Biological evaluation, overpressured layer chromatography separation, and isolation of a new acetylenic derivative compound from Prangos platychlaena ssp. platychlaena fruit essential oils

Abstract

In the present work, fruits of Prangos platychlaena Boiss. ex Tchihat. ssp. platychlaena (Apiaceae) collected from eastern (sample A) and central (sample B) parts of Turkey were subjected to hydrodistillation to yield essential oils (EOs). The chemical composition of P. platychlaena ssp. platychlaena fruit oil was analyzed by gas chromatography–flame ionization detector (GC–FID) and gas chromatography–mass spectrometry (GC–MS) techniques. An unknown compound with m/z 178 [M]+ in high percentages was detected in both EOs (45.8% and 11.2% in samples A and B, respectively). Column chromatography on silica gel was subsequently followed by the sample A and yielded a new acetylenic derivative (1), which was characterized by spectroscopic techniques as (2S)- 3,5-nonadiyne-2-yl acetate. Samples A and B oils were characterized by a series of acetylenic derivatives like 3,5-nonadiyne (24.5% and 5.8% in A and B, respectively), (Z)-3,5-nonadiyne-7-ene (0.2% in A), and (E)-3,5-nonadiyne-7-ene (0.5% in A). Monoterpenes...