VITEXIN

Possibly Marketed Outside US

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 Search

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27693342

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Hypoxia-inducible factor 1-alpha 10 Target ID: O35800 Gene ID: 29560.0 Gene Symbol: Hif1a Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17202857	Inhibitor 8504
NAD-dependent protein deacetylase sirtuin-6 1 Target ID: Q8N6T7\|\|\|Q9NRC7 Gene ID: 51548.0 Gene Symbol: SIRT6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21854049	Inhibitor 8504
Heat shock protein HSP90 35 Target ID: CHEMBL2095165 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27834134	Inhibitor 8504	353.24 nM [Ki]
Protein-tyrosine phosphatase 1B 34 Target ID: CHEMBL335 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24291393	Inhibitor 8504
Heat shock factor protein 1 3 Target ID: CHEMBL5869 Sources: http://www.impactjournals.com/oncotarget/index.php?journal=oncotarget&page=article&op=view&path[]=20113&path[]=64152	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Arrhythmia 45 Sources: https://clinicaltrials.gov/ct2/show/NCT01647984 http://www.rottapharm.it/it/service/products/otc/cardio/ritmonutra/ritmonutra.html	Primary	Approved 8583	Ritmonutra Approved Use Dietary Supplement Ritmonutra is indicated to improve cardiac functions
Diabetes mellitus 93 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28576138	Primary	Preclinical	Unknown Approved Use Unknown
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29091859	Primary	Preclinical	Unknown Approved Use Unknown
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22554436	Primary	Preclinical	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
16.61 μg/mL EXPERIMENT https://academicjournals.org/journal/AJPP/article-full-text-pdf/B80DA6F33600	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 EXPERIMENT https://academicjournals.org/journal/AJPP/article-full-text-pdf/B80DA6F33600	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 EXPERIMENT https://academicjournals.org/journal/AJPP/article-full-text-pdf/B80DA6F33600	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 EXPERIMENT https://academicjournals.org/journal/AJPP/article-full-text-pdf/B80DA6F33600	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
46.01 min EXPERIMENT https://academicjournals.org/journal/AJPP/article-full-text-pdf/B80DA6F33600	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

Doses

Dose	Population	Adverse events
360 mg 1 times / day multiple, oral Studied dose Dose: 360 mg, 1 times / day Route: oral Route: multiple Dose: 360 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14664747/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/14664747/	Sources: https://pubmed.ncbi.nlm.nih.gov/14664747/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 CYP1A2 2153 CYP2C19 2057 P-gp 1741	P-gp 2052 MRP2 252 OATP2B1 122

Drug as perpetrator

Target	Modality	Activity
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	no [IC50 >100 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	weak [IC50 >100 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	yes [IC50 13 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	yes [IC50 4 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/30955332/	yes [IC50 8 uM]
CYP1A1 272	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyMjMxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4NzQxNyJ9fQ==	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/31006447/	weak
OATP2B1 122	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/33511622/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25789809/	yes

