Hopanoids Like Sterols Form Compact but Fluid Films.

Hopanoids are pentacyclic molecules present in membranes from some bacteria, recently proposed as sterol surrogates in these organisms. Diplopterol is an abundant hopanoid that, similar to sterols, does not self-aggregate in lamellar structures when pure, but forms monolayers at the air-water interface. Here, we analyze the interfacial behavior of pure diplopterol and compare it with sterols from different organisms: cholesterol from mammals, ergosterol from fungi, and stigmasterol from plants. We prepared Langmuir monolayers of the compounds and studied their surface properties using different experimental approaches and molecular dynamics simulations. Our results indicate that the films formed by diplopterol, despite being compact with low mean molecular areas, high surface potentials, and high refractive index, depict shear viscosity values similar to that for fluid films. Altogether, our results reveal that hopanoids have similar interfacial behavior than that of sterols, and thus they may have the capacity of modulating bacterial membrane properties in a similar way sterols do in eukaryotes.