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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
Structure of MALVIDIN 3-GLUCOSIDE

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

HIDE SMILES / InChI

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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ViNitrox

Approved Use

ViNitrox™ 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.
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory.
2005 Apr
In vitro inhibition of human cGMP-specific phosphodiesterase-5 by polyphenols from red grapes.
2005 Mar 23
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
Bioassay-guided separation of an alpha-amylase inhibitor anthocyanin from Vaccinium arctostaphylos berries.
2010 Sep-Oct
Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation.
2012 Sep 30
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
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 Fri Dec 15 22:11:24 GMT 2023
Edited
by admin
on Fri Dec 15 22:11:24 GMT 2023
Record UNII
B34F52D7NB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MALVIDIN 3-GLUCOSIDE
Common Name English
1-BENZOPYRYLIUM, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, CHLORIDE (1:1)
Common Name English
NSC-70532
Code English
ENIN
Common Name English
OENIN
Common Name English
MALVIDIN-3-O-GLUCOSIDE
Common Name English
MALVINIDIN 3-GLUCOSIDE
Common Name English
Code System Code Type Description
WIKIPEDIA
OENIN
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
PRIMARY
NSC
70532
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
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FDA UNII
B34F52D7NB
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
PRIMARY
CHEBI
31799
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
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PUBCHEM
11249520
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
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EPA CompTox
DTXSID301028795
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
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ECHA (EC/EINECS)
230-631-9
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
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CAS
7228-78-6
Created by admin on Fri Dec 15 22:11:24 GMT 2023 , Edited by admin on Fri Dec 15 22:11:24 GMT 2023
PRIMARY