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Chemical Composition and Antimicrobial Activity of Volatiles from Degenia velebitica , a European Stenoendemic Plant of the Brassicaceae Family
Author(s) -
Mastelić Josip,
Blažević Ivica,
Kosalec Ivan
Publication year - 2010
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201000053
Subject(s) - chemistry , antimicrobial , glucosinolate , eugenol , chromatography , fraction (chemistry) , organic chemistry , botany , brassica , biology
Free and glucosidic bound leaf volatiles of Degenia velebitica were isolated and fractionated simultaneously into H 2 O‐soluble, H 2 O‐insoluble, and highly volatile compounds by hydrodistillation–adsorption (HDA) and analyzed by GC/MS. Among the 24 constituents identified, the main compounds obtained by the HDA method were S‐ and/or N‐atom containing compounds, i.e. , 6‐(methylsulfanyl)hexanenitrile ( 10 ; 26.78%), dimethyl trisulfide ( 6 ; 26.35%), 3,4,5‐trimethylpyrazole ( 17 ; 13.33%), hex‐5‐enenitrile ( 2 ; 10.11%), dimethyl tetrasulfide ( 8 ; 4.93%), and pent‐4‐enyl isothiocyanate ( 7 ; 4.45%). In addition, O ‐glycosidically bound volatiles and free volatiles were isolated by solvent extraction. Sixteen volatile O ‐aglycones and twelve free volatile components were identified. The main O ‐aglycones were eugenol ( 19 ; 24.15%), 2‐methoxy‐4‐vinylphenol ( 11 ; 11.50%), and benzyl alcohol ( 20 ; 9.49%), and the main free volatiles were (9 Z ,12 Z )‐octa‐9,12‐dienic acid (38.35%), hexadecanoic acid (22.64%), and phytol (5.80%). The H 2 O‐soluble volatile fraction obtained by HDA, containing mostly glucosinolate degradation products and 3,4,5‐trimethylpyrazole ( 17 ), was evaluated for antimicrobial activity by determining inhibition zones with the diffusion method as well as minimal inhibitory concentrations ( MIC ) and minimal microbicidal concentrations ( MMC ) with the micro‐dilution method. The fraction expressed activity against the tested Gram ‐positive and Gram ‐negative bacteria as well as against yeast, with MIC values equal to or lower than 16.7 μg/ml.