Phytochemical study from the roots of Ferula lutea L

A. Jabrane; H. Ben jannet; F. H. Skhiri; T. Miyamoto; M. A. Lacaille-Dubois

doi:10.1055/s-0028-1084484

Planta Medica, Table of Contents

Phytochemical study from the roots of Ferula lutea L

A Jabrane ¹^,², H Ben jannet ³, FH Skhiri ², T Miyamoto ⁴, MA Lacaille-Dubois ¹

¹Laboratoire de Pharmacognosie, Unité de Molécules d'Intérêt Biologique, UMIB, UPRES-EA 3660, U.F.R. des Sciences Pharmaceutiques et Biologiques, Université de Bourgogne, Dijon, France
²Institut Supérieur de Biotechnologie de Monastir, Université de Monastir, 5000, Monastir, Tunisie
³Laboratoire de Chimie des Substances Naturelles et de Synthèse Organique, Faculté des Sciences de Monastir, Université de Monastir, 5000 Monastir, Tunisie
⁴Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka 812–8582, Japan

Abstract

The genus Ferula belongs to the Apiaceae family with more than 150 species widespread throughout the Mediterranean area and Central Asia. Several species of this genus have been used in folk medicine to cure stomachic, febrifuge, vermifuge and carminative disorders as well as to treat skin infections and diabetes [1,2].

This genus is well documented as a good source of biologically active metabolites. Some isolated coumarins revealed significant effects such as an anti-HIV activity, inhibition of cytokine release and early events of carcinogenesis [1].

The biological importance of members of this genus, prompted us to investigate the roots of the Tunisian Ferula lutea L., which has never been studied phytochemically before. The fresh roots of this plant were extracted with MeOH at room temperature. The non-polar fraction of the methanolic extract, was submitted to successive chromatographic separations using medium-pressure liquid chromatography (MPLC) on Silica gel and CC on Sephadex LH 20 affording two furanocoumarins, Psoralen (1) and Xanthotoxin (2), a dihydrofuranocoumarin, Prantschimgin (3) as well as two phytosterols, β-sitosterol and stigmasterol.

Their structures were elucidated by extensive spectroscopic methods including 1D-(¹H and ¹³C) and 2D NMR experiments (COSY, TOCSY, HMQC, HMBC and NOESY) as well as EIMS and by comparison with literature data. Our contribution to the study of the Tunisian Ferula lutea allowed the isolation and characterization of two furanocoumarins 1 and 2 which can both serve as a chemotaxonomic marker for the genus Ferula whereas the dihydrofuranocoumarin 3 was reported for the first time in Ferula. This investigation reinforces the previous studies on the Ferula genus showing that it is a good source of coumarins.

References: 1. Abd El-Razek, M. H. et al. (2003) Heterocycles 60: 689–716 2. Iranshahi, M. et al. (2008) Phytochemistry 69:473–478.