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Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines
Author(s) -
Niezgoda Natalia,
Gliszczyńska Anna,
Kempińska Katarzyna,
Wietrzyk Joanna,
Wawrzeńczyk Czesław
Publication year - 2017
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201600470
Subject(s) - degree of unsaturation , chemistry , conjugated linoleic acid , linoleic acid , conjugated system , organic chemistry , cis–trans isomerism , stearic acid , ethyl ester , fatty acid , stereochemistry , polymer
Conjugated linoleic acid (CLA) is natural unsaturated fatty acid known for the wide biological properties therefore is available in functional food and cosmetics and as a dietary supplements. In this study a series of simple derivatives of cis ‐9, trans ‐11 and trans ‐10, cis ‐12 CLA and a mixture of those isomers have been proposed as alternative for free CLA preparations. Obtained in high yields (>72%) ethyl esters, alcohols, and their acetates have been subjected to in vitro cytotoxic assay against human tumor cells (human promyelocytic leukemia, breast cancer, and colon cancer) and compered with stearic and linoleic derivatives. Studies showed that the growth inhibitory activities depended on the degree of unsaturation. All CLA derivatives except ethyl esters showed similar activities compared to free CLA isomers. Moreover, this study showed that trans ‐10, cis ‐12 CLA derivatives have better anticancer properties against all tested tumor cells than derivatives of cis ‐9, trans ‐11 isomer and a mixture of both isomers. Practical applications : This paper make a contribution in the field of study of biological activity of CLA derivatives and completes deficiencies in spectroscopic data of known isomers of ethyl esters of CLA isomers, conjugated octadecadienoic alcohols and their acetates. Obtained compounds can be used as a components of cosmetics and food supplements. A series of simple derivatives of cis ‐9, trans ‐11 and trans ‐10, cis ‐12 CLA and a mixture of those isomers are obtained in high yields (>72%). CLA derivatives: Ethyl esters, alcohols, and their acetates are subjected to in vitro cytotoxic assay against human tumor cells. Studies show that all CLA derivatives except ethyl esters show similar activities compared to free CLA isomers. Moreover, this study show that trans ‐10, cis ‐12 CLA derivatives have better anticancer properties against all tested tumor cells than derivatives of cis ‐9, trans ‐11 isomer and a mixture of both isomers.