Abstract
A series of chiral ricinoleic and 3-hydroxynonanoic acid derivatives were synthesized in this study using various chemical and biochemical procedures. An effective method for preparation of methyl esters of 3-hydroxynonanoic acid from castor oil or methyl ricinoleate by ozonolysis and oxidation was developed. Simple, fast, and efficient procedures were applied to obtain different primary and secondary, cyclic and acyclic amides, including hydroxamic acids. Among 24 synthesized derivatives of ricinoleic and 3-hydroxynonanoic acids, i.e., methyl esters, amides, and hydroxamic acids, 16 compounds were obtained and described for the first time. The synthesized compounds showed activity against the tested cancer cells, but the best cytotoxic effect was observed for hydroxamic acid derived from 3-hydroxynonanoic acid (11) against HeLa cells. In general, most of the tested compounds were more toxic against HT29 than HeLa cancer cells. The results also showed that there was no significant difference between activities of (R)- and (S)-enantiomer of particular derivatives.
Highlights
Hydroxy fatty acids occur naturally in small amounts and the only representative of this group available in sufficient quantities is (R)-ricinoleic acid (RA) [(R,Z)-12-hydroxyoctadec-9-enoic acid] (Salywon et al 2005)
Preparation of the methyl esters of (R)-3-hydroxynonanoic acid (R-6) by ozonolysis of castor oil was previously described in literature, in all cases the product of that reaction was a mixture of compounds (Ishmuratov et al 2006, 2007, 2009)
The most interesting results were obtained for the hydroxamic acids derived from 3hydroxynonanoic acid (11), which were found to be the most cytotoxic for HeLa cancer cells
Summary
Hydroxy fatty acids occur naturally in small amounts and the only representative of this group available in sufficient quantities is (R)-ricinoleic acid (RA) [(R,Z)-12-hydroxyoctadec-9-enoic acid] (Salywon et al 2005). This hydroxy fatty acid is an important feedstock commonly used in different fields of industry. The most important source of RA is castor oil, in which it represents about 80–90% of all fatty acids In 2014 an efficient method for the preparation of (S)-RA was developed (Kula et al 2014), and its derivatives were obtained and described for the first time (Matysiak et al 2017, 2018)
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