Isoorientin

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 InfoCard 100.128.382 Edit 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 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.

Natural occurrence

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

Potential pharmacology

Isoorientin has been studied for its potential pharmacological activity. Bioassay-directed fractionation techniques led to isolation of isoorientin as the main hypoglycaemic component in Gentiana olivieri. Studies also showed that isoorientin is a potential neuroprotective compound against Alzheimer's disease.

Metabolism

The enzyme isoorientin 3'-O-methyltransferase converts isoorientin to isoscoparin in a methylation reaction using the cofactor, S-adenosyl methionine (SAM):

2D representation of the chemical structure of isoorientin .
isoorientin
+ SAM
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27102895.
isoscoparin
+ SAH
 

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.
  6. ↑ Van Brederode, J.; Kamps-Heinsbroek, R.; Mastenbroek, O. (1982). "Biochemical and Ontogenetic Evidence that the Ferulic Acid and Isoscoparin Formation in Silene are Catalyzed by Different Enzymes". Zeitschrift für Pflanzenphysiologie. 106: 43–53. doi:10.1016/S0044-328X(82)80053-6.