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Natural Product (NP) Details

General Information of the NP (ID: NP7102)
Name
Elemene
Synonyms
Cyclohexane, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1R,2R,4S)-rel-; 33880-83-0; beta-Elemene, (-)-; (- )-bete-elemene; EINECS 251-713-0; AC1L1VID; Cyclohexane, 2,4-diisopropenyl-1-methyl-1-vinyl-, (1S,2S,4R)-; OPFTUNCRGUEPRZ-UHFFFAOYSA-N; Cyclohexane, 1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-, (1S-(1-alpha,2-beta,4-beta))-; (1alpha,2beta,4beta)-1-Methyl-2,4-bis(methylvinyl)-1-vinylcyclohexane; LS-56795; EN300-296339; 1-Methyl-1-vinyl-2,4-diisopropenylcyclohexane
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Species Origin Pogostemon cablin ...     Click to Show/Hide
Pogostemon cablin
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Lamiales
Family: Lamiaceae
Genus: Pogostemon
Species: Pogostemon cablin
Atractylodes lancea
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Asterales
Family: Asteraceae
Genus: Atractylodes
Species: Atractylodes lancea
Abutilon indicum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Malvales
Family: Malvaceae
Genus: Abutilon
Species: Abutilon indicum
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Phase 1 [1]
Structure
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2D MOL

