Hyperoside

Summary

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

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
  • 482-36-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:67486 ☒N
ChemSpider
  • 4444962 ☒N
ECHA InfoCard 100.006.892 Edit this at Wikidata
KEGG
  • C10073 checkY
  • 5281643
UNII
  • 8O1CR18L82 checkY
  • 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 464.379 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).
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Infobox references

Natural occurrences edit

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 edit

  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. 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)