Page last updated: 2024-11-12

(-)-pinoresinol

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

Description

(-)-pinoresinol : An enantiomer of pinoresinol having (-)-1R,3aS,4R,6aS-configuration. [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 CID12309636
CHEMBL ID267963
CHEBI ID67245
SCHEMBL ID15481159

Synonyms (17)

Synonym
(-)-pinoresinol
chebi:67245 ,
CHEMBL267963 ,
4-[(1s,3ar,4s,6ar)-4-(4-hydroxy-3-methoxyphenyl)tetrahydro-1h,3h-furo[3,4-c]furan-1-yl]-2-methoxyphenol
bdbm50208826
C20455
(7beta,7'beta,8beta,8'beta)-3,3'-dimethoxy-7,9':7',9-diepoxylignane-4,4'-diol
4,4'-(1r,3as,4r,6as)-tetrahydro-1h,3h-furo[3,4-c]furan-1,4-diylbis(2-methoxyphenol)
SCHEMBL15481159
4-[(3r,3as,6r,6as)-6-(4-hydroxy-3-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenol
81446-29-9
Q27135716
4-[(3r,3as,6r,6as)-6-(3-methoxy-4-oxidanyl-phenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxy-phenol
GLXC-14834
(?)-pinoresinol
AKOS040760637
FS-7642
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (1)

ClassDescription
pinoresinolA lignan that is tetrahydro-1H,3H-furo[3,4-c]furan substituted at positions 1 and 4 by 4-hydroxy-3-methoxyphenyl 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]

Pathways (1)

PathwayProteinsCompounds
matairesinol biosynthesis019
matairesinol biosynthesis220

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)IC50 (µMol)34.30000.08002.50619.8500AID673422
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)Ki815.00000.00871.09573.5000AID673416; AID673417
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (45)

