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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Wogonin
PubChem CID 5281703
Molecular Weight 284.26g/mol
Synonyms

5,7-dihydroxy-8-methoxyflavone, wogonin

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 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
(1) Dictamnus dasycarpus Cold
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
(2) Scutellaria baicalensis Cold
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
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Drug(s) whose efficacy can be enhanced by this phytochemical
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Combination Pair ID: 491
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.
Drug(s) whose resistance can be reversed by this phytochemical
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Combination Pair ID: 884
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.
04. Reference
No. Title Href
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
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