Isolation and Identification of a New Phenylpropanoid Derivative from the Fruits of Pimpinella Haussknechtii Rech. f. & Riedl and GC-MS Analysis of the Essential Oil

The chemical composition of the essential oil of fruits of Pimpinella haussknechtiiBoiss.was studied by GC-MS. After GC-MS analysis, one unknown component (56.7%) was observed, which was not characterized in the GC-MS library. The essential oil of P.hauskenekhtii was injected to HPLC using YMC-Pak-Sil column (250 × 20 mm) with gradient system of hexane (A), and hexane: ethyl acetate, 9:1 (B) to yield the interested compound as a new phenylpropanoid derivative. Its structure was elucidated as 4-(prop-2-enyl)-phenyl-3'-methylbutanoate (1) based on 13C- and 1H-NMR as well as 2D-NMR, IR and different MS spectra. In the essential oil analysis, thirty-six components, comprising 94.9% of the total oil, were identified. 4-(2-propenyl)-phenyl 3'-methylbutyrate (56.7%), bicyclogermacrene (8.9%), germacrene D (7.6%), perilla aldehyde (3.5%), and β-caryophyllene (2.9%) were found to be the major constituents of the oil. The oil of the fruits of P. haussknechtii consisted of eight monoterpene hydrocarbons (1.7%), two oxygenated monoterpenes (3.9%), sixteen sesquiterpene hydrocarbons (26.8%), two oxygenated sesquiterpenes (2.1%) and five phenylpropanoids (58.7%). Three other nonterpenic compounds also comprised 1.7% of the oil.