Page last updated: 2024-11-08

malvidin-3-glucoside

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

oenin: pigment found in red wine [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

malvidin 3-O-beta-D-glucoside : An anthocyanin cation consisting of malvidin having a beta-D-glucosyl residue attached at the 3-hydroxy position. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID11249520
CHEMBL ID602754
MeSH IDM0056496
PubMed CID443652
CHEMBL ID403236
CHEBI ID31799
SCHEMBL ID6139047
MeSH IDM0056496

Synonyms (58)

Synonym
nsc-70532
oenin
7228-78-6
enin
oenin chloride
(3'-o-methyl-(3)h)malvidin-3-glucoside
oenin chloride, >=90% (hplc)
malvidin 3-glucoside
CHEMBL602754
malvidin mono-beta-d-glucopyranoside
1-benzopyrylium, 3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-, chloride, mono-beta-d-glucopyranoside
flavylium, 3,4',5,7-tetrahydroxy-3',5'-dimethoxy-, chloride, mono-beta-d-glucopyranoside
1329-33-5
malvidin beta-d-glucoside
3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride, mono-beta-d-glucopyranoside
AKOS015951116
malvidine-3-glucoside
3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-1-benzopyrylium chloride
nsc 70532
b34f52d7nb ,
unii-b34f52d7nb
einecs 230-631-9
malvidin-3-o-glucoside chloride
malvidin 3-o-glucoside chloride
malvinidin 3-glucoside
1-benzopyrylium, 3-(.beta.-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-, chloride (1:1)
malvidin-3-o-glucoside
mfcd00185576
oenin chloride, analytical standard
ligulin
enoside
(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
malvidin 3-glucoside chloride
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)chromenylium chloride
oenin chloride , hplc grade
malvidin-3-glucoside (chloride)
HY-125740
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)chromenylium chloride
CS-0093842
MS-29791
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)chromenyliumchloride
DTXSID301028795
malvidin-3-o-glucoside chloride oenin oenin chloride enin chloride cyclamin cyclamin chloride malvidin-3-beta-glucoside malvidin-3-glucoside malvidin-3-glucoside chloride malvidin-3-o-glucoside chloride 3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydr
18470-06-9
malvidin 3-o-glucoside
malvidin-3-glucoside
CHEMBL403236
chebi:31799 ,
malvidin glucoside
(2s,3r,4s,5s,6r)-2-[5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
malvidin 3-o-beta-d-glucoside
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromenium-3-yl beta-d-glucopyranoside
SCHEMBL6139047
DTXSID30332124
5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1$l^{4}-chromen-1-ylium
Q137147
1-benzopyrylium, 3-(beta-d-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-
gtpl12427

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" However few studies have been conducted to evaluate their bioavailability so their absorption mechanism remains unclear."( GLUT1 and GLUT3 involvement in anthocyanin gastric transport- Nanobased targeted approach.
Baptista, PV; Brás, N; Calhau, C; de Freitas, V; Faria, A; Fernandes, AR; Fernandes, I; Mateus, N; Oliveira, H; Roma-Rodrigues, C; Santos, A; Veigas, B, 2019
)
0.51
" Very little data are available concerning the bioavailability of anthocyanins, major sources of red pigmentation in red wine."( Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice.
Briviba, K; Bub, A; Heeb, D; Rechkemmer, G; Watzl, B, 2001
)
1.75
"M-3-G is poorly absorbed after a single ingestion of red wine, dealcoholized red wine, or red grape juice and seems to be differentially metabolized as compared to other red grape polyphenols."( Malvidin-3-glucoside bioavailability in humans after ingestion of red wine, dealcoholized red wine and red grape juice.
Briviba, K; Bub, A; Heeb, D; Rechkemmer, G; Watzl, B, 2001
)
1.75
" Overall, these data indicate that blackberry anthocyanins are excreted in urine as intact and methylated glucoside forms and that their bioavailability is very low compared with other flavonoids."( Blackberry anthocyanins are slightly bioavailable in rats.
Besson, C; Felgines, C; Fraisse, D; Lamaison, JL; Rémésy, C; Texier, O, 2002
)
0.31
" The extracts were not significantly hypoglycemic when administered without Labrasol, demonstrating its bio-enhancing effect, most likely due to increasing the bioavailability of the administered preparations."( Hypoglycemic activity of a novel anthocyanin-rich formulation from lowbush blueberry, Vaccinium angustifolium Aiton.
Grace, MH; Kuhn, P; Lila, MA; Logendra, S; Poulev, A; Raskin, I; Ribnicky, DM; Yousef, GG, 2009
)
0.35
"The bioavailability of anthocyanins is the most difficult one to assess amongst all flavonoid compounds as a result of their occurrence under different structures in equilibrium depending on pH."( A new approach on the gastric absorption of anthocyanins.
de Freitas, V; Fernandes, I; Mateus, N; Reis, C, 2012
)
0.38
" Following these studies, here we investigated possible effects of malvidin-3-glucoside, one of the main dietary anthocyanins, on NO bioavailability and on peroxynitrite-induced NF-kB activation in the same cell model."( Malvidin-3-glucoside protects endothelial cells up-regulating endothelial NO synthase and inhibiting peroxynitrite-induced NF-kB activation.
Almeida, LM; Dinis, TC; Paixão, J, 2012
)
2.06
" However, the chemical modification of anthocyanins and procyanidins (water soluble pigments) to more lipophilic compounds has the advantage of increased bioavailability in biological matrices, and to potentiate their application in food matrices and cosmetic products."( Synthesis, characterisation and antioxidant features of procyanidin B4 and malvidin-3-glucoside stearic acid derivatives.
Araújo, P; Cruz, L; de Freitas, V; Fernandes, VC; Mateus, N, 2015
)
0.65
" This study confirms the importance of the natural micro-oxidative processes that occur during the ageing of anthocyanin-containing food and their impact on their bioavailability and bioactivity properties."( Bioavailability studies and anticancer properties of malvidin based anthocyanins, pyranoanthocyanins and non-oxonium derivatives.
de Freitas, V; Fernandes, I; He, J; Mateus, N; Oliveira, H; Oliveira, J; Wang, J; Wu, N; Zhang, Q, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" We assessed accumulations of polyphenols in the rat brain following oral dosage with a Cabernet Sauvignon red wine and tested brain-targeted polyphenols for potential beneficial AD disease-modifying activities."( Identification of brain-targeted bioactive dietary quercetin-3-O-glucuronide as a novel intervention for Alzheimer's disease.
Chen, TY; Cooper, B; Ferruzzi, MG; Gong, B; Ho, L; Janle, EM; Lobo, J; Pasinetti, GM; Percival, SS; Simon, JE; Talcott, ST; Wang, J; Wu, QL, 2013
)
0.39
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (3)

