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dc.contributor.authorOrtega Muñoz, Mariano 
dc.contributor.authorRodríguez Serrano, Fernando 
dc.contributor.authorReyes Berbel, Eduardo de los
dc.contributor.authorMut Salud, Nuria
dc.contributor.authorHernández Mateo, Fernando 
dc.contributor.authorRodríguez López, Andrea
dc.contributor.authorGarrido, José M.
dc.contributor.authorLópez Jaramillo, Javier 
dc.contributor.authorSantoyo González, Francisco
dc.identifier.citationOrtega-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.es_ES
dc.description.abstractSaponins 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.es_ES
dc.description.sponsorshipThis work was supported by a grant from Ramón Areces Foundation (Madrid, Spain) and by grant CTQ2014-55474- C2-1-R from the Spanish Ministerio de Economia y Competitividad (MINECO) co-financed by FEDER funds.es_ES
dc.publisherAmerican Chemical Societyes_ES
dc.rightsAtribución-NoComercial 3.0 España*
dc.titleBiological Evaluation and Docking Studies of Synthetic Oleananetype Triterpenoidses_ES

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Atribución-NoComercial 3.0 España
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