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
CAS Number	4261-42-1;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17965 ;
ChemSpider	102753;
ECHA InfoCard	100.128.382
KEGG	C01821 ;
PubChem CID	114776;
UNII	A37342TIX1 ;
CompTox Dashboard (EPA)	DTXSID50962609 ;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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,^[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

The enzyme isoorientin 3'-O-methyltransferase converts isoorientin to isoscoparin in a methylation reaction using the cofactor, S-adenosyl methionine (SAM):^[6]

isoorientin

+ SAM

2D representation of the chemical structure of Q27102895.

isoscoparin

+ SAH

References

↑ 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.
↑ 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.

[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.

[1]

[2]

[3]

[4]

[5]

[6]

This page was redesigned at the edge.

Isoorientin

Natural occurrence

Potential pharmacology

Metabolism

See also

References