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

is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by (Pc). Interspecific hybridization between and yielded hybrids with enhanced resistance to that pathogen. The hybrids displayed distinct phenolic-compound profiles with several peaks that...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-08, Vol.24 (16), p.2910
Main Authors: Yedidia, Iris, Schultz, Keren, Golan, Avner, Gottlieb, Hugo E, Kerem, Zohar
Format: Article
Language:English
Subjects:
Crosses, Genetic
flavonoid
Flavonoids
Flowering
Flowers & plants
Glycosides
Glycosides - chemistry
Glycosides - pharmacology
High performance liquid chromatography
Hybrids
Infections
Interspecific hybridization
Kaempferol
kaempferol O-tri-glycoside
Kaempferols - chemistry
Kaempferols - pharmacology
Liquid chromatography
Mass spectrometry
Mass spectroscopy
Metabolites
NMR
Nuclear magnetic resonance
Ornithogalum
Ornithogalum - microbiology
Pectobacterium carotovorum
Pectobacterium carotovorum - growth & development
Phenolic compounds
Phenols
Plant Diseases - microbiology
Rot
Scientific imaging
soft rot
Structure-Activity Relationship
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Summary:is an ornamental flowering species that grows from a bulb and is highly susceptible to soft-rot disease caused by (Pc). Interspecific hybridization between and 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 -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 H and 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- -[4- -α-l-(3- -acetic)-rhamnopyranosyl-6- -β-d-xylopyranosyl]-β-d-glucopyranoside, kaempferol 3- -[4- -α-l-(2- -acetic)-rhamnopyranosyl-6- -β-d-xylopyranosyl]-β-d-glucopyranoside and kaempferol 3- -[4- -α-l-(2,3- -diacetic)-rhamnopyranosyl-6- -β-d-xylopyranosyl]-β-d-glucopyranoside.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules24162910