tectorigenin: tectoridin is glycosylated form [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
tectorigenin : A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 5, 7 and 4' respectively. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 5281811 |
| CHEMBL ID | 242740 |
| CHEBI ID | 9429 |
| SCHEMBL ID | 351641 |
| MeSH ID | M0307112 |
| Synonym |
|---|
| 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4h-1-benzopyran-4-one |
| 855130h9co , |
| 5-18-05-00311 (beilstein handbook reference) |
| unii-855130h9co |
| KBIO1_001185 |
| DIVK1C_006241 |
| 4',5,7-trihydroxy-6-methoxyisoflavone |
| brn 0305601 |
| tectorigenine |
| 4',5',7-trihydroxy-6-methoxyisoflavone |
| 4h-1-benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy- |
| isoflavone, 4',5,7-trihydroxy-6-methoxy- |
| k 251t |
| SPECTRUM_000761 |
| 548-77-6 |
| tectorigenin |
| KBIO2_006377 |
| KBIO2_003809 |
| KBIO2_001241 |
| KBIOSS_001241 |
| SPECPLUS_000145 |
| bdbm50241222 |
| CHEMBL242740 , |
| chebi:9429 , |
| 5,7,4'-trihydroxy-6-methoxyisoflavone |
| LMPK12050385 |
| 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one |
| S9122 |
| FT-0688353 |
| AKOS015897084 |
| tectorigenin [mi] |
| 5,7-dihydroxy-3-(4-hydroxyphenyl)-6-methoxy-4h-chromen-4-one |
| SCHEMBL351641 |
| T3729 |
| Q-100619 |
| DTXSID50203286 |
| tectorigenin, analytical standard |
| mfcd00597094 |
| gtpl9738 |
| CS-0009804 |
| HY-N0792 |
| Q3517006 |
| CCG-267463 |
| A870334 |
| AS-56397 |
| EX-A6676 |
| 5,7-dihydroxy-3-(4-hydroxy-phenyl)-6-methoxy-chromen-4-one |
| r0u , |
| 3-(4-hydroxyphenyl)-6-methoxy-5,7-bis(oxidanyl)chromen-4-one |
Tectorigenin is a novel RAR-γ-selective agonist, which inhibits UV-induced oxidative damage, inflammatory factor release and matrix metalloproteinase (MMP) production. It is a more potent antiplatelet compound than ASA and thus an interesting substance for further testing.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Tectorigenin has received attention due to its antiproliferation, anti-inflammatory, and antioxidant activities. " | ( Tectorigenin protects against experimental fulminant hepatic failure by regulating the TLR4/mitogen-activated protein kinase and TLR4/nuclear factor-κB pathways and autophagy. Fan, L; Ji, F; Li, L; Ouyang, X; Wu, D; Xie, Z; Xu, K; Zhang, L; Zhao, Y, 2019) | 3.4 |
Tectorigenin could inhibit pulmonary fibrosis and airway inflammation through TGF-β1/Smad signalling pathway and TLR4/NF-κB signalling pathway. Also can inhibit inflammation-stimulated IRS-1 serine phosphorylation and restore impaired insulin PI3K signaling.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Tectorigenin could inhibit pulmonary fibrosis and airway inflammation through TGF-β1/Smad signalling pathway and TLR4/NF-κB signalling pathway. " | ( Tectorigenin inhibits inflammation and pulmonary fibrosis in allergic asthma model of ovalbumin-sensitized guinea pigs. Jing, W; Liu, L; Liu, Z; Qi, X; Qu, W; Wang, Y; Zhang, D, 2020) | 3.44 |
| "Tectorigenin also can inhibit inflammation-stimulated IRS-1 serine phosphorylation and restore the impaired insulin PI3K signaling, leading to a decreased NO production." | ( Tectorigenin Attenuates Palmitate-Induced Endothelial Insulin Resistance via Targeting ROS-Associated Inflammation and IRS-1 Pathway. Cheng, XL; Gao, XJ; Liu, BL; Liu, K; Qin, MJ; Qin, XY; Qin, Y; Wang, Q; Xie, GY; Zhang, DY; Zhou, L, 2013) | 2.55 |
Tectorigenin significantly reduced the levels of phosphorylated retinoblastoma protein (p-RB) and decreased the expression of cyclin-dependent protein 4 (CDK4) Treatment with tectorigen in alleviated intrahepatic cholestasis by inhibiting the recruitment and activation of hepatic macrophages.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Tectorigenin treatment also significantly enhanced the expression of p21, a CDK4 inhibitor." | ( Tectorigenin Inhibits Glioblastoma Proliferation by G0/G1 Cell Cycle Arrest. Chen, CJ; Chung, YH; Hsu, LS; Yeh, LT, 2020) | 2.72 |
| "Treatment with tectorigenin clearly reduced the levels of phosphorylated retinoblastoma protein (p-RB) and decreased the expression of cyclin-dependent protein 4 (CDK4)." | ( Tectorigenin Inhibits Glioblastoma Proliferation by G0/G1 Cell Cycle Arrest. Chen, CJ; Chung, YH; Hsu, LS; Yeh, LT, 2020) | 2.34 |
| "Treatment with tectorigenin alleviated intrahepatic cholestasis by inhibiting the recruitment and activation of hepatic macrophages and by promoting the expression of bile transporters via activation of PPARγ. " | ( Tectorigenin alleviates intrahepatic cholestasis by inhibiting hepatic inflammation and bile accumulation via activation of PPARγ. Jiang, L; Kang, L; Liang, Z; Ma, C; Tao, X; Wei, L; Wu, H; Xiang, J; Yang, G; Yang, S; Zhang, W, 2021) | 2.42 |
