Isoorientin

Last updated
Isoorientin
Homoorientin.svg
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 InfoCard 100.128.382 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 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).

Isoorientin (homoorientin) is a flavone, a chemical flavonoid-like compound. It is the luteolin-6-C-glucoside.

Contents

Natural occurrence

Isoorientin can be isolated from the passion flower, [1] Vitex negundo , [2] Terminalia myriocarpa , the Açaí palm, and Swertia japonica .

Potential pharmacology

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

See also

References

  1. ↑ 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.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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
  5. ↑ 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.
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