Abstract
Thirty-two gypsogenin derivatives were synthesized and screened for their cytotoxic activities. Their structures were established using IR, 1H NMR, 13C NMR, and LC-MS spectroscopic data. In MTT assays nearly all the compounds displayed good cytotoxicity in the low μM range for several human tumour cell lines (A549, LOVO, SKOV3 and HepG2). Low IC50 values were obtained especially for the carboxamides 7a–7j, for an oxime derivative 3 and a (2,4-dinitrophenyl)hydrazono derivative 4. In particular, the IC50 values of compounds 4 (IC50 = 2.97 ± 1.13 µΜ) and 7 g (IC50 = 3.59 ± 2.04 µΜ) against LOVO cells were found to be much lower than those of the other derivatives and parent compound. These compounds were submitted to an extensive biological testing and proved compounds 4 and 7 g to act mainly by an arrest of the tumour cells in the S phase of the cell cycle. In addition, compounds 4 and 7 g triggered the apoptotic pathway in cancer cells, showing high apoptosis ratios.
Highlights
Cancer is one of the most challenging problems in medicine
Gypsogenin (3hydroxy-23-oxoolean-12-en-28-oic acid), a natural pentacyclic triterpenoid, has four active sites such as C-3 hydroxyl, ring-C double bond, C-23 aldehyde group and C-28 carboxylic acid, which are amenable for a wide range of chemical transformations
Thirty-two gypsogenin derivatives were synthesized by a series of reactions as outlined in schemes 1–3
Summary
Cancer is one of the most challenging problems in medicine. One of the several treatments is chemotherapy, and many chemotherapeutics have been developed so far. The C-28 carboxylic acid and C-23 aldehyde group were used to prepare nitrile and different types of esters These compounds are the first pentacyclic triterpenoids described as a potent AChE-selective inhibitor [17]. The C-23 aldehyde group of gypsogenin was treated with hydroxylamine hydrochloride to provide oxime This compound triggered the apoptotic pathway in cancer cells, showing high apoptosis ratios [16]. Some compounds triggered the apoptotic pathway in cancer cells, showing high apoptosis ratios These findings make oleanolic acid a promising lead compound for developing new cytotoxic/antitumour active compounds. The different types of esters and amide were designed, and synthesized at C-28 carboxylic acid They were evaluated for their cytotoxic activities against four different human cancer cell cultures. More investigations about the mechanism of cell death induced by these gypsogenin derivatives were performed
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