3D MOL

    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C15H24
PubChem CID
6918391
Canonical SMILES
CC(=C)C1CCC(C(C1)C(=C)C)(C)C=C
InChI
1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,13-14H,1-2,4,8-10H2,3,5-6H3/t13-,14+,15-/m1/s1
InChIKey
OPFTUNCRGUEPRZ-QLFBSQMISA-N
CAS Number
CAS 33880-83-0
Herb ID
HBIN024973
ETMC ID
991
SymMap ID
SMIT18326
TTD Drug ID
D04VMG
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP7  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression XIAP  Molecule Info 
Pathway MAP
                    Biological
                    Regulation
Up-regulation Cytochrome c release
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)
beta-Elemene increases cisplatin chemosensitivity of lung tumor cells by triggering apoptosis.
          Temozolomide      Brain cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ATM  Molecule Info 
Pathway MAP
Down-regulation Expression ERK1  Molecule Info 
Pathway MAP
Down-regulation Expression H2AFX  Molecule Info 
Pathway MAP
                    In-vitro Model U-87MG ATCC CVCL_0022 Glioblastoma Homo sapiens
T98G CVCL_0556 Glioblastoma Homo sapiens
U-251MG CVCL_0021 Astrocytoma Homo sapiens
LN-229 CVCL_0393 Glioblastoma Homo sapiens
C6 CVCL_0194 Rat malignant glioma Rattus norvegicus
                    Experimental
                    Result(s)
Beta-elemene enhances both radiosensitivity and chemosensitivity of glioblastoma cells through the inhibition of the ATM signaling pathway.
          Cetuximab      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression CDH1  Molecule Info 
Pathway MAP
Up-regulation Expression CDH1  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
Down-regulation Expression GLS2  Molecule Info 
Pathway MAP
Down-regulation Expression GPX4  Molecule Info 
Pathway MAP
Down-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Up-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
Down-regulation Expression SLC40A1  Molecule Info 
Pathway MAP
Down-regulation Expression SLC7A11  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI1  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI2  Molecule Info 
Pathway MAP
Down-regulation Expression TF  Molecule Info 
Pathway MAP
Up-regulation Expression TF  Molecule Info 
Pathway MAP
Down-regulation Expression VIM  Molecule Info 
Pathway MAP
                    In-vitro Model HCT 116 CVCL_0291 Colon carcinoma Homo sapiens
                    In-vivo Model A volume of 100 ul HCT116-luc cells suspension (2.5*106 cells/ml) was injected subcutaneously into right dorsal flank of mice (5-week-old female BALB/c nude mice).
                    Experimental
                    Result(s)
Combinative treatment of Beta-elemene and cetuximab is sensitive to KRAS mutant colorectal cancer cells by inducing ferroptosis and inhibiting epithelial-mesenchymal transformation.
          DC/Dribble vaccine      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression IFNG  Molecule Info 
Pathway MAP
                    In-vitro Model BNL1MEA.7R.1 Hepatocellular carcinoma Rattus norvegicus
                    Experimental
                    Result(s)
Beta-elemene combined DC/Dribble vaccine could induce specific immune cells to secrete secretory cells, thus exerting its anti-tumor effect.
          Gefitinib      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression CDH1  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
Up-regulation Expression HES1  Molecule Info 
Pathway MAP
Up-regulation Expression MYC  Molecule Info 
Pathway MAP
Up-regulation Expression NOTCH1  Molecule Info 
Pathway MAP
Up-regulation Expression SHH  Molecule Info 
Pathway MAP
Down-regulation Expression SNAI1  Molecule Info 
Pathway MAP
Up-regulation Expression SOX2  Molecule Info 
Pathway MAP
Down-regulation Expression TWIST1  Molecule Info 
Pathway MAP
Down-regulation Expression VIM  Molecule Info 
Pathway MAP
Down-regulation Expression ZEB1  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
                    Experimental
                    Result(s)
Beta-Elemene synergizes with gefitinib to inhibit stem-like phenotypes and progression of lung cancer via down-regulating EZH2.
          TNF-related apoptosis inducing ligand      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Up-regulation Expression FADD  Molecule Info 
Pathway MAP
Up-regulation Expression PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model BGC-823 CVCL_3360 Gastric cancer Homo sapiens
SGC-7901 CVCL_0520 Human gastric cancer Homo sapiens
                    Experimental
                    Result(s)
Beta-elemene increases the sensitivity of gastric cancer cells to TRAIL by promoting the formation of DISC in lipid rafts.
          Rapamycin      Multiple myeloma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
                    In-vitro Model FTC-133 CVCL_1219 Thyroid gland follicular carcinoma Homo sapiens
                    Experimental
                    Result(s)
The novel combination of mTOR inhibitor with Beta-elemene synergistically attenuates tumor cell growth in follicular thyroid cancer, which requires additional preclinical validation.
          5-fluorouracil      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation c-RAF  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation CYB5R2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Down-regulation Expression PIK3R1  Molecule Info 
Pathway MAP
                    In-vitro Model BT-549 CVCL_1092 Invasive breast carcinoma Homo sapiens
MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    In-vivo Model MDA-MB-231 cells (5*106 cells in 100 uL of PBS) were subcutaneously injected to the left flank of femal nude mice.
                    Experimental
                    Result(s)
Beta-Elemene enhances the chemotherapeutic effect of 5-Fluorouracil in triple-negative breast cancer via PI3K/AKT, RAF-MEK-ErK, and NF-KappaB signaling pathways.
          Etoposide      Testicular carcinoma     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [10]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)
Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells.
    β. A List of Drug(s) Whose Resistance can be Reversed by This NP
          Oxaliplatin      Colorectal cancer     Click to Show/Hide the Molecular Data of This Drug
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [11]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BECN1  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Up-regulation Expression MAP1LC3A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PAEP  Molecule Info 
Pathway MAP
                    In-vitro Model MHCC97-H CVCL_4972 Adult hepatocellular carcinoma Homo sapiens
HCCLM3 CVCL_6832 Adult hepatocellular carcinoma Homo sapiens
                    In-vivo Model Human HCC cell line MHCC97H were used to estabolish xenograft models in the BALB/c mice.
                    Experimental
                    Result(s)
Beta-elemene sensitizes hepatocellular carcinoma cells to oxaliplatin by preventing oxaliplatin-induced degradation of copper transporter 1.
References
Reference 1 ClinicalTrials.gov (NCT01679847) Blood Brain Barrier Penetration and Pharmacokinetics of the Elemene in Malignant Patients.. U.S. National Institutes of Health.
Reference 2 beta-Elemene, a novel plant-derived antineoplastic agent, increases cisplatin chemosensitivity of lung tumor cells by triggering apoptosis. Oncol Rep. 2009 Jul;22(1):161-70.
Reference 3 Beta-elemene enhances both radiosensitivity and chemosensitivity of glioblastoma cells through the inhibition of the ATM signaling pathway. Oncol Rep. 2015 Aug;34(2):943-51.
Reference 4 Combinative treatment of beta-elemene and cetuximab is sensitive to KRAS mutant colorectal cancer cells by inducing ferroptosis and inhibiting epithelial-mesenchymal transformation. Theranostics. 2020 Apr 6;10(11):5107-5119.
Reference 5 [Treatment of hepatic cancer in mice by beta-elemene combined DC/Dribble vaccine: an immune mechanism research]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2013 Feb;33(2):214-9.
Reference 6 Beta-Elemene Synergizes With Gefitinib to Inhibit Stem-Like Phenotypes and Progression of Lung Cancer via Down-Regulating EZH2. Front Pharmacol. 2018 Nov 30;9:1413.
Reference 7 Beta-elemene increases the sensitivity of gastric cancer cells to TRAIL by promoting the formation of DISC in lipid rafts. Cell Biol Int. 2018 Sep;42(10):1377-1385.
Reference 8 Combinatorial Antitumor Effect of Rapamycin and Beta-Elemene in Follicular Thyroid Cancer Cells. Biomed Res Int. 2016;2016:6723807.
Reference 9 beta-Elemene Enhances the Chemotherapeutic Effect of 5-Fluorouracil in Triple-Negative Breast Cancer via PI3K/AKT, RAF-MEK-ErK, and NF-kappaB Signaling Pathways. Onco Targets Ther. 2020 Jun 9;13:5207-5222.
Reference 10 Synergistic antitumor effect of Beta-elemene and etoposide is mediated via induction of cell apoptosis and cell cycle arrest in non-small cell lung carcinoma cells. Mol Med Rep. Nov-Dec 2011;4(6):1189-93.
Reference 11 Beta-elemene sensitizes hepatocellular carcinoma cells to oxaliplatin by preventing oxaliplatin-induced degradation of copper transporter 1. Sci Rep. 2016 Feb 12;6:21010.
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Cite NPCDR
Visitor Map
Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China