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Spiraeoside
Names
IUPAC name
4′-(β-D -Glucopyranosyloxy)-3,3′,5,7-tetrahydroxyflavone
Systematic IUPAC name
3,5,7-Trihydroxy-2-(3-hydroxy-4-{[(2S ,3R ,4S ,5S ,6R )-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-4H -1-benzopyran-4-one
Other names
Spiraeosid Spiraein Quercetin-4'-glucoside Quercetin 4'-O-glucoside Quercetin-4-O-β-D-glucoside
Identifiers
68011
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.039.634
EC Number
UNII
InChI=1S/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
N Key: OIUBYZLTFSLSBY-HMGRVEAOSA-N
N InChI=1/C21H20O12/c22-6-13-15(26)17(28)19(30)21(33-13)32-11-2-1-7(3-9(11)24)20-18(29)16(27)14-10(25)4-8(23)5-12(14)31-20/h1-5,13,15,17,19,21-26,28-30H,6H2/t13-,15-,17+,19-,21-/m1/s1
Key: OIUBYZLTFSLSBY-HMGRVEAOBO
c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
Properties
C21 H20 O12
Molar mass
464.37 g/mol
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Spiraeoside is a chemical compound. It can be isolated from flowers of
Filipendula ulmaria (L.) (a.k.a. Spiraea ulmaria or meadowsweet ) or from the garden onion (
Allium cepa ).
[1]
[2]
Spiraeoside is the 4'-O-
glucoside of
quercetin .
References
^ Williamson, Gary; Plumb, Geoff W.; Uda, Yasushi; Price, Keith R.; Rhodes, Michael J.C. (1996).
"Dietary quercetin glycosides: Antioxidant activity and induction of the anticarcinogenic phase II marker enzyme quinone reductase in Hepalclc7 cells" . Carcinogenesis . 17 (11): 2385–7.
doi :
10.1093/carcin/17.11.2385 .
PMID
8968052 .
^ Olsson, Marie E.; Gustavsson, Karl-Erik; Vågen, Ingunn M. (2010). "Quercetin and Isorhamnetin in Sweet and Red Cultivars of Onion (Allium cepaL.) at Harvest, after Field Curing, Heat Treatment, and Storage". Journal of Agricultural and Food Chemistry . 58 (4): 2323–30.
doi :
10.1021/jf9027014 .
PMID
20099844 .
Flavonols and their conjugates
Backbone
Flavonols
O -Methylated flavonols
Derivative flavonols
Pyranoflavonols
Furanoflavonols
Semisynthetic