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Isoorientin
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| Names | |
|---|---|
| IUPAC name
6-(β-D-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone
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| 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)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.128.382 |
| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| Properties | |
| C21H20O11 | |
| Molar mass | 448.380 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isoorientin (homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside.
Natural occurrence
[edit]Isoorientin can be isolated from the passion flower,[1] Vitex negundo,[2] Terminalia myriocarpa, the Açaí palm, and Swertia japonica.
Potential pharmacology
[edit]Isoorientin has been studied for its potential pharmacological activity.[3] Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri.[4] Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.[5]
Metabolism
[edit]See also
[edit]References
[edit]- ^ Zhang, Jie; Koike, Ryosuke; Yamamoto, Ayako; Ukiya, Motohiko; Fukatsu, Makoto; Banno, Norihiro; Miura, Motofumi; Motohashi, Shigeyasu; Tokuda, Harukuni; Akihisa, Toshihiro (2013). "Glycosidic Inhibitors of Melanogenesis from Leaves of Passiflora edulis". Chemistry & Biodiversity. 10 (10): 1851–1865. doi:10.1002/cbdv.201300181. PMID 24130028.
- ^ Sathiamoorthy, B.; Gupta, Prasoon; Kumar, Manmeet; Chaturvedi, Ashok K.; Shukla, P.K.; Maurya, Rakesh (2007). "New antifungal flavonoid glycoside from Vitex negundo". Bioorganic & Medicinal Chemistry Letters. 17 (1): 239–242. doi:10.1016/j.bmcl.2006.09.051. PMID 17027268.
- ^ Ziqubu, Khanyisani; Dludla, Phiwayinkosi V.; Joubert, Elizabeth; Muller, Christo J.F.; Louw, Johan; Tiano, Luca; Nkambule, Bongani B.; Kappo, Abidemi P.; Mazibuko-Mbeje, Sithandiwe E. (2020). "Isoorientin: A dietary flavone with the potential to ameliorate diverse metabolic complications". Pharmacological Research. 158. doi:10.1016/j.phrs.2020.104867. PMID 32407953.
- ^ 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
- ^ 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 (7): 912–923. doi:10.1021/acschemneuro.6b00059. PMC 7355085. PMID 27213824.
Flavones and their conjugates | |||||||||||||
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| Glycosides |
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| Acetylated | |||||||||||||
| Sulfated glycosides | Theograndin I and II | ||||||||||||
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