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
Unfermented rooibos tea: quantitative characterization of flavonoids by HPLC-UV and determination of the total antioxidant activity.	2003 Dec 3	14640601
High-speed countercurrent chromatography as a valuable tool to isolate C-glycosylflavones from Cecropia lyratiloba Miquel.	2003 Mar-Apr	12693634
Free radical scavengers and antioxidants from Lemongrass (Cymbopogon citratus (DC.) Stapf.).	2005 Apr 6	15796587
[HPLC fingerprinting of total glycosides of Swertia franchetiana].	2005 May	16220791
[Studies on chemical constituents of Patrinia villosa].	2006 Jan	16570799
Activity of Cecropia lyratiloba extract on contractility of cardiac and smooth muscles in Wistar rats.	2006 Jan-Feb	16445708
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 Dec	18081102
New antifungal flavonoid glycoside from Vitex negundo.	2007 Jan 1	17027268
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.	2008	19023787
[Chemical constituents from herbs of Swertia delavayi].	2008 Aug	19086635
Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.	2008 Jul	18409066
Neuropharmacological activity of the pericarp of Passiflora edulis flavicarpa degener: putative involvement of C-glycosylflavonoids.	2009 Aug	19491371
Identification and bioactivities of resveratrol oligomers and flavonoids from Carex folliculata seeds.	2009 Aug 26	19627089
[Simultaneous determination of four constituents in wild Gentiana lawrencei from Qinghai province by RP-HPLC].	2009 Nov	20209951
Gluconeogenesis inhibition and phytochemical composition of two Cecropia species.	2010 Jul 6	20420891
Antiallergic herbal composition from Scutellaria baicalensis and Phyllostachys edulis.	2010 May	19960410
Phytochemical and pharmacological review of Lagenaria sicereria.	2010 Oct	21731373
Development and validation of an HPTLC method for simultaneous quantitation of isoorientin, isovitexin, orientin, and vitexin in bamboo-leaf flavonoids.	2010 Sep-Oct	21140646
Chemical constituents of the methanolic extract of leaves of Leiothrix spiralis Ruhland and their antimicrobial activity.	2011 Dec 16	22179427
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 GMT 2023` Edited by `admin` on `Sat Dec 16 09:29:57 GMT 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