Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate
<i>Xerolekia speciosissima</i> (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remaine...
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MDPI AG
2020-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/21/4913 |
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| author | Natalia Kłeczek Janusz Malarz Barbara Gierlikowska Anna K. Kiss Anna Stojakowska |
| author_facet | Natalia Kłeczek Janusz Malarz Barbara Gierlikowska Anna K. Kiss Anna Stojakowska |
| author_sort | Natalia Kłeczek |
| collection | DOAJ |
| description | <i>Xerolekia speciosissima</i> (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remained unknown until now. A hydroalcoholic extract from the aerial parts of <i>X. speciosissima</i> was analyzed by HPLC-DAD-MS<sup>n</sup>, revealing the presence of caffeic acid derivatives and flavonoids. In all, 19 compounds, including commonly found chlorogenic acids and less frequently occurring butyryl and methylbutyryl conjugates of dicaffeoylquinic and tricaffeoylhexaric acids, plus two flavonoids, were tentatively identified. Chromatographic separation of a hydroalcoholic extract from the capitula of the plant led to the isolation of (+)-dehydrodiconiferyl alcohol 4-<i>O</i>-<i>β</i>-glucopyranoside, quercimeritrin, astragalin, isoquercitrin, 6-hydroxykaempferol-7-<i>O</i>-<i>β</i>-glucoside, quercetagitrin, methyl caffeate, caffeic acid, protocatechuic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid. Composition of a nonpolar extract from the aerial parts of the plant was analyzed by chromatographic methods supported with <sup>1</sup>H-NMR spectroscopy. The analysis revealed the presence of loliolide, reynosin, samtamarine, 2,3-dihydroaromaticin, 2-deoxy-4-<i>epi</i>-pulchellin and thymol derivatives as terpenoid constituents of the plant. One of the latter compounds—7,10-diisobutyryloxy-8,9-epoxythymyl isobutyrate—at concentrations 0.5, 1.0 and 2.5 μM, significantly reduced IL-8, IL-1β and CCL2 excretion by LPS-stimulated human neutrophils. |
| first_indexed | 2024-03-10T15:22:39Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T15:22:39Z |
| publishDate | 2020-10-01 |
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| spelling | doaj.art-6396b50795684c3c850ad8dde6bb3b7a2023-11-20T18:21:17ZengMDPI AGMolecules1420-30492020-10-012521491310.3390/molecules25214913Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl IsobutyrateNatalia Kłeczek0Janusz Malarz1Barbara Gierlikowska2Anna K. Kiss3Anna Stojakowska4Maj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, PolandMaj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, PolandDepartment of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, PolandDepartment of Pharmacognosy and Molecular Basis of Phytotherapy, Medical University of Warsaw, 1 Banacha Street, 02-097 Warsaw, PolandMaj Institute of Pharmacology, Polish Academy of Sciences, Smętna Street 12, 31-343 Kraków, Poland<i>Xerolekia speciosissima</i> (L.) Anderb., a rare plant from the north of Italy, is a member of the Inuleae-Inulinae subtribe of the Asteraceae. Despite its close taxonomic relationship with many species possessing medicinal properties, the chemical composition of the plant has remained unknown until now. A hydroalcoholic extract from the aerial parts of <i>X. speciosissima</i> was analyzed by HPLC-DAD-MS<sup>n</sup>, revealing the presence of caffeic acid derivatives and flavonoids. In all, 19 compounds, including commonly found chlorogenic acids and less frequently occurring butyryl and methylbutyryl conjugates of dicaffeoylquinic and tricaffeoylhexaric acids, plus two flavonoids, were tentatively identified. Chromatographic separation of a hydroalcoholic extract from the capitula of the plant led to the isolation of (+)-dehydrodiconiferyl alcohol 4-<i>O</i>-<i>β</i>-glucopyranoside, quercimeritrin, astragalin, isoquercitrin, 6-hydroxykaempferol-7-<i>O</i>-<i>β</i>-glucoside, quercetagitrin, methyl caffeate, caffeic acid, protocatechuic acid, chlorogenic acid and 1,5-dicaffeoylquinic acid. Composition of a nonpolar extract from the aerial parts of the plant was analyzed by chromatographic methods supported with <sup>1</sup>H-NMR spectroscopy. The analysis revealed the presence of loliolide, reynosin, samtamarine, 2,3-dihydroaromaticin, 2-deoxy-4-<i>epi</i>-pulchellin and thymol derivatives as terpenoid constituents of the plant. One of the latter compounds—7,10-diisobutyryloxy-8,9-epoxythymyl isobutyrate—at concentrations 0.5, 1.0 and 2.5 μM, significantly reduced IL-8, IL-1β and CCL2 excretion by LPS-stimulated human neutrophils.https://www.mdpi.com/1420-3049/25/21/4913<i>Buphthalmum</i>caffeic acid derivativesflavonoidsInuleaeleontopodic acidsequiterpene lactones |
| spellingShingle | Natalia Kłeczek Janusz Malarz Barbara Gierlikowska Anna K. Kiss Anna Stojakowska Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate Molecules <i>Buphthalmum</i> caffeic acid derivatives flavonoids Inuleae leontopodic acid sequiterpene lactones |
| title | Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate |
| title_full | Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate |
| title_fullStr | Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate |
| title_full_unstemmed | Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate |
| title_short | Constituents of <i>Xerolekia speciosissima</i> (L.) Anderb. (Inuleae), and Anti-Inflammatory Activity of 7,10-Diisobutyryloxy-8,9-epoxythymyl Isobutyrate |
| title_sort | constituents of i xerolekia speciosissima i l anderb inuleae and anti inflammatory activity of 7 10 diisobutyryloxy 8 9 epoxythymyl isobutyrate |
| topic | <i>Buphthalmum</i> caffeic acid derivatives flavonoids Inuleae leontopodic acid sequiterpene lactones |
| url | https://www.mdpi.com/1420-3049/25/21/4913 |
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