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

[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C2=C(O)C3=C(OC(=CC3=O)C4=CC(O)=C(O)C=C4)C=C2O

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

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 8297
detoxification of hydrogen peroxide 1 Target ID: GO:0061691 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16220571	Activator 1430
Alpha-glucosidase MAL62 4 Target ID: CHEMBL4357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19443236	Inhibitor 8297	19.7 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26669106	Inhibitor 8297	39.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Inflammation 102 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 259 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
Antimicrobial evaluation of coumarins and flavonoids from the stems of Daphne gnidium L.	2001 Jul	11515721
Naphthalene glucoside and other phenolics from the shoot and callus cultures of Drosophyllum lusitanicum.	2002 Oct	12377237
Antioxidative compounds from Crotalaria sessiliflora.	2003 Feb	12729010
Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments.	2003 Jan 29	12537462
A HPTLC densitometric determination of flavonoids from Passiflora alata, P. edulis, P. incarnata and P. caerulea and comparison with HPLC method.	2004 Jul-Aug	15311844
Salmon silk genes contribute to the elucidation of the flavone pathway in maize (Zea mays L.).	2004 May-Jun	15220389
[Studies on chemical constituents of Patrinia villosa].	2006 Jan	16570799
Resistance to Spodoptera frugiperda (Lepidoptera: Noctuidae) and Euxesta stigmatias (Diptera: Ulidiidae) in sweet corn derived from exogenous and endogenous genetic systems.	2007 Dec	18232407
Antioxidant flavone glycosides from the leaves of Sasa borealis.	2007 Feb	17366736
An anthocyanin compound in buckwheat sprouts and its contribution to antioxidant capacity.	2007 Feb	17284830
New antifungal flavonoid glycoside from Vitex negundo.	2007 Jan 1	17027268
Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts.	2007 Oct 31	17902620
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 Feb 22	18215689
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
Neural cell protective compounds isolated from Phoenix hanceana var. formosana.	2009 Jun	19628235
[Simultaneous determination of four constituents in wild Gentiana lawrencei from Qinghai province by RP-HPLC].	2009 Nov	20209951
Bioassay-guided isolation of anti-inflammatory C-glucosylflavones from Passiflora edulis.	2009 Sep	19353489
Inhibitory effect of three C-glycosylflavonoids from Cymbopogon citratus (Lemongrass) on human low density lipoprotein oxidation.	2009 Sep 30	19924037
Sasa borealis leaves extract improves insulin resistance by modulating inflammatory cytokine secretion in high fat diet-induced obese C57/BL6J mice.	2010 Apr	20461197
Hypoglycemic effects of Cecropia pachystachya in normal and alloxan-induced diabetic rats.	2010 Apr 21	20064597
Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum.	2010 Feb	20007684
Anxiolytic and sedative activities of Passiflora edulis f. flavicarpa.	2010 Mar 2	20051259
Antiallergic herbal composition from Scutellaria baicalensis and Phyllostachys edulis.	2010 May	19960410
Protective effect of isoorientin-2″-O-α-L-arabinopyranosyl isolated from Gypsophila elegans on alcohol induced hepatic fibrosis in rats.	2012 Jun	22446813

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.

Name

Type

Language

ISOORIENTIN

Common Name

English

HOMOORIENTIN

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