Title (srp)

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


Živković Stošić, Milena, 1987-


Stojanović, Gordana, 1960-
Zlatković, Bojan, 1970-
Dekić, Milan S., 1980-
Genčić, Marija S., 1985-
Radulović, Niko, 1981-

Description (srp)

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.

Description (srp)

Bibligrafija: str. 179-189. Datum odbrane: 26.08.2022. Organic chemistry and biochemistry, organic synthesis

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