Page last updated: 2024-11-07

proanthocyanidin a2

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

Description

procyanidin A2: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

proanthocyanidin A2 : A proanthocyanidin obtained by the condensation of (-)-epicatechin units. [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 CID124025
CHEMBL ID286933
CHEBI ID28472
SCHEMBL ID981582
MeSH IDM0312122

Synonyms (41)

Synonym
8,14-methano-2h,14h-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r,3r,8s,14r,15r)-
procyanidin dimer a2
procyanidin a2
procyanidol a2
(+)-epicatechin-(4.beta.-8,2.beta.-o-7)-epicatechin
dimeric catechin
8,14-methano-2h,14h-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r,3r,8s,14r,15r)-
bis(3,4-dihydroxyphenyl)[?]pentol
(+)-proanthocyanidin a2
8,14-methano-2h,14h-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2r-(2.alpha,3.alpha.,8.beta.,14.beta.,15r*)]-
epicatechin-(4.beta.-->8,2.beta.-->o-->7)epicatechin
epicatechin-(2beta->7,4beta->8)-epicatechin
41743-41-3
proanthocyanidin a2
CHEMBL286933 ,
proanthocyanidin a-2
chebi:28472 ,
(2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol
uqn6668q4r ,
unii-uqn6668q4r
8,14-methano-2h,8h,14h-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol, 2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-
2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2h,8h,14h-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol
SCHEMBL981582
procyanidina2
AC-35008
procyanidin a2, analytical standard
bdbm50478905
(+)-epicatechin-(4beta-8,2beta-o-7)-epicatechin
procyanidoepicatechin
epicatechin-(2b->7,4b->8)-epicatechin
ec-(4b,8)(2b,7)-ec
AKOS037514797
(2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
(1r,5r,6r,13s,21r)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
Q7247550
8,14-methano-2h,14h-1-benzopyrano(7,8-d)(1,3)benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2r,3r,8s,14r,15r)-
litchiderm ls-9704 component
A903788
proanthocyanidin a2;procyanidin a2; procyanidoepicatechin
MS-30365
DTXSID00904175

Research Excerpts

Effects

ExcerptReferenceRelevance
"Proanthocyanidin A2 (PA2) has multiple pharmacological activities."( Proanthocyanidin A2 attenuates the activation of hepatic stellate cells by activating the PPAR-γ signalling pathway.
Hu, M; Li, X; Liu, Y; Wang, L; Xiao, Y, 2023
)
3.07

Dosage Studied

ExcerptRelevanceReference
"5-25 kg/m(2) ) were assigned to consume a cranberry beverage containing 140 mg proanthocyanin and 35 kilocalories at 237 mL/day, according to a weekly dosing schedule for 7 weeks."( Liquid chromatography with tandem mass spectrometry quantification of urinary proanthocyanin A2 dimer and its potential use as a biomarker of cranberry intake.
Blumberg, JB; Chen, CY; McKay, DL; Polasky, DA; Ren, X; Walsh, JM; Zampariello, C, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
anti-HIV agentAn antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
angiogenesis modulating agentAn agent that modulates the physiologic angiogenesis process. This is accomplished by endogenous angiogenic proteins and a variety of other chemicals and pharmaceutical agents.
[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 (2)

ClassDescription
proanthocyanidinA flavonoid oligomer obtained by the the condensation of two or more units of hydroxyflavans.
hydroxyflavanA member of the class of flavans in which one or more ring hydrogens are replaced by hydroxy groups.
[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]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LactoperoxidaseBos taurus (cattle)Km12.66000.30001.57788.4100AID1490876
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (5)

