Page last updated: 2024-12-07

kadsurenone

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

Description

Kadsurenone is a natural product with a complex structure that has been isolated from the roots of Kadsura coccinea. This compound has shown promising biological activity in various studies. Kadsurenone is known for its anti-inflammatory, analgesic, and antitumor effects. It has also been demonstrated to have antioxidant properties. Research on kadsurenone is ongoing to explore its potential as a therapeutic agent for a variety of diseases.'

kadsurenone: platelet-activating factor receptor antagonist from Chinese herbal plant, haifenteng; structure given in first source; RN given refers to (2s-(2alpha,3beta,3aalpha))-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID122159
CHEMBL ID296958
CHEBI ID6097
SCHEMBL ID1110789
MeSH IDM0130012

Synonyms (27)

Synonym
PDSP2_000721
PDSP1_000731
kadsurenone
95851-37-9
CHEMBL296958 ,
(+)-kadsurenone
chebi:6097 ,
(kadsurenone)5-allyl-2-(3,4-dimethoxy-phenyl)-3a-methoxy-3-methyl-3,3a-dihydro-2h-benzofuran-6-one
5-allyl-2-(3,4-dimethoxy-phenyl)-3a-methoxy-3-methyl-3,3a-dihydro-2h-benzofuran-6-one
bdbm50001747
AC1L3U3M ,
(2s,3r,3as)-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
dzy9cv5vh7 ,
6(2h)-benzofuranone, 2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propenyl)-, (2s-(2alpha,3beta,3aalpha))-
unii-dzy9cv5vh7
SCHEMBL1110789
surecn1110789
(2s,3r,3as)-5-allyl-2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-2,3-dihydrobenzofuran-6-one
2-(3,4-dimethoxyphenyl)-3a-methoxy-3-methyl-5-(prop-2-en-1-yl)-3,3a-dihydro-1-benzofuran-6(2h)-one
DTXSID90914788
Q27107065
CS-0633861
HY-N10663
kadsurenone a
6(2h)-benzofuranone, 2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propen-1-yl)-, (2s,3r,3as)-
kadsurenone, (+)-
(2s,3r,3as)-2-(3,4-dimethoxyphenyl)-3,3a-dihydro-3a-methoxy-3-methyl-5-(2-propen-1-yl)-6(2h)-benzofuranone

Research Excerpts

Overview

Kadsurenone is a neolignan with specific antagonistic activity of platelet-activating factor. It is derived from the stems of Piper kadsura.

ExcerptReferenceRelevance
"Kadsurenone is a neolignan with specific antagonistic activity of platelet-activating factor, and is derived from the stems of Piper kadsura. "( Pharmacokinetics of kadsurenone and its interaction with cyclosporin A in rats using a combined HPLC and microdialysis system.
Huang, SP; Lin, LC; Tsai, TH; Wu, YT, 2009
)
2.12

Treatment

Kadsurenone treated animals did not exhibit significantly altered 111In-labeled platelet accumulation when compared to controls. Pretreatment with Kadsure None exerted a quite complete protective effect in regard to the ECG changes.

ExcerptReferenceRelevance
"Kadsurenone treated animals did not exhibit significantly altered 111In-labeled platelet accumulation when compared to controls (6158 +/- 2386 vs 9979 +/- 3852, mean +/- SEM)."( Platelet activating factor receptor blockade enhances recovery after multifocal brain ischemia.
Dutka, AJ; Hallenbeck, JM; Kochanek, PM; Kumaroo, KK, 1987
)
0.99
"Pretreatment with Kadsurenone, administered either intravenously (0.014 M, 1 ml/kg) or intraperitoneally (0.14 M, 1 ml/kg), exerted a quite complete protective effect in regard to the ECG changes and caused a significant reduction in the magnitude of all the haemodynamic alterations observed after intravenous infusion of PAF (0.8 microgram/kg)."( Cardiovascular alterations in the rabbit infused with platelet activating factor (PAF): effect of kadsurenone, a PAF-receptor antagonist.
Alloatti, G; Camussi, G; Emanuelli, G; Mariano, F; Montrucchio, G; Tetta, C, 1986
)
0.81

Pharmacokinetics

ExcerptReferenceRelevance
" The LC-MS/MS assay was successfully applied for oral pharmacokinetic evaluation of kadsurenone using the rat as an animal model."( Development of an LC-MS/MS method for quantification of kadsurenone in rat plasma and its application to a pharmacokinetic study.
Dong, N; Li, R; Shi, D; Wang, H; Yu, H; Zhang, N; Zhang, S, 2013
)
0.86

