Compounds > irisolidone
Page last updated: 2024-11-10

irisolidone

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

Description

irisolidone: isolated from the flowers and rhizomes of Pueraria thunbergiana; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
PuerariagenusA plant genus of the family FABACEAE a common weed of the southeast US. There has been folk use for alcoholism and liver protection. It contains puerarin, kakkalide, daidzein (isoflavonoids), and kudzusaponins (oleanene-type triterpene glycosides).[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID5281781
CHEMBL ID265945
CHEBI ID5972
SCHEMBL ID1974327
MeSH IDM0384413

Synonyms (27)

Synonym
2345-17-7
irisolidone
CHEMBL265945
chebi:5972 ,
LMPK12050384
4'-o-methyltectorigenin
5,7-dihydroxy-6,4'-dimethoxyisoflavone
5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)chromen-4-one
4'-o-methoxytectorigenin
081orx70zr ,
isoflavone, 5,7-dihydroxy-4',6-dimethoxy-
5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4h-chromen-4-one
unii-081orx70zr
4'-methoxytectorigenin
SCHEMBL1974327
AC-34234
5,7-dihydroxy-6-methoxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-one
AKOS037515268
HY-N2412
Q27106953
BCP33583
4'-o-methyltectorigeni
FT-0776503
CS-0022613
MS-24603
DTXSID30946104
E88606

Research Excerpts

Actions

ExcerptReferenceRelevance
"Irisolidone was found to inhibit the secretion and protein expression of MMP-9 induced by PMA in U87 MG glioma cells, accompanied by the inhibition of MMP-9 mRNA expression and promoter activity."( Inhibition of matrix metalloproteinase-9 gene expression by an isoflavone metabolite, irisolidone in U87MG human astroglioma cells.
Hyun, JW; Jung, JS; Kim, DH; Kim, HS; Kim, SY; Lee, EJ; Min, SW; Woo, MS, 2008)		1.29

Bioavailability

ExcerptReferenceRelevance
" The results indicate that urine is the primary route of kakkalide elimination in vivo and that extensive metabolism may be one of the reasons for the low bioavailability of kakkalide."( Metabolism and excretion of kakkalide and its metabolites in rat urine, bile, and feces as determined by HPLC/UV and LC/MS/MS.
Bai, X; Kano, Y; Makino, T; Sun, J; Wang, H; Yuan, D, 2013)		0.39

Dosage Studied

ExcerptRelevanceReference
" The excretion rates of Te-7G, Te-7G-4'S, Ir-7G, and Te reached a maximum between 12 and 24 h after oral dosing at 65 and 130 mg/kg."( Excretion of tectorigenin in rat urine orally administrated at different dosages by ultra-performance liquid chromatography coupled to quadrupole time-of-flight mass spectrometry.
Kano, Y; Shi, Z; Wang, S; Yuan, D; Zhang, G; Zhao, L, 2015)		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
4'-methoxyisoflavonesAny methoxyisoflavone which has a methoxy group at the 4-position of the phenyl substituent.
[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 (19)

