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Title: Recent Advances in the Chemistry and Biological Activities of the Pimpinella Species of Turkey

item Tabanca, Nurhayat
item Wedge, David

Submitted to: Journal of Pure and Applied Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 11/21/2006
Publication Date: 4/1/2007
Citation: Can Baser, K., Tabanca, N., Kirimer, N., Bedir, E., Khan, I.A., Wedge, D.E. 2007. Recent Advances in the Chemistry and Biological Activities of the Pimpinella Species of Turkey. Journal of Pure and Applied Chemistry. V. 79(4):539-556.

Interpretive Summary: Many species in Pimpinella L. (Apiaceae ) are agronomically important, particularly those species with distinctive aromas and flavors. The most widely known and cultivated Pimpinella species is P. anisum (common name=anise). Anise enjoys considerable reputation as a medicine for coughs and upper respiratory infections. In hard, dry coughs where expectoration is difficult, it is of much value. It is greatly used in the form of lozenges and the seeds have also been used for smoking, to promote expectoration. The stimulant and carminative properties of Anise make it useful in flatulency and colic. The volatile oil, mixed with spirits of wine forms the liqueur Anisette, which has a beneficial action on the bronchial tubes, and for bronchitis and spasmodic asthma. The aroma of the essential oil (up to 3% in the fruits) is dominated by trans-anethole ( up to 90%). Four new and 18 known compounds were isolated and identified from Pimpinella essential oils. Isolated compounds were also evaluated for their antimalarial, antibacterial, antifungal, estrogenic, and aphidicidal activities.

Technical Abstract: Two new phenylpropanoids [4-(2-propenyl)phenylangelate (1), 4-(3-methyloxiranyl)phenyl 2-methylbutyrate (3)], one new bisabolene-type sesquiterpenoid [1-methyl-4-(5-methyl-1-methylene-hex-4-enyl)-7-oxa-bicyclo[4.1.0] heptane = aureane (2)], and one new trinorsesquiterpene [4-(6-methyl-bicyclo[4.1.0]hept-2-en-7yl) butan-2-one=traginone (4)] were isolated and identified. Six known compounds are newly reported for Umbelliferae [4(1-propenyl)phenyl 2-methylbutanoate (5), dictamnol (6), 4,6-guaiadiene (7), 4-(1-propenyl)phenyl isobutyrate (8), alismol (9), 12-hydroxy-B-caryophyllene acetate (10)] and one known compound [trans-isoosmorhizole (11)] is newly reported for Pimpinella. Nine known phenylpropanoids were isolated from the essential oils of several Pimpinella species from Turkey. 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 the direct bioautography and micro-dilution broth assays. Various bioassays performed in these studies showed that the phenylpropanoids appeared to be more biologically active than sesquiterpenes.