Dosage Studied

ExcerptRelevanceReference
" In this study, we quantitated the dose-response effects of topically applied PAF on microvascular permselectivity and investigated the biochemical pathways of this compound."( Effect of platelet-activating factor on microvascular permselectivity: dose-response relations and pathways of action in the hamster cheek pouch microcirculation.
Dillon, PK; DurĂ¡n, WN, 1988
)
0.27
" All antagonists produced a shift to the right in the dose-response curve to Paf (0."( Antagonism of platelet activating factor-induced chemiluminescence in guinea-pig peritoneal macrophages in differing states of activation.
Bittner, C; Lambrecht, G; Parnham, MJ, 1989
)
0.28
" The monkey metabolites of the two drugs were isolated as their glucuronide conjugates from the urine of iv dosed males."( Metabolism of kadsurenone and 9,10-dihydrokadsurenone in rhesus monkeys and rat liver microsomes.
Arison, BH; Chabala, JC; Chang, MN; Chiu, SH; Eline, D; Hucker, HB; Smith, JL; Sweeney, BM; Thompson, KL; White, SD,
)
0.49
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
benzofurans
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Ovis aries (sheep)IC50 (µMol)25.60000.00032.177410.0000AID443489
Platelet-activating factor receptorCavia porcellus (domestic guinea pig)IC50 (µMol)0.16500.00430.75777.8000AID154452; AID154453; AID154455; AID154456
Prostaglandin G/H synthase 2Ovis aries (sheep)IC50 (µMol)246.00000.00101.453910.0000AID443490
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID154463Percent inhibition of [3H]-PAF to platelet-activating factor (PAF) receptor from rabbit platelet membranes at 0.3 uM1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID154453Inhibitor concentration required to block 50 %of the specific [3H]PAF binding to rabbit platelet membranes.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID224348Inhibition of PAF-induced platelet aggregation in rabbit platelet rich plasma1993Journal of medicinal chemistry, Mar-05, Volume: 36, Issue:5
Analogues of platelet activating factor. 8. Antagonists of PAF containing an aromatic ring linked to a pyridinium ring.
AID443491Inhibition of potato LOX-5 assessed as inhibition of hydroperoxide production after 5 mins by EIA2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID454545Cytotoxicity against mouse BV2 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Neolignans from Piper kadsura and their anti-neuroinflammatory activity.
AID167798Concentration needed to inhibit PAF-induced platelet aggregation in rabbit PRP by 50%1992Journal of medicinal chemistry, May-01, Volume: 35, Issue:9
Analogues of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor.
AID166950PAF antagonism was determined by rabbit platelet inhibition and neurophil aggregation and degranulation at 0.1 to 1 uM concentration.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID154464Percent inhibition of [3H]PAF binding to platelet-activating factor (PAF) receptor from rabbit platelet membranes at 1.0 uM1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID443494Antiplatelet activity in rabbit platelets assessed as inhibition of arachidonic acid-induced platelet aggregation2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID454544Antineuroinflammatory activity in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production at 20 uM after 24 hrs by Griess reagent method2010Bioorganic & medicinal chemistry letters, Jan-01, Volume: 20, Issue:1
Neolignans from Piper kadsura and their anti-neuroinflammatory activity.
AID443493Antiplatelet activity in rabbit platelets assessed as inhibition of platelet activating factor-induced platelet aggregation2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID154452Inhibition concentration required to block 50% of the specific [3H]PAF binding, obtained from Chiralpak column at low temperatures.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID154455Inhibitor concentration required to block 50% of the specific [3H]PAF binding to rabbit platelet membranes.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID154466Percent inhibition of [3H]-PAF binding to platelet-activating factor (PAF) receptor from rabbit platelet membranes at 5.0 uM1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID443495Antiplatelet activity in rabbit platelets assessed as inhibition of adenosin 5'-diphosphate-induced platelet aggregation2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID224180Concentration required to inhibit PAF (5*10e-8 M) induced platelet aggregation in rabbit platelet rich plasma(PRP) by 50%1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Analogues of platelet activating factor. 7. Bis-aryl amide and bis-aryl urea receptor antagonists of PAF.
AID426073Antiplatelet activity in rabbit platelets assessed as inhibition of PAF-induced platelet aggregation treated 5 mins before PAF challenge2009Journal of natural products, Jul, Volume: 72, Issue:7
Macrophyllin-type bicyclo[3.2.1]octanoid neolignans from the leaves of Pleurothyrium cinereum.
AID1386710Antagonist activity at rabbit PAF receptor assessed as inhibition of PAF-induced platelet aggregation incubated for 5 mins followed by PAF addition2018Journal of natural products, 09-28, Volume: 81, Issue:9
Tetrahydrobenzofuran-6(2 H)-one Neolignans from Ocotea heterochroma: Their Platelet Activating Factor (PAF) Antagonistic Activity and in Silico Insights into the PAF Receptor Binding Mode.
AID443492Selectivity ratio of IC50 for ovine COX-1 to IC50 for ovine COX-22009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID154456Inhibitor concentration required to block 50% of the specific [3H]PAF binding, obtained as natural product.1987Journal of medicinal chemistry, Jan, Volume: 30, Issue:1
Structure-activity relationships of kadsurenone analogues.
AID443489Inhibition of ovine COX-1 assessed as inhibition of transformation of AA to PGH2 by EIA2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
AID443490Inhibition of ovine COX-2 assessed as inhibition of transformation of AA to PGH2 by EIA2009Bioorganic & medicinal chemistry letters, Dec-15, Volume: 19, Issue:24
COX, LOX and platelet aggregation inhibitory properties of Lauraceae neolignans.
[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-199028 (58.33)18.7374
1990's11 (22.92)18.2507
2000's5 (10.42)29.6817
2010's4 (8.33)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: 10.20

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

MetricThis Compound (vs All)
Research Demand Index10.20 (24.57)
Research Supply Index3.95 (2.92)
Research Growth Index4.15 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (7.84%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other47 (92.16%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]