Assay IDTitleYearJournalArticle
AID323486Inhibition of hydrogen peroxide-induced lipid peroxidation in chinese hamster V79-4 cells assessed as TBARS per mg of protein at 1 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323495Protective effect on hydrogen peroxide-induced damage in chinese hamster V79-4 cells in presence of U0126 by MTT assay2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323491Decrease in hydrogen peroxide-induced 8-OHdG in chinese hamster V79-4 cells at 50 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323496Activation of ERK in chinese hamster V79-4 cells assessed as phosphorylated ERK within 6 hrs2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323481DPPH radical scavenging activity at 10 ug/ml after 30 mins2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323484ROS scavenging activity in chinese hamster V79-4 cells at 10 ug/mL after 30 mins by DCF-DA method2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323488Inhibition of hydrogen peroxide-induced lipid peroxidation in chinese hamster V79-4 cells assessed as TBARS per mg of protein at 50 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323493Protective effect on hydrogen peroxide-induced cell damage in chinese hamster V79-4 cells assessed as decrease in apoptotic sub-G1 DNA content at 50 ug/ml by flow cytometry2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323483ROS scavenging activity in chinese hamster V79-4 cells at 1 ug/mL after 30 mins by DCF-DA method2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323482DPPH radical scavenging activity at 50 ug/ml after 30 mins2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323489Decrease in hydrogen peroxide-induced 8-OHdG in chinese hamster V79-4 cells at 1 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323492Protection against hydrogen peroxide-induced apoptosis in chinese hamster V79-4 cells assessed as cell survival by MTT assay2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323498Effect on hydrogen peroxide-induced DNA damage in chinese hamster V79-4 cells assessed as decrease in phospho H2A.X expression2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323485ROS scavenging activity in chinese hamster V79-4 cells at 50 ug/mL after 30 mins by DCF-DA method2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323490Decrease in hydrogen peroxide-induced 8-OHdG in chinese hamster V79-4 cells at 10 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323494Protective effect on hydrogen peroxide-induced cell damage in chinese hamster V79-4 cells assessed as decrease in DNA fragmentation level at 50 ug/ml by ELISA2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323480DPPH radical scavenging activity at 1 ug/ml after 30 mins2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323487Inhibition of hydrogen peroxide-induced lipid peroxidation in chinese hamster V79-4 cells assessed as TBARS per mg of protein at 10 ug/mL2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
AID323497Increase in transcriptional activity of AP1 transfected in V79-4 cells by luciferase assay2008Bioorganic & medicinal chemistry, Feb-01, Volume: 16, Issue:3
Protective effect of irisolidone, a metabolite of kakkalide, against hydrogen peroxide induced cell damage via antioxidant effect.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (16)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's9 (56.25)29.6817
2010's7 (43.75)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: 19.25

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 Index19.25 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index4.45 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (19.25)

