Hyperoside

Hyperoside

Names
IUPAC name 3-(β-D-Galactopyranosyloxy)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name 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
Other names Hyperozide Hyperasid Hyperosid Hyperin quercetin galactoside Quercetin-3-galactoside Quercetin-3-O-galactoside
Identifiers
CAS Number	482-36-0  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:67486  N
ChEMBL	ChEMBL251254
ChemSpider	4444962  N
DrugBank	DB16403
ECHA InfoCard	100.006.892
EC Number	207-580-6
KEGG	C10073  Y
PubChem CID	5281643
UNII	8O1CR18L82  Y
CompTox Dashboard (EPA)	DTXSID501028789
InChI InChI=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 N Key: OVSQVDMCBVZWGM-DTGCRPNFSA-N N 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 Key: OVSQVDMCBVZWGM-DTGCRPNFBG
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
Properties
Chemical formula	C21H20O12
Molar mass	464.379 g·mol−1
Density	1.879 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

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 . ^[1] It is one of the phenolic compounds in the invasive plant Carpobrotus edulis and contributes to the antibacterial ^[2] 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 ^[3] and Taxillus kaempferi . ^[4]

References

1. Li, Shiyou; Zhang, Zhizhen; Cain, Abigail; Wang, Bo; Long, Melissa; Taylor, Josephine (2005). "Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated from Camptotheca acuminata". Journal of Agricultural and Food Chemistry. 53 (1): 32–7. Bibcode:2005JAFC...53...32L. doi:10.1021/jf0484780. PMID   15631505.
2. Van Der Watt, Elmarie; Pretorius, Johan C (2001). "Purification and identification of active antibacterial components in Carpobrotus edulis L". Journal of Ethnopharmacology. 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID   11378287.
3. Calzada, F; Cerda-García-Rojas, CM; Meckes, M; Cedillo-Rivera, R; Bye, R; Mata, R (1999). "Geranins a and B, new antiprotozoal A-type proanthocyanidins from Geranium niveum". Journal of Natural Products. 62 (5): 705–9. doi:10.1021/np980467b. PMID   10346950.
4. 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)