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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Bibliographic Details
Main Authors: Iris Yedidia, Keren Schultz, Avner Golan, Hugo E. Gottlieb, Zohar Kerem
Format: Article
Language:English
Published: MDPI AG 2019-08-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/24/16/2910
Description
Summary:<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>-&#945;-<span style="font-variant: small-caps;">l</span>-(3-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-&#946;-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-&#946;-<span style="font-variant: small-caps;">d</span>-glucopyranoside, kaempferol 3-<i>O</i>-[4-<i>O</i>-&#945;-<span style="font-variant: small-caps;">l</span>-(2-<i>O</i>-acetic)-rhamnopyranosyl-6-<i>O</i>-&#946;-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-&#946;-<span style="font-variant: small-caps;">d</span>-glucopyranoside and kaempferol 3-<i>O</i>-[4-<i>O</i>-&#945;-<span style="font-variant: small-caps;">l</span>-(2,3-<i>O</i>-diacetic)-rhamnopyranosyl-6-<i>O</i>-&#946;-<span style="font-variant: small-caps;">d</span>-xylopyranosyl]-&#946;-<span style="font-variant: small-caps;">d</span>-glucopyranoside.
ISSN:1420-3049