Apigenin
| Name | Apigenin | ||
| PubChem CID | 5280443 | ||
| Molecular Weight | 270.24g/mol | ||
| Synonyms |
Apigenin |
||
| Formula | C₁₅H₁₀O₅ | ||
| SMILES | C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O)O)O | ||
| InChI | 1S/C15H10O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-7,16-18H | ||
| InChIKey | KZNIFHPLKGYRTM-UHFFFAOYSA-N | ||
| CAS Number | 8002-66-2 | ||
| ChEMBL ID | CHEMBL28 | ||
| ChEBI ID | CHEBI:18388 | ||
| Herb ID | HBIN016408 | ||
| Drug Bank ID | DB07352 | ||
| KEGG ID | C01477 | ||
| 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
|
|
| Chineses Pinyin | QinCai | ||
| Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Dicotyledoneae
-->Order: Apiales
-->Family: Apiaceae
-->Genus: Apium
-->Species: Apium graveliens
|
||
| Pair Name | Apigenin, Doxorubicin | |||
| Partner Name | Doxorubicin | |||
| Disease Info | [ICD-11: 2C82] | Prostate cancer | Investigative | |
| Biological Phenomena | Inhibition-->Cell migration | |||
| Gene Regulation | Down-regulation | Phosphorylation | AKT1 | hsa207 |
| Up-regulation | Expression | BAX | hsa581 | |
| Down-regulation | Expression | BCL-xL | hsa598 | |
| Up-regulation | Expression | CDKN1A | hsa1026 | |
| Up-regulation | Expression | CYCS | hsa54205 | |
| Down-regulation | Phosphorylation | MAPK1 | hsa5594 | |
| Down-regulation | Expression | MMP9 | hsa4318 | |
| Down-regulation | Phosphorylation | PIK3CA | hsa5290 | |
| Up-regulation | Expression | PSMD9 | hsa5715 | |
| Up-regulation | Expression | PTEN | hsa5728 | |
| Down-regulation | Expression | SNAI1 | hsa6615 | |
| Down-regulation | Expression | TWIST1 | hsa7291 | |
| In Vitro Model | PC-3 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0035 |
| Result | Co-administration of apigenin with doxorubicin enhances anti-migration and antiproliferative effects via PI3K/PTEN/AKT pathway in prostate cancer cells | |||
| Pair Name | Apigenin, Gefitinib | |||
| Partner Name | Gefitinib | |||
| Disease Info | [ICD-11: 2C25] | Lung cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Expression | EGFR | hsa1956 |
| Down-regulation | Expression | HIF1A | hsa3091 | |
| Down-regulation | Expression | MYC | hsa4609 | |
| Down-regulation | Activity | PRKAA1 | hsa5562 | |
| Down-regulation | Expression | SLC16A1 | hsa6566 | |
| In Vitro Model | NCI-H1975 | Lung adenocarcinoma | Homo sapiens (Human) | CVCL_1511 |
| Result | Apigenin Combined With Gefitinib Blocks Autophagy Flux and Induces Apoptotic Cell Death Through Inhibition of HIF-1α, c-Myc, p-EGFR, and Glucose Metabolism in EGFR L858R+T790M-Mutated H1975 Cells | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2C82] | Prostate cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| In Vitro Model | LNCaP | Prostate carcinoma | Homo sapiens (Human) | CVCL_0395 |
| DU145 | Prostate carcinoma | Homo sapiens (Human) | CVCL_0105 | |
| Result | Apigenin markedly augmented TRAIL-mediated apoptosis in prostate cancer cells | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2A90] | Anaplastic large cell lymphoma | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Expression | CFLAR | hsa8837 |
| Up-regulation | Expression | TNFRSF10B | hsa8795 | |
| In Vitro Model | Jurkat | Childhood T acute lymphoblastic leukemia | Homo sapiens (Human) | CVCL_0065 |
| SP+ | Healthy | Homo sapiens (Human) | CVCL_1Y11 | |
| Result | Apigenin breaks TRAIL resistance in HTLV-1-associated ATL by transcriptional down-regulation of c-FLIP, a key inhibitor of death receptor signaling, and by up-regulation of TRAIL receptor 2 (TRAIL-R2) | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Up-regulation | Cleavage | CASP3 | hsa836 |
| Up-regulation | Cleavage | CASP6 | hsa839 | |
| Up-regulation | Cleavage | CASP7 | hsa840 | |
| Up-regulation | Cleavage | CASP8 | hsa841 | |
| Up-regulation | Cleavage | CASP9 | hsa842 | |
| Up-regulation | Cleavage | PARP1 | hsa142 | |
| In Vitro Model | Huh-7 | Adult hepatocellular carcinoma | Homo sapiens (Human) | CVCL_0336 |
