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Hyperoside

From Wikipedia, the free encyclopedia
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.006.892Edit this at Wikidata
EC Number
  • 207-580-6
KEGG
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 ☒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 mass464.379 g·mol−1
Density1.879 g/mL
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

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

Natural occurrences

[edit]

Hyperoside has been isolated fromDrosera rotundifolia, from the LamiaceaeStachys sp. andPrunella vulgaris, fromRumex acetosella,Cuscuta chinensis seeds, fromSt John's wort and fromCamptotheca acuminata.[1] It is one of the phenolic compounds in the invasive plantCarpobrotus edulis and contributes to the antibacterial[2] properties of the plant.

InRheum nobile andR. rhaponticum, it serves as a UV blocker found in the bracts.

It is also found inGeranium niveum[3] andTaxillus 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.Bibcode:2005JAFC...53...32L.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)
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others
Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides ofherbacetin
Glycosides ofkaempferol
Glycosides ofmyricetin
Conjugates ofquercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
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