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Keywords = tetratriacontane-16,18-dione

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22 pages, 1797 KiB  
Article
Wax Composition of Serbian Dianthus spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications
by Marko Z. Mladenović, Milenko N. Ristić, Andrija I. Bogdanović, Novica R. Ristić, Fabio Boylan and Niko S. Radulović
Plants 2023, 12(11), 2094; https://doi.org/10.3390/plants12112094 - 24 May 2023
Cited by 4 | Viewed by 2062
Abstract
Although ethnopharmacologically renowned, wax constituents of Dianthus species were sporadically studied. A combination of GC-MS analysis, synthesis, and chemical transformations enabled the identification of 275 constituents of diethyl-ether washings of aerial parts and/or flowers of six Dianthus taxa (Dianthus carthusianorum, D. [...] Read more.
Although ethnopharmacologically renowned, wax constituents of Dianthus species were sporadically studied. A combination of GC-MS analysis, synthesis, and chemical transformations enabled the identification of 275 constituents of diethyl-ether washings of aerial parts and/or flowers of six Dianthus taxa (Dianthus carthusianorum, D. deltoides, D. giganteus subsp. banaticus, D. integer subsp. minutiflorus, D. petraeus, and D. superbus) and one Petrorhagia taxon (P. prolifera) from Serbia. Seventeen of these constituents (nonacosyl benzoate, additional 12 benzoates with anteiso-branched 1-alkanols, eicosyl tiglate, triacontane-14,16-dione, dotriacontane-14,16-dione, and tetratriacontane-16,18-dione) and two additional synthesized eicosyl esters (angelate and senecioate) represent completely new compounds. The structures of the tentatively identified β-ketones were confirmed by analysis of the mass fragmentation of the corresponding pyrazoles and silyl enol ethers obtained by transformations of crude extracts and extract fractions. Silylation allowed the identification of 114 additional constituents, including a completely new natural product (30-methylhentriacontan-1-ol). The results obtained by multivariate statistical analyses showed that the chemical profile of Dianthus taxa’s surface waxes is subject to both genetic and ecological factors, whereas the latter seemingly takes a more important role for the studied Dianthus samples. Full article
(This article belongs to the Special Issue Phytochemical Composition and Biological Activity)
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