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Scandix pecten-veneris L. (Apiaceae) is a weed species used in Iran and Turkey for medicinal purposes. The latest phytochemical reports on this umbellifer date to the 1980s. Motivated by a recent discovery of a series of chemotaxonomically important volatile long-chain n-alkyl isomeric butanoates and pentanoates from a related taxon, S. balansae, the aim of this work was to reinvestigate the chemical composition of the essential oil of S. pecten-veneris. Gas chromatography (GC) and GC combined with mass spectrometry (MS) analyses of the root, aerial part and fruit essential oils revealed the presence of 14 isomeric butanoates and pentanoates of long-chain 1-alkanols (C13–C18, C21 and C23). A small synthetic library of the tentatively identified esters allowed the final identity corroboration and screening of their antimicrobial activity. Among 123 successfully identified compounds in seven samples, seven esters (n-C15, C17, C21 and C23 isobutyrates, as well as n-C13, C15 and C17 isovalerates) turned out to be new natural metabolites and these were fully spectrally characterized (nuclear magnetic resonance, infrared, MS). All detected esters were quantified by GC with flame ionization detector (FID) calibration curves: 0.02–3.27 mg of these esters per 100 g of dry roots, aerial parts or fruits. The availability of the synthetic library made it possible to examine structure–antimicrobial activity relationships. The reinvestigation of S. pecten-veneris essential oil by standard analytical methods and the application of the synthetic approach presented the possibility of identifying very rare minor plant metabolites previously unidentifiable and provided relevant data for dereplication of other related secondary metabolites. Copyright © 2014 John Wiley & Sons, Ltd. |
