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

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 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
Hypoglycemic effect of Cecropia obtusifolia on streptozotocin diabetic rats.	2001 Dec	11694359
O-Galloyl-C-glycosylflavones from Pelargonium reniforme.	2002 Feb	11830160
Naphthalene glucoside and other phenolics from the shoot and callus cultures of Drosophyllum lusitanicum.	2002 Oct	12377237
Xanthones from Swertia punctata.	2002 Oct	12377236
Antioxidative compounds from Crotalaria sessiliflora.	2003 Feb	12729010
Preparative separation of isovitexin and isoorientin from Patrinia villosa Juss by high-speed counter-current chromatography.	2005 May 13	15941046
Structure-activity relationship for antiinflammatory effect of luteolin and its derived glycosides.	2005 Sep	16220571
Activity of Cecropia lyratiloba extract on contractility of cardiac and smooth muscles in Wistar rats.	2006 Jan-Feb	16445708
Antioxidant flavone glycosides from the leaves of Sasa borealis.	2007 Feb	17366736
Induction of flavonoid production by UV-B radiation in Passiflora quadrangularis callus cultures.	2007 Jul	17512679
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.	2007 Jul 28	17537670
Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity.	2007 Jun	17520524
[Chemical constituents from herbs of Swertia delavayi].	2008 Aug	19086635
[Studies on glycosides from Gentiana veitchiorum].	2008 Nov	19149260
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
Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents.	2009 Jan	19000749
Phenolic contribution of South African herbal teas to a healthy diet.	2009 May	19445319
Bioassay-guided isolation of anti-inflammatory C-glucosylflavones from Passiflora edulis.	2009 Sep	19353489
Sasa borealis leaves extract improves insulin resistance by modulating inflammatory cytokine secretion in high fat diet-induced obese C57/BL6J mice.	2010 Apr	20461197
Spectroscopic characterization and antiproliferative activity on HepG2 human hepatoblastoma cells of flavonoid C-glycosides from Petrorhagia velutina.	2010 Dec 27	21080643
Anxiolytic and sedative activities of Passiflora edulis f. flavicarpa.	2010 Mar 2	20051259
Phytochemical and pharmacological review of Lagenaria sicereria.	2010 Oct	21731373
Protective effect of isoorientin-2″-O-α-L-arabinopyranosyl isolated from Gypsophila elegans on alcohol induced hepatic fibrosis in rats.	2012 Jun	22446813
Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy.	2012 Jun	22445328
Additive effect of zinc oxide nanoparticles and isoorientin on apoptosis in human hepatoma cell line.	2014 Mar 3	24374571

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 `Sat Dec 16 09:29:57 UTC 2023` Edited by `admin` on `Sat Dec 16 09:29:57 UTC 2023`
Record UNII	A37342TIX1
Record Status	`Validated (UNII)`
Record Version

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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