Compounds > trifolirhizin
Page last updated: 2024-12-08

trifolirhizin

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

Description

trifolirhizin: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
SophoragenusA plant genus of the family FABACEAE.[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 CID442827
CHEMBL ID454878
CHEBI ID9714
MeSH IDM0518055

Synonyms (25)

Synonym
ACON1_002295
6807-83-6
(-)-maackiain 3-o-glucoside
trifolirhizin
NCGC00169980-01
(-)-maackiain-3-o-glucoside
BRD-K43094903-001-01-3
chebi:9714 ,
CHEMBL454878 ,
trifolrhizin
sophojaponicin b2
beta-d-glucopyranoside, 6a,12a-dihydro-6h-(1,3)dioxolo(5,6)benzofuro(3,2-c)(1)benzopyran-3-yl, (6ar-cis)-
S9425
Q-100766
mfcd00238700
trifolirhizin, >=95% (lc/ms-elsd)
NCGC00169980-03
AKOS030632879
(2s,3r,4s,5s,6r)-2-(((6ar,12ar)-6a,12a-dihydro-6h-[1,3]dioxolo[4',5':5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2h-pyran-3,4,5-triol
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[[(1r,12r)-5,7,11,19-tetraoxapentacyclo[10.8.0.02,10.04,8.013,18]icosa-2,4(8),9,13(18),14,16-hexaen-16-yl]oxy]oxane-3,4,5-triol
DTXSID70987516
Q27108480
CCG-269193
HY-N0616
CS-0009612

Research Excerpts

Overview

Trifolirhizin is a compound isolated from Sophora flavescens.

ExcerptReferenceRelevance
"Trifolirhizin is a compound isolated from Sophora flavescens. "( Anti-proliferation effects of trifolirhizin on MKN45 cells and possible mechanism.
Cao, L; Lu, X; Ma, J; Qiu, H; Shen, J; Yang, L, 2016)		2.17

Pharmacokinetics

ExcerptReferenceRelevance
" The method was successfully applied to a pharmacokinetic study involving oral administration of trifolirhizin to rats."( Determination of trifolirhizin in rat plasma by UPLC: Application to a pharmacokinetic study.
Hu, GX; Huang, XC; Ni, KH; Wang, CX; Wen, ZD; Ye, TT; Zhou, MT, 2015)		0.97
" This study investigates the pharmacokinetic properties of SKI3301 extract in rats."( Pharmacokinetic properties of trifolirhizin, (-)-maackiain, (-)-sophoranone and 2-(2,4-dihydroxyphenyl)-5,6-methylenedioxybenzofuran after intravenous and oral administration of Sophora tonkinensis extract in rats.
Bae, SH; Bae, SK; Choi, WK; Jang, SM; Kang, M; Kim, D; Min, JS; Park, JB; Ryu, KH; Yoo, H, 2015)		0.71

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019)		0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
pterocarpansMembers of the class of benzofurochromene with a 6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene skeleton and its substituted derivatives. They generally bear structural resemblance to isoflavanoids that possess antibiotic activity and are produced by plant tissues in response to infection. They are the 3,4-dihydroderivatives of coumestans.
[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
maackiain conjugates interconversion017

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID403549Antiviral activity against HSV1 in african green monkey Vero cells assessed as virus-induced cytopathic effect after 3 days by MTT assay1998Journal of natural products, Dec, Volume: 61, Issue:12
A new prenylated flavonol from the roots of Sophora flavescens.
AID410031Inhibition of Clostridium perfringens neuraminidase2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID1238084Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at IC50 by MTT assay2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Chemical constituents isolated from the Mongolian medicinal plant Sophora alopecuroides L. and their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages.
AID403550Antiviral activity against HSV2 in african green monkey Vero cells assessed as virus-induced cytopathic effect after 3 days by MTT assay1998Journal of natural products, Dec, Volume: 61, Issue:12
A new prenylated flavonol from the roots of Sophora flavescens.
AID410032Inhibition of Clostridium perfringens neuraminidase by Lineweaver-Burke plot2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID1238082Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated nitric oxide production after 24 hrs by Griess method2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Chemical constituents isolated from the Mongolian medicinal plant Sophora alopecuroides L. and their inhibitory effects on LPS-induced nitric oxide production in RAW 264.7 macrophages.
AID1432767Enhancement of GLUT4 translocation at plasma membrane of rat L6 cells expressing pIRAP-mOrange at 10 uM after 30 mins by fluorescence assay relative to control2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Chemical constituents from Sophora tonkinensis and their glucose transporter 4 translocation activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.17)18.2507
2000's4 (16.67)29.6817
2010's12 (50.00)24.3611
2020's7 (29.17)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.65

