Structural Elucidation of Irish Ale Bioactive Polar Lipids with Antithrombotic Properties

Abstract

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.

Beneficial Anti-Platelet and Anti-Inflammatory Properties of Irish Apple Juice and Cider Bioactives

“…These results come also in accordance with previously reported ones for similar differences observed in the anti-platelet properties against PAF of TL, NL and PL extracts from other plant-derived beverages such as wine, beer and tea [8,9,16,17]. More specifically, the PL from all these apple-based beverages were found to be less active but within the same order of magnitude when compared to the PL from wine [8] and beer [9,16] against PAF inflammatory and platelet aggregation pathways.…”

“…These results come also in accordance with previously reported ones for similar differences observed in the anti-platelet properties against PAF of TL, NL and PL extracts from other plant-derived beverages such as wine, beer and tea [8,9,16,17]. More specifically, the PL from all these apple-based beverages were found to be less active but within the same order of magnitude when compared to the PL from wine [8] and beer [9,16] against PAF inflammatory and platelet aggregation pathways. Moreover, the activities of PL from both apple juice and cider samples against the PAF pathways are of similar potency with previously reported ones for PL extracts derived from tea [17] and from several other food sources, such as olive oil and fish [2,12,18].…”

“…These results concerning the fatty acid composition of PL from apple juice and apple cider are in accordance with previously reported ones for lipids from apple juice and cider [22,23], but also in PL from other plant-derived food sources used for beverages products, such as beer and tea [9,17].…”

“…In other beverages that are also derived from fermentation of plant/fruit sources, such as red and white wine and relative musts and yeasts for their production, as well as beer, they have all been found to contain bioactive PL like phospholipids and glycolipids with cardio-protective abilities against the inflammatory and thrombotic mediator platelet-activating factor (PAF) and its associated pathways [8]. The same was also shown in beers that were found to contain specific PL subclasses and molecular species with beneficial bioactivities against inflammation and thrombosis, as a result of fermentation, in comparison to their raw materials [9].…”

Bioactive Lipids of Marine Microalga Chlorococcum sp. SABC 012504 with Anti-Inflammatory and Anti-Thrombotic Activities

“…seem to be attributed to a synergism of highly bioactive polar lipid molecules that coexist in Chlorococcum sp. For this reason, apart from the fatty acid composition, the overall structures of bioactive molecules present in these most bioactive lipid fractions were also elucidated through LC-MS analysis as previously described [ 21 , 22 , 31 ].…”