Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticancer activity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 and C-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGH of hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. New derivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomeric forms by the Barbier-Grignard procedure and three of them were found to be active toward all of the three targets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed for the more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpress NF−κB.

Gianfranco Fontana, Maurizio Bruno, Monica Notarbartolo, Manuela Labbozzetta, Paola Poma, Alberto Spinella, et al. (2019). Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement. BIOORGANIC CHEMISTRY, 90, 1-8 [10.1016/j.bioorg.2019.103054].

Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement

Gianfranco Fontana
;
Maurizio Bruno
;
Monica Notarbartolo;Manuela Labbozzetta;Paola Poma;Alberto Spinella;Sergio Rosselli
2019-01-01

Abstract

Oleanolic and ursolic acids are two ubiquitous isomeric triterpene phytochemicals known for their anticancer activity. A set of derivatives of the two compounds with a modified oxidation state and lipophylicity at C-3 and C-28 positions, were prepared and tested as anticancer agents versus the lines HepG2, Hep3B and HA22T/VGH of hepatocarcinoma, a strongly aggressive tumor that is not responsive toward the standard therapies. New derivatives containing a three carbons side chain on the C-3 position were synthetized in both stereoisomeric forms by the Barbier-Grignard procedure and three of them were found to be active toward all of the three targets. The implication of the transcriptional nuclear factor NF−κB in the mechanism of action was assessed for the more active compounds in the set, as hepatocellular carcinoma (HCC) cyto-types are known to overexpress NF−κB.
Settore BIO/14 - Farmacologia
Settore BIO/15 - Biologia Farmaceutica
Settore CHIM/06 - Chimica Organica
Gianfranco Fontana, Maurizio Bruno, Monica Notarbartolo, Manuela Labbozzetta, Paola Poma, Alberto Spinella, et al. (2019). Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement. BIOORGANIC CHEMISTRY, 90, 1-8 [10.1016/j.bioorg.2019.103054].
File in questo prodotto:
File Dimensione Formato  
bioor chem 2019.pdf

Solo gestori archvio

Descrizione: articolo principale
Tipologia: Versione Editoriale
Dimensione 700.81 kB
Formato Adobe PDF
700.81 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
Manuscript revised 20190523.pdf

Solo gestori archvio

Descrizione: Articolo
Tipologia: Post-print
Dimensione 712.12 kB
Formato Adobe PDF
712.12 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/361992
Citazioni
  • ???jsp.display-item.citation.pmc??? 10
  • Scopus 18
  • ???jsp.display-item.citation.isi??? 20
social impact