Effect of Erythrodiol, A Natural Pentacyclic Triterpene from Olive Oil, on the Lipid Membrane Properties

Abstract

The effect of erythrodiol, a natural pentacyclic triterpene to which humans are exposed through nutrients, on the lipid membranes is studied using liposomes as a membrane model. Empty and erythrodiol-loaded liposomes were prepared by the reverse phase evaporation method followed by the extrusion and by the thin film hydration method. Liposomes were characterized in terms of size and zeta potential and were imaged by transmission electron microscopy (TEM) and atomic force microscopy (AFM). The effect of erythrodiol on thermotropic behavior of DPPC bilayers is also examined by differential scanning calorimetry (DSC). The DSC thermograms suggested that erythrodiol interacted with the polar head groups of phospholipids and may produce a disruption of the ordering of the alkyl chains. The diffraction light scattering analysis showed that erythrodiol-loaded liposomes presented a decrease in the vesicle size when compared to blank liposomes. Images obtained by TEM confirmed the formation of unilamellar and spherical liposomes. AFM images showed spherical vesicles and single lipid bilayers. The latter were more abundant in the preparations containing erythrodiol than in the blank ones. Moreover, erythrodiol-loaded liposomes tended to rupture into single lipid bilayers during scanning. The study may provide a better understanding of pentacyclic triterpenes-membrane interaction.

Nutrigenomics of extra‐virgin olive oil: A review

“…The triterpenes are bioactive molecules found in olive skin and in the leaves of olive trees. Hydroxyl pentacyclic triterpene acids (HPTA) (oleanolic and maslinic acid) and dialcohols (uvaol and erythrodiol) are responsible for several biological activities attributed to VOO, such as anti‐inflammatory, hepatoprotective, anticancer, antiviral, anti‐HIV, anti‐microbial, antifungal, anti‐diabetic, gastroprotective and hypolipidemic . Recent findings demonstrated also neuroprotective effects exerted by maslinic and oleanolic acid .…”

Wastewater technology attenuates the toxicity of shisha smoking

“…Liposomes have found applications in pharmacology for drug delivery, and in food for the delivery of flavors and nutrients. They are also used as models to study the interaction of chemicals with biological cells (Habib et al 2015). Concerning the encapsulation of contaminants, 1-aminopyrene and 1-hydroxymethylpyrene bind strongly on neutral liposomes composed of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (Macii et al 2019).…”

Pentacyclic triterpenes modulate liposome membrane fluidity and permeability depending on membrane cholesterol content

“…Among the very few studies, it has been reported that pentacyclic TTPs affect the membrane phase properties, alter the CHOL-rich domains, and may affect the function of membrane-associated proteins (Prades et al, 2011). Also, it has been demonstrated that the interaction of ER (Abboud et al, 2016;Habib et al, 2015) and the tetracyclic TTPs like cucurbitacin E (Habib et al, 2013) and corticoids (Abboud et al, 2016(Abboud et al, , 2015Kaddah et al, 2018b) affect the membrane dynamics.…”