Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i>
<i>Ornithogalum</i> is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by <i>Pectobacterium carotovorum</i> (Pc). Interspecific hybridization between <i>O. thyrsoides</i> and <i>O. dubium</i>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/16/2910 |
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| author | Iris Yedidia Keren Schultz Avner Golan Hugo E. Gottlieb Zohar Kerem |
| author_facet | Iris Yedidia Keren Schultz Avner Golan Hugo E. Gottlieb Zohar Kerem |
| author_sort | Iris Yedidia |
| collection | DOAJ |
| description | <i>Ornithogalum</i> is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by <i>Pectobacterium carotovorum</i> (Pc). Interspecific hybridization between <i>O. thyrsoides</i> and <i>O. dubium</i> yielded hybrids with enhanced resistance to that pathogen. The hybrids displayed distinct phenolic-compound profiles with several peaks that were specifically heightened following Pc infection. Three of these compounds were isolated and identified as novel kaempferol <i>O-tri</i>-glycosides. The structures of these compounds were elucidated using reversed phase high-performance liquid chromatography (RP-LC), RP-LC coupled to high-resolution mass spectrometry (RP-LC-MS), and nuclear magnetic resonance (NMR) (1D <sup>1</sup>H and <sup>13</sup>C, DEPT, HMQC, HMBC, COSY, and NOE), in order to achieve pure and defined compounds data. The new compounds were finally identified as kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(3-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside, kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(2-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside and kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(2,3-<i>O</i>-diacetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside. |
| first_indexed | 2024-12-11T13:20:20Z |
| format | Article |
| id | doaj.art-e346f04ba3664d809e1df21f0e420e12 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T13:20:20Z |
| publishDate | 2019-08-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e346f04ba3664d809e1df21f0e420e122022-12-22T01:05:52ZengMDPI AGMolecules1420-30492019-08-012416291010.3390/molecules24162910molecules24162910Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i>Iris Yedidia0Keren Schultz1Avner Golan2Hugo E. Gottlieb3Zohar Kerem4Department of Ornamental Horticulture, ARO, Volcani Center, Derech Hamacabim 20 P.O. Box 6, 50250 Bet-Dagan, IsraelInstitute of Biochemistry, Food Science and Nutrition, The Robert H Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, P.O. Box 12, 7610001 Rehovot, IsraelDepartment of Ornamental Horticulture, ARO, Volcani Center, Derech Hamacabim 20 P.O. Box 6, 50250 Bet-Dagan, IsraelDepartment of Chemistry, Bar Ilan University, 52900 Ramat-Gan, IsraelInstitute of Biochemistry, Food Science and Nutrition, The Robert H Smith Faculty of Agriculture, Food and Environment, The Hebrew University of Jerusalem, P.O. Box 12, 7610001 Rehovot, Israel<i>Ornithogalum</i> is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by <i>Pectobacterium carotovorum</i> (Pc). Interspecific hybridization between <i>O. thyrsoides</i> and <i>O. dubium</i> yielded hybrids with enhanced resistance to that pathogen. The hybrids displayed distinct phenolic-compound profiles with several peaks that were specifically heightened following Pc infection. Three of these compounds were isolated and identified as novel kaempferol <i>O-tri</i>-glycosides. The structures of these compounds were elucidated using reversed phase high-performance liquid chromatography (RP-LC), RP-LC coupled to high-resolution mass spectrometry (RP-LC-MS), and nuclear magnetic resonance (NMR) (1D <sup>1</sup>H and <sup>13</sup>C, DEPT, HMQC, HMBC, COSY, and NOE), in order to achieve pure and defined compounds data. The new compounds were finally identified as kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(3-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside, kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(2-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside and kaempferol 3-<i>O</i>-[4-<i>O</i>-α-<span style="font-variant: small-caps;">l</span>-(2,3-<i>O</i>-diacetic)-rhamnopyranosyl-6-<i>O</i>-β-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-β-<span style="font-variant: small-caps;">d</span>-glucopyranoside.https://www.mdpi.com/1420-3049/24/16/2910flavonoidkaempferol <i>O-tri</i>-glycoside<i>Ornithogalum</i><i>Pectobacterium carotovorum</i>soft rot |
| spellingShingle | Iris Yedidia Keren Schultz Avner Golan Hugo E. Gottlieb Zohar Kerem Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> Molecules flavonoid kaempferol <i>O-tri</i>-glycoside <i>Ornithogalum</i> <i>Pectobacterium carotovorum</i> soft rot |
| title | Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> |
| title_full | Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> |
| title_fullStr | Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> |
| title_full_unstemmed | Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> |
| title_short | Structural Elucidation of Three Novel Kaempferol <i>O-tri</i>-Glycosides that Are Involved in the Defense Response of Hybrid <i>Ornithogalum</i> to <i>Pectobacterium carotovorum</i> |
| title_sort | structural elucidation of three novel kaempferol i o tri i glycosides that are involved in the defense response of hybrid i ornithogalum i to i pectobacterium carotovorum i |
| topic | flavonoid kaempferol <i>O-tri</i>-glycoside <i>Ornithogalum</i> <i>Pectobacterium carotovorum</i> soft rot |
| url | https://www.mdpi.com/1420-3049/24/16/2910 |
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