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=C3OC(=CC(=O)C3=C(O)C=C2O)C4=CC=C(O)C=C4
InChI
InChIKey=SGEWCQFRYRRZDC-VPRICQMDSA-N
InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,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 |
Vitexin, identified as apigenin-8-C-β-D-glucopyranoside, is a flavonoid compound found in Anthurium versicolor, Ficaria verna Huds. (Ranunculaceae), Cucumis sativus L. (Cucurbitaceae), and Acer palmatum (Aceraceae). Vitexin is an active component of many traditional Chinese medicines. Vitexin has recently received increased attention due to its wide range of pharmacological effects, including but not limited to anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects.
Originator
Sources: https://books.google.com/books?id=EmmHcz_mWdwC&printsec=frontcover&hl=ru#v=onepage&q&f=false
Curator's Comment: 1900
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: O35800 Gene ID: 29560.0 Gene Symbol: Hif1a Target Organism: Rattus norvegicus (Rat) |
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Target ID: Q8N6T7|||Q9NRC7 Gene ID: 51548.0 Gene Symbol: SIRT6 Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL2095165 |
353.24 nM [Ki] | ||
Target ID: CHEMBL335 |
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Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Ritmonutra Approved UseDietary Supplement Ritmonutra is indicated to improve cardiac functions |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
16.61 μg/mL |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
VITEXIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
0.51 μg/mL |
30 mg/kg single, oral dose: 30 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
VITEXIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
327.11 μg × min/mL |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
VITEXIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
42.7 μg × min/mL |
30 mg/kg single, oral dose: 30 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
VITEXIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
46.01 min |
10 mg/kg single, intravenous dose: 10 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
VITEXIN plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [IC50 >100 uM] | ||||
| no | ||||
| weak [IC50 >100 uM] | ||||
| yes [IC50 13 uM] | ||||
| yes [IC50 4 uM] | ||||
| yes [IC50 8 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| weak | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vitexin, an HIF-1alpha inhibitor, has anti-metastatic potential in PC12 cells. | 2006 Dec 31 |
|
| [Study on the chemical constituents of the leaves from Crataegus pinnatifida Bge. var. major N. E. Br]. | 2006 Nov |
|
| A rapid ultra-performance liquid chromatography-electrospray ionization tandem mass spectrometric method for the qualitative and quantitative analysis of the constituents of the flower of Trollius ledibouri Reichb. | 2006 Nov 24 |
|
| Anti-inflammatory effects of flavonoids: genistein, kaempferol, quercetin, and daidzein inhibit STAT-1 and NF-kappaB activations, whereas flavone, isorhamnetin, naringenin, and pelargonidin inhibit only NF-kappaB activation along with their inhibitory effect on iNOS expression and NO production in activated macrophages. | 2007 |
|
| Quantitative LC/MS/MS method and in vivo pharmacokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn. | 2007 Apr |
|
| Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents. | 2007 Apr |
|
| Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors. | 2007 Aug 8 |
|
| Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench). | 2007 Aug 8 |
|
| 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 |
|
| 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 |
|
| Preparative separation of vitexin and isovitexin from pigeonpea extracts with macroporous resins. | 2007 Jan 19 |
|
| A new flavonol from Sophora tonkinensis. | 2007 Jan-Feb |
|
| Induction of flavonoid production by UV-B radiation in Passiflora quadrangularis callus cultures. | 2007 Jul |
|
| The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions. | 2007 Jul 28 |
|
| [Studies on chemical constituents from stellaria media. I]. | 2007 Jun |
|
| Anti HIV-1 flavonoid glycosides from Ochna integerrima. | 2007 Jun |
|
| Composition and content of seed flavonoids in forage and grain legume crops. | 2007 Mar |
|
| Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. | 2007 Mar |
|
| Simultaneous determination of vitexin-4''-O-glucoside and vitexin-2''-O-rhamnoside from Hawthorn leaves flavonoids in rat plasma by HPLC method and its application to pharmacokinetic studies. | 2007 May 9 |
|
| Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts. | 2007 Nov 28 |
|
| A predictive tool for assessing (13)C NMR chemical shifts of flavonoids. | 2007 Oct |
|
| Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts. | 2007 Oct 31 |
|
| 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 |
|
| 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 |
|
| Inhibition of tobacco mosaic virus infection by quercetin and vitexin. | 2008 |
|
| Mechanisms of vitexin preconditioning effects on cultured neonatal rat cardiomyocytes with anoxia and reoxygenation. | 2008 |
|
| 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 |
|
| Chemical constituents from the leaves of Broussonetia papyrifera. | 2008 Feb |
|
| Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS. | 2008 Feb |
|
| Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves. | 2008 Jan-Feb |
|
| 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 |
|
| Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis. | 2008 May |
|
| Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2''-O-rhamnoside from Crataegus monogyna Jacq. (hawthorn). | 2008 Nov-Dec |
|
| [Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC]. | 2008 Oct |
|
| Pharmacokinetic study of three active flavonoid glycosides in rat after intravenous administration of Trollius ledebourii extract by liquid chromatography. | 2008 Oct |
|
| Antiradical activities of the extract of Passiflora incarnata. | 2008 Sep-Oct |
|
| Anti-arthritic potential of the plant Justicia gendarussa Burm F. | 2009 |
|
| Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice. | 2009 |
|
| Some solutions to obtain very efficient separations in isocratic and gradient modes using small particles size and ultra-high pressure. | 2009 Apr 10 |
|
| 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 |
|
| Vitexins, nature-derived lignan compounds, induce apoptosis and suppress tumor growth. | 2009 Aug 15 |
|
| Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies. | 2009 Dec |
|
| [Studies on chemical constituents of roots of Linum usitatissimum]. | 2009 Mar |
|
| HPLC determination of eight polyphenols in the leaves of Crataegus pinnatifida Bge. var. major. | 2009 Mar |
|
| Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves. | 2009 Mar 4 |
Sample Use Guides
Rats in the vitexin-treated group were administered 30 mg/kg oral vitexin once daily at doses for 4 weeks.
Recommended dosage of Dietary Supplement Ritmonutra ® containing among other components 5.4 mg of vitexin is two capsules a day.
Route of Administration:
Oral
HCT-116 cells treated with vitexin (10, 25 and 50 μM) for 24 h caused remarkable changes with majority of cells to become shrink and show distorted morphology characteristics of programmed cell death, with significant cell death as evidenced by reduction in cell viability and enhanced LDH activity
| Substance Class |
Chemical
Created
by
admin
on
Edited
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| Record UNII |
9VP70K75OK
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| Record Status |
Validated (UNII)
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| Record Version |
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1982 (Number of products:3)
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16954
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VITEXIN
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222-963-8
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5280441
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1717708
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3681-93-4
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DTXSID90190287
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300000037469
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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 was 14,800 +/- 451.
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 | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
