Lupane-type pentacyclic triterpenes (lupeol, betulin, and betulinic acid) are
natural products isolated from various plant sources. The terpenes exhibit a vast spectrum
of biological activity and are applied in therapies for different diseases, among which the
anticancer, anti-HIV, antihypercholest
eremic, and antiinflammatory are the most
promising. These chemicals possess amphiphilic structure and were proved to interact
strongly with biomembranes, which can be the key stage in their mechanism of action. In
our studies, we applied Langmuir monolayers as versatile models of biomembranes. It
turned out that the three investigated terpenes are capable of stable monolayer formation;
however, these monolayers differ profoundly regarding their physicochemical character-
istics. In our research, we applied the Langmuir technique (surface pressure
−
mean
molecular area (
π
−
A) isotherm registration) coupled with Brewster angle microscopy
(BAM), but the main focus was on the synchrotron radiation scattering method, grazing
incidence X-ray diffraction (GIXD), which provides information on the amphiphilic
molecule ordering in the angstro
m scale. It was proved that all the investigated terpenes
form crystalline phases in their monolayers. In the case of lupeol, only the closely packed upright phase was observed, whereas for
betulin and betulinic acid, the phase situation was more complex. Betulinic acid molecules can be organized in an upright phase,
which is crystalline, and in a tilted phase, which is amorphous. The betulin film is a conglomerate of an upright crystalline
monolayer phase, tilted amorphous monolayer phase, and a crystalline tilted bilayer. In our paper, we discuss the factors leading
to the formation of the observed phases and the implications of our results to the therapeutic applications of the native lupane-
type triterpenes.
departmental parameterization:
35
affiliation:
Wydział Chemii : Zakład Chemii Fizycznej i Elektrochemii, Wydział Chemii : Zakład Chemii Środowiska