hyperoside
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 451447904
| Name = Hyperoside
| ImageFile = Hyperoside.svg
| ImageSize = 250px
| ImageName =
| IUPACName = 3-(β-D-Galactopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
| SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
| OtherNames= Hyperozide
Hyperasid
Hyperosid
Hyperin
quercetin galactoside
Quercetin-3-galactoside
Quercetin-3-O-galactoside
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 482-36-0
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 67486
| ChEMBL = 251254
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444962
| DrugBank = DB16403
| EC_number = 207-580-6
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10073
| PubChem = 5281643
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 8O1CR18L82
| SMILES = c1cc(c(cc1c2c(c(=O)c3c(cc(cc3o2)O)O)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O)O
| InChI = 1/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1
| InChIKey = OVSQVDMCBVZWGM-DTGCRPNFBG
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15+,17+,18-,21+/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OVSQVDMCBVZWGM-DTGCRPNFSA-N
}}
|Section2={{Chembox Properties
| C=21 | H=20 | O=12
| Density = 1.879 g/mL
| MeltingPt =
| BoilingPt =
}}
}}
Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.
Natural occurrences
Hyperoside has been isolated from Drosera rotundifolia, from the Lamiaceae Stachys sp. and Prunella vulgaris, from Rumex acetosella, Cuscuta chinensis seeds, from St John's wort and from Camptotheca acuminata.{{cite journal | doi = 10.1021/jf0484780 | title = Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated from Camptotheca acuminata | year = 2005 | last1 = Li | first1 = Shiyou | last2 = Zhang | first2 = Zhizhen | last3 = Cain | first3 = Abigail | last4 = Wang | first4 = Bo | last5 = Long | first5 = Melissa | last6 = Taylor | first6 = Josephine | journal = Journal of Agricultural and Food Chemistry | volume = 53 | pages = 32–7 | pmid = 15631505 | issue = 1| bibcode = 2005JAFC...53...32L | url = https://scholarworks.sfasu.edu/cgi/viewcontent.cgi?article=1091&context=biology | url-access = subscription }} It is one of the phenolic compounds in the invasive plant Carpobrotus edulis and contributes to the antibacterial{{Cite journal|doi=10.1016/S0378-8741(01)00197-0|title=Purification and identification of active antibacterial components in Carpobrotus edulis L|year=2001|last1=Van Der Watt|first1=Elmarie|last2=Pretorius|first2=Johan C|journal=Journal of Ethnopharmacology|volume=76|pages=87–91|pmid=11378287|issue=1}} properties of the plant.
In Rheum nobile and R. rhaponticum, it serves as a UV blocker found in the bracts.
It is also found in Geranium niveum{{Cite journal|pmid=10346950|year=1999|last1=Calzada|first1=F|last2=Cerda-García-Rojas|first2=CM|last3=Meckes|first3=M|last4=Cedillo-Rivera|first4=R|last5=Bye|first5=R|last6=Mata|first6=R|title=Geranins a and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum|volume=62|issue=5|pages=705–9|doi=10.1021/np980467b|journal=Journal of Natural Products}} and Taxillus kaempferi.The constituents of Taxillus kaempferi and the host, Pinus thunbergii. I. Catechins and flavones of Taxillus kaempferi. Konishi T, Nishio T, Kiyosawa S, Fujiwara Y and Konoshima T, Yakugaku Zasshi., February 1996, volume 116, issue 2, pages 148-157 (article in Japanese)
References
{{Reflist|2}}
{{Opioidergics}}
{{Flavonol}}
Category:Flavonoid galactosides
Category:Kappa-opioid receptor antagonists