Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.11889/3975
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dc.contributor.authorBjoroy, Orjan-
dc.contributor.authorRayyan, Saleh-
dc.contributor.authorFossen, Torgils-
dc.contributor.authorAndersen, Øyvind M.-
dc.date.accessioned2016-12-21T12:07:32Z-
dc.date.available2016-12-21T12:07:32Z-
dc.date.issued2009-08-
dc.identifier.citationBjorey, Orjan, Slaeh Rayyan, Torgils Fossen, and Oyvind M. Anderson. "Structural properties of anthocyanins : rearrangement of 2 C -Glycosyl-3-deoxyanthocyani dins in acidic aqueous solutions." Journal of Agricultural and Food Chemistry 30.20 (2009): A-J. Web.en_US
dc.identifier.urihttp://hdl.handle.net/20.500.11889/3975-
dc.description.abstractSeven C-glycosyl-3-deoxyanthocyanidins were made from their corresponding C-glycosylflavones. The structures of their rearrangement products, which were formed in acidic aqueous solutions, were elucidated. Rotameric conformers were detected for all of the 8-C-glycosyldeoxyanthocyani- dins but were absent for their isomeric 6-C-analogues in acidified methanolic NMR solvent. A correlation method based on HPLC-DAD and NMR integration of similar samples made it possible for the first time to determine accurately the proportions of two isomeric 6-C- and 8-C-glycosyl- flavonoids occurring in mixtures. Each of the C-glycosyldeoxyanthocyanidins established fixed equilibrium proportions with their corresponding A-ring isomer in aqueous solutions, even under relatively strong acidic conditions (pH ∼1), whether one started with pure 6-C- or 8-C-glycosyl- 3-deoxyanthocyanidin. The nature of the aglycone, C-glycosyl moiety, and temperature were found to affect the equilibrium proportions. Increased water content (to a certain level) and temperatures were shown to increase the isomerization rates. The flavylium cations were the only equilibrium forms present at detectable quantities. The significance of rotation of the A-ring during isomerization was confirmed by lack of rearrangement of both 6-C- and 8-C-glycosyl-3-deoxy-5-carboxypyra- noanthocyanidins. The intermediary C-ring open forms of the C-glycosyldeoxyanthocyanidins experience fast ring closure to their cyclic forms, which may reduce irreversible degradation reported for open chalcone forms of the common anthocyanins. The stable C-glycosyl-3-deoxyanthocyani-dins may thus attract interest as possible colorants in the food industry, etc.en_US
dc.language.isoen_USen_US
dc.subjectAnthocyanins - Structureen_US
dc.subjectAnthocyanins - Solubilityen_US
dc.subjectC -Glycosyl-3-deoxyanthocyani dins - Coloringen_US
dc.subjectC -Glycosyl-3-deoxyanthocyanidins - Coloring matter in fooden_US
dc.titleStructural properties of anthocyanins : rearrangement of C-Glycosyl-3-deoxyanthocyanidins in acidic aqueous solutionsen_US
dc.typeArticleen_US
newfileds.departmentScienceen_US
newfileds.item-access-typeopen_accessen_US
newfileds.thesis-prognoneen_US
newfileds.general-subjectNatural Sciences | العلوم الطبيعيةen_US
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item.grantfulltextopen-
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