title: Bioactive constituents from Turkish Pimpinella species.
abstract: A new 'phenylpropanoid', 4-(3-methyloxiran-2-yl)phenyl 2-methylbutanoate (1), a new trinorsesquiterpene, 4-(6-methylbicyclo[4.1.0]hept-2-en-7-yl)butan-2-one (2), and eight known compounds (3-10) were isolated from the essential oils of several Pimpinella species growing in Turkey. The structures of the new compounds were determined by 1D- and 2D-NMR analyses. The absolute configuration of 1 was established via comparison of its optical rotation with that of 'epoxypseudoisoeugenyl 2-methylbutyrate' (11), the absolute configuration of which was determined by chemical degradation and an appropriate Mosher ester formation. Direct bioautography revealed antifungal activity of 1 and 11 against Colletotrichum acutatum, C. fragariae, and C. gloesporioides. Subsequent evaluation of antifungal compounds in a 96-well microtiter assay showed that compounds 1 and 11 produced the most-significant growth inhibition in Phomopsis spp., Colletotrichum spp., and Botrytis cinerea. Compounds 1 and 6 displayed antimicrobial activities against Mycobacterium intracellulare, with IC50 values of 2.78 and 1.29 microM, respectively.
authors.affiliation: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
authors.forename: Nurhayat
authors.initials: N
authors.lastname: Tabanca
authors.forename: Erdal
authors.initials: E
authors.lastname: Bedir
authors.forename: Daneel
authors.initials: D
authors.lastname: Ferreira
authors.forename: Desmond
authors.initials: D
authors.lastname: Slade
authors.forename: David E
authors.initials: DE
authors.lastname: Wedge
authors.forename: Melissa R
authors.initials: MR
authors.lastname: Jacob
authors.forename: Shabana I
authors.initials: SI
authors.lastname: Khan
authors.forename: Nese
authors.initials: N
authors.lastname: Kirimer
authors.forename: K Husnu Can
authors.initials: KH
authors.lastname: Baser
authors.forename: Ikhlas A
authors.initials: IA
authors.lastname: Khan
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D009822:Oils, Volatile / Q000737:chemistry / Q000494:pharmacology; D028042:Pimpinella / Q000737:chemistry*; D010938:Plant Oils / Q000737:chemistry* / Q000494:pharmacology; D014421:Turkey
chemical_list: D000900:Anti-Bacterial Agents; D009822:Oils, Volatile; D010938:Plant Oils