PubMed

Title	Date	PubMed
Effects of dimethylaminoethanol pyroglutamate (DMAE p-Glu) against memory deficits induced by scopolamine: evidence from preclinical and clinical studies.	2009-12	19756528
Vitexins, nature-derived lignan compounds, induce apoptosis and suppress tumor growth.	2009-08-15	19671865
Antioxidant activity of the dihydrochalcones Aspalathin and Nothofagin and their corresponding flavones in relation to other Rooibos ( Aspalathus linearis ) Flavonoids, Epigallocatechin Gallate, and Trolox.	2009-08-12	19722573
Quantitation of chafurosides A and B in tea leaves and isolation of prechafurosides A and B from oolong tea leaves.	2009-08-12	19572651
Screening and structural characterization of alpha-glucosidase inhibitors from hawthorn leaf flavonoids extract by ultrafiltration LC-DAD-MS(n) and SORI-CID FTICR MS.	2009-08	19443236
Some solutions to obtain very efficient separations in isocratic and gradient modes using small particles size and ultra-high pressure.	2009-04-10	19251260
Antioxidant activities of extracts and main components of Pigeonpea [Cajanus cajan (L.) Millsp.] leaves.	2009-03-04	19305357
[Studies on chemical constituents of roots of Linum usitatissimum].	2009-03	19624013
HPLC determination of eight polyphenols in the leaves of Crataegus pinnatifida Bge. var. major.	2009-03	19298706
Anti-arthritic potential of the plant Justicia gendarussa Burm F.	2009	19488595
Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice.	2009	18989825
Antiradical activities of the extract of Passiflora incarnata.	2008-12-05	19051605
Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system.	2008-12	19006051
[Simultaneous determination of four glycosylflavones from Lophatherum gracile by RP-HPLC].	2008-10	19166010
Pharmacokinetic study of three active flavonoid glycosides in rat after intravenous administration of Trollius ledebourii extract by liquid chromatography.	2008-10	18651602
Therapeutic biology of Jatropha curcas: a mini review.	2008-08	18691091
Influence of the extraction mode on the yield of hyperoside, vitexin and vitexin-2''-O-rhamnoside from Crataegus monogyna Jacq. (hawthorn).	2008-07-12	18618435
Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.	2008-07	18409066
Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis.	2008-05	18418586
Isoflavonoid glycosides and rotenoids from Pongamia pinnata leaves.	2008-04-05	18386479
HPLC-PDA-MS and NMR characterization of C-glycosyl flavones in a hydroalcoholic extract of Citrus aurantifolia leaves with antiplatelet activity.	2008-03-12	18278866
Chemical constituents from the leaves of Broussonetia papyrifera.	2008-02	18507345
Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS.	2008-02	18196523
Fructose-amino acid conjugate and other constituents from Cyperus rotundus L.	2008	19023813
Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis.	2008	19023787
Inhibition of tobacco mosaic virus infection by quercetin and vitexin.	2008	18564899
Mechanisms of vitexin preconditioning effects on cultured neonatal rat cardiomyocytes with anoxia and reoxygenation.	2008	18457368
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).	2007-12	18081102
Use of cyclic voltammetry, photochemiluminescence, and spectrophotometric methods for the measurement of the antioxidant capacity of buckwheat sprouts.	2007-11-28	17966982
Trace element water improves the antioxidant activity of buckwheat (Fagopyrum esculentum Moench) sprouts.	2007-10-31	17902620
A predictive tool for assessing (13)C NMR chemical shifts of flavonoids.	2007-10	17729229
The spasmolytic effect of Aloysia citriodora, Palau (South American cedrón) is partially due to its vitexin but not isovitexin on rat duodenums.	2007-09-05	17640836
Anticonvulsant effects of aerial parts of Passiflora incarnata extract in mice: involvement of benzodiazepine and opioid receptors.	2007-08-08	17686156
Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench).	2007-08-08	17630762
The antimutagenic activity of the major flavonoids of rooibos (Aspalathus linearis): some dose-response effects on mutagen activation-flavonoid interactions.	2007-07-28	17537670
Induction of flavonoid production by UV-B radiation in Passiflora quadrangularis callus cultures.	2007-07	17512679
[Studies on chemical constituents from stellaria media. I].	2007-06	17672340
Anti HIV-1 flavonoid glycosides from Ochna integerrima.	2007-06	17562490
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.	2007-05-09	17329058
Quantitative LC/MS/MS method and in vivo pharmacokinetic studies of vitexin rhamnoside, a bioactive constituent on cardiovascular system from hawthorn.	2007-04	17294503
Diterpenoids and flavonoids from the fruits of Vitex agnus-castus and antioxidant activity of the fruit extracts and their constituents.	2007-04	17262892
A new flavonol from Sophora tonkinensis.	2007-03-17	17365189
Composition and content of seed flavonoids in forage and grain legume crops.	2007-03	17444218
Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats.	2007-03	17313710
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.	2007-02	17311228
Preparative separation of vitexin and isovitexin from pigeonpea extracts with macroporous resins.	2007-01-19	17140590
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	18274639
Vitexin, an HIF-1alpha inhibitor, has anti-metastatic potential in PC12 cells.	2006-12-31	17202857
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.	2006-11-24	17723770
[Study on the chemical constituents of the leaves from Crataegus pinnatifida Bge. var. major N. E. Br].	2006-11	17228656

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 19:55:35 GMT 2025` Edited by `admin` on `Mon Mar 31 19:55:35 GMT 2025`
Record UNII	9VP70K75OK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VITEXIN

Official Name

English

APIGENIN-8-C-.BETA.-D-GLUCOPYRANOSIDE

Preferred 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

4H-1-BENZOPYRAN-4-ONE, 8-.BETA.-D-GLUCOPYRANOSYL-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-

Systematic Name

English

Classification Tree Code System Code

DSLD

1982 (Number of products:3)