Cytotoxicity of oleanolic and ursolic acid derivatives toward hepatocellular carcinoma and evaluation of NF-κB involvement.
Antineoplastic Agents, Phytogenic
/ pharmacology
Apoptosis
Carcinoma, Hepatocellular
/ drug therapy
Cell Proliferation
Humans
Liver Neoplasms
/ drug therapy
Malus
/ chemistry
NF-kappa B
/ metabolism
Olea
/ chemistry
Oleanolic Acid
/ pharmacology
Plant Extracts
/ pharmacology
Triterpenes
/ pharmacology
Tumor Cells, Cultured
Ursolic Acid
Antitumor activity
HA22T/VGH
Hep3B
HepG2
NF−κB
Oleanolic acid
Ursolic acid
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
09 2019
09 2019
Historique:
received:
01
03
2019
revised:
29
05
2019
accepted:
06
06
2019
pubmed:
19
6
2019
medline:
21
10
2020
entrez:
19
6
2019
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 31212180
pii: S0045-2068(19)30275-5
doi: 10.1016/j.bioorg.2019.103054
pii:
doi:
Substances chimiques
Antineoplastic Agents, Phytogenic
0
NF-kappa B
0
Plant Extracts
0
Triterpenes
0
Oleanolic Acid
6SMK8R7TGJ
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103054Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.