ISOORIENTIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O11
Molecular Weight	448.3769
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=C(O)C=C3OC(=CC(=O)C3=C2O)C4=CC=C(O)C(O)=C4

InChI

InChIKey=ODBRNZZJSYPIDI-VJXVFPJBSA-N

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

HIDE SMILES / InChI

Molecular Formula	C21H20O11
Molecular Weight	448.3769
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23220614 | https://www.ncbi.nlm.nih.gov/pubmed/21870321 | https://www.ncbi.nlm.nih.gov/pubmed/26462718 | https://www.ncbi.nlm.nih.gov/pubmed/28243356

Isoorientin is a common C-glycosyl flavone in the human diet. It has been isolated from several plant species, including Phyllostachys pubescens, Crataegus monogyna and Crataegus pentagyna, Patrinia villosa Juss, Drosophyllum lusitanicum, buckwheat, Arum palaestinum, and Rumex and Swertia. Isoorientin possesses significant anti-nociceptive and anti-inflammatory activities. Significantly protected PC12 nerve cells from 6-OHDA-induced apoptotic neurotoxicity and reduced the proliferation of HepG2 cells. Isoorientin showed anti-RSV (respiratory syncytial virus) activity.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Thromboxane B2 synthesis 1 Target ID: Thromboxane B2 synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/16220571	Inhibitor 8504
detoxification of hydrogen peroxide 1 Target ID: GO:0061691 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16220571	Activator 1447
Alpha-glucosidase MAL62 4 Target ID: CHEMBL4357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19443236	Inhibitor 8504	19.7 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26669106	Inhibitor 8504	39.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Inflammation 105 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16220571 https://www.ncbi.nlm.nih.gov/pubmed/28243356 https://www.ncbi.nlm.nih.gov/pubmed/26669106	Primary	Preclinical	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19443236	Primary	Basic research	Unknown Approved Use Unknown
Liver cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23220614 https://www.ncbi.nlm.nih.gov/pubmed/24841907 https://www.ncbi.nlm.nih.gov/pubmed/26462718	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Additive effect of zinc oxide nanoparticles and isoorientin on apoptosis in human hepatoma cell line.	2014-03-03	24374571
Protective effect of isoorientin-2″-O-α-L-arabinopyranosyl isolated from Gypsophila elegans on alcohol induced hepatic fibrosis in rats.	2012-06	22446813
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012-06	22445328
Chemical constituents of the methanolic extract of leaves of Leiothrix spiralis Ruhland and their antimicrobial activity.	2011-12-16	22179427
Spectroscopic characterization and antiproliferative activity on HepG2 human hepatoblastoma cells of flavonoid C-glycosides from Petrorhagia velutina.	2010-12-27	21080643
Development and validation of an HPTLC method for simultaneous quantitation of isoorientin, isovitexin, orientin, and vitexin in bamboo-leaf flavonoids.	2010-12-15	21140646
Antiedematogenic activity and phytochemical composition of preparations from Echinodorus grandiflorus leaves.	2010-12-15	20637578
Phytochemical and pharmacological review of Lagenaria sicereria.	2010-10	21731373
Gluconeogenesis inhibition and phytochemical composition of two Cecropia species.	2010-07-06	20420891
The compound isolated from the leaves of Phyllostachys nigra protects oxidative stress-induced retinal ganglion cells death.	2010-06	20381571
Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart.	2010-06	20347919
[Determination of five active constituents in aerial part of Tibetan medicine Gentiana straminea by HPLC].	2010-05	20707196
Natural products from Scorzonera aristata (Asteraceae).	2010-05	20521536
Antiallergic herbal composition from Scutellaria baicalensis and Phyllostachys edulis.	2010-05	19960410
Randomized clinical trial of a phytotherapic compound containing Pimpinella anisum, Foeniculum vulgare, Sambucus nigra, and Cassia augustifolia for chronic constipation.	2010-04-30	20433751
Hypoglycemic effects of Cecropia pachystachya in normal and alloxan-induced diabetic rats.	2010-04-21	20064597
Sasa borealis leaves extract improves insulin resistance by modulating inflammatory cytokine secretion in high fat diet-induced obese C57/BL6J mice.	2010-04	20461197
