New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices
Species of the genus <i>Doronicum</i> are known for their pharmacological properties and essential oils, the chemical composition of which remains inadequately studied. In this work, GC-MS analysis, synthesis, and spectral techniques (UV, IR, MS, and NMR) were employed to identify 83 con...
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2025-01-01
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| author | Milan Ž. Dimitrijević Marko Z. Mladenović Milica D. Nešić Milan S. Dekić Vidak N. Raičević Niko S. Radulović |
| author_facet | Milan Ž. Dimitrijević Marko Z. Mladenović Milica D. Nešić Milan S. Dekić Vidak N. Raičević Niko S. Radulović |
| author_sort | Milan Ž. Dimitrijević |
| collection | DOAJ |
| description | Species of the genus <i>Doronicum</i> are known for their pharmacological properties and essential oils, the chemical composition of which remains inadequately studied. In this work, GC-MS analysis, synthesis, and spectral techniques (UV, IR, MS, and NMR) were employed to identify 83 constituents in the essential oil from <i>D. columnae</i> roots, which accounted for 98.1% of the total GC-peak area. The major components were thymyl isobutyrate (32.8%) and thymyl 2-methylbutyrate (22.8%), while the minor constituents were methoxy-<i>p</i>-cymene derivatives. Six new natural products were identified through synthesis, GC co-injection experiments and spectral characterization, including esters (isobutyrate, 2-methylbutyrate, and/or isovalerate) of 2-methoxycuminol, 6-methoxythymol, and 6-hydroxythymyl methyl ether, as well as methyl 3-methoxycuminate. Their identification was made possible by synthesis efforts, as isolating pure compounds was impracticable because of their low abundance and the overall structural similarity within the highly complex mixture that was the essential oil. |
| format | Article |
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| institution | Kabale University |
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| language | English |
| publishDate | 2025-01-01 |
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| spelling | doaj-art-91c36176fd0e40409b58117684c22bf42025-01-24T13:43:29ZengMDPI AGMolecules1420-30492025-01-0130230210.3390/molecules30020302New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex MatricesMilan Ž. Dimitrijević0Marko Z. Mladenović1Milica D. Nešić2Milan S. Dekić3Vidak N. Raičević4Niko S. Radulović5Department of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaDepartment of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaDepartment of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaDepartment of Sciences and Mathematics, State University of Novi Pazar, Vuka Karadžića 9, 36300 Novi Pazar, SerbiaFaculty of Medicine, University of Novi Sad, Hajduk Veljkova 3, 21000 Novi Sad, SerbiaDepartment of Chemistry, Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, SerbiaSpecies of the genus <i>Doronicum</i> are known for their pharmacological properties and essential oils, the chemical composition of which remains inadequately studied. In this work, GC-MS analysis, synthesis, and spectral techniques (UV, IR, MS, and NMR) were employed to identify 83 constituents in the essential oil from <i>D. columnae</i> roots, which accounted for 98.1% of the total GC-peak area. The major components were thymyl isobutyrate (32.8%) and thymyl 2-methylbutyrate (22.8%), while the minor constituents were methoxy-<i>p</i>-cymene derivatives. Six new natural products were identified through synthesis, GC co-injection experiments and spectral characterization, including esters (isobutyrate, 2-methylbutyrate, and/or isovalerate) of 2-methoxycuminol, 6-methoxythymol, and 6-hydroxythymyl methyl ether, as well as methyl 3-methoxycuminate. Their identification was made possible by synthesis efforts, as isolating pure compounds was impracticable because of their low abundance and the overall structural similarity within the highly complex mixture that was the essential oil.https://www.mdpi.com/1420-3049/30/2/302<i>Doronicum columnae</i>volatile constituentsNMRGC-MSstructure elucidation |
| spellingShingle | Milan Ž. Dimitrijević Marko Z. Mladenović Milica D. Nešić Milan S. Dekić Vidak N. Raičević Niko S. Radulović New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices Molecules <i>Doronicum columnae</i> volatile constituents NMR GC-MS structure elucidation |
| title | New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices |
| title_full | New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices |
| title_fullStr | New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices |
| title_full_unstemmed | New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices |
| title_short | New Oxygenated Methoxy-<i>p</i>-Cymene Derivatives from Leopard’s Bane (<i>Doronicum columnae</i> Ten., Asteraceae) Essential Oil: Synthesis Facilitating the Identification of Isomeric Minor Constituents in Complex Matrices |
| title_sort | new oxygenated methoxy i p i cymene derivatives from leopard s bane i doronicum columnae i ten asteraceae essential oil synthesis facilitating the identification of isomeric minor constituents in complex matrices |
| topic | <i>Doronicum columnae</i> volatile constituents NMR GC-MS structure elucidation |
| url | https://www.mdpi.com/1420-3049/30/2/302 |
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