Recent advances in the chemistry and biological activities of the Pimpinella species of Turkey*
K. Husnu Can Baser1, Nurhayat Tabanca1,3,5, Nese Kirimer1, Erdal Bedir2, Ikhlas A. Khan3,4, and David E. Wedge5
1Department of Pharmacognosy, Faculty of Pharmacy, Anadolu University, 26470, Eskisehir, Turkey; 2Department of Bioengineering, Faculty of Engineering,Ege University, Bornova, Izmir 35100, Turkey; 3National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, The University of Mississippi, University, MS 38677, USA; 4Department of Pharmacognosy,School of Pharmacy, The University of Mississippi, University, MS 38677, USA; 5USDA-ARS-NPURU, 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.
Keywords: Pimpinella; essential oils; GC; GC/MS; phenylpropanoids; sesquiterpenes; monoterpenes.
*Pure Appl. Chem. 79, 467-823 (2007) pp. 467-823. An issue of reviews and research papers based on lectures presented at the 25th International Symposium on Chemistry of Natural Products (ISCNP-25) and 5th International Conference on Biodiversity (ICOB-5), held jointly in Kyoto, Japan, 23-28 July 2006, on the theme of natural products.