Hyperoside
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| Names | |
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| 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
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| Other names
Hyperozide
Hyperasid Hyperosid Hyperin quercetin galactoside Quercetin-3-galactoside Quercetin-3-O-galactoside |
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| Identifiers | |
482-36-0  |
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| ChEBI | CHEBI:67486  |
| ChemSpider | 4444962 |
| ECHA InfoCard | 100.006.892 |
| Jmol 3D model | Interactive image |
| PubChem | 5281643 |
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| Properties | |
| C21H20O12 | |
| Molar mass | 464.38 g·mol−1 |
| Density | 1.879 g/mL |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| 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] 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]
Uses and actions[edit]
It can have a protective antioxidant effect on cultured PC12 cells.[5]
Like various other flavonoids, hyperoside has been found to possess antagonist activity at the κ-opioid receptor.[6]
References[edit]
- ^ 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.
- ^ 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.
- ^ 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.
- ^ 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)
- ^ 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): 481–490. doi:10.1016/j.biopha.2005.06.009.
- ^ 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.
