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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Emodin
PubChem CID 3220
Molecular Weight 270.24g/mol
Synonyms

Archin, Casanthranol, Emodin, Emodin, Frangula, Emodin, Rheum, Frangula Emodin, Frangulic Acid, Peristim, Rheum Emodin

Formula C₁₅H₁₀O₅
SMILES CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
InChI 1S/C15H10O5/c1-6-2-8-12(10(17)3-6)15(20)13-9(14(8)19)4-7(16)5-11(13)18/h2-5,16-18H,1H3
InChIKey RHMXXJGYXNZAPX-UHFFFAOYSA-N
CAS Number 518-82-1
ChEMBL ID CHEMBL289277
ChEBI ID CHEBI:42223
Herb ID HBIN025041
Drug Bank ID DB07715
KEGG ID C10343
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
Rheum palmatum Cold
Chineses Pinyin ZhangYeDaHuang
Use Part Root and rhizome
Habitat GanSu, SiChuan, QingHai, YunNan, XiZang
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Caryophyllales
    -->Family: Polygonaceae
     -->Genus: Rheum
      -->Species: Rheum palmatum
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: 289
Pair Name Emodin, Vinblastine
Partner Name Vinblastine
Disease Info [ICD-11: 2C77] Cervical cancer Investigative
Biological Phenomena Induction-->Blockade of cell cycle in G2/M phase
Gene Regulation Down-regulation Activity ATM hsa472
Down-regulation Expression BCL2 hsa596
Up-regulation Activity CASP3 hsa836
Up-regulation Activity CASP7 hsa840
Up-regulation Expression ROS1 hsa6098
In Vitro Model HeLa Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_0030
Result Emodin Sensitizes Cervical Cancer Cells to Vinblastine by Inducing Apoptosis and Mitotic Death
Combination Pair ID: 290
Pair Name Emodin, Doxorubicin
Partner Name Doxorubicin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->DNA damage
Gene Regulation Down-regulation Expression AKT1 hsa207
Down-regulation Expression PARP1 hsa142
Down-regulation Expression RAD51 hsa5888
Up-regulation Expression TP53 hsa7157
Down-regulation Expression XRCC1 hsa7515
In Vitro Model MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
Result Emodin Interferes With AKT1-Mediated DNA Damage and Decreases Resistance of Breast Cancer Cells to Doxorubicin
Combination Pair ID: 291
Pair Name Emodin, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C25] Lung cancer Investigative
Biological Phenomena Induction-->DNA damage
Gene Regulation Down-regulation Expression ABCB1 hsa5243
In Vitro Model A-549 Lung adenocarcinoma Homo sapiens (Human) CVCL_0023
NCI-H460 Lung large cell carcinoma Homo sapiens (Human) CVCL_0459
Result The results from the present study demonstrated that emodin can increase A549 and H460 cell sensitivity to cisplatin by inhibiting Pgp expression. Emodin may therefore be considered as an effective adjuvant for cisplatin treatment.
Combination Pair ID: 729
Pair Name Emodin, Cytarabine
Partner Name Cytarabine
Disease Info [ICD-11: 2A60.Z] Acute myeloid leukemia Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Phosphorylation AKT1 hsa207
Up-regulation Expression BAX hsa581
Down-regulation Expression BCL2 hsa596
Down-regulation Expression BID hsa637
Up-regulation Cleavage CASP3 hsa836
Down-regulation Phosphorylation MAPK1 hsa5594
Down-regulation Phosphorylation MAPK3 hsa5595
Down-regulation Phosphorylation MTOR hsa2475
Down-regulation Phosphorylation RPS6KB1 hsa6198
In Vitro Model HL-60 Adult acute myeloid leukemia Homo sapiens (Human) CVCL_0002
ARAC-8C Childhood T acute lymphoblastic leukemia Homo sapiens (Human) CVCL_GZ09
Jurkat Childhood T acute lymphoblastic leukemia Homo sapiens (Human) CVCL_0065
MOLT-4 Adult T acute lymphoblastic leukemia Homo sapiens (Human) CVCL_0013
CA46 Burkitt lymphoma Homo sapiens (Human) CVCL_1101
In Vivo Model Around 1.5×10⁷ HL-60/H3 cells were subcutaneously injected into the right flank of BALB/C-nude mice.
