C2/C3, the influence of the aglycone, and the bulky nature of the substituents in C28. OA bearing a α-D-mannose moiety at C28 (compound 18) focused our interest because the estimated inhibitory concentration 50 was similar to that reported for ginsenoside Rh2 against colon cancer cells and it inhibits the G1−S phase transition affecting the cell viability and apoptosis. Considering that triterpenoids from natural sources have been identified as inhibitors of nuclear factor kappa-light-chain-enhancer of activated B cell (NF-κB) signaling, docking studies were conducted to evaluate whether NF-κB may be a potential target. Results are consistent with the biological study and predict a similar binding mode of MA and compound 18 to the p52 subunit from NF- κB but not for OA. The fact that the binding site is shared by the NF-κB inhibitor 6,6-dimethyl-2-(phenylimino)-6,7- dihydrobenzo[d][1,3]oxathiol-4(5H)-one supports the result and points to NF-κB as a potential target of both MA and compound 18. 2019-11-12T10:17:30Z 2019-11-12T10:17:30Z 2018-09-20 info:eu-repo/semantics/article Ortega-Muñoz, M., Rodríguez-Serrano, F., De los Reyes-Berbel, E., Mut-Salud, N., Hernández-Mateo, F., Rodríguez-López, A., ... & Santoyo-González, F. (2018). Biological Evaluation and Docking Studies of Synthetic Oleanane-type Triterpenoids. ACS omega, 3(9), 11455-11468. http://hdl.handle.net/10481/57839 10.1021/acsomega.8b01034 eng http://creativecommons.org/licenses/by-nc/3.0/es/ info:eu-repo/semantics/openAccess Atribución-NoComercial 3.0 España American Chemical Society