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Isoorientin

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Isoorientin
Names
IUPAC name
6-(β-D-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-1-benzopyran-4-one
Other names
Luteolin-6-C-glucoside
homoorientin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.128.382Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1
    Key: ODBRNZZJSYPIDI-VJXVFPJBSA-N
  • C1=CC(=C(C=C1C2=CC(=O)C3=C(C(=C(C=C3O2)O)C4C(C(C(C(O4)CO)O)O)O)O)O)O
Properties
C21H20O11
Molar mass448.38 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Isoorientin (or homoorientin) is aflavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside.Bioassay-directed fractionation techniques led to isolation of isoorientin as the mainhypoglycaemic component inGentiana olivieri.[1] Studies also showed that isoorientin is a potentialneuroprotective compound againstAlzheimer's disease.[2]

Natural occurrences

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Isoorientin can be isolated from thepassion flower,Vitex negundo,Terminalia myriocarpa, theAçaí palm andSwertia japonica.

Metabolism

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See also

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References

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  1. ^Hypoglycaemic activity of Gentiana olivieri and isolation of the active constituent through bioassay- directed fractionation techniques. Ekrem Sezik, Mustafa Aslan, Erdem Yesilada, Shigeru Ito, Life Sciences, 28 January 2005, Volume 76, Issue 11, Pages 1223–1238,doi:10.1016/j.lfs.2004.07.024
  2. ^Zhibin Liang; Bei Zhang; Wei Wen Su; Philip G Williams; Qing X Li (July 2016)."C-Glycosylflavones Alleviate Tau Phosphorylation and Amyloid Neurotoxicity through GSK3β Inhibition".ACS Chemical Neuroscience.7: 912–923.doi:10.1021/acschemneuro.6b00059.PMC 7355085.PMID 27213824.


Flavones and their conjugates
Aglycones
Monohydroxyflavone
Dihydroxyflavones
Trihydroxyflavones
Tetrahydroxyflavones
Pentahydroxyflavones
O-methylated flavones
Glycosides
of apigenin
of baicalein
of hypolaetin
of luteolin
Acetylated
Sulfated glycosides
Polymers
Drugs


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