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
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 |
|||
| Preventing | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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| Characterization of the polyphenolic composition of purple loosestrife (Lythrum salicaria). | 2001 Jan-Feb |
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| Unfermented rooibos tea: quantitative characterization of flavonoids by HPLC-UV and determination of the total antioxidant activity. | 2003 Dec 3 |
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| Flavone C-glycoside, phenolic acid, and nitrogen contents in leaves of barley subject to organic fertilization treatments. | 2003 Jan 29 |
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| Flavonoids of Crotalaria sessiliflora. | 2004 May |
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| Inhibitory effects of a rice hull constituent on tumor necrosis factor alpha, prostaglandin E2, and cyclooxygenase-2 production in lipopolysaccharide-activated mouse macrophages. | 2005 May |
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| Distinction of the C-glycosylflavone isomer pairs orientin/isoorientin and vitexin/isovitexin using HPLC-MS exact mass measurement and in-source CID. | 2005 Sep-Oct |
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| [Studies on chemical constituents of Patrinia villosa]. | 2006 Jan |
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| Activity of Cecropia lyratiloba extract on contractility of cardiac and smooth muscles in Wistar rats. | 2006 Jan-Feb |
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| An extract of Lannea microcarpa: composition, activity and evaluation of cutaneous irritation in cell cultures and reconstituted human epidermis. | 2006 Jul |
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| Flavonoid glycosides in bergamot juice (Citrus bergamia Risso). | 2006 May 31 |
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| Antioxidant, anti-inflammatory, anti-nociceptive activities and composition of Lythrum salicaria L. extracts. | 2007 Apr 4 |
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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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| Phenolic constituents in dried flowers of aloe vera (Aloe barbadensis) and their in vitro antioxidative capacity. | 2007 Jun |
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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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| 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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| Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis. | 2008 |
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| Therapeutic biology of Jatropha curcas: a mini review. | 2008 Aug |
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| Aldose-reductase- and protein-glycation-inhibitory principles from the whole plant of Duchesnea chrysantha. | 2008 Feb |
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| Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity. | 2008 Jul |
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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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| 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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| Neural cell protective compounds isolated from Phoenix hanceana var. formosana. | 2009 Jun |
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| Phytochemical and antifungal studies on Terminalia mollis and Terminalia brachystemma. | 2009 Sep |
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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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| Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints. | 2010 Mar 2 |
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| Topical and systemic anti-inflammatory effects of Echinodorus macrophyllus (Kunth) Micheli (Alismataceae). | 2010 Oct |
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.
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DSLD |
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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SUBSTANCE RECORD
