Page last updated: 2024-11-10

astringin

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

Description

astringin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

trans-astringin : A stilbenoid that is piceatannol substituted at position 3 by a beta-D-glucosyl residue. [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 CID5281712
CHEMBL ID358769
CHEBI ID2899
SCHEMBL ID501245
MeSH IDM0334406

Synonyms (32)

Synonym
astringin
29884-49-9
LMPK13090007
CHEMBL358769
chebi:2899 ,
(e)-astringin
4er6ykm4yl ,
beta-d-glucopyranoside, 3-(2-(3,4-dihydroxyphenyl)ethenyl)-5-hydroxyphenyl, (e)-
unii-4er6ykm4yl
trans-astringin
3,4,3',5'-tetrahydroxystilbene 3'-glucoside
(2s,3r,4s,5s,6r)-2-[3-[(e)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
(2s,3r,4s,5s,6r)-2-[3-[(e)-2-(3,4-dihydroxyphenyl)vinyl]-5-hydroxy-phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
piceatannol 3-o-beta-d-glucoside
3-[(e)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenyl beta-d-glucopyranoside
piceatannol 3-beta-glucoside
piceatannol 3-beta-d-glucoside
SCHEMBL501245
e-astringin
Q4811458
mfcd03427331
CS-0032099
HY-N4093
MS-26957
(2s,3r,4s,5s,6r)-2-(3-((e)-3,4-dihydroxystyryl)-5-hydroxyphenoxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
(2s,3r,4s,5s,6r)-2-[3-[(e)-2-(3,4-dihydroxyphenyl)ethenyl]-5-hydroxyphenoxy]-6-(hydroxymethyl) oxane-3,4,5-triol
DTXSID401029689
3-[(e)-2-(3,4-dihydroxyphenyl)vinyl]-5-hydroxyphenyl beta-d-glucopyranoside
(2s,3r,4s,5s,6r)-2-(3-((e)-2-(3,4-dihydroxyphenyl)ethenyl)-5-hydroxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
3-((1e)-2-(3,4-dihydroxyphenyl)ethenyl)-5-hydroxyphenyl .beta.-d-glucopyranoside
.beta.-d-glucopyranoside, 3-((1e)-2-(3,4-dihydroxyphenyl)ethenyl)-5-hydroxyphenyl
AKOS040760281

Research Excerpts

Overview

Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol. It is mainly found in the bark of Picea sitchensis.

ExcerptReferenceRelevance
"Astringin is a stilbenoid, the 3-β-D-glucoside of piceatannol, mainly found in the bark of Picea sitchensis."( Astringin protects LPS-induced toxicity by suppressing oxidative stress and inflammation via suppression of PI3K/AKT/NF-κB pathway for pediatric acute lung injury.
Jiang, S; Li, X; Lin, T; Qin, T; Wang, L, 2023
)
3.07
"(E)-astringin is a high added value compound found in plants and wine."( Highly regioselective hydroxylation of polydatin, a resveratrol glucoside, for one-step synthesis of astringin, a piceatannol glucoside, by P450 BM3.
Ahn, T; Doan, TT; Jang, HH; Joung, YH; Kang, HS; Le, TK; Lee, GY; Nguyen, HT; Park, KD; Yun, CH, 2017
)
1.15

Bioavailability

ExcerptReferenceRelevance
" It would be important in the future to investigate the origins of the differences in wine stilbene levels in relation to the vine varieties, and the bioavailability of the newly extracted stilbene delta-viniferin in plasma after consumption of different types of wines."( Determination of stilbenes (delta-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, epsilon-viniferin) in Brazilian wines.
Bornet, A; Delaunay, JC; Mérillon, JM; Richard, T; Teissédre, PL; Valls, J; Vanderlinde, R; Vitrac, X, 2005
)
0.58
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
[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 (4)