| "Pretreatment with tectorigenin significantly reduced the serum levels of alanine aminotransferase (ALT) and aspartate aminotransferase (AST), histological injury, apoptosis, and the mortality of FHF mice, by suppressing the production of inflammatory cytokines such as TNF-α and IL-6." | ( Tectorigenin protects against experimental fulminant hepatic failure by regulating the TLR4/mitogen-activated protein kinase and TLR4/nuclear factor-κB pathways and autophagy. Fan, L; Ji, F; Li, L; Ouyang, X; Wu, D; Xie, Z; Xu, K; Zhang, L; Zhao, Y, 2019) | 2.28 |
| "Treatment with tectorigenin inhibited the nuclear translocation of NFκB and the expression of NFκB-dependent genes such as FLIP, XIAP, Bcl-2, Bcl-xL and COX-2, which are known to be associated with chemoresistance." | ( Tectorigenin sensitizes paclitaxel-resistant human ovarian cancer cells through downregulation of the Akt and NFκB pathway. Choi, JH; Choi, YS; Kim, TJ; Lee, KT; Park, HJ; Shih, IeM; Yang, YI, 2012) | 2.16 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " in mice and no toxic symptoms were observed at doses up to 300 mg/kg in a subacute toxicity test during 28-day treatment." | ( Toxicity, analgesic and anti-inflammatory activities of tectorigenin. Dat, NT; Ha, le M; Huyen, do TT; Long, PQ; Que, do TN, 2013) | 0.64 |
| "We demonstrated that tectorigenin is a safe and promising analgesic and anti-inflammatory agent." | ( Toxicity, analgesic and anti-inflammatory activities of tectorigenin. Dat, NT; Ha, le M; Huyen, do TT; Long, PQ; Que, do TN, 2013) | 0.96 |
Tectorigenin is a metabolite of tectoridin. It exhibits poor bioavailability after oral administration of I. The main metabolic pathways in rats are glucuronidation, sulfation and demethylation.
| Excerpt | Reference | Relevance |
|---|---|---|
| " This method was successfully applied to a pharmacokinetic study of the three isoflavones after oral administration of Rhizoma Belamcandae extract to rats." | ( Simultaneous determination of tectorigenin, irigenin and irisflorentin in rat plasma and urine by UHPLC-MS/MS: application to pharmacokinetics. Gu, Y; Wang, R; Wang, XJ; Yang, WJ; Zhang, WD, 2011) | 0.66 |
| " Pharmacokinetic studies have demonstrated that the main metabolic pathways in rats for tectorigenin are glucuronidation, sulfation, demethylation and methoxylation, but that it exhibits poor bioavailability." | ( Tectorigenin: A Review of Its Sources, Pharmacology, Toxicity, and Pharmacokinetics. Du, D; Fu, F; Han, C; Rong, J; Wu, Y; Xia, Q, 2023) | 2.58 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "A novel methodology for the identification of tetorigenin and its metabolites in rat bile has been created using liquid chromatography (LC) combined with time-of-flight (TOF) and ion trap multiple mass spectrometry (IT-MSn)." | ( Identification of the major metabolites of tectorigenin in rat bile by liquid chromatography combined with time-of-flight and ion trap tandem mass spectrometry. Huang, WZ; Li, P; Qi, LW; Yang, XL; Yang, ZL; Zhang, WD, 2008) | 0.61 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " 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 |
| " To increase the aqueous solubility and oral bioavailability of TG, we prepared the solid dispersions of tectorigenin (TG-SD) using a simple solvent evaporation process with TG, polyvinylpyrrolidone (PVP) and PEG4000 at weight ratio of 7:54:9 after tested in several ratios." | ( Preparation, characterization and in vitro/vivo evaluation of tectorigenin solid dispersion with improved dissolution and bioavailability. Huang, Q; Lan, K; Shuai, S; Wang, W; Yang, J; Ye, L; Yue, S, 2016) | 0.89 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " at the same dosage for 10 days to ICR mice bearing sarcoma 180, caused a significant suppression in tumor weight by 44." | ( Anti-angiogenic and anti-tumor activities of isoflavonoids from the rhizomes of Belamcanda chinensis. Jung, SH; Kim, YS; Lee, S; Lee, YS; Lim, SS; Ohuchi, K; Shin, KH, 2003) | 0.32 |
| " Different dosage tectorigenin was added into VEC and the activity of VEC was observed by MTT colorimetry." | ( [Effect of tectorigenin on MCP-1 and ICAM-1 mRNA expression in injured vascular endothelial cells]. Hou, M; Wang, F; Wang, G; Wang, J; Wang, S; Yang, C; Zhang, Y, 2010) | 1.08 |