Processvia Protein(s)Taxonomy
response to oxidative stressLactoperoxidaseBos taurus (cattle)
thiocyanate metabolic processLactoperoxidaseBos taurus (cattle)
antibacterial humoral responseLactoperoxidaseBos taurus (cattle)
hydrogen peroxide catabolic processLactoperoxidaseBos taurus (cattle)
cellular oxidant detoxificationLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
peroxidase activityLactoperoxidaseBos taurus (cattle)
calcium ion bindingLactoperoxidaseBos taurus (cattle)
heme bindingLactoperoxidaseBos taurus (cattle)
thiocyanate peroxidase activityLactoperoxidaseBos taurus (cattle)
lactoperoxidase activityLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (2)

Processvia Protein(s)Taxonomy
extracellular spaceLactoperoxidaseBos taurus (cattle)
cytoplasmLactoperoxidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (52)

Assay IDTitleYearJournalArticle
AID358165Cytotoxicity against human PRMI7951 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID380214Antimicrobial activity against Mycobacterium fortuitum1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID377249Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 2.4 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID377251Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.6 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID358166Cytotoxicity against human KB cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID358168Cytotoxicity against human HCT8 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID380216Antimicrobial activity against Salmonella paratyphi1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID730068Cytotoxicity against human MCF7 cells after 24 to 72 hrs by MTT assay2013Journal of natural products, Jan-25, Volume: 76, Issue:1
Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities.
AID380212Antimicrobial activity against Candida albicans1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID1490876Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Km using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1151282Bactericidal activity against BacLight Green labeled Escherichia coli up to 30 ug/ml2014Journal of natural products, May-23, Volume: 77, Issue:5
Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells.
AID380213Antimicrobial activity against Staphylococcus aureus1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID730063Binding affinity to recombinant VEGFA (unknown origin) measured for 60 seconds by surface plasmon resonance assay2013Journal of natural products, Jan-25, Volume: 76, Issue:1
Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities.
AID380217Antimicrobial activity against Pseudomonas aeruginosa1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID380215Antimicrobial activity against Enterobacter cloacae1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID377252Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.3 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID646549Antibacterial activity against Staphylococcus aureus ATCC 6538P assessed as inhibition of planktonic growth at sub-MIC measured up to 25 hrs2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID730066Binding affinity to recombinant PIGF1 (unknown origin) measured for 60 seconds by surface plasmon resonance assay2013Journal of natural products, Jan-25, Volume: 76, Issue:1
Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities.
AID380206Selectivity index, ratio of CC50 for human MT4 cells to IC50 for HIV infected in human MT4 cells1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID380218Antimicrobial activity against Escherichia coli1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID380211Antimicrobial activity against Streptococcus pyogenes1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID380220Modulation of alternative complement pathway system assessed as hemoglobin release by spectrophotometry1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID646563Antibacterial activity against Staphylococcus epidermidis ATCC 35984 assessed as disappearance of bacterial surface proteins level at sub-MIC by zymographic analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID1490877Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring substrate Kcat using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID1490878Induction of H2O2-inactivated bovine milk lactoperoxidase pseudo-halogenating activity assessed as increase in hypothiocyanate formation by measuring ratio of Kcat to Km for substrate using thiocyanate as substrate by Lineweaver-Burk plot2017Journal of natural products, 05-26, Volume: 80, Issue:5
Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
AID646551Antibacterial activity against Staphylococcus aureus ATCC 6538P assessed as inhibition of biofilm formation after 24 hrs by crystal violet staining2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID380219Modulation of classical complement pathway system assessed as hemoglobin release by spectrophotometry1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID377253Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 0.15 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID1151279Inhibition of BacLight Green labeled Escherichia coli adherence to human UEC after 1 hr by flow cytometry analysis2014Journal of natural products, May-23, Volume: 77, Issue:5