ClassDescription
polyphenolMembers of the class of phenols that contain 2 or more benzene rings each of which is substituted by at least one hydroxy group.
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
beta-D-glucosideAny D-glucoside in which the anomeric centre has beta-configuration.
monosaccharide derivativeA carbohydrate derivative that is formally obtained from a monosaccharide.
[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 (20)

Assay IDTitleYearJournalArticle
AID1374190Estrogenic activity at ERalpha/ERbeta (unknown origin) expressed in human HepG2 cells co-expressing ERE-dependent promoter assessed as increase in ER-mediated transcriptional activation at 10 uM incubated for 24 hrs by luciferase reporter gene assay relat2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.
AID1374189Estrogenic activity at ERalpha/ERbeta (unknown origin) expressed in human HepG2 cells co-expressing ERE-dependent promoter assessed as increase in ER-mediated transcriptional activation at 1 uM incubated for 24 hrs by luciferase reporter gene assay relati2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Estrogenic activity of constituents from the rhizomes of Rheum undulatum Linné.
AID401039Antioxidant activity assessed as DPPH radical scavenging activity1998Journal of natural products, May, Volume: 61, Issue:5
Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from vitis vinifera cell cultures
AID226690Free radical scavenging activity of DPPH was determined; value taken from reference 112004Bioorganic & medicinal chemistry letters, Jan-19, Volume: 14, Issue:2
Syntheses and radical scavenging activities of resveratrol derivatives.
AID458145Antimicrobial activity against Streptococcus sanguinis NCTC 9811 at 50 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID458148Antimicrobial activity against Streptococcus sanguinis NCTC 9811 at 400 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID458141Antimicrobial activity against Streptococcus mutans KCTC 3065 at 100 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID458144Antimicrobial activity against Streptococcus mutans KCTC 3065 at 600 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID1354555Inhibition of PI3K/Akt in mouse J774 cells assessed as reduction in LPS-induced Akt phosphorylation at Ser473 at 100 uM after 4 hrs by Western blot analysis2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID458143Antimicrobial activity against Streptococcus mutans KCTC 3065 at 400 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID458147Antimicrobial activity against Streptococcus sanguinis NCTC 9811 at 200 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID234680Free radical scavenging activity of DPPH relative to resveratrol was determined2004Bioorganic & medicinal chemistry letters, Jan-19, Volume: 14, Issue:2
Syntheses and radical scavenging activities of resveratrol derivatives.
AID1354545Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced MCP1 expression at 30 uM after 24 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID458140Antimicrobial activity against Streptococcus mutans KCTC 3065 at 50 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID458146Antimicrobial activity against Streptococcus sanguinis NCTC 9811 at 100 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID401040Antioxidant activity against cupric ion-induced lipid peroxidation in human LDL by TBA assay1998Journal of natural products, May, Volume: 61, Issue:5
Isolation, identification, and antioxidant activity of three stilbene glucosides newly extracted from vitis vinifera cell cultures
AID458142Antimicrobial activity against Streptococcus mutans KCTC 3065 at 200 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID1354544Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced IL6 expression at 30 uM after 24 hrs by ELISA2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
AID458149Antimicrobial activity against Streptococcus sanguinis NCTC 9811 at 600 ug/ml after 20 hrs by disk diffusion method2010Bioorganic & medicinal chemistry letters, Feb-01, Volume: 20, Issue:3
The antimicrobial activity of compounds from the leaf and stem of Vitis amurensis against two oral pathogens.
AID1354543Antiinflammatory activity in mouse J774 cells assessed as reduction in LPS-induced nitric oxide production at 30 uM after 24 hrs by Griess assay2018Journal of natural products, 05-25, Volume: 81, Issue:5
Natural Stilbenoids Have Anti-Inflammatory Properties in Vivo and Down-Regulate the Production of Inflammatory Mediators NO, IL6, and MCP1 Possibly in a PI3K/Akt-Dependent Manner.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (9.52)18.2507
2000's3 (14.29)29.6817
2010's14 (66.67)24.3611
2020's2 (9.52)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.67

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 Index27.67 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.02 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.67)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]