Taxonomic group: plant / Streptophyta
(Phylum: Streptophyta)
Publication DOI: 10.1002/(SICI)1522-2675(20000216)83:2<428::AID-HLCA428>3.0.CO;2-JJournal NLM ID: 2985094RPublisher: Verlag Helvetica Chimica Acta
Correspondence: dangles
univ-lyon1.fr
Institutions: Université Claude Bernard-Lyon I, UMR-CNRS 5078, Laboratoire des Polyphénols, Villeurbanne, France, Université Cadi Ayyad, Faculté des Sciences et Techniques-Guéliz, Marrakech, Maroc
Water-soluble derivatives of rutin, a very common glycoside of quercetin (=3,3′,4′,5,7-pentahydroxyflavone=2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one) and a potent plant antioxidant from the flavonol family, were synthesized by simple chemical procedures aimed at introducing carboxy or sulfo groups at the sugar moiety (Scheme 1). Such derivatives form stable molecular complexes with malvin, a polyphenolic pigment from the anthocyanin family, and thereby prove to be very effective in the enhancement (hyperchromism) and variation (bathochromism) of natural colours. The H2O-solubilizing carboxylate and sulfate groups are shown to deeply modify the enthalpy-entropy balance of the pigment-flavonol complexation (copigmentation). A molecular interpretation of the complexation-induced bathochromic shift in the pigment VIS band is proposed. Finally, the H2O-soluble rutin derivatives are shown to retain the high antioxidant ability of rutin as evidenced by their efficient trapping of the coloured radical DPPH (=2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl).
chemical synthesis, derivatives, rutin, malvin, natural pigments
Structure type: oligomer
C
27H
30O
16Location inside paper: abstract
Trivial name: rutin, rutoside, rutin, quercetin rutinoside, rutoside, quercetin 3-O-rutinose, quercetin-3-O-rutinoside, quercetin 3-O-rutinoside
Compound class: saponin glycoside, glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144144,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, chemical synthesis, UV, acetylation, fluorescence spectroscopy, column chromatography, antioxidant activities, spectrophotometry, derivatization
NCBI Taxonomy refs (TaxIDs): 35493Reference(s) to other database(s): CCSD:
50720, CBank-STR:3399
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
report error