| " 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) | 0.79 |
| Role | Description |
|---|---|
| anti-inflammatory agent | Any compound that has anti-inflammatory effects. |
| plant metabolite | Any 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] | |
| Class | Description |
|---|---|
| 7-hydroxyisoflavones | A hydroxyisoflavone compound having a hydroxy group at the 7-position. |
| methoxyisoflavone | Members of the class of isoflavones with at least one methoxy 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] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Epidermal growth factor receptor | Homo sapiens (human) | IC50 (µMol) | 3.3000 | 0.0000 | 0.5369 | 10.0000 | AID378668 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID469799 | Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol after 96 hrs by alamar blue assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID469802 | Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol after 96 hrs by alamar blue assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID490349 | Antiallergic activity in human HMC1 cells assessed as inhibition of IgE FcgammaR1 receptor mRNA expression after 72 hrs by RT-PCR | 2010 | Bioorganic & medicinal chemistry letters, Jul-01, Volume: 20, Issue:13 | Inhibitors for expression of IgE receptor on human mast cell from Puerariae Flos. |
| AID469804 | Estrogenic activity in luciferase transfected human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by luciferase reporter gene assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID1507014 | Antiviral activity against Hepatitis B virus assessed as inhibition of HBsAg secretion | 2017 | European journal of medicinal chemistry, Aug-18, Volume: 136 | Design, synthesis and primary biological evaluation of the novel 2-pyridone derivatives as potent non-nucleoside HBV inhibitors. |
| AID469806 | Estrogenic activity in luciferase transfected human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by luciferase reporter gene assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID469800 | Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol after 96 hrs by alamar blue assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID377455 | Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by alamar blue assay | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines. |
| AID378668 | Inhibition of EGFR | 2006 | Journal of natural products, Jan, Volume: 69, Issue:1 | A common protein fold topology shared by flavonoid biosynthetic enzymes and therapeutic targets. |
| AID338974 | Inhibition of cow milk xanthine oxidase at 50 ug/mL | |||
| AID377457 | Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by alamar blue assay | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines. |
| AID469805 | Estrogenic activity in luciferase transfected human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by luciferase reporter gene assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID377458 | Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by alamar blue assay | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines. |
| AID469803 | Estrogenic activity in luciferase transfected human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 10 pM estradiol by luciferase reporter gene assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID377456 | Estrogenic activity in human MCF7 cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol by alamar blue assay | 2005 | Journal of natural products, Mar, Volume: 68, Issue:3 | Phenolic constituents of the rhizomes of the Thai medicinal plant Belamcanda chinensis with proliferative activity for two breast cancer cell lines. |
| AID469801 | Estrogenic activity in human T47D cells assessed as drug level causing stimulation of cell proliferation equivalent to 100 pM estradiol after 96 hrs by alamar blue assay | 2009 | Journal of natural products, Dec, Volume: 72, Issue:12 | Flavonoids from the heartwood of the Thai medicinal plant Dalbergia parviflora and their effects on estrogenic-responsive human breast cancer cells. |
| AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 4 (4.21) | 18.2507 |
| 2000's | 30 (31.58) | 29.6817 |
| 2010's | 41 (43.16) | 24.3611 |
| 2020's | 20 (21.05) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (27.89) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (1.04%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 95 (98.96%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||