Bioactive constituents from Turkish Pimpinella species.
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.
Tabanca
Nurhayat
N
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.
Bedir
Erdal
E
Ferreira
Daneel
D
Slade
Desmond
D
Wedge
David E
DE
Jacob
Melissa R
MR
Khan
Shabana I
SI
Kirimer
Nese
N
Baser
K Husnu Can
KH
Khan
Ikhlas A
IA
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
D000900:Anti-Bacterial Agents; D009822:Oils, Volatile; D010938:Plant Oils