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Structural Elucidation of Three Novel Kaempferol O-tri-Glycosides that Are Involved in the Defense Response of Hybrid Ornithogalum to Pectobacterium carotovorum

1
Department of Ornamental Horticulture, ARO, Volcani Center, Derech Hamacabim 20 P.O. Box 6, 50250 Bet-Dagan, Israel
2
Institute 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
3
Department of Chemistry, Bar Ilan University, 52900 Ramat-Gan, Israel
*
Author to whom correspondence should be addressed.
Academic Editors: Martin C. Gruhlke and Alan J. Slusarenko
Molecules 2019, 24(16), 2910; https://doi.org/10.3390/molecules24162910
Received: 9 July 2019 / Revised: 5 August 2019 / Accepted: 9 August 2019 / Published: 10 August 2019
(This article belongs to the Special Issue Natural Products in Plant Protection)
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Abstract

Ornithogalum is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by Pectobacterium carotovorum (Pc). Interspecific hybridization between O. thyrsoides and O. dubium 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 O-tri-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 1H and 13C, DEPT, HMQC, HMBC, COSY, and NOE), in order to achieve pure and defined compounds data. The new compounds were finally identified as kaempferol 3-O-[4-O-α-l-(3-O-acetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside, kaempferol 3-O-[4-O-α-l-(2-O-acetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside and kaempferol 3-O-[4-O-α-l-(2,3-O-diacetic)-rhamnopyranosyl-6-O-β-d-xylopyranosyl]-β-d-glucopyranoside. View Full-Text
Keywords: flavonoid; kaempferol O-tri-glycoside; Ornithogalum; Pectobacterium carotovorum; soft rot flavonoid; kaempferol O-tri-glycoside; Ornithogalum; Pectobacterium carotovorum; soft rot
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Yedidia, I.; Schultz, K.; Golan, A.; Gottlieb, H.E.; Kerem, Z. Structural Elucidation of Three Novel Kaempferol O-tri-Glycosides that Are Involved in the Defense Response of Hybrid Ornithogalum to Pectobacterium carotovorum. Molecules 2019, 24, 2910.

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