https://doi.org/10.15255/KUI.2006.029
Published: Kem. Ind. 56 (4) (2007) 199–207
Paper reference number: KUI-29/2006
Paper type: Review
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Contribution to the Research of Free and Glycosidically Bound Volatiles from 2001 to 2006

I. Jerković

Abstract

This review paper presents a contribution to the research of free and glycosidically bound volatiles in the 2001–2006 period obtained by work in the Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Croatia. Many terpene structures, phenylpropane derivatives (Fig. 6), as well as aliphatic hydrocarbons, alcohols, carbonyls, fatty acids and others were identified (Fig. 5). The chemotypes of Origanum vulgare ssp. hirtum, Artemisia absinthium and Myrtus communis were determined and some uninvestigated or insufficiently investigated plants (Micromeria juliana, Sequaoiadendron giganteum, Populus nigra, Prunus mahaleb, Ailanthus altissima and others) were analyzed. A newly developed method of co-distillation enabled isolation of unstable volatile compounds without formation of artefacts (Fig. 1). The volatile aglycones liberated by enzymatic hydrolysis of the corresponding glycosides were aliphatic and phenylpropanoic derivatives, as well as monoterpenes, sesquiterpenes and others (Fig. 7). Only partial similarity was observed in the composition of volatile aglycones and corresponding free volatiles of the same plant. Furthermore, glucosides of ubiquitous monoterpene and aliphatic alcohols and phenols were prepared by Koenigs-Knorr glucosylation (Fig. 8), by enzymatic condensation and transglucosidation from cellobiose (Fig. 11) and by direct glucosylation with FeCl3 (Fig. 13). The products were characterized by GC-MS analysis of prepared tetraacetyl glucosides. Fragment ion characteristics of the aglucone moiety were present in all mass spectra, along with the fragments obtained from acetylated glucose (Fig. 12 and Fig. 14). Acetylated glucosides were separable on the HP-101 column, Fig. 9 (even diastereomeric tetraacetyl
-glucosides of enantiomeric alcohols, Fig. 10).

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Keywords

essential oils, glycosidically bound volatiles, O-glycosides synthesis, GC-MS