Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity

Plant sterols, also referred as phytosterols, have been known as bioactive compounds which have cholesterol-lowering properties in human blood. It has been established that a diet rich in plant sterols or their esters alleviates cardiovascular diseases (CVD), and also may inhibit breast, colon and l...

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Autores principales:	Magdalena Rudzińska, Aleksandra Grudniewska, Anna Chojnacka, Witold Gładkowski, Gabriela Maciejewska, Anna Olejnik, Katarzyna Kowalska
Formato:	article
Lenguaje:	EN
Publicado:	MDPI AG 2021
Materias:	phytosterols stigmasterol acylglycerols synthesis identification cytotoxicity Organic chemistry QD241-441
Acceso en línea:	https://doaj.org/article/f0edc853a7dc4d6880cbda4aa4b52d4b
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spelling	oai:doaj.org-article:f0edc853a7dc4d6880cbda4aa4b52d4b2021-11-25T18:27:38ZDistigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity10.3390/molecules262268371420-3049https://doaj.org/article/f0edc853a7dc4d6880cbda4aa4b52d4b2021-11-01T00:00:00Zhttps://www.mdpi.com/1420-3049/26/22/6837https://doaj.org/toc/1420-3049Plant sterols, also referred as phytosterols, have been known as bioactive compounds which have cholesterol-lowering properties in human blood. It has been established that a diet rich in plant sterols or their esters alleviates cardiovascular diseases (CVD), and also may inhibit breast, colon and lung carcinogenesis. Phytosterols, in their free and esterified forms, are prone to thermo-oxidative degradation, where time and temperature affect the level of degradation. Looking for new derivatives of phytosterols with high thermo-oxidative stability for application in foods, our idea was to obtain novel structured acylglycerols in which two fatty acid parts are replaced by stigmasterol residues. In this work, asymmetric (1,2- and 2,3-) distigmasterol-modified acylglycerols (dStigMAs) were synthesized by the covalent attachment of stigmasterol residues to <i>sn</i>-1 and <i>sn</i>-2 or <i>sn</i>-2 and <i>sn</i>-3 positions of 3-palmitoyl-<i>sn</i>-glycerol or 1-oleoyl-<i>sn</i>-glycerol, respectively, using a succinate or carbonate linker. The chemical structures of the synthesized compounds were identified by NMR, HR-MS, and IR data. Moreover, the cytotoxicity of the obtained compounds was determined. The dStigMAs possessing a carbonate linker showed potent cytotoxicity to cells isolated from the small intestine and colon epithelium and liver, whereas the opposite results were obtained for compounds containing a succinate linker.Magdalena RudzińskaAleksandra GrudniewskaAnna ChojnackaWitold GładkowskiGabriela MaciejewskaAnna OlejnikKatarzyna KowalskaMDPI AGarticlephytosterolsstigmasterolacylglycerolssynthesisidentificationcytotoxicityOrganic chemistryQD241-441ENMolecules, Vol 26, Iss 6837, p 6837 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	phytosterols stigmasterol acylglycerols synthesis identification cytotoxicity Organic chemistry QD241-441
spellingShingle	phytosterols stigmasterol acylglycerols synthesis identification cytotoxicity Organic chemistry QD241-441 Magdalena Rudzińska Aleksandra Grudniewska Anna Chojnacka Witold Gładkowski Gabriela Maciejewska Anna Olejnik Katarzyna Kowalska Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
description	Plant sterols, also referred as phytosterols, have been known as bioactive compounds which have cholesterol-lowering properties in human blood. It has been established that a diet rich in plant sterols or their esters alleviates cardiovascular diseases (CVD), and also may inhibit breast, colon and lung carcinogenesis. Phytosterols, in their free and esterified forms, are prone to thermo-oxidative degradation, where time and temperature affect the level of degradation. Looking for new derivatives of phytosterols with high thermo-oxidative stability for application in foods, our idea was to obtain novel structured acylglycerols in which two fatty acid parts are replaced by stigmasterol residues. In this work, asymmetric (1,2- and 2,3-) distigmasterol-modified acylglycerols (dStigMAs) were synthesized by the covalent attachment of stigmasterol residues to <i>sn</i>-1 and <i>sn</i>-2 or <i>sn</i>-2 and <i>sn</i>-3 positions of 3-palmitoyl-<i>sn</i>-glycerol or 1-oleoyl-<i>sn</i>-glycerol, respectively, using a succinate or carbonate linker. The chemical structures of the synthesized compounds were identified by NMR, HR-MS, and IR data. Moreover, the cytotoxicity of the obtained compounds was determined. The dStigMAs possessing a carbonate linker showed potent cytotoxicity to cells isolated from the small intestine and colon epithelium and liver, whereas the opposite results were obtained for compounds containing a succinate linker.
format	article
author	Magdalena Rudzińska Aleksandra Grudniewska Anna Chojnacka Witold Gładkowski Gabriela Maciejewska Anna Olejnik Katarzyna Kowalska
author_facet	Magdalena Rudzińska Aleksandra Grudniewska Anna Chojnacka Witold Gładkowski Gabriela Maciejewska Anna Olejnik Katarzyna Kowalska
author_sort	Magdalena Rudzińska
title	Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
title_short	Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
title_full	Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
title_fullStr	Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
title_full_unstemmed	Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity
title_sort	distigmasterol-modified acylglycerols as new structured lipids—synthesis, identification and cytotoxicity
publisher	MDPI AG
publishDate	2021
url	https://doaj.org/article/f0edc853a7dc4d6880cbda4aa4b52d4b
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_version_	1718411170657861632

Distigmasterol-Modified Acylglycerols as New Structured Lipids—Synthesis, Identification and Cytotoxicity

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