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%
Other16 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tert-butylhydroperoxide
tert-Butylhydroperoxide: A direct-acting oxidative stress-inducing agent used to examine the effects of oxidant stress on Ca(2+)-dependent signal transduction in vascular endothelial cells. It is also used as a catalyst in polymerization reactions and to introduce peroxy groups into organic molecules.. tert-butyl hydroperoxide : An alkyl hydroperoxide in which the alkyl group is tert-butyl. It is widely used in a variety of oxidation processes.		2.0210alkyl hydroperoxideantibacterial agent;
oxidising agent
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.0510D-glucopyranoseepitope;
mouse metabolite
tyloxapol
tyloxapol: non-ionic detergent with surface-active properties; incompatible with metals; surfactant also used in inhalation therapy; N1 is from CA Vol 90 Form Index; N1 in Chemline is same as synonym 8. tyloxapol : A polymeric compound resulting from the reaction of 4-(1,1,3,3-tetramethylbutyl)phenol with formaldehyde to give a chain in which 6-8 molecules are linked together by CH2 groups ortho to the phenolic hydroxy groups, which have then undergone reaction with oxirane to give polyoxyethyleneoxy moieties, Ar(OCH2CH2)xOH, where x = 8-10. A nonionic liquic polymer, it inhibits lipoprotein lipase and hence clearance of triglyceride from the plasma, so is used to induce hyperlipidaemia in test animals. Also used as a surfactant to aid liquefaction and removal of mucus- and pus-containing bronchopulmonary secretions.		2.0310
homoorientin
homoorientin: isolated from Swertia japonica; structure given in first source		2.0510flavone C-glycoside;
tetrahydroxyflavone		antineoplastic agent;
radical scavenger
isoflavanone
isoflavanone: structure given in first source; RN from CA Index Guide. isoflavanone : Isoflavone in which the double bond between positions 2 and 3 has been reduced to a single bond.		2.0410isoflavanones
isovitexin
[no description available]		2.0510C-glycosyl compound;
trihydroxyflavone		EC 3.2.1.20 (alpha-glucosidase) inhibitor;
metabolite
glycosides
[no description available]		3.4570
dinoprostone
prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.		2.0610prostaglandins Ehuman metabolite;
mouse metabolite;
oxytocic
apigenin
Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.		2.0510trihydroxyflavoneantineoplastic agent;
metabolite
luteolin
[no description available]		2.05103'-hydroxyflavonoid;
tetrahydroxyflavone		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
apoptosis inducer;
c-Jun N-terminal kinase inhibitor;
EC 2.3.1.85 (fatty acid synthase) inhibitor;
immunomodulator;
nephroprotective agent;
plant metabolite;
radical scavenger;
vascular endothelial growth factor receptor antagonist
genistein
[no description available]		2.44207-hydroxyisoflavonesantineoplastic agent;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
geroprotector;
human urinary metabolite;
phytoestrogen;
plant metabolite;
tyrosine kinase inhibitor
irilone
irilone: structure in first source. irilone : A hydroxyisoflavone that is 6,7-methylenedioxyisoflavone substituted by hydroxy groups at positions 5 and 4'.		2.0510hydroxyisoflavone;
organic heterotricyclic compound;
oxacycle		antineoplastic agent;
immunomodulator;
metabolite
tectoridin
tectoridin: glycosylated tectorigenin. tectoridin : A glycosyloxyisoflavone that is tectorigenin substituted by a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage.		2.03107-hydroxyisoflavones 7-O-beta-D-glucoside;
hydroxyisoflavone;
methoxyisoflavone;
monosaccharide derivative		plant metabolite
tectorigenin
tectorigenin: tectoridin is glycosylated form. tectorigenin : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4' respectively.		2.96407-hydroxyisoflavones;
methoxyisoflavone		anti-inflammatory agent;
plant metabolite
mocetinostat
mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).		2.1510aminopyrimidine;
benzamides;
pyridines;
secondary amino compound;
secondary carboxamide;
substituted aniline		antineoplastic agent;
apoptosis inducer;
autophagy inducer;
cardioprotective agent;
EC 3.5.1.98 (histone deacetylase) inhibitor;
hepatotoxic agent
interleukin-8
Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.		2.1510
kakkalide
kakkalide: hepatoprotective isoflavonoid from Pueraria;		3.4570
phytoestrogens
Phytoestrogens: Compounds derived from plants, primarily ISOFLAVONES that mimic or modulate endogenous estrogens, usually by binding to ESTROGEN RECEPTORS.		2.0310
ConditionIndicatedRelationship StrengthStudiesTrials
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.1110
Gastritis
Inflammation of the GASTRIC MUCOSA, a lesion observed in a number of unrelated disorders.		02.1510
Innate Inflammatory Response
[description not available]		02.0610
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		07.0610
Acute Liver Injury, Drug-Induced
[description not available]		02.0210
Liver Dysfunction
[description not available]		02.0210
Liver Diseases
Pathological processes of the LIVER.		02.0210
Chemical and Drug Induced Liver Injury
A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.		02.0210
Polyomavirus Infections
Infections with POLYOMAVIRUS, which are often cultured from the urine of kidney transplant patients. Excretion of BK VIRUS is associated with ureteral strictures and CYSTITIS, and that of JC VIRUS with progressive multifocal leukoencephalopathy (LEUKOENCEPHALOPATHY, PROGRESSIVE MULTIFOCAL).		02.0310
Encephalitis, JC Polyomavirus
[description not available]		02.0310
Leukoencephalopathy, Progressive Multifocal
An opportunistic viral infection of the central nervous system associated with conditions that impair cell-mediated immunity (e.g., ACQUIRED IMMUNODEFICIENCY SYNDROME and other IMMUNOLOGIC DEFICIENCY SYNDROMES; HEMATOLOGIC NEOPLASMS; IMMUNOSUPPRESSION; and COLLAGEN DISEASES). The causative organism is JC Polyomavirus (JC VIRUS) which primarily affects oligodendrocytes, resulting in multiple areas of demyelination. Clinical manifestations include DEMENTIA; ATAXIA; visual disturbances; and other focal neurologic deficits, generally progressing to a vegetative state within 6 months. (From Joynt, Clinical Neurology, 1996, Ch26, pp36-7)		02.0310
Hyperlipemia
[description not available]		02.0310
Hyperlipidemias
Conditions with excess LIPIDS in the blood.		02.0310
Anaplastic Astrocytoma
[description not available]		02.0410
Astrocytoma
Neoplasms of the brain and spinal cord derived from glial cells which vary from histologically benign forms to highly anaplastic and malignant tumors. Fibrillary astrocytomas are the most common type and may be classified in order of increasing malignancy (grades I through IV). In the first two decades of life, astrocytomas tend to originate in the cerebellar hemispheres; in adults, they most frequently arise in the cerebrum and frequently undergo malignant transformation. (From Devita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2013-7; Holland et al., Cancer Medicine, 3d ed, p1082)		02.0410