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1. (Article ID: 12175)
Fossen T, Slimestad R, Øvstedal DO, Andersen ØM
Covalent anthocyanin-flavonol complexes from flowers of chive, Allium schoenoprasum
Phytochemistry 54(3) (2000)
317-323
The structures of eight anthocyanins have been determined in acidified methanolic extract of pale-purple flowers of chive, Allium schoenoprasum. Four of them have been identified as the anthocyanin-flavonol complexes (cyanidin 3-O-β-glucosideAII) (kaempferol 3-O-(2-O-β-glucosylFIII-β-glucosideFII)-7-O-β-glucosiduronic acidFIV) malonateAIII (AII-6→AIII-1, FIV-2→AIII-3), 1, (cyanidin 3-O-(3-O-acetyl-β-glucosideAII) (kaempferol 3-O-(2-O-β-glucosylFIII-β-glucosideFII)-7-O-β-gl ucosiduronic acidFIV) malonateAIII (AII-6→AIII-1, FIV-2→AIII-3), 2, and their 7-O-(methyl-O-β-glucosiduronateFIV) analogous, 3 and 4. Pigments 1 and 2 are the first final identification of covalent complexes between an anthocyanin and a flavonol, while 3 and 4 are formed during the isolation process. The other four anthocyanins (5-8) were found to be the 3-acetylglucoside, 3-glucoside, 3-(6-malonylglucoside) and 3-(3,6-dimalonylglucoside) of cyanidin. The three latter pigments have earlier been identified as the major anthocyanins of the chive stem. The covalent anthocyanin-flavonol complexes show intramolecular association between the anthocyanidin (cyanidin) and flavonol (kaempferol) units, which influence the colour.
acetylation, Liliaceae, flower colour, Allium schoenoprasum, covalent anthocyanin-flavonol complexes, (cyanidin 3-glucoside)(kaempferol 3-(2-glucosylglucoside)-7-glucosiduronic acid) malonate, co-pigmentation, intramolecular association
NCBI PubMed ID: 10870187Publication DOI: 10.1016/s0031-9422(00)00102-3Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: oyvind.anderson

kj.uib.no
Institutions: Department of Chemistry, University of Bergen, Bergen, Norway, Polyphenols AS, Hanabryggene Technology Centre, Sandnes, Norway, Department of Botany, University of Bergen, Bergen, Norway
Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, HPLC, UV, extraction, CC, spectrophotometry, evaporation
The publication contains the following compound(s):
- Compound ID: 26794
Structure type: monomer
Compound class: glycoside, flavonoid glycoside, anthocyanin glycoside, anthocyanin glucoside
Reference(s) to other database(s): CCSD:
43647, CBank-STR:930
- Compound ID: 31575
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31625
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
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Cyanidin-(3-1)-b-D-Glcp-(6-3)-Mal-(1-3)-b-D-GlcpA-(1-7)-Kaempferol |
Show graphically |
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31626
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b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
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Cyanidin-(3-1)-b-D-Glcp3Ac-(6-3)-Mal-(1-3)-b-D-GlcpA-(1-7)-Kaempferol |
Show graphically |
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31627
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
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Cyanidin-(3-1)-b-D-Glcp-(6-3)-Mal-(1-3)-b-D-GlcpA6Me-(1-7)-Kaempferol |
Show graphically |
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31628
|
b-D-Glcp-(1-2)-b-D-Glcp-(1-3)-+
|
Cyanidin-(3-1)-b-D-Glcp3Ac-(6-3)-Mal-(1-3)-b-D-GlcpA6Me-(1-7)-Kaempferol |
Show graphically |
Structure type: oligomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31629
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
- Compound ID: 31630
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
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