3,3',4',5,7-pentahydroxyflavone, dikvertin, Quercetin
Name | Quercetin | ||
PubChem CID | 5280343 | ||
Molecular Weight | 302.23g/mol | ||
Synonyms |
3,3',4',5,7-pentahydroxyflavone, dikvertin, Quercetin |
||
Formula | C₁₅H₁₀O₇ | ||
SMILES | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O)O)O | ||
InChI | 1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H | ||
InChIKey | REFJWTPEDVJJIY-UHFFFAOYSA-N | ||
CAS Number | 117-39-5 | ||
ChEMBL ID | CHEMBL50 | ||
ChEBI ID | CHEBI:16243 | ||
Herb ID | HBIN041495 | ||
Drug Bank ID | DB04216 | ||
KEGG ID | C00389 | ||
Toxicity | Organism | Test Type | Route(Dose) |
rat | LD50 | intraperitoneal(165 mg/kg) | |
mouse | LD50 | intraperitoneal(254 mg/kg) | |
rat | LD50 | oral(322 mg/kg) | |
Structure |
Download
2D
MOL
3D
MOL
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Chineses Pinyin | JingDaJi | ||
Use Part | Root | ||
Habitat | JiangSu, SiChuan, JiangXi, GuangXi | ||
Flavor | Bitter | ||
Meridian Tropism | Lung, Spleen, Kidney | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Malpighiales
-->Family: Euphorbiaceae
-->Genus: Euphorbia
-->Species: Euphorbia pekinensis
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Chineses Pinyin | Cha | ||
Use Part | Tender leaf or tender bud | ||
Habitat | JiangSu, AnHui, ZheJiang, JiangXi, HuBei, SiChuan, GuiZhou, YunNan, Shaanxi | ||
Flavor | Sweet; Bitter | ||
Meridian Tropism | Lung; Stomach; Heart | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Ericales
-->Family: Theaceae
-->Genus: Camellia
-->Species: Camellia sinensis
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Pair Name | Quercetin, Cisplatin | |||
Partner Name | Cisplatin | |||
Disease Info | [ICD-11: 2C73] | Ovarian cancer | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Up-regulation | Cleavage | CASP3 | hsa836 |
Up-regulation | Cleavage | CASP7 | hsa840 | |
Up-regulation | Cleavage | CASP9 | hsa842 | |
Down-regulation | Phosphorylation | MTOR | hsa2475 | |
Up-regulation | Cleavage | PARP1 | hsa142 | |
Down-regulation | Phosphorylation | STAT3 | hsa6774 | |
Down-regulation | Expression | Trx1 | KEGG ID N.A. | |
Down-regulation | Expression | Trx2 | KEGG ID N.A. | |
Down-regulation | Expression | TrxR | KEGG ID N.A. | |
In Vitro Model | SK-OV-3 | Ovarian serous cystadenocarcinoma | Homo sapiens (Human) | CVCL_0532 |
SKOV-3/CDDP | Cisplatin-resistant ovarian serous cystadenocarcinoma | Homo sapiens (Human) | N.A. | |
Result | This study provides further new data for the mechanism by which the QU pre-treatment re-sensitizes SKOV-3/CDDP cells to cisplatin. |
Pair Name | Quercetin, Doxorubicin | |||
Partner Name | Doxorubicin | |||
Disease Info | [ICD-11: 2A60.Z] | Acute myeloid leukemia | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Down-regulation | Expression | ABCB1 | hsa5243 |
Down-regulation | Expression | BCL2 | hsa596 | |
Up-regulation | Expression | CASP3 | hsa836 | |
Up-regulation | Expression | CASP8 | hsa841 | |
Up-regulation | Expression | CASP9 | hsa842 | |
In Vitro Model | K-562 | Blast phase chronic myelogenous leukemia | Homo sapiens (Human) | CVCL_0004 |
Result | These findings demonstrated that quercetin is important in MDR and may be developed into a new reversal agent for cancer chemotherapy. |
Pair Name | Quercetin, Doxorubicin | |||
Partner Name | Doxorubicin | |||
Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Down-regulation | Expression | ABCB1 | hsa5243 |
In Vitro Model | MCF-7 | Invasive breast carcinoma of no special type | Homo sapiens (Human) | CVCL_0031 |
Result | These findings demonstrated that quercetin is important in MDR and may be developed into a new reversal agent for cancer chemotherapy. |
Pair Name | Quercetin, Doxorubicin | |||
Partner Name | Doxorubicin | |||
Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
Biological Phenomena | Inhibition-->ROS accumulation | |||
Gene Regulation | Up-regulation | Cleavage | CASP3 | hsa836 |
Down-regulation | Phosphorylation | MAPK1 | hsa5594 | |
Down-regulation | Expression | MMP9 | hsa4318 | |
Down-regulation | Expression | MYC | hsa4609 | |
In Vitro Model | MDA-MB-231 | Breast adenocarcinoma | Homo sapiens (Human) | CVCL_0062 |
