Identifikacija i sinteza odabranih sastojaka voskova biljnih vrsta Prima veris L., Primula acaulis(L.) L. (Primulaceae) I Liriodendron tulipifera L. (Magnoliaceae)
This doctoral dissertation presents the chemical composition of thewashings of Primula veris L., Primula acaulis (L.) L. andLiriodendron tulipifera L. The studied Primula species were rich inlong-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. Evennumberediso-alkanes and 2-alkanones, and iso-odd-numbered fattyacid benzyl esters, are unique for Primula spp. Washings of P. veriscontained 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 (66new), and 77 long-chain n-, iso-, anteiso-, 2-methyl-, and 3-methylfatty acids. All long-chain 2-methyl- and 3-methyl acids werefound in the Plant Kingdom for the first time. Benzyl esters lower thewax 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 DMDSadducts MS. Where possible, the configuration was inferred from theNMR analysis of cyclopropanation adducts. 10/11-Hydroxy-16-hentriacontanones were identified based on the analysis oftrimethylsilyl derivatives of hydroxy-ketone and bis(trimethylsilyl)derivatives of hentriacontanediols MSes. GC-MS analysis of L.tulipifera leaf washings samples revealed that the main constituentwas palmitone, while separate GC-MS analyses of petals, sepals, andpistils with anthers, revealed palmitone to be predominant on thepetal and sepal surfaces.
Bibligrafija: str. 179-189. Datum odbrane: 26.08.2022. Organic chemistry and biochemistry, organic synthesis
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