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
[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
| 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 |
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Target ID: WP254 |
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Target ID: CHEMBL1900 |
0.13 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors. | 2007 Aug 8 |
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| Chemosystematic value of flavonoids from Crataegus x macrocarpa (Rosaceae) with special emphasis on (R)- and (S)-eriodictyol-7-O-glucuronide and luteolin-7-O-glucuronide. | 2007 Feb |
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| The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions. | 2007 Jul 28 |
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| [Studies on chemical constituents from stellaria media. I]. | 2007 Jun |
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| Selective inducible nitric oxide synthase suppression by new bracteanolides from Murdannia bracteata. | 2007 Jun 13 |
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| Aromatic diglycosides from Cladogynos orientalis. | 2007 Mar |
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| [Chemical constituents from a Tibetan medicine Arenaria kansuensis I]. | 2007 May |
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| Flavonoid biosynthesis in barley primary leaves requires the presence of the vacuole and controls the activity of vacuolar flavonoid transport. | 2007 May |
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| Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts. | 2007 Nov 28 |
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| Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts. | 2007 Oct 31 |
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| Flavonoids from Acacia pennata and their cyclooxygenase (COX-1 and COX-2) inhibitory activities. | 2007 Sep |
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| The spasmolytic effect of Aloysia citriodora, Palau (South American cedrón) is partially due to its vitexin but not isovitexin on rat duodenums. | 2007 Sep 5 |
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| Fructose-amino acid conjugate and other constituents from Cyperus rotundus L. | 2008 |
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| Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis. | 2008 |
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| [Chemical constituents from herbs of Swertia delavayi]. | 2008 Aug |
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| Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system. | 2008 Dec |
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| Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl. | 2008 Jan |
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| Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity. | 2008 Jul |
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| [Studies on glycosides from Gentiana veitchiorum]. | 2008 Nov |
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| [Studies on HPLC fingerprint chromatogram of Folium Fici Microcarpa]. | 2008 Oct |
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| [Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC]. | 2008 Oct |
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| Antiradical activities of the extract of Passiflora incarnata. | 2008 Sep-Oct |
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| New bioactive compounds from Aloe hijazensis. | 2009 |
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| Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice. | 2009 |
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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 Aug |
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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 Aug 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 Aug 12 |
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| Chemical constituents of the fruits of Gleditschia australis Hemsl. | 2009 Feb |
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| Protection against neurodegenerative diseases of Iris pseudopumila extracts and their constituents. | 2009 Jan |
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| Anti-inflammatory activity of flavonoids from Cayaponia tayuya roots. | 2009 Jan 21 |
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| Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes. | 2009 Jul-Aug |
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| Neural cell protective compounds isolated from Phoenix hanceana var. formosana. | 2009 Jun |
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| Rapid identification of polyphenol C-glycosides from Swertia franchetiana by HPLC-ESI-MS-MS. | 2009 Mar |
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| Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma. | 2009 Sep |
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| Pharmacognosy and chemotypes of passionflower (Passiflora incarnata L.). | 2010 |
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| Anti-secretory, anti-inflammatory and anti-Helicobacter pylori activities of several fractions isolated from Piper carpunya Ruiz & Pav. | 2010 Apr 21 |
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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 Apr 30 |
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| Analysis of rare flavonoid C-glycosides in Celtis australis L. by micellar electrokinetic chromatography. | 2010 Apr 6 |
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| Potential insulin secretagogue effects of isovitexin and swertisin isolated from Wilbrandia ebracteata roots in non-diabetic rats. | 2010 Dec |
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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 Dec 1 |
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| Antiedematogenic activity and phytochemical composition of preparations from Echinodorus grandiflorus leaves. | 2010 Dec 15 |
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| Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum. | 2010 Feb |
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| A new flavone C-glycoside from Clematis rehderiana. | 2010 Jan 29 |
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| Secondary plant substances in various extracts of the leaves, fruits, stem and bark of Caraipa densifolia Mart. | 2010 Jun |
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| A new lignan dimer from Mallotus philippensis. | 2010 Mar |
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| Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010 Mar 2 |
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| The constituents of Urtica cannabina used in Uighur medicine. | 2010 May |
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| Topical and systemic anti-inflammatory effects of Echinodorus macrophyllus (Kunth) Micheli (Alismataceae). | 2010 Oct |
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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 Oct 5 |
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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 Oct 8 |
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
Sat Dec 16 09:58:09 GMT 2023
by
admin
on
Sat Dec 16 09:58:09 GMT 2023
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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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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 | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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