Hyperoside
 | |
| 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  | |
| ChEBI | CHEBI:67486  |
| ChemSpider | 4444962 |
| Jmol interactive 3D | Image |
| PubChem | 5281643 |
| |
| |
| 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). | |
| verify (what is ?) | |
| 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
- ↑ 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.
- ↑ Ibtissem, Bouftira (2012). "Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts". Advances in Chemical Engineering and Science 02 (3): 359–365. doi:10.4236/aces.2012.23042.
- ↑ 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.
| ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
This article is issued from Wikipedia - version of the Friday, January 29, 2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.