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
SMILES
OC[C@H]1O[C@H]([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
| 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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: WP408 |
|||
Target ID: WP254 |
|||
Target ID: CHEMBL1900 |
0.13 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antiedematogenic activity and phytochemical composition of preparations from Echinodorus grandiflorus leaves. | 2010-12-15 |
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| Chemical composition of the SFE-CO extracts from Cajanus cajan (L.) Huth and their antimicrobial activity in vitro and in vivo. | 2010-12-01 |
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| Potential insulin secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats. | 2010-12 |
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| 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. | 2010-10-08 |
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| Extracts from the Mongolian traditional medicinal plants Dianthus versicolorFisch. and Lilium pumilum Delile stimulate bile flow in an isolated perfused rat liver model. | 2010-10-05 |
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| Topical and systemic anti-inflammatory effects of Echinodorus macrophyllus (Kunth) Micheli (Alismataceae). | 2010-10 |
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| Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart. | 2010-06 |
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| The constituents of Urtica cannabina used in Uighur medicine. | 2010-05 |
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| Randomized clinical trial of a phytotherapic compound containing Pimpinella anisum, Foeniculum vulgare, Sambucus nigra, and Cassia augustifolia for chronic constipation. | 2010-04-30 |
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| Anti-secretory, anti-inflammatory and anti-Helicobacter pylori activities of several fractions isolated from Piper carpunya Ruiz & Pav. | 2010-04-21 |
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| Analysis of rare flavonoid C-glycosides in Celtis australis L. by micellar electrokinetic chromatography. | 2010-04-06 |
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| Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010-03-02 |
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| A new lignan dimer from Mallotus philippensis. | 2010-03 |
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| Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum. | 2010-02 |
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| A new flavone C-glycoside from Clematis rehderiana. | 2010-01-29 |
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| Pharmacognosy and chemotypes of passionflower (Passiflora incarnata L.). | 2010 |
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| Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes. | 2009-10-02 |
|
| Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma. | 2009-09 |
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| Antioxidant activity of the dihydrochalcones Aspalathin and Nothofagin and their corresponding flavones in relation to other Rooibos ( Aspalathus linearis ) Flavonoids, Epigallocatechin Gallate, and Trolox. | 2009-08-12 |
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| Quantitation of chafurosides A and B in tea leaves and isolation of prechafurosides A and B from oolong tea leaves. | 2009-08-12 |
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| Screening and structural characterization of alpha-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MS(n) and SORI-CID FTICR MS. | 2009-08 |
|
| Neural cell protective compounds isolated from Phoenix hanceana var. formosana. | 2009-06 |
|
| Rapid identification of polyphenol C-glycosides from Swertia franchetiana by HPLC-ESI-MS-MS. | 2009-03 |
|
| Chemical constituents of the fruits of Gleditschia australis Hemsl. | 2009-02 |
|
| Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots. | 2009-01-21 |
|
| Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents. | 2009-01 |
|
| New bioactive compounds from Aloe hijazensis. | 2009 |
|
| Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice. | 2009 |
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| Antiradical activities of the extract of Passiflora incarnata. | 2008-12-05 |
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| Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system. | 2008-12 |
|
| [Studies on glycosides from Gentiana veitchiorum]. | 2008-11 |
|
| [Studies on HPLC fingerprint chromatogram of Folium Fici Microcarpa]. | 2008-10 |
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| [Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC]. | 2008-10 |
|
| [Chemical constituents from herbs of Swertia delavayi]. | 2008-08 |
|
| Therapeutic biology of Jatropha curcas: a mini review. | 2008-08 |
|
| Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity. | 2008-07 |
|
| HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. | 2008-03-12 |
|
| 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 |
|
| Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha. | 2008-02 |
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| Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS. | 2008-02 |
|
| Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl. | 2008-01 |
|
| Flavonoids in the leaves of Oxalis corniculata and sequestration of the flavonoids in the wing scales of the pale grass blue butterfly, Pseudozizeeria maha. | 2008-01 |
|
| 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 |
|
| Priming of antimicrobial phenolics during induced resistance response towards Pectobacterium carotovorum in the ornamental monocot calla lily. | 2007-12-12 |
|
| 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 |
|
| Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts. | 2007-11-28 |
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| Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts. | 2007-10-31 |
|
| 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 |
|
| Flavonoids from Acacia pennata and their cyclooxygenase (COX-1 and COX-2) inhibitory activities. | 2007-09 |
Patents
Sample Use Guides
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
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admin
on
Edited
Mon Mar 31 22:56:09 GMT 2025
by
admin
on
Mon Mar 31 22:56:09 GMT 2025
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| Record UNII |
KTQ9R9MS0Q
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| Record Status |
Validated (UNII)
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| Record Version |
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4451 (Number of products:1)
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KTQ9R9MS0Q
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DTXSID60952152
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Isovitexin
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162350
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38953-85-4
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58447
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| Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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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.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
