Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial activity of 7-prenyloxycoumarins against promastigotes.
Two new sesquiterpene coumarins, named szowitsiacoumarin A (1) and szowitsiacoumarin B (2), and a phenylpropanoid derivative, 2-epihelmanticine (3), together with nine known compounds, auraptene (4), umbelliprenin (5), galbanic acid (6), methyl galbanate (7), farnesiferol B (8), farnesiferol C (9), persicasulfide A (10), beta-sitosterol and stigmasterol were isolated from the roots of Ferula szowitsiana. The structures of these compounds were elucidated by extensive spectroscopic methods including 1D-((1)H and (13)C) and 2D-NMR experiments (DQF-COSY, HSQC, HMBC, and ROESY) as well as HR-MALDI-MS analysis. Since the configuration of 2-epihelmanticine was previously only partly determined, a relative configurational analysis of its four stereocenters was carried out on the basis of the recently reported J-based method. The inhibiting activity of prenylated coumarins, auraptene (4) and umbelliprenin (5), in addition to galbanic acid (6), as major component, and of the Me(2)CO extract of Ferula szowitsiana (Apiaceae) roots has been evaluated against promastigotes of Leishmania major. Umbelliprenin and auraptene showed significant activity with IC(50) values of 4.9microg/ml (13.3microM) and 5.1microg/ml (17.1microM) after 48h incubation, respectively.
Iranshahi
Mehrdad
M
Department of Pharmacognosy and Biotechnology, Faculty of Pharmacy, Mashhad, Iran. Iransham@sina.tums.ac.ir
Arfa
Peyman
P
Ramezani
Mohammad
M
Jaafari
Mahmoud Reza
MR
Sadeghian
Hamid
H
Bassarello
Carla
C
Piacente
Sonia
S
Pizza
Cosimo
C
D003374:Coumarins / Q000737:chemistry* / Q000302:isolation & purification; D005309:Ferula / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D003374:Coumarins; D012717:Sesquiterpenes