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1. (Article ID: 10631)
Nielsen JK, Olsen CE, Petersen MK
Acylated flavonol glycosides from cabbage leaves
Phytochemistry 34 (1993)
539-544
Seven flavonol glycosides were isolated from a leaf extract of cabbage and characterized by chemical and spectroscopic methods including 1H and 13C NMR and negative ion FAB-MS. Five compounds were new Natural products or were fully characterized for the first time. They are derivatives of kaempferol-3-O-β-D-sophoroside-7-O-β-D-glucoside acylated at C-2"' with either caffeic acid, p-coumaric acid or ferulic acid, and of quercetin-3-O-β-D-sophoroside-7-O-β-D-glucoside acylated with either caffeic acid or ferulic acid. Kaempferol-3-O-β-D- sophoroside-7-O-β-D-glucoside and kaempferol-3-O-β-D-(2-sinapoylsophoroside)-7-O-β-D-glucoside were found for the first time in cabbage, but they have previously been found in other Brassica species.
acylated, flavonol glycosides, Brassica oleracea, Cruciferae, cabbage, caffeoyl, p-coumaroyl, feruloyl, sinapoyl
NCBI PubMed ID: 7764144Publication DOI: 10.1016/0031-9422(93)80042-QJournal NLM ID: 0151434Publisher: Elsevier
Institutions: Chemistry Department, Royal Veterinary and Agricultural University, Frederiksberg, Denmark
Methods: 13C NMR, 1H NMR, FAB-MS, TLC, acid hydrolysis, HPLC, UV, PC
The publication contains the following compound(s):
- Compound ID: 26248
Structure type: oligomer
; 771 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38838, CBank-STR:7476
- Compound ID: 26249
|
b-D-Glcp-(1-7)-+
|
Sin-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Kaempferol
Sin = sinapinic acid |
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Structure type: oligomer
; 977 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38839, CBank-STR:9483
- Compound ID: 26250
|
b-D-Glcp-(1-7)-+
|
Fer-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Kaempferol
Fer = ferulic acid |
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Structure type: oligomer
; 947 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38841, CBank-STR:9485
- Compound ID: 26251
|
b-D-Glcp-(1-7)-+
|
pCoum-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Kaempferol
pCoum = p-coumaric acid |
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Structure type: oligomer
; 917 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38842, CBank-STR:9486
- Compound ID: 26252
|
b-D-Glcp-(1-7)-+
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Caf-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Kaempferol
Caf = caffeic acid |
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Structure type: oligomer
; 933 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38843, CBank-STR:9482
- Compound ID: 26253
|
b-D-Glcp-(1-7)-+
|
Fer-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Quercetin
Fer = ferulic acid |
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Structure type: oligomer
; 963 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38844, CBank-STR:9484
- Compound ID: 26254
|
b-D-Glcp-(1-7)-+
|
Caf-(9-2)-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Quercetin
Caf = caffeic acid |
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Structure type: oligomer
; 949 [M-H]-
Compound class: flavonol glycoside
Reference(s) to other database(s): CCSD:
38845, CBank-STR:9481
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2. (Article ID: 11406)
Wilson KE, Wilson MI, Greenberg BM
Identification of the flavonoid glycosides that accumulate in Brassica napus L. cv. Topas specifically in response to ultraviolet B radiation
Photochemistry and Photobiology 67(5) (1998)
547-553
We have shown in previous work that Brassica napus synthesizes epidermal flavonoids in response to UVB radiation (290-320 nm) and that these compounds are effective at screening the leaf mesophyll from UVB (Wilson and Greenberg, Photochem. Photobiol, 57, 556-563, 1993), This route of acclimation is common to many plant species. However, flavonoids are a highly diverse group of compounds that vary greatly from species to species, and little is known about the specific flavonoids synthesized in response to UVB, To address this, we extracted flavonoids from the leaves of B. napus plants exposed to photosynthetically active radiation (PAR: 400-700 nm), PAR + UVA (320-400 nm) and PAR + WA + UVB, The compounds were resolved by HPLC and their structures were elucidated. Twelve distinct flavonoid glucosides with quercetin and kaempferol backbones were found. In some cases, a hydroxycinnamic acid moiety was linked via an ester bridge to a glucose. Of the 12 compounds identified, the leaf concentrations of 6 increased in response to UVB: kaempferol-3-O-sophoroside (K2), kaempferol-3-O-sophoroside-7-O-glucoside (K3), quercetin-3-O-sophoroside (Q2), quercetin-3-O-sophoroside-7-O-glucoside (Q3), K3-coumaroyl ester and Q3-caffeoyl ester, Of these six compounds, K2, K3, Q2 and Q3 accumulated to high enough concentrations to contribute to UVB screening. Interestingly, the extractable amounts of the other six compounds identified were lower in the plants exposed to UVA or WA + UVB compared to plants exposed only to PAR. Thus, in B. napus UV exposure seems to cause a shift in the population of flavonoid glycosides, with four of the UVB-induced flavonoids being generated in high concentrations.
sensitivity, protection, Plants, UV-B, penetration, epidermal-transmittance, secale-cereale, rye seedlings, primary leaf, acclimation
Publication DOI: 10.1111/j.1751-1097.1998.tb09092.xJournal NLM ID: 0376425Publisher: Lawrence KS: American Society for Photobiology
Correspondence: Greenberg BM
sciborg.uwaterloo.ca>
Institutions: Department of Biology, University of Waterloo, Waterloo, Ontario, Canada
Methods: ESI-MS, HPLC, extraction, hydrolysis
The publication contains the following compound(s):
- Compound ID: 29017
|
b-D-Glcp-(1-7)-+
|
/Variants 0/-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Quercetin
/Variants 0/ is:
?%Fer-(9-2)-
OR (exclusively)
?%Caf-(9-2)- |
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Structure type: oligomer
; 789, 951, 965
Compound class: glycoside
- Compound ID: 29018
|
b-D-Glcp-(1-7)-+
|
/Variants 0/-b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-Kaempferol
/Variants 0/ is:
?%pCoum-(9-2)-
OR (exclusively)
?%Sin-(9-2)-
OR (exclusively)
?%Fer-(9-2)-
OR (exclusively)
?%Caf-(9-2)- |
Show graphically |
Structure type: oligomer
; 773, 935, 979, 949, 919
Compound class: glycoside
- Compound ID: 29019
|
/Variants 0/-+
|
b-D-Glcp-(1-2)-b-D-Glcp
/Variants 0/ is:
Quercetin-(3-1)-
OR (exclusively)
Kaempferol-(3-1)- |
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Structure type: oligomer
; 627, 610
Compound class: glycoside
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