In Vivo Model | Into the right hind limb of each nude mouse, 2×10⁶ 4 T1 TNBC cells were injected subcutaneously. One week later, the mice were randomly divided into four groups (n = 3): control group (0.9% saline); Que group (50 mg/kg Que); AC group (5 mg/kg Dox plus 50 mg/kg Cyc); and AC plus Que group (5 mg/kg Dox plus 50 mg/kg Cyc plus 50 mg/kg Que). | |||
Result | Que could attenuate AC-induced cardiotoxicity by inhibiting ROS accumulation and activating ERK1/2 pathway in cardiomyocytes, but interestingly, Que could enhance the antitumor activity of AC by inhibiting ROS accumulation and ERK1/2 pathway in TNBC cells. In addition,in vivo studies further confirmed that Que could enhance the chemotherapeutic effect of AC against TNBC while it reduced the injury of cardiotoxicity induced by AC |
Pair Name | Quercetin, Anti-PD-1 antibody | |||
Partner Name | Anti-PD-1 antibody | |||
Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
Biological Phenomena | Reshaped-->Tumor immune microenvironment | |||
Gene Regulation | Up-regulation | Expression | ARG1 | hsa383 |
Up-regulation | Expression | CD4 | hsa920 | |
Up-regulation | Expression | CD8A | hsa925 | |
Up-regulation | Expression | IFNG | hsa3458 | |
Up-regulation | Expression | IL10 | hsa3586 | |
Down-regulation | Expression | IL12A | hsa3592 | |
Down-regulation | Expression | IL1B | hsa3553 | |
Down-regulation | Expression | IL4 | hsa3565 | |
Down-regulation | Expression | IL6 | hsa3569 | |
Up-regulation | Expression | ITGAM | hsa3684 | |
Up-regulation | Expression | MMP9 | hsa4318 | |
Down-regulation | Expression | NFKBIA | hsa4792 | |
Down-regulation | Expression | RELA | hsa5970 | |
Up-regulation | Expression | TGFB1 | hsa7040 | |
Down-regulation | Expression | TLR4 | hsa7099 | |
Down-regulation | Expression | TNF | hsa7124 | |
In Vivo Model | Orthotopically transplanted HCC tumors in mice were treated with quercetin, anti-PD-1 antibody, or a combination of both therapies. | |||
Result | Quercetin/anti-PD-1 antibody combination therapy reshaped HCC tumor microenvironment in mice in parallel with regulating the GM and macrophage immunity. |
Pair Name | Quercetin, Docetaxel | |||
Partner Name | Docetaxel | |||
Disease Info | [ICD-11: 2C82] | Prostate cancer | Investigative | |
Biological Phenomena | Induction-->Proliferation and apoptosis | |||
In Vitro Model | DU145 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0105 |
PC-3 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0035 | |
Result | Combination Modality Using Quercetin to Enhance the Efficacy of Docetaxel in Prostate Cancer Cells |
Pair Name | Quercetin, Oxaliplatin | |||
Partner Name | Oxaliplatin | |||
Disease Info | [ICD-11: 2B91] | Colorectal cancer | Investigative | |
Gene Regulation | Up-regulation | Expression | BAX | hsa581 |
Down-regulation | Expression | BCL2 | hsa596 | |
Up-regulation | Cleavage | CASP3 | hsa836 | |
Up-regulation | Expression | CYCS | hsa54205 | |
Up-regulation | Cleavage | PARP1 | hsa142 | |
In Vitro Model | HCT 116 | Colon carcinoma | Homo sapiens (Human) | CVCL_0291 |
In Vivo Model | To generate HCT116 xenografts in BALB/c nude mice, 3×10⁶ HCT116 cells were subcutaneously injected into the left and right flanks of each mouse. | |||
Result | These findings suggest that the depletion of intracellular glutathione by quercetin and sulforaphane could strengthen the anti-cancer efficacy of oxaliplatin. |
Pair Name | Quercetin, Cyclophosphamide | |||
Partner Name | Cyclophosphamide | |||
Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
Biological Phenomena | Induction-->Immunomodulatory | |||
In Vitro Model | 4T1 | Malignant neoplasms of the mouse mammary gland | Mus musculus (Mouse) | CVCL_0125 |
In Vivo Model | 4T1 cells (5×10³) in 100 µL of phosphate-buffered saline (PBS) were injected into one axillary mammary fat pad per mouse of 5–6-week-old female immunocompetent BALB/c mice. | |||
Result | Complementarity between Microbiome and Immunity May Account for the Potentiating Effect of Quercetin on the Antitumor Action of Cyclophosphamide in a Triple-Negative Breast Cancer Model |
Pair Name | Quercetin, Docetaxel | |||
Partner Name | Docetaxel | |||
Disease Info | [ICD-11: 2E02] | Metastatic prostate cancer | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Down-regulation | Expression | ABCB1 | hsa5243 |
Down-regulation | Phosphorylation | AKT1 | hsa207 | |
Down-regulation | Expression | AR | hsa367 | |