Result Emodin and its combination with Ara-C may be considered a promising therapeutic approach in AML and worthy of further investigation.
Combination Pair ID: 730
Pair Name Emodin, Gemcitabine
Partner Name Gemcitabine
Disease Info [ICD-11: 2C10] Pancreatic cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression CDH13 hsa1012
Down-regulation Expression NFKB1 hsa4790
Down-regulation Expression XIAP hsa331
In Vitro Model SW1990 Pancreatic adenocarcinoma Homo sapiens (Human) CVCL_1723
Result This study suggests that emodin enhances the antitumor effect of gemcitabine in SW1990 pancreatic cancer in vitro and in vivo, which may be via the downregulation of NF-κB expression, thus inhibiting the expression of XIAP.
Combination Pair ID: 740
Pair Name Emodin, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Inhibition-->Cell metastasis
Gene Regulation Up-regulation Expression CDH1 hsa999
Down-regulation Expression MMP2 hsa4313
Down-regulation Expression MMP9 hsa4318
Down-regulation Expression VIM hsa7431
In Vitro Model Hep-G2 Hepatoblastoma Homo sapiens (Human) CVCL_0027
Result We found that emodin inhibited hepatocellular carcinoma (HCC) metastasis. Compared with either cisplatin or emodin alone, the combination of both showed a more significant synergistic effect. Emodin can enhance the sensitivity of HepG2 HCC cells to cisplatin by inhibiting epithelial-mesenchymal transition, and thus, play a role in preventing recurrence and metastasis in HCC.
Combination Pair ID: 844
Pair Name Emodin, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C94] Bladder cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression GSS hsa2937
Down-regulation Expression MRP1 KEGG ID N.A.
Up-regulation Expression ROS1 hsa6098
In Vitro Model T24 Bladder carcinoma Homo sapiens (Human) CVCL_0554
In Vivo Model 3×10⁶ T24 cells were harvested, washed, and resuspended in serum-free optimum medium and then injected subcutaneously into 6-week old BALB/c-nu/nu mice
Result This study revealed that emodin could increase the cisplatin-induced cytotoxicity against T24 and J82 cells via elevating the cellular ROS level and downregulating MRP1 expression. We suggest that emodin could serve as an effective adjuvant agent for the cisplatin-based chemotherapy of bladder cancer
04. Reference
No. Title Href
1 Emodin Sensitizes Cervical Cancer Cells to Vinblastine by Inducing Apoptosis and Mitotic Death. Int J Mol Sci. 2022 Jul 31;23(15):8510. doi: 10.3390/ijms23158510. Click
2 Emodin interferes with AKT1-mediated DNA damage and decreases resistance of breast cancer cells to doxorubicin. Front Oncol. 2023 Dec 7;13:1337635. doi: 10.3389/fonc.2023.1337635. Click
3 Emodin enhances cisplatin sensitivity in non-small cell lung cancer through Pgp downregulation. Oncol Lett. 2021 Mar;21(3):230. doi: 10.3892/ol.2021.12491. Click
4 Emodin and Its Combination with Cytarabine Induce Apoptosis in Resistant Acute Myeloid Leukemia Cells in Vitro and in Vivo. Cell Physiol Biochem. 2018;48(5):2061-2073. doi: 10.1159/000492544. Click
5 Enhanced antitumor efficacy by the combination of emodin and gemcitabine against human pancreatic cancer cells via downregulation of the expression of XIAP in vitro and in vivo. Int J Oncol. 2011 Nov;39(5):1123-31. doi: 10.3892/ijo.2011.1115. Click
6 Effect of emodin combined with cisplatin on the invasion and migration of HepG2 hepatoma cells. J Physiol Pharmacol. 2023 Aug;74(4). doi: 10.26402/jpp.2023.4.04. Click
7 Emodin enhances cisplatin-induced cytotoxicity in human bladder cancer cells through ROS elevation and MRP1 downregulation. BMC Cancer. 2016;16:578. Published 2016 Aug 2. doi:10.1186/s12885-016-2640-3 Click
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