TY - JOUR
T1 - Structural elucidation of three novel kaempferol otri-glycosides that are involved in the defense response of hybrid ornithogalum to pectobacterium carotovorum
AU - Yedidia, Iris
AU - Schultz, Keren
AU - Golan, Avner
AU - Gottlieb, Hugo E.
AU - Kerem, Zohar
N1 - Publisher Copyright:
© 2019 MDPI AG. All rights reserved.
PY - 2019/8/10
Y1 - 2019/8/10
N2 - 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.
AB - 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.
KW - Flavonoid
KW - Kaempferol O-tri-glycoside
KW - Ornithogalum
KW - Pectobacterium carotovorum
KW - Soft rot
UR - http://www.scopus.com/inward/record.url?scp=85070707956&partnerID=8YFLogxK
U2 - 10.3390/molecules24162910
DO - 10.3390/molecules24162910
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C2 - 31405174
AN - SCOPUS:85070707956
SN - 1420-3049
VL - 24
JO - Molecules
JF - Molecules
IS - 16
M1 - 2910
ER -