Anxiolytic and sedative activities of Passiflora edulis f. flavicarpa.	2010-03-02	20051259
Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum.	2010-02	20007684
A new flavone C-glycoside from Clematis rehderiana.	2010-01-29	20335937
[Simultaneous determination of four constituents in wild Gentiana lawrencei from Qinghai province by RP-HPLC].	2009-11	20209951
Inhibitory effect of three C-glycosylflavonoids from Cymbopogon citratus (Lemongrass) on human low density lipoprotein oxidation.	2009-09-30	19924037
Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.	2009-09	19446614
Bioassay-guided isolation of anti-inflammatory C-glucosylflavones from Passiflora edulis.	2009-09	19353489
Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds.	2009-08-26	19627089
Neuropharmacological activity of the pericarp of Passiflora edulis flavicarpa degener: putative involvement of C-glycosylflavonoids.	2009-08	19491371
Neural cell protective compounds isolated from Phoenix hanceana var. formosana.	2009-06	19628235
Phenolic contribution of South African herbal teas to a healthy diet.	2009-05	19445319
Rapid identification of polyphenol C-glycosides from Swertia franchetiana by HPLC-ESI-MS-MS.	2009-03	19298704
Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents.	2009-01	19000749
Further studies on the chemical constituents of Chinese folk medicine Gentiana apiata N.E. Br.	2009	19431015
Verticilliside, a new flavone C-glucoside from Enicostemma verticillatum.	2009	19408150
Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice.	2009	18989825
[Studies on glycosides from Gentiana veitchiorum].	2008-11	19149260
[Chemical constituents from herbs of Swertia delavayi].	2008-08	19086635
Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.	2008-07	18409066
Characterization of phenolic compounds in rooibos tea.	2008-05-14	18399640
Anemonin, from Clematis crassifolia, potent and selective inducible nitric oxide synthase inhibitor.	2008-03-28	18281171
Further knowledge on barley (Hordeum vulgare L.) leaves O-glycosyl-C-glycosyl flavones by liquid chromatography-UV diode-array detection-electrospray ionisation mass spectrometry.	2008-02-22	18215689
Compounds from Vitex polygama active against kidney diseases.	2008-01-17	17981413
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.	2008	19023787
Isoorientin induces Nrf2 pathway-driven antioxidant response through phosphatidylinositol 3-kinase signaling.	2007-12	18254247
Resistance to Spodoptera frugiperda (Lepidoptera: Noctuidae) and Euxesta stigmatias (Diptera: Ulidiidae) in sweet corn derived from exogenous and endogenous genetic systems.	2007-12	18232407
4'''-Acetylvitexin-2''-O-rhamnoside, isoorientin, orientin, and 8-methoxykaempferol-3-O-glucoside as markers for the differentiation of Crataegus monogyna and Crataegus pentagyna from Crataegus laevigata (Rosaceae).	2007-12	18081102
Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts.	2007-11-28	17966982
Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts.	2007-10-31	17902620
Isovitexin-2'-O-beta-[6-O-E-p-coumaroylglucopyranoside] from UV-B irradiated leaves of rice, Oryza sativa L. inhibits fertility of Helicoverpa armigera.	2007-09-21	17880511
A new pyrrole alkaloid isolated from Arum palaestinum Boiss. and its biological activities.	2007-08	17879743
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.	2007-07-28	17537670
Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity.	2007-06	17520524

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10 or 20 mg/Kg body weight

Route of Administration: Intraperitoneal

In Vitro Use Guide

Isoorientin was active as quorum sensing (QS) inhibitor when tested on the E. coli biosensor model. It presented moderate activity - 45 ug/disc. The result of QS inhibition assay with Isoorientin using C.violaceum as biosensor was - 40 ug/disc.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:41:40 GMT 2025` Edited by `admin` on `Mon Mar 31 22:41:40 GMT 2025`
Record UNII	A37342TIX1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HOMOORIENTIN

Preferred Name

English

ISOORIENTIN

Common Name

English

ISO-ORIENTIN

Common Name

English

LESPECAPITIOSIDE

Common Name

English

LUTONARETIN

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 2-(3,4-DIHYDROXYPHENYL)-6-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID50962609