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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Tangeretin
PubChem CID 68077
Molecular Weight 372.4g/mol
Synonyms

4',5,6,7,8-pentamethoxy-flavone, 4',5,6,7,8-pentamethoxyflavone, tangeretin, tangeritin

Formula C₂₀H₂₀O₇
SMILES COC1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C(=C(C(=C3OC)OC)OC)OC
InChI 1S/C20H20O7/c1-22-12-8-6-11(7-9-12)14-10-13(21)15-16(23-2)18(24-3)20(26-5)19(25-4)17(15)27-14/h6-10H,1-5H3
InChIKey ULSUXBXHSYSGDT-UHFFFAOYSA-N
CAS Number 481-53-8
ChEMBL ID CHEMBL73930
ChEBI ID CHEBI:9400
Herb ID HBIN045469
KEGG ID C10190
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 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
Citrus reticulata Warm
Chineses Pinyin GanJu
Use Part Fruit; Peel; Juice
Habitat JiangSu, ZheJiang, AnHui, JiangXi, HuBei, HuNan, GuangDong, GuangXi, HaiNan, SiChuan, GuiZhou, YunNan, TaiWan
Flavor Sour
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Sapindales
    -->Family: Rutaceae
     -->Genus: Citrus
      -->Species: Citrus reticulata
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: 86
Pair Name Tangeretin, Metformin
Partner Name Metformin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->ROS accumulation
Gene Regulation Down-regulation Phosphorylation ABCB1 hsa5243
Down-regulation Phosphorylation ABCC1 hsa4363
Down-regulation Phosphorylation AKT1 hsa207
Up-regulation Cleavage CASP3 hsa836
Up-regulation Cleavage CASP7 hsa840
Down-regulation Expression CDK2 hsa1017
Down-regulation Expression CDK4 hsa1019
Down-regulation Phosphorylation MAPK1 hsa5594
Up-regulation Cleavage PARP1 hsa142
Up-regulation Phosphorylation PRKAA1 hsa5562
Up-regulation Activity ROS1 hsa6098
In Vitro Model MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
Result The current work underscores the importance of metformin as an ERMA in tackling breast cancer and as a novel approach to boost its anticancer activity via a synergistic combination with tangeretin.
Combination Pair ID: 645
Pair Name Tangeretin, Fluorouracil
Partner Name Fluorouracil
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->DNA damage
Gene Regulation Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Down-regulation Expression BID hsa637
Up-regulation Expression CASP9 hsa842
Down-regulation Expression MAP1LC3A hsa84557
Up-regulation Phosphorylation MAPK8 hsa5599
Up-regulation Cleavage PARP1 hsa142
Up-regulation Phosphorylation RB1 hsa5925
Up-regulation Phosphorylation TP53 hsa7157
Down-regulation Expression TXN KEGG ID N.A.
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
HCT 15 Colon adenocarcinoma Homo sapiens (Human) CVCL_0292
KM12-C Colon carcinoma Homo sapiens (Human) CVCL_9547
Result To our knowledge gained from literature, this study is the first to describe synergistic activity of TAN and 5-FU against colorectal cancer cells.
04. Reference
No. Title Href
1 Tangeretin boosts the anticancer activity of metformin in breast cancer cells via curbing the energy production. Phytomedicine. 2021 Mar;83:153470. doi: 10.1016/j.phymed.2021.153470. Click
2 Synergistic therapy with tangeretin and 5-fluorouracil accelerates the ROS/JNK mediated apoptotic pathway in human colorectal cancer cell. Food Chem Toxicol. 2020 Sep;143:111529. doi: 10.1016/j.fct.2020.111529. Click
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