The Equilibria of Diosgenin–Phosphatidylcholine and Diosgenin–
Cholesterol in Monolayers at the Air/Water Interface
Aneta Dorota Petelska
Received: 2 February 2016 / Accepted: 15 June 2016 / Published online: 27 June 2016
Ó The Author(s) 2016. This article is published with open access at Springerlink.com
Abstract Diosgenin (Dio) has shown many treatment
properties, but the most important property is cytotoxic
activity in cancer cells. In this study, we investigated
monolayers of Dio, cholesterol (Ch), and phosphatidyl-
choline (PC) at the air/water interface. The measurements
were carried with a Langmuir Teﬂon trough and a Nima
9000 tensiometer program. The surface tension values of
pure and mixed monolayers were used to calculate p–A
isotherms and determine molecular surface areas. We were
able to demonstrate the formation of complexes between
Dio and PC and Dio and Ch molecules also. We considered
the equilibrium between individual components and the
formed complexes. In addition, we established that dios-
genin and the lipids formed highly stable 1:1 complexes.
Keywords Diosgenin Á Phosphatidylcholine Á Cholesterol Á
Complex formation equilibria Á Monolayer Á Langmuir
Since the dawn of time, the plants were the main source of
drugs. The World Health Organization (WHO) announced
the list of 21,000 plants, which have medicinal effects
worldwide (Patel et al. 2012). One of the medicinal plants
species are saponins which can be found in Agavaceae,
Dioscoreaceae, Liliaceae, Solanaceae, Scrophulariaceae,
Amaryryllidaceae, Leguminosae, and Rhamnaceae (Chen
et al. 2015). The Dioscoreaceae Family is known as yams.
Plants of genus Dioscorea are an essential component of
food for many populations in Africa, Asia, and tropical
America. The leading production comes from West Africa
contributing to 95 % of the world production (Contreras–
Pacheco et al. 2013).
For the ﬁrst time, diosgenin (Dio) was discovered in 1935
by Fujii and Matsukawa in Dioscorea Tokoro Makino.This
substance is a steroidal sapogenin predominantly found in
yams, fenugreek, and Costus speciosus. Dio molecule
(Fig. 1) is structurally similar to cholesterol (Ch) and other
steroids (Hostettmann and Marston 1995). In the pharma-
ceutical industry, Dio is a very important source of steroidal
hormones. The saponin is a precursor of sex hormones
(progesterone), corticosteroids (corticosone), and contra-
ceptives (Djerassi et al. 1952). Many studies have shown that
Dio plays an important role in Ch metabolism (Liu et al.
2005, Chen et al. 2015). Dio has both antioxidant property
and anticholesterolomic activity (Selim and Jaouni 2015).
Dio has been used as an antihypercholesterolemia, antihy-
pertriacylglycerolemia, antidiabetes, and antihyperglicemia
agent (Chen et al. 2011). In addition, Dio possesses anti-
cancer properties. Many studies showed that Dio inhibits
proliferation and induces apoptosis in a variety of tumor cells
such as osteosarcoma, colon carcinoma, hepatoma, leuke-
mia, and breast carcinoma (Moalic et al. 2001; Chiang et al.
2007; Li et al. 2010; He et al. 2014).
The objective of the present work was to examine the
possible effect of Dio on the lipid monolayer from phos-
phatidylcholine (PC) or Ch. The molecular interactions
between Dio and PC and Dio and Ch were also studied.
The interaction was checked by analyzing physicochemical
properties for binary mixed monolayers (lipid–Dio), treated
as the simplest model of a half of the biological membrane.
In this paper, we present evidence for the formation of 1:1
& Aneta Dorota Petelska
Institute of Chemistry, University of Bialystok, K.
Ciolkowskiego 1K, 15-245 Bialystok, Poland
J Membrane Biol (2016) 249:585–590