Recent advances in the chemistry and biological activities of the <i>Pimpinella</i> species of Turkey

Baser, K. Hüsnü Can; Tabanca, Nurhayat; Kirimer, Nese; Bedir, Erdal; Khan, Ikhlas A.; Wedge, David E.

doi:10.1351/pac200779040539

Pure Appl. Chem., 2007, Vol. 79, No. 4, pp. 539-556

http://dx.doi.org/10.1351/pac200779040539

Recent advances in the chemistry and biological activities of the Pimpinella species of Turkey

K. Hüsnü Can Baser¹, Nurhayat Tabanca^1,2,3, Nese Kirimer¹, Erdal Bedir⁴, Ikhlas A. Khan^2,5 and David E. Wedge³

¹ Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey
² National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA
³ USDA-ARS-NPURU, The University of Mississippi, University, MS 38677, USA
⁴ Department of Bioengineering, Faculty of Engineering,Ege University, Bornova, Izmir 35100, Turkey
⁵ Department of Pharmacognosy,School of Pharmacy, The University of Mississippi, University, MS 38677, USA

Abstract: Two new natural products incorporating a phenylpropyl subunit ("phenylpropanoids"), [4-(prop-2-enyl)phenyl angelate and 4-(3-methyloxiranyl)phenyl 2-methylbutyrate], one new bisabolene-type sesquiterpenoid [1-methyl-4-(6-methylhepta-1,5-dien-2-yl)-7-oxabicyclo[4.1.0]heptane ("aureane")], and one new trinorsesquiterpene [4-(6-methylbicyclo[4.1.0]hept-2-en-7yl)butan-2-one ("traginone")] have been isolated from the essential oils of Pimpinella species occurring in Turkey, together with nine known phenylpropanoids and other natural products. Six of the known compounds are newly reported for Umbelliferae, whilst one is newly reported for Pimpinella species. Compound structures were determined by 1D and 2D NMR analysis. Isolated compounds were evaluated for antimalarial, antimicrobial, estrogenic, and aphidicidal activities. Pure compounds were also tested for antifungal activity against strawberry anthracnose-causing fungal plant pathogens Colletotrichum acutatum, C. fragariae, and C. gloeosporioides using direct bioautography and microdilution broth assays.