Antileishmanial activity of anthranoïds from Psorospermum genus (Hypericaceae) used in traditional medicine and their structural analogues
Nicolas Wasser  1@  , Jean-Baptiste Gallé  2@  , Bruno Ndjakou-Lenta  3@  , Marcel Kaiser  4  , Philippe Loiseau  5, 6  , Eric Deharo  7  , Lucie Paloque  8@  , Catherine Vonthron-Sénécheau  2@  , Nicolas Girard  1@  
1 : Laboratoire d'Innovation Thérapeutique  (LIT)  -  Site web
université de Strasbourg, CNRS : UMR7200
Université de Strasbourg Faculté de Pharmacie 74 route du Rhin BP 60024 67401 Illkirch Cedex -  France
2 : Laboratoire d'Innovation Thérapeutique  (LIT)
université de Strasbourg, CNRS : UMR7200
Université de Strasbourg Faculté de Pharmacie 74 route du Rhin BP 60024 67401 Illkirch Cedex -  France
3 : Département de Chimie, Ecole Normale Supérieure, Université de Yaoundé I
Yaoundé -  Cameroun
4 : Swiss Tropical and Public Health Institute
5 : BioCIS
Université Paris-Sud
6 : Molécules bioactives, conception, isolement et synthèse  (MBCIS)  -  Site web
CNRS : UMR8076, Université Paris XI - Paris Sud
tour D.3 et D.5 Rue J.B Clément 92296 CHATENAY MALABRY CEDEX -  France
7 : Pharmacochimie et Pharmacologie Pour le Développement  (PHARMA-DEV)  -  Site web
CNRS : UMR152, Université Paul Sabatier (UPS) - Toulouse III, Institut de recherche pour le développement (IRD)
IRD UMR 152 Université Paul Sabatier 35 Chemin des Maraîchers 31400 Toulouse -  France
8 : Laboratoire de chimie de coordination  (LCC)  -  Site web
CNRS : UPR8241
205 Route de Narbonne 31077 TOULOUSE CEDEX 4 -  France

An ethnopharmacological study allowed the selection of three Psorospermum species for the strong antileishmanial activity of their bark extracts. Then phytochemical studies led to the isolation and characterization of several anthranoid compounds active on amastigotes of visceral forms of Leishmania (L. donovani, L. infantum). Deacetylvismione H exhibited the strongest antileishmanial activity (IC50=0.031 µM against L. donovani axenic amastigotes, Selectivity Index=112). The activity seemed to be directed by the nature of the anthranoid moiety and the position and the nature of the substitution groups. In order to understand the mechanism of action and improve both the activity and selectivity of the molecules, we synthesized several analogues of natural anthranoid compounds. One new analogue substituted with a prenyl group on a key position has already been synthetized with improved pharmacological profile (IC50=0.010 µM, SI=401). These data demonstrate for the first time the in vitro and in vivo antileishmanial effect of natural vismiones. SAR study revealed that vismione core substituted with prenyl group on position 3 and free hydroxyl groups on positions 1, 6 and 9 is strongly associated to antileishmanial activity against visceral species. To find out the mechanism of action in silico approaches and proteomic studies are under way.


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