title: New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire.
abstract: A phytochemical investigation of the roots of Ferula lutea (Poir.) Maire led to the isolation of new dihydrofuranocoumarins as two inseparable isomers, (-)-5-hydroxyprantschimgin 1 and (-)-5-hydroxydeltoin 2, together with eight known compounds, (-)-prantschimgin 3, (-)-deltoin 4, psoralen 5, xanthotoxin 6, umbelliferone 7, caffeic acid 8, β-sitosterol 9 and stigmasterol 10. Their structures were elucidated on the basis of extensive spectroscopic methods, including 1D and 2D NMR experiments and mass spectroscopy analysis, as well as by comparison with literature data. The anti-acetylcholinesterase and cytotoxic effects of the isolates and antioxidant activities of the mixture (1+2) were also evaluated in this work. Results showed that the mixture (1+2) has the most cytotoxic activity with IC50 values 0.29±0.05 and 1.61±0.57μM against the cell lines HT-29 and HCT 116, respectively. The greatest acetylcholinesterase inhibitory activity (IC50=0.76±0.03) was exhibited by the xanthotoxin 6. In addition, the mixture (1+2) was investigated for its antioxidant activity and showed IC50 values 18.56, 13.06, 7.59, and 4.81μM towards DPPH free radical scavenging, ABTS radical monocation, singlet oxygen and hydrogen peroxide, respectively.
authors.affiliation: Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity, Team: Medicinal Chemistry and Natural Products, Faculty of Sciences, University of Monastir, Monastir, Tunisia.
authors.forename: Saoussen
authors.initials: S
authors.lastname: Ben Salem
authors.forename: Aymen
authors.initials: A
authors.lastname: Jabrane
authors.forename: Fethia
authors.initials: F
authors.lastname: Harzallah-Skhiri
authors.forename: Hichem
authors.initials: H
authors.lastname: Ben Jannet
mesh_terms: D000110:Acetylcholinesterase / Q000737:chemistry / Q000378:metabolism; D000975:Antioxidants / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D002470:Cell Survival / Q000187:drug effects; D003374:Coumarins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D005309:Ferula / Q000737:chemistry*; D045325:HCT116 Cells; D019073:HT29 Cells; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry
chemical_list: D000975:Antioxidants; D003374:Coumarins; D000110:Acetylcholinesterase