Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis
In course of our studies of the aerial parts of Artemisia abrotanum the major methoxyflavonol could be isolated. However, by NMR structural analysis it became obvious that the substitution pattern in ring B differs from reports for casticin (2). The position of methoxyl and hydroxyl groups are inter...
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| Language: | English |
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Elsevier
2023-11-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844023095178 |
| _version_ | 1797429729628782592 |
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| author | Olaf Kunert Fabian Alperth Elisabeth Pabi Franz Bucar |
| author_facet | Olaf Kunert Fabian Alperth Elisabeth Pabi Franz Bucar |
| author_sort | Olaf Kunert |
| collection | DOAJ |
| description | In course of our studies of the aerial parts of Artemisia abrotanum the major methoxyflavonol could be isolated. However, by NMR structural analysis it became obvious that the substitution pattern in ring B differs from reports for casticin (2). The position of methoxyl and hydroxyl groups are interchanged, i.e., the major flavone is actually chrysosplenetin (1). Three structures in A. abrotanum and A. frigida had to be revised. Use of pyridine-d5 instead of DMSO‑d6 made the resolution of the B-ring 1H and 13C NMR signals possible and enabled correct structural assignment by 2D NMR experiments.Results from NMR structure elucidation for A. abrotanum were confirmed by LC-PDA-ESI-MSn analysis when a PFP (pentafluorophenyl) stationary phase with an optimized gradient elution was applied for separation of 1 and 2 instead of a corresponding C-18 phase. Electrospray mass spectrometry (positive and negative mode) with subsequent fragmentation (ESI-MSn) revealed distinctive mass spectral features of both compounds, especially at MS4 level. Several Artemisia extracts including A. annua were analysed on the PFP phase for the presence of 1 and 2. |
| first_indexed | 2024-03-09T09:17:22Z |
| format | Article |
| id | doaj.art-f5ff1549164c40b3928c2f1fff8f20c4 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-03-09T09:17:22Z |
| publishDate | 2023-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-f5ff1549164c40b3928c2f1fff8f20c42023-12-02T07:05:43ZengElsevierHeliyon2405-84402023-11-01911e22309Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysisOlaf Kunert0Fabian Alperth1Elisabeth Pabi2Franz Bucar3Institute of Pharmaceutical Sciences, Department of Pharmaceutical Chemistry, University of Graz, Universitätsplatz 1, 8010, Graz, AustriaInstitute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Beethovenstraße 8, 8010, Graz, AustriaInstitute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Beethovenstraße 8, 8010, Graz, AustriaInstitute of Pharmaceutical Sciences, Department of Pharmacognosy, University of Graz, Beethovenstraße 8, 8010, Graz, Austria; Corresponding author. University of Graz, Institute of Pharmaceutical Sciences, Department of Pharmacognosy, Beethovenstraße 8, 8010, Graz, Austria.In course of our studies of the aerial parts of Artemisia abrotanum the major methoxyflavonol could be isolated. However, by NMR structural analysis it became obvious that the substitution pattern in ring B differs from reports for casticin (2). The position of methoxyl and hydroxyl groups are interchanged, i.e., the major flavone is actually chrysosplenetin (1). Three structures in A. abrotanum and A. frigida had to be revised. Use of pyridine-d5 instead of DMSO‑d6 made the resolution of the B-ring 1H and 13C NMR signals possible and enabled correct structural assignment by 2D NMR experiments.Results from NMR structure elucidation for A. abrotanum were confirmed by LC-PDA-ESI-MSn analysis when a PFP (pentafluorophenyl) stationary phase with an optimized gradient elution was applied for separation of 1 and 2 instead of a corresponding C-18 phase. Electrospray mass spectrometry (positive and negative mode) with subsequent fragmentation (ESI-MSn) revealed distinctive mass spectral features of both compounds, especially at MS4 level. Several Artemisia extracts including A. annua were analysed on the PFP phase for the presence of 1 and 2.http://www.sciencedirect.com/science/article/pii/S2405844023095178Artemisia sp.AsteraceaeFlavonoidsCasticinChrysosplenetinNMR |
| spellingShingle | Olaf Kunert Fabian Alperth Elisabeth Pabi Franz Bucar Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis Heliyon Artemisia sp. Asteraceae Flavonoids Casticin Chrysosplenetin NMR |
| title | Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis |
| title_full | Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis |
| title_fullStr | Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis |
| title_full_unstemmed | Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis |
| title_short | Highly oxidized flavones in Artemisia species – structure revisions and improved UHPLC-MSn analysis |
| title_sort | highly oxidized flavones in artemisia species structure revisions and improved uhplc msn analysis |
| topic | Artemisia sp. Asteraceae Flavonoids Casticin Chrysosplenetin NMR |
| url | http://www.sciencedirect.com/science/article/pii/S2405844023095178 |
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