Kleinwächter Isabel S, Pannwitt Stefanie, Centi Alessia, Hellmann Nadja, Thines Eckhard, Bereau Tristan, Schneider Dirk
Department of Chemistry, Biochemistry, Johannes Gutenberg University Mainz, Hanns-Dieter-Hüsch-Weg 17, 55128 Mainz, Germany.
Max Planck Institute for Polymer Research, 55128 Mainz, Germany.
Membranes (Basel). 2021 Mar 31;11(4):254. doi: 10.3390/membranes11040254.
The hydrophobic tails of aliphatic primary alcohols do insert into the hydrophobic core of a lipid bilayer. Thereby, they disrupt hydrophobic interactions between the lipid molecules, resulting in a decreased lipid order, i.e., an increased membrane fluidity. While aromatic alcohols, such as 2-phenylethanol, also insert into lipid bilayers and disturb the membrane organization, the impact of aromatic alcohols on the structure of biological membranes, as well as the potential physiological implication of membrane incorporation has only been studied to a limited extent. Although diverse targets are discussed to be causing the bacteriostatic and bactericidal activity of 2-phenylethanol, it is clear that 2-phenylethanol severely affects the structure of biomembranes, which has been linked to its bacteriostatic activity. Yet, in fungi some 2-phenylethanol derivatives are also produced, some of which appear to also have bacteriostatic activities. We showed that the 2-phenylethanol derivatives phenylacetic acid, phenyllactic acid, and methyl phenylacetate, but not Tyrosol, were fully incorporated into model membranes and affected the membrane organization. Furthermore, we observed that the propensity of the herein-analyzed molecules to partition into biomembranes positively correlated with their respective bacteriostatic activity, which clearly linked the bacteriotoxic activity of the substances to biomembranes.
脂肪族伯醇的疏水尾部确实会插入脂质双层的疏水核心。由此，它们破坏了脂质分子之间的疏水相互作用，导致脂质有序性降低，即膜流动性增加。虽然芳香醇，如2-苯乙醇，也会插入脂质双层并扰乱膜结构，但芳香醇对生物膜结构的影响以及膜整合的潜在生理意义仅在有限程度上得到研究。尽管人们讨论了多种靶点导致2-苯乙醇的抑菌和杀菌活性，但很明显，2-苯乙醇会严重影响生物膜的结构，这与其抑菌活性有关。然而，在真菌中也会产生一些2-苯乙醇衍生物，其中一些似乎也具有抑菌活性。我们发现，2-苯乙醇衍生物苯乙酸、苯乳酸和苯乙酸甲酯，但酪醇不会，能完全整合到模型膜中并影响膜结构。此外，我们观察到本文分析的分子分配到生物膜中的倾向与其各自的抑菌活性呈正相关，这清楚地将这些物质的抑菌活性与生物膜联系起来。
