<i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil
Motivated by the ethnopharmacological use of <i>Pulicaria dysenterica</i>, in the present study, the antimicrobial potential of the extracted essential oil was investigated against a panel of eighteen microorganism strains. Additionally, anti-acetylcholinesterase and antispasmodic (isola...
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MDPI AG
2022-12-01
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| Series: | Plants |
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| author | Niko S. Radulović Marko Z. Mladenović Dušan R. Vukićević Nikola M. Stojanović Pavle J. Randjelović Zorica Z. Stojanović-Radić Fabio Boylan |
| author_facet | Niko S. Radulović Marko Z. Mladenović Dušan R. Vukićević Nikola M. Stojanović Pavle J. Randjelović Zorica Z. Stojanović-Radić Fabio Boylan |
| author_sort | Niko S. Radulović |
| collection | DOAJ |
| description | Motivated by the ethnopharmacological use of <i>Pulicaria dysenterica</i>, in the present study, the antimicrobial potential of the extracted essential oil was investigated against a panel of eighteen microorganism strains. Additionally, anti-acetylcholinesterase and antispasmodic (isolated rat distal colon) activities, general acute toxicity (<i>Artemia salina</i> model), and immunomodulatory properties (cytotoxicity on isolated mouse macrophages) were studied. Detailed analyses of the essential oil led to the identification of 3-methoxycuminyl 2-methylbutanoate (a new natural product) and 3-methoxycuminyl 3-methylbutanoate (a rare natural product). The obtained esters and intermediates in the synthesis of the starting alcohol (3-methoxycuminol) were subjected to a battery of 1D- and 2D-NMR experiments. The synthesized esters were additionally characterized by GC–MS, IR, and UV–Vis. The synthesized compounds (ten in total) were biologically tested in the same way as the extracted <i>P. dysenterica</i> essential oil. The obtained low acute toxicity and promising antimicrobial potential suggest that the <i>P. dysenterica</i> essential oil might partially explain the ethnopharmacological application of <i>P. dysenterica</i> plant material for the treatment of gastrointestinal infections. |
| first_indexed | 2024-03-09T17:34:30Z |
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| institution | Directory Open Access Journal |
| issn | 2223-7747 |
| language | English |
| last_indexed | 2024-03-09T17:34:30Z |
| publishDate | 2022-12-01 |
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| series | Plants |
| spelling | doaj.art-1688094eeb824202abf5e8431fd93aca2023-11-24T11:56:19ZengMDPI AGPlants2223-77472022-12-011123334010.3390/plants11233340<i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential OilNiko S. Radulović0Marko Z. Mladenović1Dušan R. Vukićević2Nikola M. Stojanović3Pavle J. Randjelović4Zorica Z. Stojanović-Radić5Fabio Boylan6Department of Chemistry, Faculty of Sciences and Mathematics, University of Nis, Višegradska 33, 18000 Nis, SerbiaDepartment of Chemistry, Faculty of Sciences and Mathematics, University of Nis, Višegradska 33, 18000 Nis, SerbiaFaculty of Medicine, University of Kragujevac, Svetozara Markovića 69, 34000 Kragujevac, SerbiaDepartment of Physiology, Faculty of Medicine, University of Nis, Zorana Ðinđica 81, 18000 Nis, SerbiaDepartment of Physiology, Faculty of Medicine, University of Nis, Zorana Ðinđica 81, 18000 Nis, SerbiaDepartment of Biology and Ecology, Faculty of Sciences and Mathematics, University of Nis, Visegradska 33, 18000 Nis, SerbiaSchool of Pharmacy and Pharmaceutical Sciences, Panoz Institute, Trinity College, Westland Row, 2 Dublin, IrelandMotivated by the ethnopharmacological use of <i>Pulicaria dysenterica</i>, in the present study, the antimicrobial potential of the extracted essential oil was investigated against a panel of eighteen microorganism strains. Additionally, anti-acetylcholinesterase and antispasmodic (isolated rat distal colon) activities, general acute toxicity (<i>Artemia salina</i> model), and immunomodulatory properties (cytotoxicity on isolated mouse macrophages) were studied. Detailed analyses of the essential oil led to the identification of 3-methoxycuminyl 2-methylbutanoate (a new natural product) and 3-methoxycuminyl 3-methylbutanoate (a rare natural product). The obtained esters and intermediates in the synthesis of the starting alcohol (3-methoxycuminol) were subjected to a battery of 1D- and 2D-NMR experiments. The synthesized esters were additionally characterized by GC–MS, IR, and UV–Vis. The synthesized compounds (ten in total) were biologically tested in the same way as the extracted <i>P. dysenterica</i> essential oil. The obtained low acute toxicity and promising antimicrobial potential suggest that the <i>P. dysenterica</i> essential oil might partially explain the ethnopharmacological application of <i>P. dysenterica</i> plant material for the treatment of gastrointestinal infections.https://www.mdpi.com/2223-7747/11/23/3340<i>Pulicaria dysenterica</i>essential oil3-methoxycuminyl estersantimicrobial activityacetylcholinesterase inhibitory activityantispasmodic activity |
| spellingShingle | Niko S. Radulović Marko Z. Mladenović Dušan R. Vukićević Nikola M. Stojanović Pavle J. Randjelović Zorica Z. Stojanović-Radić Fabio Boylan <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil Plants <i>Pulicaria dysenterica</i> essential oil 3-methoxycuminyl esters antimicrobial activity acetylcholinesterase inhibitory activity antispasmodic activity |
| title | <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil |
| title_full | <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil |
| title_fullStr | <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil |
| title_full_unstemmed | <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil |
| title_short | <i>Pulicaria dysenterica</i> (L.) Bernh.—Rightfully Earned Name? Identification and Biological Activity of New 3-Methoxycuminyl Esters from <i>P. dysenterica</i> Essential Oil |
| title_sort | i pulicaria dysenterica i l bernh rightfully earned name identification and biological activity of new 3 methoxycuminyl esters from i p dysenterica i essential oil |
| topic | <i>Pulicaria dysenterica</i> essential oil 3-methoxycuminyl esters antimicrobial activity acetylcholinesterase inhibitory activity antispasmodic activity |
| url | https://www.mdpi.com/2223-7747/11/23/3340 |
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