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=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
| 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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Radioprotective effects of vitexina for breast cancer patients undergoing radiotherapy with cobalt-60. | 2002 Mar |
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| [Research of the amounts of flavonoids accumulated in the buds of single-styled hawthorn]. | 2004 |
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| ent-Kaurene diterpenoids from Isodon oresbius. | 2004 Apr |
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| Novel dammarane-type glycosides from Gynostemma pentaphyllum. | 2004 Dec |
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| A HPTLC densitometric determination of flavonoids from Passiflora alata, P. edulis, P. incarnata and P. caerulea and comparison with HPLC method. | 2004 Jul-Aug |
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| Norisoprenoids and hepatoprotective flavone glycosides from the aerial parts of Beta vulgaris var. cicla. | 2004 Jun |
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| Trollioside, a new compound from the flowers of Trollius chinensis. | 2004 Jun |
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| [Determination of orientin and vitexin in Trollius chinesis preparation by HPLC]. | 2004 Nov |
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| Optimization of "Askoeziuofito" tablets. | 2005 |
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| [Crataegus oxyacantha (aubepine) in the use as herb medicine in France]. | 2005 Apr |
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| Phytotoxic activity of bibenzyl derivatives from the orchid Epidendrum rigidum. | 2005 Aug 10 |
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| The isolation and antioxidative effects of vitexin from Acer palmatum. | 2005 Feb |
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| 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 |
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| LC and UV determination of flavonoids from Passiflora alata medicinal extracts and leaves. | 2005 Feb 23 |
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| Kakispyrol, a new biphenyl derivative from the leaves of Diospyros kaki. | 2005 Jun |
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| Flavone C-glycosides from flowers of Trollius ledebouri. | 2005 May |
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| 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 |
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| Anti-HIV activity of dibenzylbutyrolactone-type lignans from Phenax species endemic in Costa Rica. | 2005 Sep |
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| 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 |
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| Capillary electrophoretic analysis of flavonoids in single-styled hawthorn (Crataegus monogyna Jacq.) ethanolic extracts. | 2006 Apr 21 |
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| 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 |
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| Exudation of allelopathic substances in buckwheat (Fagopyrum esculentum Moench). | 2007 Aug 8 |
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| 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 |
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| [Studies on chemical constituents from stellaria media. I]. | 2007 Jun |
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| Anti HIV-1 flavonoid glycosides from Ochna integerrima. | 2007 Jun |
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| Metabolism of flavone C-glucosides and p-coumaric acid from antioxidant of bamboo leaves (AOB) in rats. | 2007 Mar |
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| 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 |
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| Fructose-amino acid conjugate and other constituents from Cyperus rotundus L. | 2008 |
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| Two new 11alpha,12alpha-epoxy-ursan-28,13beta-olides and other triterpenes from Cecropia catharinensis. | 2008 |
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| Anxiolytic activity of a phytochemically characterized Passiflora incarnata extract is mediated via the GABAergic system. | 2008 Dec |
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| Determination of vitexin and isovitexin in pigeonpea using ultrasonic extraction followed by LC-MS. | 2008 Feb |
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| 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 |
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| Anti-arthritic potential of the plant Justicia gendarussa Burm F. | 2009 |
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| Gastric anti-ulcer activity of leaf fractions obtained of polar extract from Wilbrandia ebracteata in mice. | 2009 |
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| 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 |
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
Thu Jul 06 02:47:12 UTC 2023
by
admin
on
Thu Jul 06 02:47:12 UTC 2023
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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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9VP70K75OK
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222-963-8
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5280441
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57963
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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 |
