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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O10
Molecular Weight 432.3775
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOVITEXIN

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=C(O)C=C4)C=C2O

InChI

InChIKey=MYXNWGACZJSMBT-VJXVFPJBSA-N
InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14-,17-,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H20O10
Molecular Weight 432.3775
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Isovitexin (apigenin-6-C-glucoside), an isomer of vitexin, is found in plants such as pigeon pea, Passiflora, bamboo, mimosa, wheat leaves, rice hull of Oryza sativa and others. Isovitexin is poorly absorbed in the gastrointestinal tract. The highest level of intravenously administrated isovitexin was examined in kidney, liver, lung, and lowest in the brain. Isovitexin helps to stimulate apoptotic cell death and autophagy of various cancer cells through the upstream regulation of Bax, PARP, p-JNK, and MAPK and the downstream regulation of the caspases Bcl-2 and ERK1/2. Isovitexin has been proved to have various activities, such as anti-oxidant, anti-inflammatory, anti-Alzheimer's disease and others.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rats. Human data not available. Lowest level

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.13 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
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
Priming of antimicrobial phenolics during induced resistance response towards Pectobacterium carotovorum in the ornamental monocot calla lily.
2007 Dec 12
Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts.
2007 Nov 28
Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts.
2007 Oct 31
Flavonoids from Acacia pennata and their cyclooxygenase (COX-1 and COX-2) inhibitory activities.
2007 Sep
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 Sep-Oct
Fructose-amino acid conjugate and other constituents from Cyperus rotundus L.
2008
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.
2008
[Chemical constituents from herbs of Swertia delavayi].
2008 Aug
Therapeutic biology of Jatropha curcas: a mini review.
2008 Aug
Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system.
2008 Dec
Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha.
2008 Feb
Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS.
2008 Feb
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
Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl.
2008 Jan
Flavonoids in the leaves of Oxalis corniculata and sequestration of the flavonoids in the wing scales of the pale grass blue butterfly, Pseudozizeeria maha.
2008 Jan
Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.
2008 Jul
HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity.
2008 Mar 12
[Studies on glycosides from Gentiana veitchiorum].
2008 Nov
[Studies on HPLC fingerprint chromatogram of Folium Fici Microcarpa].
2008 Oct
[Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC].
2008 Oct
Antiradical activities of the extract of Passiflora incarnata.
2008 Sep-Oct
New bioactive compounds from Aloe hijazensis.
2009
Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice.
2009
Screening and structural characterization of alpha-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MS(n) and SORI-CID FTICR MS.
2009 Aug
Antioxidant activity of the dihydrochalcones Aspalathin and Nothofagin and their corresponding flavones in relation to other Rooibos ( Aspalathus linearis ) Flavonoids, Epigallocatechin Gallate, and Trolox.
2009 Aug 12
Quantitation of chafurosides A and B in tea leaves and isolation of prechafurosides A and B from oolong tea leaves.
2009 Aug 12
Chemical constituents of the fruits of Gleditschia australis Hemsl.
2009 Feb
Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents.
2009 Jan
Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots.
2009 Jan 21
Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes.
2009 Jul-Aug
Neural cell protective compounds isolated from Phoenix hanceana var. formosana.
2009 Jun
Rapid identification of polyphenol C-glycosides from Swertia franchetiana by HPLC-ESI-MS-MS.
2009 Mar
Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma.
2009 Sep
Pharmacognosy and chemotypes of passionflower (Passiflora incarnata L.).
2010
Anti-secretory, anti-inflammatory and anti-Helicobacter pylori activities of several fractions isolated from Piper carpunya Ruiz & Pav.
2010 Apr 21
Randomized clinical trial of a phytotherapic compound containing Pimpinella anisum, Foeniculum vulgare, Sambucus nigra, and Cassia augustifolia for chronic constipation.
2010 Apr 30
Analysis of rare flavonoid C-glycosides in Celtis australis L. by micellar electrokinetic chromatography.
2010 Apr 6
Potential insulin secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats.
2010 Dec
Chemical composition of the SFE-CO extracts from Cajanus cajan (L.) Huth and their antimicrobial activity in vitro and in vivo.
2010 Dec 1
Antiedematogenic activity and phytochemical composition of preparations from Echinodorus grandiflorus leaves.
2010 Dec 15
Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum.
2010 Feb
A new flavone C-glycoside from Clematis rehderiana.
2010 Jan 29
Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart.
2010 Jun
A new lignan dimer from Mallotus philippensis.
2010 Mar
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
The constituents of Urtica cannabina used in Uighur medicine.
2010 May
Topical and systemic anti-inflammatory effects of Echinodorus macrophyllus (Kunth) Micheli (Alismataceae).
2010 Oct
Extracts from the Mongolian traditional medicinal plants Dianthus versicolorFisch. and Lilium pumilum Delile stimulate bile flow in an isolated perfused rat liver model.
2010 Oct 5
Comparative study of the flavonoids of some Verbena species cultivated in Egypt by using high-performance liquid chromatography coupled with ultraviolet spectroscopy and atmospheric pressure chemical ionization mass spectrometry.
2010 Oct 8
Patents

Patents

Sample Use Guides

Rat: 0.1 or 0.25 mg/kg
Route of Administration: Intragastric
Isovitexin inhibited the release of TNF-alpha, a proinflammatory cytokine, upon LPS activation of RAW 264.7 macrophages with a 50% inhibitory concentration (IC50) of 78.6 uM. Isovitexin markedly reduced LPS-stimulated PGE2 production in a concentration-dependent manner, with an IC50 of 80.0 uM.
Substance Class Chemical
Created
by admin
on Thu Jul 06 15:29:18 UTC 2023
Edited
by admin
on Thu Jul 06 15:29:18 UTC 2023
Record UNII
KTQ9R9MS0Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ISOVITEXIN
Common Name English
4H-1-BENZOPYRAN-4-ONE, 6-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
Systematic Name English
Isovitexin [WHO-DD]
Common Name English
AVROSIDE
Common Name English
ISOVITEXIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]
Common Name English
ISOAVROSIDE
Common Name English
APIGENIN-6-C-GLUCOSIDE
Common Name English
SAPONARETIN
Common Name English
6-C-.BETA.-D-GLUCOPYRANOSYLAPIGENIN
Common Name English
Classification Tree Code System Code
DSLD 4451 (Number of products:1)
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
Code System Code Type Description
CHEBI
18330
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
FDA UNII
KTQ9R9MS0Q
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID60952152
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
WIKIPEDIA
Isovitexin
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
PUBCHEM
162350
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
CAS
38953-85-4
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
CHEBI
58447
Created by admin on Thu Jul 06 15:29:19 UTC 2023 , Edited by admin on Thu Jul 06 15:29:19 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
ORAC value expressed as umol TE/g for this compound is 22404.5 +/- 1322.1. ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP