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Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties

The structures of bioactive polar lipids (PLs) of Irish ale with potent antithrombotic and cardioprotective properties were elucidated. Ale PL was fractionated by preparative thin layer chromatography (TLC) into subclasses, and their antithrombotic effect was assessed against human platelet aggregat...

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Autores principales: Tsoupras, Alexandros, Lordan, Ronan, O’Keefe, Eoin, Shiels, Katie, Saha, Sushanta Kumar, Zabetakis, Ioannis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7407377/
https://www.ncbi.nlm.nih.gov/pubmed/32708453
http://dx.doi.org/10.3390/biom10071075
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author Tsoupras, Alexandros
Lordan, Ronan
O’Keefe, Eoin
Shiels, Katie
Saha, Sushanta Kumar
Zabetakis, Ioannis
author_facet Tsoupras, Alexandros
Lordan, Ronan
O’Keefe, Eoin
Shiels, Katie
Saha, Sushanta Kumar
Zabetakis, Ioannis
author_sort Tsoupras, Alexandros
collection PubMed
description The structures of bioactive polar lipids (PLs) of Irish ale with potent antithrombotic and cardioprotective properties were elucidated. Ale PL was fractionated by preparative thin layer chromatography (TLC) into subclasses, and their antithrombotic effect was assessed against human platelet aggregation induced by the pro-inflammatory mediator, platelet-activating factor (PAF). The fatty acid content and the overall structures of ale PL were elucidated by liquid chromatography mass spectrometry (LC-MS). Phosphatidylcholines (PC) and molecules of the sphingomyelin (SM) family exhibited the strongest anti-PAF effects, followed by phosphatidylethanolamines (PE). PC contained higher amounts of omega-3 polyunsaturated fatty acids (n-3 PUFA) and thus the lowest n-6/n-3 ratio. Bioactive diacyl and alkyl-acyl PC and PE molecules bearing n-3 PUFA at their sn-2 position, especially docosahexaenoic acid (DHA) and α-linolenic acid (ALA) but mostly oleic acid (OA), were identified in both PC and PE subclasses. Eicosapentaenoic acid (EPA) was present only in bioactive PC molecules and not in PE, explaining the lower anti-PAF effects of PE. Bioactive sphingolipid and glycolipid molecules with reported anti-inflammatory and anti-tumour properties, such as specific ceramides and glucosylcerebrosides with sphingosine, phytosphingosine and dihydrosphingosine bases but also specific monogalactodiglycerides and SM species bearing ALA at their sn-2 position, were identified in the SM subclass, providing a rational for its strong bioactivities against the PAF pathway. Further studies are required on the health benefits of bioactive PL from beer and brewery by-products.
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spelling pubmed-74073772020-08-11 Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties Tsoupras, Alexandros Lordan, Ronan O’Keefe, Eoin Shiels, Katie Saha, Sushanta Kumar Zabetakis, Ioannis Biomolecules Article The structures of bioactive polar lipids (PLs) of Irish ale with potent antithrombotic and cardioprotective properties were elucidated. Ale PL was fractionated by preparative thin layer chromatography (TLC) into subclasses, and their antithrombotic effect was assessed against human platelet aggregation induced by the pro-inflammatory mediator, platelet-activating factor (PAF). The fatty acid content and the overall structures of ale PL were elucidated by liquid chromatography mass spectrometry (LC-MS). Phosphatidylcholines (PC) and molecules of the sphingomyelin (SM) family exhibited the strongest anti-PAF effects, followed by phosphatidylethanolamines (PE). PC contained higher amounts of omega-3 polyunsaturated fatty acids (n-3 PUFA) and thus the lowest n-6/n-3 ratio. Bioactive diacyl and alkyl-acyl PC and PE molecules bearing n-3 PUFA at their sn-2 position, especially docosahexaenoic acid (DHA) and α-linolenic acid (ALA) but mostly oleic acid (OA), were identified in both PC and PE subclasses. Eicosapentaenoic acid (EPA) was present only in bioactive PC molecules and not in PE, explaining the lower anti-PAF effects of PE. Bioactive sphingolipid and glycolipid molecules with reported anti-inflammatory and anti-tumour properties, such as specific ceramides and glucosylcerebrosides with sphingosine, phytosphingosine and dihydrosphingosine bases but also specific monogalactodiglycerides and SM species bearing ALA at their sn-2 position, were identified in the SM subclass, providing a rational for its strong bioactivities against the PAF pathway. Further studies are required on the health benefits of bioactive PL from beer and brewery by-products. MDPI 2020-07-18 /pmc/articles/PMC7407377/ /pubmed/32708453 http://dx.doi.org/10.3390/biom10071075 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Tsoupras, Alexandros
Lordan, Ronan
O’Keefe, Eoin
Shiels, Katie
Saha, Sushanta Kumar
Zabetakis, Ioannis
Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title_full Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title_fullStr Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title_full_unstemmed Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title_short Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties
title_sort structural elucidation of irish ale bioactive polar lipids with antithrombotic properties
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7407377/
https://www.ncbi.nlm.nih.gov/pubmed/32708453
http://dx.doi.org/10.3390/biom10071075
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