| Properties | Information | |
|---|---|---|
| PhytoCAT-ID | PhytoCAT-1284 | |
| Phytochemical name or plant extracts | Biochanin A | |
| PMID | 17970592 | |
| Literature evidence | The coadministration of quercetin and EGCG significantly increased the BCA area under the plasma concentration vs time curve (AUC) in rats, after both iv and oral administration of BCA. | |
| IUPAC name | 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one | |
| Phytochemicals’ class or type of plant extracts | Flavonoid | |
| Source of phytochemicals or plant Extracts | Trifolium pratense | |
| Geographical availability | Afghanistan, Albania, Algeria, Altay, Austria, Azores, Baltic States, Belarus, Belgium, Bulgaria, Buryatiya, Canary Is., Central European Russia, Corse, Czechoslovakia, Denmark, East European Russia, East Himalaya, Finland, France, Føroyar, Germany, Great Britain, Greece, Hungary, India, Iran, Iraq, Ireland, Irkutsk, Italy, Kazakhstan, Kirgizstan, Krasnoyarsk, Krym, Madeira, Mongolia, Morocco, Nepal, Netherlands, North Caucasus, North European Russia, Northwest European R, Norway, Pakistan, Poland, Portugal, Romania, Sardegna, Sicilia, South European Russia, Spain, Sweden, Switzerland, Tadzhikistan, Transcaucasus, Tunisia, Turkey-in-Europe, Turkmenistan, Tuva, Ukraine, Uzbekistan, West Himalaya, West Siberia, Xinjiang, Yugoslavia | |
| Plant parts | NA | |
| Other cancers | Breast cancer, Cervical cancer, Lung cancer | |
| Target gene or protein | hTERT, c-MYC, Bcl-2, Ha-ras, QR, C3, COX7RP, p18, MSH2, NF2, WT1, ER?, miR-375, Aromatase | |
| Gene or Protein evidence | A collection of primary estrogen receptor (ER)-regulated genes by estradiol (E2), including hTERT, c-MYC, BCL2 and Ha-ras (oncogenic) and quinone reductase (QR), human complement 3 (C3) and COX7RP (non-oncogenic) were selected as marker genes for a MCF-7 cell-based endogenous gene expression assay, After treatment with biochanin A, ER, miR-375, and Bcl-2 expression was significantly upregulated. In this brief review, we summarize the studies on phytochemicals such as biochanin A, genistein, quercetin, isoliquiritigenin, resveratrol, and grape seed extracts related to their effect on the activation of breast cancer-associated aromatase promoters and discuss their aromatase inhibitory potential to be used as safer chemotherapeutic agents for specific hormone-dependent breast cancer. | |
| Target pathways | Inhibits P-gp-mediated cellular efflux in MCF-7 and MDA435/LCC6 cell lines Promotes ER?-positive cell proliferation through miR-375 activation and this mechanism is possibly involving in a miR-375 and ER? feedback loop, and causes upregulation in Bcl-2 expression Significantly increases uterin weight in mice (IN VIVO, in ovariectomized mice) Causes an increase in in a number of tumor suppressor genes (p18, MSH2, NF2, and WT1) in HMEC and MCF12A cells | |
| IC50 | 44.0+10.10 µM against MDA-MB-468 25 µM against MCF-7 | |
| Potency | Many of the tested flavonoids (including biochanin A, genistein, and epigallocatechin-3-gallate) significantly inhibited [3H]DHEAS uptake in a concentration-dependent manner in OATP1B1-expressing cells, with biochanin A being one of the most potent inhibitors with an IC50 of 11.3 +/- 3.22 microM." | |
| Cell line/ mice model | MCF-7, MDA435/LCC6 , MCF-7/ADR, T47-D, MDA-MB-468, MCF-7 MX100,SK-BR3,MCF12A HeLa, NCI-H460, HMEC | |
| Additional information | Potentiates doxorubicin cytotoxicity in P-gp positive cells Significantly decreases the IC50 value of DNM - daunomycin (DNM), a P-gp substrate, causes high increase in [3H]-DNM accumulation, increasing by 454.3 +/- 19.5% in the resistant cells, significantly decreases DNM efflux from MCF-7/ADR cells - may reverse MDR8. At 20-80 microM, sharply inhibits DNA synthesis in MDA-MB-231 cells, at 20-90 microM inhibits DNA synthesis by 50% in MCF-7 cells by inhibiting the P-gp function. Displays anti-estrogenic effects on E2-induced transcriptions of hTERT, c-MYC, BCL2 and Ha-ras (oncogenic) and quinone reductase (QR), human complement 3 (C3) and COX7RP (non-oncogenic) genes in a MCF-7 cell culture system Causes 11% apoptosis and growth inhibition in MDA-MB-468 cells Inhibits serum-stimulated growth in both T-47D and MCF-7 breast cancer cells at 10-100 microM Causes aromatase inhibition in MCF-7 breast tumor cells Exhibits significant inhibition (>50%) on BCRP in BCRP-MDCKII cells, which reduces the BCRP-mediated efflux of doxorubicin and temozolomide, accordingly increasing their cytotoxicity. At 20-80 microM, sharply inhibits DNA synthesis in MDA-MB-231 cells, at 20-90 microM inhibits DNA synthesis by 50% in MCF-7 cells Significantly inhibits [3H]DHEAS uptake in a concentration-dependent manner in OATP1B1-expressing cells Increases the cytotoxicity of mitoxantrone in BCRP-overexpressing breast cancer cells Significantly increases the intracellular level of mitoxantrone in both murine and human BCRP-expressing Madin-Darby canine kidney (MDCK) cells, has no impact on the concentration of mitoxantrone in plasma and most tissues collected (brain, heart, liver and lung), decreases the concentrations of mitoxantrone in spleen and kidney (IN VIVO) ERbeta-selective agonists of transcriptional repression and activation at physiological levels. The molecular mechanism for ERbeta selectivity by isoflavones involves their capacity to create an activation function-2 surface of ERbeta that has a greater affinity for coregulators than ERalpha. Potent BCRP inhibitor, producing significant increases in mitoxantrone accumulation at concentrations of 0.5 or 1.0 microM and in mitoxantrone cytotoxicity at a concentration of 2.5 microM. Synergistically increased the potency of 5-FU in both MCF-7 and MDA-MB231 cell lines, 5-FU/Bio-A combination causes 75% reduction in tumor volume after two treatment cycles (IN VIVO) due to Bio-A-mediated suppression of ER-?/Akt axis and the augmentation of 5-FU-mediated proapoptotic effects Inhibits aromatase enzyme activity and reduce mRNA expression in SK-BR3 cells | |
| PubChem ID | 5280373 | |
| Additional PMIDs | 12604704 16114498 35112408 25613180 16081670 10601582 15069695 15876415 19928832 21693041 11279159 22256760 9631496 17948189 10523716 24508860 17482226 24067281 17516862 17970592 23286459 9625730 23982890 15102949 15290869 26059153 31493543 9343831 17108059 10989984 20369276 20535833 8105867 | |
| Additional sources of information | https://powo.science.kew.org/taxon/urn:lsid:ipni.org:names:523575-1 | |
| Safety | NA |