| Result | Apigenin sensitizes cells to TRAIL-induced apoptosis by activating both intrinsic and extrinsic apoptotic pathway-related caspases. The augmented apoptotic effect by TRAIL/apigenin combination was accompanied by triggering mitochondria-dependent signaling pathway, as indicated by Bax/Bcl-2 ratio up-regulation | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2D10.Z] | Thyroid cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Expression | AKT1 | hsa207 |
| Down-regulation | Expression | BCL2 | hsa596 | |
| Up-regulation | Phosphorylation | MAPK3 | hsa5595 | |
| Up-regulation | Cleavage | PARP1 | hsa142 | |
| In Vitro Model | 8505C | Thyroid gland anaplastic carcinoma | Homo sapiens (Human) | CVCL_1054 |
| CAL-62 | Thyroid gland anaplastic carcinoma | Homo sapiens (Human) | CVCL_1112 | |
| Result | Apigenin synergizes with TRAIL through regulation of Bcl2 family proteins in inducing cytotoxicity, and suppression of AKT potentiates synergistic cytotoxicity of apigenin with TRAIL in ATC cells | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2C25] | Lung cancer | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Expression | AKT1 | hsa207 |
| Up-regulation | Expression | BAD | hsa572 | |
| Up-regulation | Expression | BAX | hsa581 | |
| Down-regulation | Expression | BCL2 | hsa596 | |
| Down-regulation | Expression | BCL-xL | hsa598 | |
| Down-regulation | Expression | CDH13 | hsa1012 | |
| Down-regulation | Expression | MAPK3 | hsa5595 | |
| Up-regulation | Expression | TNFRSF10B | hsa8795 | |
| In Vitro Model | A-549 | Lung adenocarcinoma | Homo sapiens (Human) | CVCL_0023 |
| NCI-H1299 | Lung large cell carcinoma | Homo sapiens (Human) | CVCL_0060 | |
| Result | Apigenin enhances TRAIL-induced antitumor activity in NSCLC cells by APG via inhibition of the NF-kappaB, AKT and ERK prosurvival regulators | |||
| Pair Name | Apigenin, TNF-related apoptosis inducing ligand | |||
| Partner Name | TNF-related apoptosis inducing ligand | |||
| Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Up-regulation | Expression | TNFRSF10B | hsa8795 |
| In Vitro Model | Hep-G2 | Hepatoblastoma | Homo sapiens (Human) | CVCL_0027 |
| Result | Sub-toxic dose of apigenin sensitizes HepG2 cells to TRAIL through ERK-dependent up-regulation of TRAIL receptor DR5 | |||
| No. | Title | Href |
|---|---|---|
| 1 | Co-administration of apigenin with doxorubicin enhances anti-migration and antiproliferative effects via PI3K/PTEN/AKT pathway in prostate cancer cells. Exp Oncol. 2021 Jun;43(2):125-134. doi: 10.32471/exp-oncology.2312-8852.vol-43-no-2.16096. | Click |
| 2 | Apigenin Combined With Gefitinib Blocks Autophagy Flux and Induces Apoptotic Cell Death Through Inhibition of HIF-1α, c-Myc, p-EGFR, and Glucose Metabolism in EGFR L858R+T790M-Mutated H1975 Cells. Front Pharmacol. 2019 Mar 22;10:260. doi: 10.3389/fphar.2019.00260. | Click |
| 3 | Ethanolic Extract of Propolis Augments TRAIL-Induced Apoptotic Death in Prostate Cancer Cells. Evid Based Complement Alternat Med. 2011;2011:535172. doi: 10.1093/ecam/nep180. | Click |
| 4 | Wogonin and related natural flavones overcome tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) protein resistance of tumors by down-regulation of c-FLIP protein and up-regulation of TRAIL receptor 2 expression. J Biol Chem. 2012 Jan 2;287(1):641-649. doi: 10.1074/jbc.M111.286526. | Click |
| 5 | Apigenin Sensitizes Huh-7 Human Hepatocellular Carcinoma Cells to TRAIL-induced Apoptosis. Biomol Ther (Seoul). 2012 Jan;20(1):62-7. doi: 10.4062/biomolther.2012.20.1.062. | Click |
| 6 | Suppression of AKT Potentiates Synergistic Cytotoxicity of Apigenin with TRAIL in Anaplastic Thyroid Carcinoma Cells. Anticancer Res. 2015 Dec;35(12):6529-37. | Click |
| 7 | Apigenin potentiates TRAIL therapy of non-small cell lung cancer via upregulating DR4/DR5 expression in a p53-dependent manner. Sci Rep. 2016 Oct 18;6:35468. doi: 10.1038/srep35468. | Click |
| 8 | Sub-toxic dose of apigenin sensitizes HepG2 cells to TRAIL through ERK-dependent up-regulation of TRAIL receptor DR5. Mol Cells. 2013 Jan;35(1):32-40. doi: 10.1007/s10059-013-2175-2. | Click |