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 Index22.65 (24.57)
Research Supply Index3.26 (2.92)
Research Growth Index5.32 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.65)

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%
Other25 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
formic acid
formic acid: RN given refers to parent cpd. formic acid : The simplest carboxylic acid, containing a single carbon. Occurs naturally in various sources including the venom of bee and ant stings, and is a useful organic synthetic reagent. Principally used as a preservative and antibacterial agent in livestock feed. Induces severe metabolic acidosis and ocular injury in human subjects.		2.110monocarboxylic acidantibacterial agent;
astringent;
metabolite;
protic solvent;
solvent
pimagedine
pimagedine: diamine oxidase & nitric oxide synthase inhibitor; an advanced glycosylation end product inhibitor; used in the treatment of diabetic complications; structure. aminoguanidine : A one-carbon compound whose unique structure renders it capable of acting as a derivative of hydrazine, guanidine or formamide.		2.1110guanidines;
one-carbon compound		EC 1.14.13.39 (nitric oxide synthase) inhibitor;
EC 1.4.3.4 (monoamine oxidase) inhibitor
1-methyl-3-isobutylxanthine
1-Methyl-3-isobutylxanthine: A potent cyclic nucleotide phosphodiesterase inhibitor; due to this action, the compound increases cyclic AMP and cyclic GMP in tissue and thereby activates CYCLIC NUCLEOTIDE-REGULATED PROTEIN KINASES. 3-isobutyl-1-methylxanthine : An oxopurine that is xanthine which is substituted at positions 1 and 3 by methyl and isobutyl groups, respectively.		2.04103-isobutyl-1-methylxanthine
acetonitrile
acetonitrile: RN given refers to unlabeled cpd. acetonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a methyl group.		2.110aliphatic nitrile;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
NMR chemical shift reference compound;
polar aprotic solvent
phenyl acetate
phenyl acetate: The ester formed between phenol and acetic acid. Don't confuse with phenylacetic acid derivatives listed under PHENYLACETATES.. phenyl acetate : An acetate ester obtained by the formal condensation of phenol with acetic acid.		2.110benzenes;
phenyl acetates
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.		5.16160D-glucopyranoseepitope;
mouse metabolite
dictamnine
dictamnine: furanoquinoline alkaloid; crosslinks DNA in presence of ultraviolet light		3.0310alkaloid antibiotic;
organic heterotricyclic compound;
organonitrogen heterocyclic compound;
oxacycle
vexibinol
vexibinol: flavanol from Sophora; structure in first source; RN given refers to (S-(R*,S*))-isomer. sophoraflavanone G : A tetrahydroxyflavanone having a structure of naringenin bearing an additional hydroxyl substituent at position 2' as well as a (2R)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl (lavandulyl) substituent at position 8'.		2.7730(2S)-flavan-4-one;
4'-hydroxyflavanones;
tetrahydroxyflavanone		antimalarial;
antimicrobial agent;
antioxidant;
plant metabolite
inermin
inermin: phytoalexin produced in plants after injection with fungi; RN given refers to (cis-(+-))-isomer; RN for cpd without isomeric designation; structure. (-)-maackiain : The (-)-enantiomer of maackiain.		4.4170maackiain
syringaresinol
[no description available]		2.2510aromatic ether;
furofuran;
lignan;
polyether;
polyphenol		plant metabolite
obacunone
obacunone: from bark of Chinese plant Phellodendron amurense; shortens sleeping time induced in mice by alpha-chloralose-urethane		3.0310limonoid
fraxinellone
fraxinellone: structure given in first source; RN given for (3R-cis)-isomer		3.03102-benzofurans
