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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O10
Molecular Weight 432.3783
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VITEXIN

SMILES

c1cc(ccc1-c2cc(=O)c3c(cc(c(c3o2)[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C21H20O10
Molecular Weight 432.3783
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.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: O35800
Gene ID: 29560.0
Gene Symbol: Hif1a
Target Organism: Rattus norvegicus (Rat)
Target ID: Q8N6T7|||Q9NRC7
Gene ID: 51548.0
Gene Symbol: SIRT6
Target Organism: Homo sapiens (Human)
353.24 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Ritmonutra

Approved Use

Dietary Supplement Ritmonutra is indicated to improve cardiac functions
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Capillary electrophoretic analysis of flavonoids in single-styled hawthorn (Crataegus monogyna Jacq.) ethanolic extracts.
2006 Apr 21
Vitexin, an HIF-1alpha inhibitor, has anti-metastatic potential in PC12 cells.
2006 Dec 31
An extract of Lannea microcarpa: composition, activity and evaluation of cutaneous irritation in cell cultures and reconstituted human epidermis.
2006 Jul
[Study on the chemical constituents of the leaves from Crataegus pinnatifida Bge. var. major N. E. Br].
2006 Nov
Antispasmodic effects of Rooibos tea (Aspalathus linearis) is mediated predominantly through K+ -channel activation.
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
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
Prenylation enhances cytotoxicity of apigenin and liquiritigenin in rat H4IIE hepatoma and C6 glioma cells.
2007 Jan
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
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
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
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
Patents

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 Sat Jun 26 03:29:23 UTC 2021
Edited
by admin
on Sat Jun 26 03:29:23 UTC 2021
Record UNII
9VP70K75OK
Record Status Validated (UNII)
Record Version
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Name Type Language
VITEXIN
USP-RS  
Common Name English
VITEXIN [USP-RS]
Common Name English
VITEXINE
Common Name English
VITEXINA
Common Name English
VITEXIN (CONSTITUENT OF HAWTHORN LEAF WITH FLOWER) [DSC]
Common Name English
ORIENTOSIDE
Common Name English
APIGENIN-8-C-GLUCOSIDE
Common Name English
FLAVONE, 8-.BETA.-D-GLUCOPYRANOSYL-4',5,7-TRIHYDROXY-
Common Name English
VITEXIN [INCI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 8-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
Systematic Name English
APIGENIN-8-C-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
VITEXIN [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 1982 (Number of products:3)
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
Code System Code Type Description
USP_CATALOG
1717708
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
VITEXIN
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
FDA UNII
9VP70K75OK
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
222-963-8
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
PUBCHEM
5280441
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
CAS
3681-93-4
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
EPA CompTox
3681-93-4
Created by admin on Sat Jun 26 03:29:23 UTC 2021 , Edited by admin on Sat Jun 26 03:29:23 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT