# Isoorientin

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> Markdown URL: https://mediated.wiki/source/Isoorientin.md
> Source: https://en.wikipedia.org/wiki/Isoorientin
> Source revision: 1351351441
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{{chembox
| ImageFile = Homoorientin.svg
| ImageSize = 250px
| IUPACName = 6-(β-<small>D</small>-Glucopyranosyl)-3′,4′,5,7-tetrahydroxyflavone
| SystematicName = 2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-6-[(2''S'',3''R'',4''R'',5''S'',6''R'')-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4''H''-1-benzopyran-4-one
| OtherNames = [Luteolin](/source/Luteolin)-6-C-glucoside<br>Homoorientin
|Section1={{Chembox Identifiers
| CASNo_Ref = 
| CASNo = 4261-42-1
| UNII_Ref= {{fdacite|correct|FDA}}
| UNII = A37342TIX1
| 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
| InChIKey = ODBRNZZJSYPIDI-VJXVFPJBSA-N
| PubChem = 114776
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17965
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01821
| ChemSpiderID = 102753
| ChEMBL_Ref = 
| ChEMBL = 
| 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
  }}
|Section2={{Chembox Properties
| C=21 | H=20 | O=11
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

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

== Natural occurrence ==
Isoorientin can be isolated from the [passion flower](/source/passion_flower),<ref>{{cite journal | doi = 10.1002/cbdv.201300181 | title = Glycosidic Inhibitors of Melanogenesis from Leaves of ''Passiflora edulis'' | date = 2013 | last1 = Zhang | first1 = Jie | last2 = Koike | first2 = Ryosuke | last3 = Yamamoto | first3 = Ayako | last4 = Ukiya | first4 = Motohiko | last5 = Fukatsu | first5 = Makoto | last6 = Banno | first6 = Norihiro | last7 = Miura | first7 = Motofumi | last8 = Motohashi | first8 = Shigeyasu | last9 = Tokuda | first9 = Harukuni | last10 = Akihisa | first10 = Toshihiro | journal = Chemistry & Biodiversity | volume = 10 | issue = 10 | pages = 1851–1865 | pmid = 24130028 }}</ref> ''[Vitex negundo](/source/Vitex_negundo)'',<ref>{{cite journal | doi = 10.1016/j.bmcl.2006.09.051 | title = New antifungal flavonoid glycoside from Vitex negundo | date = 2007 | last1 = Sathiamoorthy | first1 = B. | last2 = Gupta | first2 = Prasoon | last3 = Kumar | first3 = Manmeet | last4 = Chaturvedi | first4 = Ashok K. | last5 = Shukla | first5 = P.K. | last6 = Maurya | first6 = Rakesh | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 1 | pages = 239–242 | pmid = 17027268 }}</ref> ''[Terminalia myriocarpa](/source/Terminalia_myriocarpa)'', the [Açaí palm](/source/A%C3%A7a%C3%AD_palm), and ''[Swertia japonica](/source/Swertia_japonica)''.

== Potential pharmacology==
Isoorientin has been studied for its potential pharmacological activity.<ref>{{Cite journal | doi = 10.1016/j.phrs.2020.104867 | title = Isoorientin: A dietary flavone with the potential to ameliorate diverse metabolic complications | date = 2020 | last1 = Ziqubu | first1 = Khanyisani | last2 = Dludla | first2 = Phiwayinkosi V. | last3 = Joubert | first3 = Elizabeth | last4 = Muller | first4 = Christo J.F. | last5 = Louw | first5 = Johan | last6 = Tiano | first6 = Luca | last7 = Nkambule | first7 = Bongani B. | last8 = Kappo | first8 = Abidemi P. | last9 = Mazibuko-Mbeje | first9 = Sithandiwe E. | journal = Pharmacological Research | volume = 158 | pmid = 32407953 }}</ref>  [Bioassay-directed fractionation](/source/Bioassay-directed_fractionation) techniques led to isolation of isoorientin as the main [hypoglycaemic](/source/hypoglycaemic) component in ''[Gentiana olivieri](/source/Gentiana_olivieri)''.<ref>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}}</ref> Studies also showed that isoorientin is a potential [neuroprotective](/source/neuroprotective) compound against [Alzheimer's disease](/source/Alzheimer's_disease).<ref>{{cite journal |author1=Zhibin Liang |author2=Bei Zhang |author3=Wei Wen Su |author4=Philip G Williams |author5=Qing X Li |title=C-Glycosylflavones Alleviate Tau Phosphorylation and Amyloid Neurotoxicity through GSK3β Inhibition |journal=ACS Chemical Neuroscience |volume=7 |date=July 2016 |issue=7 |pages=912–923 |pmid=27213824 |doi=10.1021/acschemneuro.6b00059 |pmc=7355085 }}</ref>

== Metabolism ==
The enzyme [isoorientin 3'-O-methyltransferase](/source/isoorientin_3'-O-methyltransferase) converts isoorientin to isoscoparin in a [methylation](/source/methylation) reaction using the [cofactor](/source/cofactor_(biochemistry)), [S-adenosyl methionine](/source/S-adenosyl_methionine) (SAM):<ref>{{cite journal |last1=Van Brederode |first1=J. |last2=Kamps-Heinsbroek |first2=R. |last3=Mastenbroek |first3=O. |title=Biochemical and Ontogenetic Evidence that the Ferulic Acid and Isoscoparin Formation in Silene are Catalyzed by Different Enzymes |journal=Zeitschrift für Pflanzenphysiologie |date=1982 |volume=106 |pages=43–53 |doi=10.1016/S0044-328X(82)80053-6 }}</ref>

{{chemrxn|width=70%|
{{chemrxn/cpd|isoorientin }}
{{chemrxn/txt|+ [SAM](/source/S-adenosyl_methionine) }}
{{chemrxn/arw| }}
{{chemrxn/cpd|qid=Q27102895|caption=[isoscoparin](/source/isoscoparin) }}
{{chemrxn/txt|+ [SAH](/source/S-Adenosyl-L-homocysteine) }}
}}

== See also==
* [Orientin](/source/Orientin), the 8-C [glucoside](/source/glucoside) of [luteolin](/source/luteolin).

== References ==
{{Reflist}}

{{flavone}}

Category:Flavone glucosides
Category:C-glycoside natural phenols

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Adapted from the Wikipedia article [Isoorientin](https://en.wikipedia.org/wiki/Isoorientin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Isoorientin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.