limonin
[no description available]		3.0310epoxide;
furans;
hexacyclic triterpenoid;
lactone;
limonoid;
organic heterohexacyclic compound		inhibitor;
metabolite;
volatile oil component
isobavachin
isobavachin: RN given for (S)-isomer; structure in first source		2.1110flavanones
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		3.9640
medicarpin
(-)-medicarpin : The (-)-enantiomer of medicarpin.		2.1510medicarpinplant metabolite
sophoranone
sophoranone: a flavonoid compound with isoprenoid side chains; extracted from a traditional Chinese medicine Shan Dou Gen, isolated from the roots of Sophora subprostrata; structure in first source. sophoranone : A dihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7 and 4' and prenyl groups at positions 3' and 5' respectively.		2.81304'-hydroxyflavanones;
dihydroxyflavanone		plant metabolite
rutaevin
rutaevin: from root bark of Dictamnus daycarpus Turcz.		3.0310steroid lactone
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.2510
ferulic acid
ferulate : A monocarboxylic acid anion obtained by the deprotonation of the carboxy group of ferulic acid.		2.0310ferulic acidsanti-inflammatory agent;
antioxidant;
apoptosis inhibitor;
cardioprotective agent;
MALDI matrix material;
plant metabolite
gamma-sitosterol
clionasterol : A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3.		2.03103beta-hydroxy-Delta(5)-steroid;
3beta-sterol;
phytosterols		marine metabolite;
plant metabolite
pallidol
pallidol: isolated from Ciccus pallida; structure in first source. pallidol : A tetracyclic stilbenoid that is a homodimer obtained by cyclodimerisation of resveratrol.		2.1110carbopolycyclic compound;
polyphenol;
stilbenoid		antifungal agent;
antioxidant;
plant metabolite
8-isopentenylnaringenin
8-isopentenylnaringenin: a non-steroidal phytoestrogen from Anaxagorea luzonensis; structure in first source		2.1110flavanones
ammonium acetate
ammonium acetate : An ammonium salt obtained by reaction of ammonia with acetic acid. A deliquescent white crystalline solid, it has a relatively low melting point (114degreeC) for a salt. Used as a food acidity regulator, although no longer approved for this purpose in the EU.		2.110acetate salt;
ammonium salt		buffer;
food acidity regulator
cytellin
cytellin: a phytosterol preparation of mainly B-sitosterol, that was marketed by Eli Lilly to lower cholesterol 1957 to 1982		2.0310
quercetin
[no description available]		2.15107-hydroxyflavonol;
pentahydroxyflavone		antibacterial agent;
antineoplastic agent;
antioxidant;
Aurora kinase inhibitor;
chelator;
EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor;
geroprotector;
phytoestrogen;
plant metabolite;
protein kinase inhibitor;
radical scavenger
7,3'-dihydroxy-4'-methoxyisoflavone
7,3'-dihydroxy-4'-methoxyisoflavone: isolated from Astragali radix; structure in first source. calycosin : A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at the 3' position and a methoxy group at the 4' position.		2.25104'-methoxyisoflavones;
7-hydroxyisoflavones		antioxidant;
metabolite
mangiferin
shamimin: isolated from the leaves of Bombax ceiba; structure in first source		2.0410C-glycosyl compound;
xanthones		anti-inflammatory agent;
antioxidant;
hypoglycemic agent;
plant metabolite
aurone
[no description available]		2.2510aurones;
cyclic ketone
sophoflavescenol
sophoflavescenol: a prenylated flavonol from the roots of Sophora flavescens; structure in first source		1.9910
glabrol
glabrol: from Glycyrrhiza glabra hairy root; structure in first source		2.1510flavanones
oxymatrine
oxymatrine: structure in first source; has anti-apoptosis effects		2.3110
kurarinone
