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 images Image
PubChem 5281643
Properties
C21H20O12
Molar mass 464.38 g·mol−1
Density 1.879 g/mL
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
Infobox references

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

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] 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[edit]

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

Like various other flavonoids, hyperoside has been found to possess activity at the opioid receptors.[7] Specifically, it acts as an antagonist of the κ- and μ-opioid receptors.[7]

References[edit]

  1. ^ Li, Shiyou; Zhang, Zhizhen; Cain, Abigail; Wang, Bo; Long, Melissa; Taylor, Josephine (2005). "Antifungal Activity of Camptothecin, Trifolin, and Hyperoside Isolated fromCamptotheca 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. ^ Ibtissem, Bouftira (2012). "Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts". Advances in Chemical Engineering and Science 02 (3): 359. doi:10.4236/aces.2012.23042. 
  4. ^ 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. 
  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. ^ Liu, Zhiyong; Tao, Xinyi; Zhang, Chongwei; Lu, Yanhua; Wei, Dongzhi (2005). "Protective effects of hyperoside (quercetin-3-o-galactoside) to PC12 cells against cytotoxicity induced by hydrogen peroxide and tert-butyl hydroperoxide". Biomedicine & Pharmacotherapy 59 (9): 481. doi:10.1016/j.biopha.2005.06.009. 
  7. ^ a b Katavic PL, Lamb K, Navarro H, Prisinzano TE (August 2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J. Nat. Prod. 70 (8): 1278–82. doi:10.1021/np070194x. PMC 2265593. PMID 17685652.