Assay IDTitleYearJournalArticle
AID673420Competitive inhibition of rat intestinal maltase using maltose as substrate assessed as enzyme-inhibitor complex formation at 0.1 to 1 mg/ml by Lineweaver-Burk plot analysis2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID404181Cytotoxicity against mouse LLC cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID1291762Cytotoxicity in rat C6 cells assessed as cell viability at 20 uM after 24 hrs by MTT assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID404180Cytotoxicity against mouse B16-BL6 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID1291758Cytotoxicity against human SK-MEL-2 cells by SRB assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID1291763Neuroprotective activity in rat C6 cells assessed as NGF secretion at 20 uM after 24 hrs by ELISA2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID1434704Antineuroinflammatory activity in mouse N9 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap.
AID735305Cytotoxicity against C57BL/6 mouse BMDCs at 2 to 50 microM by MTT assay2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.
AID1062030Inhibition of Streptococcus mutans OMZ65 recombinant sortase A delta-40 mutant using Dabcyl-QALPETGEE-Edans as substrate after 1 hr by fluorescence spectrophotometry2014Bioorganic & medicinal chemistry letters, Jan-01, Volume: 24, Issue:1
Sortase A inhibitory metabolites from the roots of Pulsatilla koreana.
AID404182Cytotoxicity against human A549 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID638450Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess method2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Inhibitory constituents of Nardostachys chinensis on nitric oxide production in RAW 264.7 macrophages.
AID381214Cytotoxicity against human HL-60 cells after 72 hrs by MTT assay1999Journal of natural products, Sep, Volume: 62, Issue:9
Triterpene saponins and lignans from the roots of Pulsatilla chinensis and their cytotoxic activity against HL-60 cells.
AID404184Cytotoxicity against human HT1080 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID735306Antiinflammatory activity in C57BL/6 mouse BMDCs assessed as inhibition of LPS-stimulated IL-12p40 production treated 1 hr before LPS challenge measured 18 hrs post stimulation by ELISA2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.
AID1434705Cytotoxicity against LPS-induced mouse N9 cells assessed as decrease in cell viability at 1 to 100 ug/ml after 24 hrs by MTT assay2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap.
AID341223Cytotoxicity against human SK-MEL-2 cells after 48 hrs by SRB assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
AID1272762Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
Bioactive lignan derivatives from the stems of Firmiana simplex.
AID673417Competitive inhibition of rat intestinal maltase using maltose as substrate assessed as dissociation of enzyme-inhibitor complex at 0.1 to 1 mg/ml by Dixon plot analysis2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID341224Cytotoxicity against mouse B16F1 cells after 48 hrs by SRB assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
AID313354Cytotoxicity against human PANC1 cells in nutrient deprived medium after 24 hrs2008Bioorganic & medicinal chemistry, Jan-01, Volume: 16, Issue:1
Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition.
AID1190588Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production after 24 hrs by Griess assay2015Bioorganic & medicinal chemistry letters, Feb-15, Volume: 25, Issue:4
Inhibitory constituents of Sophora tonkinensis on nitric oxide production in RAW 264.7 macrophages.
AID357032Cytotoxicity against human H9 cells2001Journal of natural products, Jul, Volume: 64, Issue:7
Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives.
AID673419Inhibition of rat intestinal sucrase using sucrose as substrate at 10 mg/ml preincubated for 10 mins before substrate addition by glucose oxidase method2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID341221Inhibition of actin polymerization in human HaCaT cells assessed as aggregate-like structure at 40 ug/mL by immunofluorescence technique2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
AID1291757Cytotoxicity against human SKOV3 cells by SRB assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID673418Non-competitive inhibition of rat intestinal maltase using maltose as substrate assessed as enzyme-substrate-inhibitor complex formation at 0.1 to 1 mg/ml by Lineweaver-Burk plot analysis2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID325509Inhibition of HIV1 5'-long terminal repeat promoter expression in human 293T cells by luciferase assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Low molecular weight lignin suppresses activation of NF-kappaB and HIV-1 promoter.
AID1291759Cytotoxicity against human XF498 cells by SRB assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID325510Inhibition of TNF-induced NF-kappaB activation in human 239T cells by luciferase assay2008Bioorganic & medicinal chemistry, Mar-01, Volume: 16, Issue:5
Low molecular weight lignin suppresses activation of NF-kappaB and HIV-1 promoter.
AID735307Antiinflammatory activity in C57BL/6 mouse BMDCs assessed as inhibition of LPS-stimulated IL12 production treated 1 hr before LPS challenge measured 18 hrs post stimulation by ELISA2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.
AID673424Inhibition of bakers yeast alpha-glucosidase using p-nitrophenyl-(alpha-D-glucopyranoside) as substrate preincubated for 10 mins before substrate addition by microplate reader2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID1291761Cytotoxicity against mouse BV2 cells assessed as cell viability at 20 uM by MTT assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID1190589Cytotoxicity against mouse RAW264.7 cells after 24 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Feb-15, Volume: 25, Issue:4
Inhibitory constituents of Sophora tonkinensis on nitric oxide production in RAW 264.7 macrophages.
AID673416Non-competitive inhibition of rat intestinal maltase using maltose as substrate assessed as dissociation of enzyme-substrate-inhibitor complex at 0.1 to 1 mg/ml by secondary plot analysis2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID357033Antiviral activity against HIV1 in human H9 cells assessed as inhibition of viral replication2001Journal of natural products, Jul, Volume: 64, Issue:7
Anti-AIDS agents. 46. Anti-HIV activity of harman, an anti-HIV principle from Symplocos setchuensis, and its derivatives.
AID1291760Anti-neuroinflammatory activity in LPS-activated mouse BV2 cells assessed as inhibition of NO production after 24 hrs by Griess assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID735308Antiinflammatory activity in C57BL/6 mouse BMDCs assessed as inhibition of LPS-stimulated TNF-alpha production treated 1 hr before LPS challenge measured 18 hrs post stimulation by ELISA2013Journal of natural products, Apr-26, Volume: 76, Issue:4
Diarylheptanoids and flavonoids from viscum album inhibit LPS-stimulated production of pro-inflammatory cytokines in bone marrow-derived dendritic cells.
AID341222Cytotoxicity against human A549 cells after 48 hrs by SRB assay2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
Hanultarin, a cytotoxic lignan as an inhibitor of actin cytoskeleton polymerization from the seeds of Trichosanthes kirilowii.
AID673422Inhibition of rat intestinal maltase using maltose as substrate preincubated for 10 mins before substrate addition by glucose oxidase method2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID1291756Cytotoxicity against human A549 cells by SRB assay2016Bioorganic & medicinal chemistry letters, Apr-15, Volume: 26, Issue:8
Bioactive lignan constituents from the twigs of Sambucus williamsii.
AID638451Cytotoxicity against mouse RAW264.7 cells by CCK assay2012Bioorganic & medicinal chemistry letters, Jan-01, Volume: 22, Issue:1
Inhibitory constituents of Nardostachys chinensis on nitric oxide production in RAW 264.7 macrophages.
AID404179Cytotoxicity against mouse colon 26-L5 cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID404183Cytotoxicity against human HeLa cells after 72 hrs by MTT assay2008Bioorganic & medicinal chemistry, May-15, Volume: 16, Issue:10
Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship.
AID673415Mixed type inhibition of rat intestinal maltase using maltose as substrate at 0.1 to 1 mg/ml2012Bioorganic & medicinal chemistry letters, Aug-15, Volume: 22, Issue:16
(+)-Pinoresinol is a putative hypoglycemic agent in defatted sesame (Sesamum indicum) seeds though inhibiting α-glucosidase.
AID1272763Cytotoxicity against LPS-stimulated mouse BV2 cells assessed as cell viability at 20 uM by MTT assay relative to control2016Bioorganic & medicinal chemistry letters, Feb-01, Volume: 26, Issue:3
Bioactive lignan derivatives from the stems of Firmiana simplex.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.14)18.2507
2000's5 (35.71)29.6817
2010's8 (57.14)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.15

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.15 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.11 (4.65)
Search Engine Demand Index53.49 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (39.15)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]