Hyperoside

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Hyperoside
Hyperoside.svg
Names
IUPAC name
2-(3,4-dihydroxyphenyl)-3-[(3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-chromene-4,5,7-triol
Other names
Hyperozide
Hyperasid
Hyperosid
Hyperin
quercetin galactoside
Quercetin-3-galactoside
Quercetin-3-O-galactoside
Identifiers
482-36-0 YesY
ChEBI CHEBI:67486 N
ChemSpider 4444962 N
Jmol 3D model Interactive image
PubChem 5281643
  • 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
  • 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
C21H20O12
Molar mass 464.38 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 YesYN ?)
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] and antioxidant[3] 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[4] and Taxillus kaempferi.[5]

Uses and actions

It can have a protective antioxidant effect on cultured PC12 cells.[6]

Like various other flavonoids, hyperoside has been found to possess antagonist activity at the κ-opioid receptor.[7]

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 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)
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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