Hyperoside

Last updated
Hyperoside
Hyperoside.svg
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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.892 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • 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 X mark.svgN
    Key: OVSQVDMCBVZWGM-DTGCRPNFSA-N X mark.svgN
  • 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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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] 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]

Related Research Articles

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<span class="mw-page-title-main">Avicularin</span> Chemical compound

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<span class="mw-page-title-main">Taxillusin</span> Chemical compound

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<span class="mw-page-title-main">Pawhuskin A</span> Chemical compound

Pawhuskin A is a naturally occurring prenylated stilbene isolated from Dalea purpurea which acts as a competitive silent antagonist of the κ-, μ-, and δ-opioid receptors. The compound was named after Pawhuska, Oklahoma, a place near where the samples of Dalea purpurea that led to its discovery were taken from. Other isolates of the plant with affinity for opioid receptors include Pawhuskin B and Pawhuskin C, though these compounds produce comparatively weak opioid receptor displacement relative to Pawhuskin A. Dalea purpurea was used in traditional Native American medicine to treat various ailments, and pawhuskin A and related isolates may be some of the constituents of the plant which underlay this use.

<span class="mw-page-title-main">Viridiflorol</span> Chemical compound

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References

  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)