Page last updated: 2024-11-12

kirenol

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

Description

kirenol: an antirheumatic agent isolated from Siegebeckia; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID15736732
CHEMBL ID1089731
CHEBI ID192213
SCHEMBL ID19051009
MeSH IDM0559873

Synonyms (22)

Synonym
52659-56-0
kirenol
CHEMBL1089731
(1r)-1-[(2s,4ar,4bs,6s,8r,8as)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-4,4a,5,6,7,8a,9,10-octahydro-3h-phenanthren-2-yl]ethane-1,2-diol
CHEBI:192213
S9297
AKOS025311590
K0059
AC-34582
Q-100596
SCHEMBL19051009
mfcd00210519
HY-N0559
kirenol 100 microg/ml in acetonitrile
(r)-1-((2s,4ar,4bs,6s,8r,8as)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl)ethane-1,2-diol
CCG-267903
kirel
CS-0009086
A870938
(r)-1-((2s,4as,4bs,6s,8r,8as)-6-hydroxy-8-(hydroxymethyl)-2,4b,8-trimethyl-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthren-2-yl)ethane-1,2-diol
AS-55945
bdbm50465842

Research Excerpts

Overview

Kirenol (KRL) is a biologically active substance extracted from Herba Siegesbeckiae. Kirenol is a bioactive compound present in the Sieges beckia sps.

ExcerptReferenceRelevance
"Kirenol is a bioactive substance isolated from Herba Siegesbeckiae. "( Kirenol inhibits inflammation challenged by lipopolysaccharide through the AMPK-mTOR-ULK1 autophagy pathway.
Chen, H; Ding, L; Kou, R; Mao, C; Shen, X; Wang, K; Xiao, J; Zhai, L, 2023
)
3.8
"Kirenol is a bioactive compound present in the Sieges beckia sps."( Kirenol Exhibits the Protective Role against N-Methyl-N-Nitrosourea-Induced Gastric Cancer in Rats via Modulating the Oxidative Stress and Inflammatory Markers.
Li, C; Li, Y; Liu, W, 2020
)
2.72
"Kirenol (KRL) is a biologically active substance extracted from Herba Siegesbeckiae. "( Cardiac Protective Effect of Kirenol against Doxorubicin-Induced Cardiac Hypertrophy in H9c2 Cells through Nrf2 Signaling via PI3K/AKT Pathways.
Alzahrani, AM; Hanieh, H; Rajendran, P; Veeraraghavan, VP, 2021
)
2.36
"Kirenol (Kr) is an ent-pimarane type diterpenoid that has been reported from Siegesbeckiaorientalis, S. "( Kirenol: A promising bioactive metabolite from siegesbeckia species: A detailed review.
Abdallah, HM; Altyar, AE; El-Agamy, DS; Ibrahim, SRM; Mohamed, GA; Mohamed, SGA; Sindi, IA, 2021
)
3.51
"Kirenol is a biologically active substance isolated from Herba Siegesbeckiae. "( Kirenol, a compound from Herba Siegesbeckiae, induces apoptosis in human chronic myeloid leukemia K562 cells.
Chen, Y; Fu, H; Lu, Y; Qian, R; Xiao, J; Xu, D, 2014
)
3.29
"Kirenol is a diterpenoid compound purified from the Chinese Herba Siegesbeckiae. "( Kirenol upregulates nuclear annexin-1 which interacts with NF-κB to attenuate synovial inflammation of collagen-induced arthritis in rats.
Fu, HZ; Lu, Y; Qian, RQ; Wang, ZM; Wu, ZW; Zhu, SG, 2011
)
3.25
"Kirenol is a major diterpenoid components of Herba Siegesbeckiae, which has been applied for arthritic therapy for centuries."( Kirenol exerts a potent anti-arthritic effect in collagen-induced arthritis by modifying the T cells balance.
Chen, YY; Fu, HZ; Hu, J; Lu, Y; Qian, RQ; Wang, ZM; Wu, ZW; Xiao, J, 2012
)
2.54