ClassDescription
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
anthocyanin cationAny flavonoid that is a glycoside derivative of an anthocyanidin cation.
aromatic etherAny ether in which the oxygen is attached to at least one aryl substituent.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID456317Antioxidant activity assessed as trolox equivalent by TEAC assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Reliability of bond dissociation enthalpy calculated by the PM6 method and experimental TEAC values in antiradical QSAR of flavonoids.
AID601033Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601212Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601297Drug uptake in Wistar rat bile assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601303Drug excretion in Wistar rat urine assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by mass spectrometry analysis2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601034Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601291Drug uptake in Wistar rat urine assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601029Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601128Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level by assuming kidney mass was 2.4 gram at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601215Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level by assuming liver mass was 7 grams at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601209Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level by assuming liver mass was 7 grams at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601125Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601032Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601031Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601213Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level by assuming liver mass was 7 grams at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601123Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601286Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601211Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level by assuming liver mass was 7 grams at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID320802Inhibition of beta amyloid 25-35 fibril formation2008Bioorganic & medicinal chemistry letters, Jan-15, Volume: 18, Issue:2
New polyphenols active on beta-amyloid aggregation.
AID601122Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level by assuming kidney mass was 2.4 gram at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601391Ratio of drug uptake in urine to kidney in Wistar rat assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by mass spectrometry analysis2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601292Drug uptake in Wistar rat urine assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601127Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID320801Inhibition of beta amyloid 25-35 fibril formation at 10 uM2008Bioorganic & medicinal chemistry letters, Jan-15, Volume: 18, Issue:2
New polyphenols active on beta-amyloid aggregation.
AID601035Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level by assuming plasma volume was 8.8 mL at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601210Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601126Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level by assuming kidney mass was 2.4 gram at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601030Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level at 0.67 umol, iv after 0.25 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601214Drug uptake in Wistar rat liver assessed as malvidin 3-glucoside level at 0.67 umol, iv after 5 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601396Ratio of drug uptake in bile to liver in Wistar rat assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by mass spectrometry analysis2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601386Drug excretion in Wistar rat bile assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by mass spectrometry analysis2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601298Drug uptake in Wistar rat bile assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601129Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601124Drug uptake in Wistar rat kidney assessed as malvidin 3-glucoside level by assuming kidney mass was 2.4 gram at 0.67 umol, iv after 1 min by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
AID601036Drug uptake in Wistar rat plasma assessed as malvidin 3-glucoside level at 0.67 umol, iv after 15 mins by tandem mass spectrometry2011Journal of natural products, May-27, Volume: 74, Issue:5
Exceptionally fast uptake and metabolism of cyanidin 3-glucoside by rat kidneys and liver.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (135)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (0.74)18.7374
1990's2 (1.48)18.2507
2000's46 (34.07)29.6817
2010's71 (52.59)24.3611
2020's15 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 33.84

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index33.84 (24.57)
Research Supply Index4.85 (2.92)
Research Growth Index5.68 (4.65)
Search Engine Demand Index42.06 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (33.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Trials2 (1.60%)5.53%
Reviews0 (0.00%)6.00%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Observational0 (0.00%)0.25%
Other10 (100.00%)84.16%
Other123 (98.40%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]