Development of a fluorometric microplate antiadhesion assay using uropathogenic Escherichia coli and human uroepithelial cells.
AID1176782Antioxidant activity assessed as DPPH radical scavenging activity after 30 mins by UV-spectrophotometry2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Unusual C,O-Fused Glycosylapigenins from Serjania marginata Leaves.
AID646557Antibacterial activity against Staphylococcus aureus ATCC 6538P assessed as change in bacterial surface protein level at sub-MIC by SDS-PAGE analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID379279Inhibition of HIV1 protease2000Journal of natural products, Feb, Volume: 63, Issue:2
Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia.
AID1266151Inhibition of porcine pancreatic alpha-amylase assessed as starch digestion up to 370 uM up to 120 mins by turbidity assay2015Bioorganic & medicinal chemistry, Dec-15, Volume: 23, Issue:24
Phenolic group on A-ring is key for dracoflavan B as a selective noncompetitive inhibitor of α-amylase.
AID646552Antibacterial activity against Staphylococcus epidermidis ATCC 35984 incubated in drug free medium for 18 hrs after MIC determination by broth microdilution method2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID646559Antibacterial activity against Staphylococcus aureus ATCC 6538P assessed as change in bacterial surface protein level at sub-MIC by zymographic analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID646553Antibacterial activity against Staphylococcus epidermidis ATCC 35984 by broth microdilution method2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID646558Antibacterial activity against Staphylococcus epidermidis ATCC 35984 assessed as disappearance of bacterial surface protein level at sub-MIC by SDS-PAGE analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID358169Cytotoxicity against human TE671 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID380203Antioxidant activity assessed as superoxide radical anion scavenging activity1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID646550Antibacterial activity against Staphylococcus epidermidis ATCC 35984 assessed as inhibition of biofilm formation after 24 hrs by crystal violet staining2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID646556Antibacterial activity against Staphylococcus epidermidis ATCC 35984 assessed as inhibition of planktonic growth at sub-MIC measured up to 25 hrs2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID338965Inhibition of PHA-stimulated human PBMC proliferation assessed as [3H]thymidine uptake after 3 days by scintillation counting2002Journal of natural products, Apr, Volume: 65, Issue:4
Immunomodulatory proanthocyanidins from Ecdysanthera utilis.
AID730067Cytotoxicity against human Jurkat cells after 24 to 72 hrs by MTT assay2013Journal of natural products, Jan-25, Volume: 76, Issue:1
Bioassay-guided isolation of proanthocyanidins with antiangiogenic activities.
AID379280Inhibition of HIV1 protease at 100 ug/ml2000Journal of natural products, Feb, Volume: 63, Issue:2
Inhibitory effects on HIV-1 protease of constituents from the wood of Xanthoceras sorbifolia.
AID380207Antiviral activity against HIV infected in human MT4 cells assessed as inhibition of virus-induced cytopathic effect by MTT assay1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID646555Antibacterial activity against Staphylococcus aureus ATCC 6538P incubated in drug free medium for 18 hrs after MIC determination by broth microdilution method2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID646554Antibacterial activity against Staphylococcus aureus ATCC 6538P by broth microdilution method2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds.
AID377250Antiadherent activity against P-fimbriated Escherichia coli in human erythrocyte assessed as suppression of agglutination using latex beads coated with P receptor analogue at 1.2 mg/ml2000Journal of natural products, Sep, Volume: 63, Issue:9
A-Type proanthocyanidin trimers from cranberry that inhibit adherence of uropathogenic P-fimbriated Escherichia coli.
AID380204Antiviral activity against HSV up to 200 ug/mL by extracellular virucidal assay1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID380208Antimicrobial activity against Bacillus cereus1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
AID358167Cytotoxicity against human A549 cells by tetrazolium salt-based colorimetric assay1992Journal of natural products, Aug, Volume: 55, Issue:8
Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents.
AID380205Cytotoxicity against human MT4 cells by MTT assay1999Journal of natural products, Jul, Volume: 62, Issue:7
Biological evaluation of proanthocyanidin dimers and related polyphenols.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (48)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (4.17)18.2507
2000's8 (16.67)29.6817
2010's32 (66.67)24.3611
2020's6 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.13

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 Index32.13 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index5.19 (4.65)
Search Engine Demand Index41.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.13)

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%
Other48 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]