Cytotoxic and genotoxic effects of (R)‐ and (S)‐ricinoleic acid derivatives

Abstract

(R)‐ricinoleic acid is the main component of castor oil from Ricinus communis L. Due to the presence of the hydroxyl group in homoallylic position and asymmetrically substituted carbon atom, it may undergo a number of chemical and biochemical transformations resulting in the products with some specific bioactivities. Conversion of (R)‐ricinoleic acid into its (S)‐enantiomer enables synthesis of both (R)‐ and (S)‐ricinoleic acid derivatives and comparison of their biological activities. In the present research, (R)‐ and (S)‐ricinoleic acid amides synthesized from methyl ricinoleates and ethanolamine or pyrrolidine as well as acetate derivatives of ethanolamine amides were studied to demonstrate their biological activities using HT29 cancer cells. Double staining of cells with fluorochromes (Hoechst 33258/propidium iodide) as well as 2,′7′‐dichlorodihydrofluorescein (DCF) and comet assays were performed. Both the tested amides and acetates caused DNA damage and induced apoptotic and necrotic cell death. In the case of (R)‐ and (S)‐enantiomers of one of the tested acetates, significant difference in the ability to induce DNA damage was observed, which showed the impact of the stereogenic center on the activities of these compounds.

Analysis of metabolites of bactrain camel milk in Alxa of China before and after fermentation with fermenting agent TR1 based on untargeted LC-MS/MS based metabolomics

“…Down-regulated organic acids mainly included ricinoleic acid, deoxycholic acid, lauric acid, phosphocreatine, pentadecanoic acid, citric acid. Ricinoleic acid had a certain cytotoxicity on cells, and may lead to cell apoptosis [ 39 ]. The reduction of this substance after fermentation may significantly enhance the biological activity of LAB and thereby enhancing the probiotic function in fermented camel milk.…”

Analogues of Anticancer Natural Products: Chiral Aspects

“…Blaszczyk and co-workers [ 89 ] reported the synthesis and cytotoxic activity of both ( R )- and ( S )-enantiomers of ricinoleic acid amides and their acetates. The ricinoleic acid amides as well as acetate derivatives of ethanolamine amides were studied ( 15 – 22 ) ( Figure 10 ) to demonstrate the influence of the stereogenic centre on their potential anticancer activity.…”

“…In most cases, only slight differences between the activities of the two enantiomers were observed. In the case of ( R )- and ( S )-enantiomers of one of the tested acetates ( 21 , 22 ), a significant difference in the ability to induce DNA damage was observed, which showed the impact of the stereogenic centre on the activities of these compounds [ 89 ].…”