Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications
Although ethnopharmacologically renowned, wax constituents of <i>Dianthus</i> 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 flower...
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MDPI AG
2023-05-01
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| Series: | Plants |
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| Online Access: | https://www.mdpi.com/2223-7747/12/11/2094 |
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| author | Marko Z. Mladenović Milenko N. Ristić Andrija I. Bogdanović Novica R. Ristić Fabio Boylan Niko S. Radulović |
| author_facet | Marko Z. Mladenović Milenko N. Ristić Andrija I. Bogdanović Novica R. Ristić Fabio Boylan Niko S. Radulović |
| author_sort | Marko Z. Mladenović |
| collection | DOAJ |
| description | Although ethnopharmacologically renowned, wax constituents of <i>Dianthus</i> 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 <i>Dianthus</i> taxa (<i>Dianthus carthusianorum</i>, <i>D. deltoides</i>, <i>D. giganteus</i> subsp. <i>banaticus</i>, <i>D. integer</i> subsp. <i>minutiflorus</i>, <i>D. petraeus</i>, and <i>D. superbus</i>) and one <i>Petrorhagia</i> taxon (<i>P. prolifera</i>) from Serbia. Seventeen of these constituents (nonacosyl benzoate, additional 12 benzoates with <i>anteiso</i>-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 <i>Dianthus</i> taxa’s surface waxes is subject to both genetic and ecological factors, whereas the latter seemingly takes a more important role for the studied <i>Dianthus</i> samples. |
| first_indexed | 2024-03-11T02:59:28Z |
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| id | doaj.art-479d90f2a0e94797af7865cb77719b96 |
| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-03-11T02:59:28Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
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| series | Plants |
| spelling | doaj.art-479d90f2a0e94797af7865cb77719b962023-11-18T08:23:16ZengMDPI AGPlants2223-77472023-05-011211209410.3390/plants12112094Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic ImplicationsMarko Z. Mladenović0Milenko N. Ristić1Andrija I. Bogdanović2Novica R. Ristić3Fabio Boylan4Niko S. Radulović5Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaFaculty of Natural Science and Mathematics, University of Priština, Lole Ribara 29, 38220 Kosovska Mitrovica, SerbiaDepartment of Biology and Ecology, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaFaculty of Natural Science and Mathematics, University of Priština, Lole Ribara 29, 38220 Kosovska Mitrovica, SerbiaSchool of Pharmacy and Pharmaceutical Sciences, Panoz Institute, and Trinity Biomedical Sciences Institute, Trinity College Dublin, D02 PN40 Dublin, IrelandDepartment of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaAlthough ethnopharmacologically renowned, wax constituents of <i>Dianthus</i> 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 <i>Dianthus</i> taxa (<i>Dianthus carthusianorum</i>, <i>D. deltoides</i>, <i>D. giganteus</i> subsp. <i>banaticus</i>, <i>D. integer</i> subsp. <i>minutiflorus</i>, <i>D. petraeus</i>, and <i>D. superbus</i>) and one <i>Petrorhagia</i> taxon (<i>P. prolifera</i>) from Serbia. Seventeen of these constituents (nonacosyl benzoate, additional 12 benzoates with <i>anteiso</i>-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 <i>Dianthus</i> taxa’s surface waxes is subject to both genetic and ecological factors, whereas the latter seemingly takes a more important role for the studied <i>Dianthus</i> samples.https://www.mdpi.com/2223-7747/12/11/2094<i>Dianthus</i>waxbranched long-chain benzoatesβ-diketonestriacontane-14,16-dionedotriacontane-14,16-dione |
| spellingShingle | Marko Z. Mladenović Milenko N. Ristić Andrija I. Bogdanović Novica R. Ristić Fabio Boylan Niko S. Radulović Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications Plants <i>Dianthus</i> wax branched long-chain benzoates β-diketones triacontane-14,16-dione dotriacontane-14,16-dione |
| title | Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications |
| title_full | Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications |
| title_fullStr | Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications |
| title_full_unstemmed | Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications |
| title_short | Wax Composition of Serbian <i>Dianthus</i> spp. (Caryophyllaceae): Identification of New Metabolites and Chemotaxonomic Implications |
| title_sort | wax composition of serbian i dianthus i spp caryophyllaceae identification of new metabolites and chemotaxonomic implications |
| topic | <i>Dianthus</i> wax branched long-chain benzoates β-diketones triacontane-14,16-dione dotriacontane-14,16-dione |
| url | https://www.mdpi.com/2223-7747/12/11/2094 |
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