Up-regulation | Expression | BAX | hsa581 | |
Down-regulation | Expression | BCL2 | hsa596 | |
Down-regulation | Expression | PIK3CA | hsa5290 | |
In Vitro Model | PC-3-R | Prostate carcinoma | Homo sapiens (Human) | CVCL_C0QS |
PC-3 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0035 | |
LNCaP | Prostate carcinoma | Homo sapiens (Human) | CVCL_0395 | |
In Vivo Model | 5×10⁵ PC-3 cells were suspended in 100 μL PBS, or 2×108 LNCaP cells were suspended in 100 μL of matrigel, while PBS mixture (1:1) were injected subcutaneously into the right axillary fossa of mice. | |||
Result | Quercetin reverses docetaxel resistance in prostate cancer via androgen receptor and PI3K/Akt signaling pathways |
Pair Name | Quercetin, Fluorouracil | |||
Partner Name | Fluorouracil | |||
Disease Info | [ICD-11: 2B90] | Colon cancer | Investigative | |
Biological Phenomena | Induction-->Apoptosis | |||
Gene Regulation | Down-regulation | Expression | HMOX1 | hsa3162 |
Down-regulation | Expression | NFE2L2 | hsa4780 | |
In Vitro Model | HCT 116 | Colon carcinoma | Homo sapiens (Human) | CVCL_0291 |
Result | Our results suggest that Que reverses 5-FU resistance in CC cells via modulating the Nrf2/HO-1 pathway. |
Pair Name | Quercetin, Fluorouracil | |||
Partner Name | Fluorouracil | |||
Disease Info | [ICD-11: 2B90] | Colon cancer | Investigative | |
In Vitro Model | HT-29 | Colon adenocarcinoma | Homo sapiens (Human) | CVCL_0320 |
In Vivo Model | Rats were assigned to two groups. The 5-FU/quercetin group received intraperitoneal quercetin (10 mg/kg) and the Tween was injected to the control group for 14 consecutive days. On the 15th day, both groups received 50 mg/kg of 5-FU. | |||
Result | Interaction of quercetin and 5-fluorouracil: cellular and pharmacokinetic study |
No. | Title | Href |
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1 | Interaction of quercetin and 5-fluorouracil: cellular and pharmacokinetic study. Toxicol Mech Methods. 2023 Nov;33(6):502-511. doi: 10.1080/15376516.2023.2188928. | Click |
2 | Potentiation of Cisplatin Cytotoxicity in Resistant Ovarian Cancer SKOV3/Cisplatin Cells by Quercetin Pre-Treatment. Int J Mol Sci. 2023;24(13):10960. Published 2023 Jun 30. doi:10.3390/ijms241310960 | Click |
3 | Quercetin enhances adriamycin cytotoxicity through induction of apoptosis and regulation of mitogen-activated protein kinase/extracellular signal-regulated kinase/c-Jun N-terminal kinase signaling in multidrug-resistant leukemia K562 cells. Mol Med Rep. 2015 Jan;11(1):341-8. doi: 10.3892/mmr.2014.2734. | Click |
4 | Quercetin potentiates the effect of adriamycin in a multidrug-resistant MCF-7 human breast-cancer cell line: P-glycoprotein as a possible target. Cancer Chemother Pharmacol. 1994;34(6):459-64. doi: 10.1007/BF00685655. | Click |
5 | Quercetin attenuates the cardiotoxicity of doxorubicin-cyclophosphamide regimen and potentiates its chemotherapeutic effect against triple-negative breast cancer. Phytother Res. 2022;36(1):551-561. doi:10.1002/ptr.7342 | Click |
6 | Quercetin/Anti-PD-1 Antibody Combination Therapy Regulates the Gut Microbiota, Impacts Macrophage Immunity and Reshapes the Hepatocellular Carcinoma Tumor Microenvironment. Front Biosci (Landmark Ed). 2023 Dec 1;28(12):327. doi: 10.31083/j.fbl2812327. | Click |
7 | Combination Modality Using Quercetin to Enhance the Efficacy of Docetaxel in Prostate Cancer Cells. Cancers (Basel). 2023 Jan 31;15(3):902. doi: 10.3390/cancers15030902. | Click |
8 | Quercetin-Induced Glutathione Depletion Sensitizes Colorectal Cancer Cells to Oxaliplatin. Foods. 2023 Apr 21;12(8):1733. doi: 10.3390/foods12081733. | Click |
9 | Complementarity between Microbiome and Immunity May Account for the Potentiating Effect of Quercetin on the Antitumor Action of Cyclophosphamide in a Triple-Negative Breast Cancer Model. Pharmaceuticals (Basel). 2023 Oct 6;16(10):1422. doi: 10.3390/ph16101422. | Click |
10 | Quercetin reverses docetaxel resistance in prostate cancer via androgen receptor and PI3K/Akt signaling pathways. Int J Biol Sci. 2020 Feb 10;16(7):1121-1134. doi: 10.7150/ijbs.41686. | Click |
11 | Quercetin reverses 5-fluorouracil resistance in colon cancer cells by modulating the NRF2/HO-1 pathway. Eur J Histochem. 2023 Aug 7;67(3):3719. doi: 10.4081/ejh.2023.3719. | Click |