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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
Structure of VITEXIN

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=C(O)C=C(O)C3=C2OC(=CC3=O)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

HIDE SMILES / InChI

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.

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
Radioprotective effects of vitexina for breast cancer patients undergoing radiotherapy with cobalt-60.
2002 Mar
[Research of the amounts of flavonoids accumulated in the buds of single-styled hawthorn].
2004
ent-Kaurene diterpenoids from Isodon oresbius.
2004 Apr
Novel dammarane-type glycosides from Gynostemma pentaphyllum.
2004 Dec
A HPTLC densitometric determination of flavonoids from Passiflora alata, P. edulis, P. incarnata and P. caerulea and comparison with HPLC method.
2004 Jul-Aug
Norisoprenoids and hepatoprotective flavone glycosides from the aerial parts of Beta vulgaris var. cicla.
2004 Jun
Trollioside, a new compound from the flowers of Trollius chinensis.
2004 Jun
[Determination of orientin and vitexin in Trollius chinesis preparation by HPLC].
2004 Nov
Optimization of "Askoeziuofito" tablets.
2005
[Crataegus oxyacantha (aubepine) in the use as herb medicine in France].
2005 Apr
Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum.
2005 Aug 10
The isolation and antioxidative effects of vitexin from Acer palmatum.
2005 Feb
Determination of flavone C-glucosides in antioxidant of bamboo leaves (AOB) fortified foods by reversed-phase high-performance liquid chromatography with ultraviolet diode array detection.
2005 Feb 18
LC and UV determination of flavonoids from Passiflora alata medicinal extracts and leaves.
2005 Feb 23
Kakispyrol, a new biphenyl derivative from the leaves of Diospyros kaki.
2005 Jun
Flavone C-glycosides from flowers of Trollius ledebouri.
2005 May
Isolation and purification of flavonoid glycosides from Trollius ledebouri using high-speed counter-current chromatography by stepwise increasing the flow-rate of the mobile phase.
2005 Oct 28
Anti-HIV activity of dibenzylbutyrolactone-type lignans from Phenax species endemic in Costa Rica.
2005 Sep
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
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
Isolation and HPLC quantitative analysis of antioxidant flavonoids from Alternanthera tenella Colla.
2006 Jan-Feb
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
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
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
[Studies on chemical constituents from stellaria media. I].
2007 Jun
Anti HIV-1 flavonoid glycosides from Ochna integerrima.
2007 Jun
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
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
Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system.
2008 Dec
Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS.
2008 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
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
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
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
[Studies on chemical constituents of roots of Linum usitatissimum].
2009 Mar
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 Thu Jul 06 02:47:12 UTC 2023
Edited
by admin
on Thu Jul 06 02:47:12 UTC 2023
Record UNII
9VP70K75OK
Record Status Validated (UNII)
Record Version
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Name Type Language
VITEXIN
USP-RS  
Common Name English
Vitexin [WHO-DD]
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
Classification Tree Code System Code
DSLD 1982 (Number of products:3)
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
Code System Code Type Description
CHEBI
16954
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
WIKIPEDIA
VITEXIN
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
FDA UNII
9VP70K75OK
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
222-963-8
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
PUBCHEM
5280441
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
CHEBI
57963
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1717708
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
CAS
3681-93-4
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID90190287
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
SMS_ID
300000037469
Created by admin on Thu Jul 06 02:47:12 UTC 2023 , Edited by admin on Thu Jul 06 02:47:12 UTC 2023
PRIMARY
Related Record Type Details
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
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT