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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27693342
Curator's Comment: Known to be CNS penetrant in rats. Human data not available.
Lowest level
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27693342 |
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Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28891090 |
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Target ID: CHEMBL1900 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24291393 |
0.13 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors. | 2007 Aug 8 |
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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 |
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Priming of antimicrobial phenolics during induced resistance response towards Pectobacterium carotovorum in the ornamental monocot calla lily. | 2007 Dec 12 |
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[Studies on chemical constituents from stellaria media. I]. | 2007 Jun |
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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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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 |
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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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Therapeutic biology of Jatropha curcas: a mini review. | 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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Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha. | 2008 Feb |
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Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS. | 2008 Feb |
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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 |
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Megastigmane and flavone glycosides from Strophioblachia fimbricalyx Boerl. | 2008 Jan |
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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 |
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Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity. | 2008 Jul |
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HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity. | 2008 Mar 12 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25096710
Rat: 0.1 or 0.25 mg/kg
Route of Administration:
Intragastric
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15965085
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
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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Related Record | Type | Details | ||
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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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