Effects

ExcerptReferenceRelevance
"Kirenol has been reported to possess anti-oxidant, anti-inflammatory, anti-allergic, anti-adipogenic, and anti-arthritic activities; however, its effect on osteoblast differentiation has not yet been reported. "( Kirenol stimulates osteoblast differentiation through activation of the BMP and Wnt/β-catenin signaling pathways in MC3T3-E1 cells.
Hwang, JK; Kim, MB; Song, Y, 2014
)
3.29

Treatment

Kirenol significantly decreased high glucose-induced cardiofibroblasts proliferation and increased the cardiomyocytes viability. Kirenol treatment markedly delayed onset of disease and reduced clinical scores in EAE mice.

ExcerptReferenceRelevance
"Kirenol treatment significantly decreased high glucose-induced cardiofibroblasts proliferation and increased the cardiomyocytes viability, prevented the loss of mitochondrial membrane potential and further attenuated cardiomyocytes apoptosis, accompanied by a reduction in apoptosis-related protein expression."( Attenuation of diabetic cardiomyopathy by relying on kirenol to suppress inflammation in a diabetic rat model.
Fan, XH; Gui, R; Huang, CQ; Huang, XY; Li, L; Li, PC; Wang, S; Wu, B; Xiao, J, 2019
)
1.48
"Kirenol treatment significantly down-regulated the secretion of IFN-γ, IL-17A, IL-6 and TNF-α by the MLNs lymphocytes and increased the apoptosis of lymphocytes, especially CD4"( [Kirenol relieves dextran sulfate sodium-induced ulcerative colitis in mice by inhibiting inflammatory cytokines and inducing CD4
Guomei, D; Guoxing, L; Juan, X; Xin, T; Xiuhong, L; Yajun, DU, 2019
)
2.15
"Kirenol treatment appreciably improved the body weight and diminished the tumor volume and incidences in the MNG-challenged rats. "( Kirenol Exhibits the Protective Role against N-Methyl-N-Nitrosourea-Induced Gastric Cancer in Rats via Modulating the Oxidative Stress and Inflammatory Markers.
Li, C; Li, Y; Liu, W, 2020
)
3.44
"Kirenol treatment markedly delayed onset of disease and reduced clinical scores in EAE mice."( Kirenol attenuates experimental autoimmune encephalomyelitis by inhibiting differentiation of Th1 and th17 cells and inducing apoptosis of effector T cells.
Deng, W; Fan, X; Liu, W; Xiao, J; Yang, L; Yang, R, 2015
)
2.58
"Kirenol treatment reduces pro-inflammatory cytokine secretion, increases anti-inflammatory cytokine production, inhibits cell proliferation and induces apoptosis of CII-specific lymphocytes in vitro, suggesting the potential of kirenol as an immunosuppressant."( Effects of kirenol on bovine type II collagen-induced rat lymphocytes in vivo and in vitro.
Chen, Y; Fu, H; Lu, Y; Qian, R; Wang, Z; Wu, Z; Xiao, J, 2012
)
2.21

Pharmacokinetics

The present method was successfully applied to the pharmacokinetic study of kirenol in male Sprague-Dawley rats after oral administration at a dose of 50 mg/kg.

ExcerptReferenceRelevance
" The present method was successfully applied to the pharmacokinetic study of kirenol in male Sprague-Dawley rats after oral administration at a dose of 50 mg/kg."( A rapid and simple RP-HPLC method for quantification of kirenol in rat plasma after oral administration and its application to pharmacokinetic study.
Fu, HZ; Qian, RQ; Song, XL; Wang, ZM; Zhang, QY, 2011
)
0.84
" The validated method was successfully applied to a comparative pharmacokinetic study of the two diterpenoids in rat plasma after intragastric administration of Kirenol, DHKA and Herba Siegesbeckiae extract."( Simultaneous quantification of Kirenol and ent-16β,17-dihydroxy-kauran-19-oic acid from Herba Siegesbeckiae in rat plasma by liquid chromatography-tandem mass spectrometry and its application to pharmacokinetic studies.
Guo, X; Huo, L; Jiang, Z; Lei, M; Wang, X, 2013
)
0.87
" The pharmacokinetic parameters of different medication administration teams were analyzed with SPSS statistics 13."( [Pharmacokinetics study of two active diterpenoids from Herba Siegesbeckiae in rat plasma].
Jiang, Z; Sun, Y; Yin, Y, 2016
)
0.43

