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Int. J. Mol. Sci. 2019, 20(4), 832; https://doi.org/10.3390/ijms20040832

Hexadecenoic Fatty Acid Positional Isomers and De Novo PUFA Synthesis in Colon Cancer Cells

1
Consiglio Nazionale delle Ricerche, ISOF, Area della Ricerca, 40129 Bologna, Italy
2
Department of Experimental, Diagnostic and Specialty Medicine-DIMES, Alma Mater Studiorum, University of Bologna, 40126 Bologna, Italy
3
Istituto di Fisica, Fondazione Policlinico Universitario A.Gemelli IRCSS, 00168 Roma, Italy
4
Istituto di Fisica, Università Cattolica del Sacro Cuore, 00168 Roma, Italy
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
These authors contributed equally to this work.
Received: 15 January 2019 / Revised: 7 February 2019 / Accepted: 11 February 2019 / Published: 15 February 2019
(This article belongs to the Section Biochemistry)
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Abstract

Palmitic acid metabolism involves delta-9 and delta-6 desaturase enzymes forming palmitoleic acid (9cis-16:1; n-7 series) and sapienic acid (6cis-16:1; n-10 series), respectively. The corresponding biological consequences and lipidomic research on these positional monounsaturated fatty acid (MUFA) isomers are under development. Furthermore, sapienic acid can bring to the de novo synthesis of the n-10 polyunsaturated fatty acid (PUFA) sebaleic acid (5cis,8cis-18:2), but such transformations in cancer cells are not known. The model of Caco-2 cell line was used to monitor sapienic acid supplementation (150 and 300 μM) and provide evidence of the formation of n-10 fatty acids as well as their incorporation at levels of membrane phospholipids and triglycerides. Comparison with palmitoleic and palmitic acids evidenced that lipid remodelling was influenced by the type of fatty acid and positional isomer, with an increase of 8cis-18:1, n-10 PUFA and a decrease of saturated fats in case of sapienic acid. Cholesteryl esters were formed only in cases with sapienic acid. Sapienic acid was the less toxic among the tested fatty acids, showing the highest EC50s and inducing death only in 75% of cells at the highest concentration tested. Two-photon fluorescent microscopy with Laurdan as a fluorescent dye provided information on membrane fluidity, highlighting that sapienic acid increases the distribution of fluid regions, probably connected with the formation of 8cis-18:1 and the n-10 PUFA in cell lipidome. Our results bring evidence for MUFA positional isomers and de novo PUFA synthesis for developing lipidomic analysis and cancer research. View Full-Text
Keywords: positional isomerism; PUFA biosynthesis; membrane remodelling; membrane lipidomics; lipidomic analysis; fluidity; functional two-photon microscopy positional isomerism; PUFA biosynthesis; membrane remodelling; membrane lipidomics; lipidomic analysis; fluidity; functional two-photon microscopy
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Scanferlato, R.; Bortolotti, M.; Sansone, A.; Chatgilialoglu, C.; Polito, L.; De Spirito, M.; Maulucci, G.; Bolognesi, A.; Ferreri, C. Hexadecenoic Fatty Acid Positional Isomers and De Novo PUFA Synthesis in Colon Cancer Cells. Int. J. Mol. Sci. 2019, 20, 832.

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