U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Study of biochemical prevalence indicators for the assessment of iodine deficiency disorders in adults at field conditions in Gujarat (India).
2001
Characterization of the polyphenolic composition of purple loosestrife (Lythrum salicaria).
2001 Jan-Feb
Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.).
2002 Feb
[Studies on chemical constituents from Phyllostachys pubescens].
2003 Aug
Determination of flavones in Crataegus pinnatifida by capillary zone electrophoresis.
2003 Feb
C-glucoside flavonoids from the leaves of Crataegus pinnatifida Bge. var. major N.E.Br.
2003 Jun
Evidence for estrogen receptor beta-selective activity of Vitex agnus-castus and isolated flavones.
2003 Oct
Optimization of "Askoeziuofito" tablets.
2005
The isolation and antioxidative effects of vitexin from Acer palmatum.
2005 Feb
LC and UV determination of flavonoids from Passiflora alata medicinal extracts and leaves.
2005 Feb 23
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
Isolation and HPLC quantitative analysis of antioxidant flavonoids from Alternanthera tenella Colla.
2006 Jan-Feb
Antispasmodic effects of Rooibos tea (Aspalathus linearis) is mediated predominantly through K+ -channel activation.
2006 Nov
Quantitative LC/MS/MS method and in vivo pharmacokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn.
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
Preparative separation of vitexin and isovitexin from pigeonpea extracts with macroporous resins.
2007 Jan 19
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.
2007 Jul 28
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
Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts.
2007 Oct 31
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
HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity.
2008 Mar 12
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
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
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
  • Download
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