Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H25O12.Cl |
Molecular Weight | 528.89 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Cl-].COC1=CC(=CC(OC)=C1O)C2=[O+]C3=C(C=C2O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(O)=CC(O)=C3
InChI
InChIKey=YDIKCZBMBPOGFT-DIONPBRTSA-N
InChI=1S/C23H24O12.ClH/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23;/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27);1H/t17-,19-,20+,21-,23-;/m1./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C23H24O12 |
Molecular Weight | 492.4295 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Malvidin-3-O-glucoside is a polyphenolic anthocyanin. Anthocyanins are flavonoids widely distributed in fruits and vegetables that exhibit antioxidative and anti-inflammatory bioactivities. Among other polyphenolic components, malvidin-3-glucoside is present in ViNitrox™ a natural dietary supplement from apple and grape, it offers a number of exceptional sports nutrition properties including enhanced and lasting performance.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19663426 | https://www.ncbi.nlm.nih.gov/pubmed/26235983
Curator's Comment: In combination, quercetin and malvidin-3-glucoside significantly attenuated sleep deprivation-induced cognitive impairment in -a mouse model of acute sleep deprivation. However, malvidin-3-glucoside was not detectable in the mouse brain after oral administration of bilberry extract containing anthocyanins including malvidin-3-glucoside.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27935050 |
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Target ID: GO:0006954 |
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Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15769121 |
35.4 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | ViNitrox Approved UseViNitrox™ is a natural dietary supplement containing apple and grape polyphenols including proanthocyanidins (as catechins, B2 dimer), phenolic acids (as chlorogenic acids, gallic acids) and anthocyanins (as malvidin-3-glucoside). It offers a number of exceptional sports nutrition properties including enhanced and lasting performance. |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory. | 2005 Apr |
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In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes. | 2005 Mar 23 |
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Antioxidant activity of wine pigments derived from anthocyanins: hydrogen transfer reactions to the dpph radical and inhibition of the heme-induced peroxidation of linoleic acid. | 2009 Jul 8 |
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Bioassay-guided separation of an alpha-amylase inhibitor anthocyanin from Vaccinium arctostaphylos berries. | 2010 Sep-Oct |
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Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation. | 2012 Sep 30 |
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Stilbenes and anthocyanins reduce stress signaling in BV-2 mouse microglia. | 2013 Jun 26 |
Patents
Sample Use Guides
Vinitrox™, supplied by Nexira (France) is a combination of specific profile polyphenols from grape and apple. Vinitrox™ is a purified extract with low lipids, fibers and proteins content (respectively 0.5%, 1.4% and 5.5%) and more than 60% of total polyphenols (Folin method—expressed as gallic acid equivalent) with antioxidant properties demonstrated by ORAC value (12,000 μMtrolox equivalent per gram of ingredient). The main polyphenol classes are proanthocyanidins (as catechins, B2 dimer), phenolic acids (as chlorogenic acids, gallic acids) and anthocyanins (as malvidin-3-glucoside). Nexira’s latest clinical study on 50 athletes, 25-45 years old, demonstrated that under intensive effort, 500 mg/day of ViNitrox™ improves physical capabilities: increases physical training time by 10%, delays the fatigue barrier by 13%.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23731018
1 mg/mL blueberry extract significantly reduced LPS-induced nitric oxide release in BV-2 mouse microglia; this concentration of blueberry extract contains 2.6 μM malvidin-3-O-glucoside, but when malvidin-3-O-glucoside was tested individually, 20 μM was necessary to observe a significant reduction in nitric oxide release.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 22:11:24 GMT 2023
by
admin
on
Fri Dec 15 22:11:24 GMT 2023
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Record UNII |
B34F52D7NB
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Record Status |
Validated (UNII)
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Record Version |
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