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Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties

1
Department of Biological Sciences, University of Limerick, V94 T9PX Limerick, Ireland
2
Health Research Institute, University of Limerick, V94 T9PX Limerick, Ireland
3
Bernal Institute, University of Limerick, V94 T9PX Limerick, Ireland
4
Shannon Applied Biotechnology Centre, Limerick Institute of Technology, Moylish Park, V94 E8YF Limerick, Ireland
*
Author to whom correspondence should be addressed.
Biomolecules 2020, 10(7), 1075; https://doi.org/10.3390/biom10071075
Received: 28 May 2020 / Revised: 14 July 2020 / Accepted: 16 July 2020 / Published: 18 July 2020
(This article belongs to the Section Natural and Bio-inspired Molecules)
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. View Full-Text
Keywords: beer; CVD; PAF; polar lipids; platelet aggregation; fatty acids; PUFA; anti-inflammatory beer; CVD; PAF; polar lipids; platelet aggregation; fatty acids; PUFA; anti-inflammatory
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MDPI and ACS Style

Tsoupras, A.; Lordan, R.; O'Keefe, E.; Shiels, K.; Saha, S.K.; Zabetakis, I. Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties. Biomolecules 2020, 10, 1075. https://doi.org/10.3390/biom10071075

AMA Style

Tsoupras A, Lordan R, O'Keefe E, Shiels K, Saha SK, Zabetakis I. Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties. Biomolecules. 2020; 10(7):1075. https://doi.org/10.3390/biom10071075

Chicago/Turabian Style

Tsoupras, Alexandros, Ronan Lordan, Eoin O'Keefe, Katie Shiels, Sushanta K. Saha, and Ioannis Zabetakis. 2020. "Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties" Biomolecules 10, no. 7: 1075. https://doi.org/10.3390/biom10071075

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