Bioavailability

ExcerptReferenceRelevance
" For DHKA, the absorption rate of DHKA increased rapidly after administration of the extract."( [Pharmacokinetics study of two active diterpenoids from Herba Siegesbeckiae in rat plasma].
Jiang, Z; Sun, Y; Yin, Y, 2016
)
0.43
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diterpenoidAny terpenoid derived from a diterpene. The term includes compounds in which the C20 skeleton of the parent diterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl 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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Coagulation factor XHomo sapiens (human)IC50 (µMol)2.53400.00030.593710.0000AID1414363; AID1602882
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
proteolysisCoagulation factor XHomo sapiens (human)
blood coagulationCoagulation factor XHomo sapiens (human)
positive regulation of cell migrationCoagulation factor XHomo sapiens (human)
positive regulation of TOR signalingCoagulation factor XHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityCoagulation factor XHomo sapiens (human)
calcium ion bindingCoagulation factor XHomo sapiens (human)
protein bindingCoagulation factor XHomo sapiens (human)
phospholipid bindingCoagulation factor XHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
extracellular regionCoagulation factor XHomo sapiens (human)
endoplasmic reticulum lumenCoagulation factor XHomo sapiens (human)
Golgi lumenCoagulation factor XHomo sapiens (human)
plasma membraneCoagulation factor XHomo sapiens (human)
external side of plasma membraneCoagulation factor XHomo sapiens (human)
extracellular spaceCoagulation factor XHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID1602882Inhibition of human factor Xa using Z-D-Arg-Gly-Arg-pNA.2HCl as substrate preincubated for 15 mins followed by substrate addition by UV absorption analysis2019Bioorganic & medicinal chemistry, 04-01, Volume: 27, Issue:7
Semisynthesis of epoxy-pimarane diterpenoids from kirenol and their FXa inhibition activities.
AID469809Cytotoxicity against mouse B16 cells after 44 hrs by MTT assay2010Journal of natural products, Jan, Volume: 73, Issue:1
ent-kaurane and ent-pimarane diterpenoids from Siegesbeckia pubescens.
AID469807Cytotoxicity against rat HSC-T6 cells after 44 hrs by MTT assay2010Journal of natural products, Jan, Volume: 73, Issue:1
ent-kaurane and ent-pimarane diterpenoids from Siegesbeckia pubescens.
AID1437541Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by Griess assay2017Journal of natural products, 01-27, Volume: 80, Issue:1
ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens.
AID1414363Inhibition of human coagulation factor 10a using Z-D-Arg-Gly-Arg-pNA.2HCl as substrate preincubated for 15 mins followed by substrate addition by UV absorption assay2018Bioorganic & medicinal chemistry letters, 12-15, Volume: 28, Issue:23-24
Semisynthesis of ent-norstrobane diterpenoids as potential inhibitor for factor Xa.
AID1437542Antiinvasive activity in human MDA-MB-231 cells assessed as inhibition of EGF-induced cell invasion after 3.5 hrs2017Journal of natural products, 01-27, Volume: 80, Issue:1
ent-Strobane and ent-Pimarane Diterpenoids from Siegesbeckia pubescens.
AID469808Cytotoxicity against human HeLa cells after 44 hrs by MTT assay2010Journal of natural products, Jan, Volume: 73, Issue:1
ent-kaurane and ent-pimarane diterpenoids from Siegesbeckia pubescens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (2.63)18.2507
2000's0 (0.00)29.6817
2010's20 (52.63)24.3611
2020's17 (44.74)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.06

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 Index26.06 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index6.39 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (26.06)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (5.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other36 (94.74%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]