Identifikacija i sinteza odabranih sastojaka voskova biljnih vrsta Prima veris L., Primula acaulis(L.) L. (Primulaceae) I Liriodendron tulipifera L. (Magnoliaceae)

Abstract

This doctoral dissertation presents the chemical composition of the washings of Primula veris L., Primula acaulis (L.) L. and Liriodendron tulipifera L. The studied Primula species were rich in long-chain branched alkanes. For the first time, 19 new long-chain n-, iso-, and anteiso-benzyl alkanoates, as well as 8 iso- and 6 anteiso-2- alkanones were identified in samples of natural origin. Evennumbered iso-alkanes and 2-alkanones, and iso-odd-numbered fatty acid benzyl esters, are unique for Primula spp. Washings of P. veris contained new: 16 syn-1-phenylalkane-1,3-diyl diacetates, 7 3-oxo-1- phenylalkan-1-yl acetates, 8 1-phenylalkane-1,3-diones, and 10 1- Hydroxy-1-phenylalkan-3-ones, with n-, iso- and anteiso-chaintermini. Also, 79 n-, iso-, and anteiso-sec-alcohols were identified (66 new), and 77 long-chain n-, iso-, anteiso-, 2-methyl-, and 3- methylfatty acids. All long-chain 2-methyl- and 3-methyl acids were found in the Plant Kingdom for the first time. Benzyl esters lower the wax melting point, which increases the permeability of the cuticle, and reduce the harmful effects of UV-C radiation. Washings of L. tulipifera flowers, among the most abundant palmitone, contained nalkanes, (E)-n-alkenes, regioisomeric alk(en)als, alkanones, and (Z)- alk(en)-1-ols. Double bond regiochemistry was inferred from DMDS adducts MS. Where possible, the configuration was inferred from the NMR analysis of cyclopropanation adducts. 10/11-Hydroxy-16- hentriacontanones were identified based on the analysis of trimethylsilyl derivatives of hydroxy-ketone and bis(trimethylsilyl) derivatives of hentriacontanediols MSes. GC-MS analysis of L. tulipifera leaf washings samples revealed that the main constituent was palmitone, while separate GC-MS analyses of petals, sepals, and pistils with anthers, revealed palmitone to be predominant on the petal and sepal surfaces.