4th EucheMs chemistry congress

Poster Session 1
s1025
chem. Listy 106, s587–s1425 (2012)
Poster session 1 - organic chemistry
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SyntheSiS of ruSCozePine A And B, noveL
nAturAL ProduCtS iSoLAted froM ButCher’S
BrooM
J. herrMAnn 1 , G. JürGenLieMK 2 , J. heiLMAnn 2 ,
B. KÖniG 1
1 Institute of Organic Chemistry, Department of Chemistry and
Pharmacy, Regensburg, Germany
2 Institute of Pharmacy, Department of Chemistry and
Pharmacy, Regensburg, Germany
The novel natural products, Ruscozepine A and B, have been
isolated from Ruscus aculeatus L., also called Butcher’s Broom. [1]
An extract from the roots of this shrub is already used for the
treatment of various diseases, including chronic venous
insufficiency [2] and hemorrhoids. [3] The pharmacological activity
is mostly ascribed to the steroidal saponins and ruscinogens, being
the main constituents of the Rusci rhizoma extract. However,
nothing is known about the influence on the pharmacological
effects of the novel found Benzoxepines. Because of the low
availability of these compounds by isolation, a synthetic approach
was needed to guarantee the supply for extensive pharmacological
testing. Beside the synthesis of the isolated compounds a few
analogues substances, e. g. Benzazepines, are synthesized to
create a small substance library.
references:
1. Barbic, M., Schmidt, T. J., Jürgenliemk, G., Novel
Phenyl-1-benzoxepinols from Butcher’s Broom
(Rusci rhizoma). Chemistry & Biodiversity in press, doi:
10.1002/cbdv.201100158
2. Abascal, K.; Yarnell, E., Botanicals for Chronic Venous
Insufficiency. Alternative and Complementary Therapies
2007, 13 (6), 304 - 311.
3. MacKay, D., Hemorrhoids and varicose veins: a review of
treatment options. Altern Med Rev 2001, 6 (2), 126-40.
Keywords: Natural products; Enantioselectivity; Biological
activity; Synthetic methods;
4 th EucheMs chemistry congress
P - 0 3 2 8
ControLLed SyntheSiS of SMArt druG
deLivery SySteM froM veGetABLe oiL
L. heSPeL 1 , G. MorAndi 1 , L. LeCAMP 1 , f. BureL 1
1 Institut national des sciences appliquée de Rouen,
Seine-Maritime, Saint Etienne du Rouvray, France
Email: louise.hespel@insa-rouen.fr
Since liposomes were first described in the 1960s and
proposed as carriers of proteins and drugs for disease treatment,
they have been extensively studied and their efficiency as drug
delivery systems has been demonstrated. [1] However liposomology
still faces major deficiencies, partly due to their large size. [2]
Developing new vectorisation systems of smaller size, typically
micelles, but having the same affinity with cells membrane is then
of great interest and our group is consequently interested in
synthesis of amphiphilic block copolymers containing a
hydrophobic block based on a lipid chain. In that purpose, an
original synthetic pathway in two main steps was chosen: (1) the
vegetable oil is first chemically modified to introduce an initiating
site for Atom Transfer Radical Polymerization (ATRP) leading to
a lipoinitiator and (2) a synthetic hydrophilic block is added to
the lipid block using ATRP.
The final amphiphilic copolymers are soluble in water,
leading to uncolored and foaming solutions. The properties and
structure of this innovating micellar system are studied. The
micelles present low critical micelle concentrations with a strong
dependence to the pH value and a linear dependence to the
hydrophilic block length. The micelles ability to encapsulate
hydrophobic molecules has been demonstrated and their release
properties are currently under investigation as well the
polymerization of other monomers to access “intelligent” systems.
references:
1. D. Lasic & D. Papahadjopoulos, Medical applications of
liposomes, Amsterdam, 1998.
2. Y. Barenholz Curr. Opin. Colloid Interface Sci. 2001, 6,
66-77.
Keywords: Drug delivery; amphiphiles; lipid; renewable
resources; Polymers;
AUGUst 26–30, 2012, PrAGUE, cZEcH rEPUbLIc