kurarinone: cytotoxic lavandulyl flavanone from Sophora flavescens; structure in first source		2.0810
kuraridin
kuraridin: isolated from Sophora flavescens; structure in first source		1.9910
Kushenol A
kushenol A: a tyrosinase inhibitor derived from Sophora flavescens		2.5120flavanones
kurarinol
kurarinol: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source. kurarinol : A trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4' , a methoxy group at position 5 and a (2S)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl group at position 8 respectively.		7.71304'-hydroxyflavanones;
monomethoxyflavanone;
trihydroxyflavanone		anti-inflammatory agent;
antioxidant;
plant metabolite
leachianone a
leachianone A: isolated from the Chinese herbal medicine Radix Sophorae; structure in first source. leachianone A : A trihydroxyflavanone that is (2S)-flavanone substituted by a lavandulyl group at position 8, hydroxy groups at positions 5, 7 and 4' and a methoxy group at position 2'. Isolated from the roots of Sophora flavescens and Sophora leachiana, it exhibits antineoplastic and antimalarial activity.		2.47204'-hydroxyflavanones;
monomethoxyflavanone;
trihydroxyflavanone		antimalarial;
antineoplastic agent;
metabolite
ConditionIndicatedRelationship StrengthStudiesTrials
Congenital Zika Syndrome
[description not available]		02.2510
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.7220
Zika Virus Infection
A viral disease transmitted by the bite of AEDES mosquitoes infected with ZIKA VIRUS. Its mild DENGUE-like symptoms include fever, rash, headaches and ARTHRALGIA. The viral infection during pregnancy, in rare cases, is associated with congenital brain and ocular abnormalities, called Congenital Zika Syndrome, including MICROCEPHALY and may also lead to GUILLAIN-BARRE SYNDROME.		02.2510
Colitis Gravis
[description not available]		02.4110
Innate Inflammatory Response
[description not available]		02.4110
Colitis
Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.		07.4110
Colitis, Ulcerative
Inflammation of the COLON that is predominantly confined to the MUCOSA. Its major symptoms include DIARRHEA, rectal BLEEDING, the passage of MUCUS, and ABDOMINAL PAIN.		02.4110
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.		07.4110
Nasopharyngeal Carcinoma
A carcinoma that originates in the EPITHELIUM of the NASOPHARYNX and includes four subtypes: keratinizing squamous cell, non-keratinizing, basaloid squamous cell, and PAPILLARY ADENOCARCINOMA. It is most prevalent in Southeast Asian populations and is associated with EPSTEIN-BARR VIRUS INFECTIONS. Somatic mutations associated with this cancer have been identified in NPCR, BAP1, UBAP1, ERBB2, ERBB3, MLL2, PIK3CA, KRAS, NRAS, and ARID1A genes.		07.610
Cancer of Nasopharynx
[description not available]		02.610
Nasopharyngeal Neoplasms
Tumors or cancer of the NASOPHARYNX.		02.610
Cancer of Colon
[description not available]		02.2510
Colonic Neoplasms
Tumors or cancer of the COLON.		02.2510
Asthma, Bronchial
[description not available]		02.0810
Asthma
A form of bronchial disorder with three distinct components: airway hyper-responsiveness (RESPIRATORY HYPERSENSITIVITY), airway INFLAMMATION, and intermittent AIRWAY OBSTRUCTION. It is characterized by spasmodic contraction of airway smooth muscle, WHEEZING, and dyspnea (DYSPNEA, PAROXYSMAL).		02.0810
Muscle Contraction
A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.		07.0810
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
Cancer of Stomach
[description not available]		02.1310
Stomach Neoplasms
Tumors or cancer of the STOMACH.		02.1310
B16 Melanoma
[description not available]		02.0410