5,7-dihydroxy-8-methoxyflavone, wogonin
Name | Wogonin | ||
PubChem CID | 5281703 | ||
Molecular Weight | 284.26g/mol | ||
Synonyms |
5,7-dihydroxy-8-methoxyflavone, wogonin |
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Formula | C₁₆H₁₂O₅ | ||
SMILES | COC1=C(C=C(C2=C1OC(=CC2=O)C3=CC=CC=C3)O)O | ||
InChI | 1S/C16H12O5/c1-20-15-12(19)7-10(17)14-11(18)8-13(21-16(14)15)9-5-3-2-4-6-9/h2-8,17,19H,1H3 | ||
InChIKey | XLTFNNCXVBYBSX-UHFFFAOYSA-N | ||
CAS Number | 632-85-9 | ||
ChEMBL ID | CHEMBL16171 | ||
ChEBI ID | CHEBI:10043 | ||
Herb ID | HBIN048372 | ||
KEGG ID | C10197 | ||
Structure |
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2D
MOL
3D
MOL
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Chineses Pinyin | BaiXianPi | ||
Use Part | Root Cortex | ||
Habitat | HeiLongJiang, JiLin, LiaoNing, NeiMengGu | ||
Flavor | Bitter | ||
Meridian Tropism | Spleen, Stomach, Bladder | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Sapindales
-->Family: Rutaceae
-->Genus: Dictamnus
-->Species: Dictamnus dasycarpus
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Chineses Pinyin | HuangQin | ||
Use Part | Root | ||
Habitat | HeiLongJiang, LiaoNing, NeiMengGu, HeBei, HeNan, GanSu, Shaanxi, ShanXi, ShanDong, SiChuan | ||
Flavor | Bitter | ||
Meridian Tropism | Lung; Large Intestine; Stomach; Small Intestine; Gallbladder | ||
Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Lamiales
-->Family: Lamiaceae
-->Genus: Scutellaria
-->Species: Scutellaria baicalensis
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Pair Name | Wogonin, Cisplatin | |||
Partner Name | Cisplatin | |||
Disease Info | Head and neck cancer | / | ||
Biological Phenomena | Induction-->ROS accumulation | |||
Gene Regulation | Up-regulation | Expression | / | KEGG ID N.A. |
Up-regulation | Expression | BAX | hsa581 | |
Up-regulation | Phosphorylation | MAPK8 | hsa5599 | |
Down-regulation | Expression | MCL1 | hsa4170 | |
Down-regulation | Expression | NFE2L2 | hsa4780 | |
Down-regulation | Expression | NQO1 | hsa1728 | |
Up-regulation | Cleavage | PARP1 | hsa142 | |
In Vitro Model | HN4-cisR | Cisplatin-resistant human head and neck cancer | Homo sapiens (Human) | N.A. |
HN9-cisR | Cisplatin-resistant human head and neck cancer | Homo sapiens (Human) | N.A. | |
In Vivo Model | AMC-HN4-cisR or HN9-cisR cells (5×10⁶) were injected subcutaneously into the flank. Tumor volumes and body weights were measured every 3 days. | |||
Result | Wogonin induced selective cell death by targeting the antioxidant defense mechanisms enhanced in the resistant HNC cells and activating cell death pathways involving PUMA and PARP. Hence, wogonin significantly sensitized resistant HNC cells to cisplatin both in vitro and in vivo. Wogonin is a promising anticancer candidate that induces ROS accumulation and selective cytotoxicity in HNC cells and can help to overcome cisplatin-resistance in this cancer. |
Pair Name | Wogonin, Doxorubicin | |||
Partner Name | Doxorubicin | |||
Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
Gene Regulation | Down-regulation | Expression | NFE2L2 | hsa4780 |
In Vitro Model | MCF-7(DOX/R) | Invasive breast carcinoma of no special type | Homo sapiens (Human) | CVCL_C4M9 |
Result | Wogonin reversed drug resistance and its reversal mechanism might be due to the suppression of Nrf2 signaling pathway, indicating the feasibility of using Nrf2 inhibitors to increase efficacy of chemotherapeutic drugs. |
No. | Title | Href |
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1 | Targeting Nrf2 with wogonin overcomes cisplatin resistance in head and neck cancer. Apoptosis. 2016;21(11):1265-1278. doi:10.1007/s10495-016-1284-8 | Click |
2 | Drug resistance associates with activation of Nrf2 in MCF-7/DOX cells, and wogonin reverses it by down-regulating Nrf2-mediated cellular defense response. Mol Carcinog. 2013;52(10):824-834. doi:10.1002/mc.21921 | Click |