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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Evodiamine
PubChem CID 442088
Molecular Weight 303.4g/mol
Synonyms

evodiamine, evodiamine, (S)-isomer, isoevodiamine

Formula C₁₉H₁₇N₃O
SMILES CN1C2C3=C(CCN2C(=O)C4=CC=CC=C41)C5=CC=CC=C5N3
InChI 1S/C19H17N3O/c1-21-16-9-5-3-7-14(16)19(23)22-11-10-13-12-6-2-4-8-15(12)20-17(13)18(21)22/h2-9,18,20H,10-11H2,1H3/t18-/m0/s1
InChIKey TXDUTHBFYKGSAH-SFHVURJKSA-N
CAS Number 518-17-2
ChEMBL ID CHEMBL463165
ChEBI ID CHEBI:4948
Herb ID HBIN026264
KEGG ID C09187
Structure 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
(1) Dendrobium nobile Cold
Chineses Pinyin ShiHu
Use Part Stem
Habitat GuangXi, GuiZhou, YunNan, HuBei
Flavor Sweet
Meridian Tropism Stomach, Kidney
Species
>Kingdom: Viridiplantae
 -->Phylum: Streptophyta
  -->Class: Equisetopsida
   -->Order: Asparagales
    -->Family: Orchidaceae
     -->Genus: Dendrobium
      -->Species: Dendrobium nobile
(2) Euodia rutaecarpa Hot
Chineses Pinyin WuZhuYu
Use Part Fruit
Habitat GuangDong, GuangXi, HaiNan, Hongkong , Shaanxi, GuiZhou, HuNan, YunNan, ZheJiang, SiChuan
Flavor Pungent, Bitter
Meridian Tropism Liver, Spleen, Stomach, Kidney
(3) Evodia austrosinensis Hot
Chineses Pinyin HuaNanWuZhuYu
Use Part Fruit
Habitat GuiZhou, GuangXi, HuNan, YunNan, Shaanxi, ZheJiang, SiChuan
Flavor Pungent, Bitter
Meridian Tropism Liver, Spleen, Stomach, Kidney
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: 21
Pair Name Evodiamine, Gemcitabine
Partner Name Gemcitabine
Disease Info [ICD-11: 2B62.Z] Tongue cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression BCL2 hsa596
Down-regulation Expression BCL-xL hsa598
Down-regulation Expression RELA hsa5970
In Vitro Model CAL-27 Tongue adenosquamous carcinoma Homo sapiens (Human) CVCL_1107
Tca8113 Human papillomavirus-related cervical adenocarcinoma Homo sapiens (Human) CVCL_6851
In Vivo Model CAL-27 cells (2×10⁶) were injected subcutaneously into the right armpit regions of nude mice.
Result The results of this study showed that EVO may inhibit cancer cells by suppressing NF-κB activity, and in combination with GEM, it may increase the chemosensitivity of tongue squamous cancer cells, thereby improving the treatment response.
Combination Pair ID: 22
Pair Name Evodiamine, Doxorubicin
Partner Name Doxorubicin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Down-regulation Expression BIRC2 hsa329
Down-regulation Expression BIRC5 hsa332
Up-regulation Activity CASP7 hsa840
Up-regulation Activity CASP9 hsa842
Down-regulation Expression KRAS hsa3845
Down-regulation Phosphorylation MAP2K7 hsa5609
Down-regulation Phosphorylation MAPK1 hsa5594
Up-regulation Activity PARP1 hsa142
Down-regulation Expression XIAP hsa331
In Vitro Model MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
Result Our results indicated that EVO enhanced the apoptotic action of DOX by inhibiting the Ras/MEK/ERK cascade and the expression of IAPs without inhibiting the expression and activity of P-glycoprotein (P-gp). Taken together, our data indicate that EVO, a natural product, may be useful applied alone or in combination with DOX for the treatment of resistant breast cancer.
04. Reference
No. Title Href
1 Evodiamine inactivates NF-κB and potentiates the antitumor effects of gemcitabine on tongue cancer both in vitro and in vivo. Onco Targets Ther. 2018;12:257-267. Published 2018 Dec 27. doi:10.2147/OTT.S181062 Click
2 Evodiamine synergizes with doxorubicin in the treatment of chemoresistant human breast cancer without inhibiting P-glycoprotein. PLoS One. 2014 May 15;9(5):e97512. doi: 10.1371/journal.pone.0097512. Click
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