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β-Elemene

Alias: β-Elemene; (-)-β-Elemene; Levo-β-elemene
Cat No.:V40349 Purity: ≥98%
β-Elemene ((-)-β-Elemene; Levo-β-elemene) is found in the natural plant Curcuma aromatica and has anti-tumor activity.
β-Elemene
β-Elemene Chemical Structure CAS No.: 515-13-9
Product category: Apoptosis
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
β-Elemene ((-)-β-Elemene; Levo-β-elemene) is found in the natural plant Curcuma aromatica and has anti-tumor activity. β-Elemene ((-)-β-Elemene; Levo-β-elemene; β-Elemen) can cause apoptosis.
β-Elemene is a natural sesquiterpene isolated from the plant Curcuma aromatica. With a molecular weight of 204.35 g/mol and a formula of C15H24, it has been studied for its potential anticancer, anti-inflammatory, and antioxidant properties. β-Elemene exerts cytotoxic effects on cancer cells by inducing apoptosis and inhibiting tumor growth. It has also shown promise in enhancing the efficacy of other chemotherapy drugs.
Biological Activity I Assay Protocols (From Reference)
Targets
β-Elemene does not have a single defined target but acts through multiple mechanisms. It induces cell apoptosis and inhibits tumor growth. It has been shown to enhance cisplatin-induced apoptosis in bladder cancer cells through the ROS-AMPK signaling pathway. Its anticancer effects are mediated through the induction of apoptosis and modulation of various signaling pathways involved in cell survival and proliferation.
ln Vitro
β-elemene (0 - 200 μg/mL; 24 hours) had IC50 values of 72.8 μg/mL; 47.4 against SV-HUC-1, T24, 5637, TCCSUP, J82, UMUC-3, RT4, and SW780 cells, respectively; 61.5 μg/mL; 3.661 μg/mL; 68 μg/mL; and 72.12 μg/mL[1]. β-elemene (0-75 μg/mL; 24 hours) caused a dose-dependent G1 workforce in T24 cells, significantly decreased the proportion of S phase, and started to diminish cell counts at 50 μg/ml with a considerable decrease at 75 μg/ml [1]. In T24 cells, β-elemene (50 μg/mL; 12 hours) upregulates the expression of p21 and p27 and duplicates the expression levels of p-STAT3 and cell cycle-related proteins, cyclin D1, CDK4, and CDK6 [1]. β-elemene readily increases cisplatin by triggering ROS-AMPK signaling (50 μg/mL; 24 hours).
In vitro, β-Elemene has demonstrated cytotoxic effects against various cancer cell lines by inducing apoptosis. It inhibits tumor cell growth. It has been shown to enhance the efficacy of other chemotherapy drugs, such as cisplatin, in bladder cancer cells. Its anti-inflammatory and antioxidant properties have also been reported. These activities make it a valuable compound for cancer research.
ln Vivo
In vivo, β-Elemene has shown antitumor activity in animal models. It can inhibit tumor growth and enhance the effects of other chemotherapeutics. Its ability to induce apoptosis and modulate signaling pathways translates to in vivo efficacy. The compound's natural origin and broad biological activities make it a subject of interest for developing new cancer therapies, though it is not currently approved as a drug in many countries.
Enzyme Assay
In vitro assays for β-Elemene typically involve cell viability and apoptosis assays. Cancer cell lines are treated with increasing concentrations of the compound, and cell viability is measured by MTT or CellTiter-Glo assays. Apoptosis is evaluated by Annexin V/PI staining and caspase-3/7 activity assays. The compound's effects on signaling pathways, such as ROS-AMPK, are assessed by Western blot.
Cell Assay
Cell Viability Assay[2]
Cell Types: T24, 5637, TCCSUP, J82, UM-UC-3, RT4 and SW780 cells
Tested Concentrations: 0, 6.25, 12.5, 25, 50, 100 Induced cells are sterile[1]. , 150 and 200 µg/ml
Incubation Duration: 24 hrs (hours)
Experimental Results: Inhibits the proliferation of RT4, SW780, J82, UMUC-3, TCCSUP, 5637 and T24 human bladder cancer cells and SV-HUC-1 human urothelial cells.
Cell cycle analysis[2]
Cell Types: T24 and 5637 Cell
Tested Concentrations: 0, 25, 50 and 75 µg/ml
Incubation Duration: 24 hrs (hours)
Experimental Results: The percentage of cells in S phase was induced in a dose-dependent manner.
Western Blot Analysis[2]
Cell Types: T24 Cell
Tested Concentrations: 50 µg/ml
Incubation Duration: 24 hrs (hours)
Experimental Results: Downregulation of p-STAT3 and cell cycle related proteins.
For in vitro cell-based assays, various cancer cell lines are cultured and treated with β-Elemene. Its effects on cell proliferation, apoptosis, and signaling pathways are evaluated. The compound's ability to enhance the cytotoxicity of other drugs, like cisplatin, is also tested in combination studies. Cell viability, apoptosis, and changes in protein expression are measured using standard assays.
Animal Protocol
In vivo animal studies with β-Elemene typically use mouse xenograft models of cancer. Tumors are implanted subcutaneously, and the compound is administered orally or intraperitoneally. Tumor growth inhibition is monitored. The compound can be used alone or in combination with other chemotherapeutics to assess its potential as an adjuvant therapy. Its effects on tumor apoptosis and signaling pathways are analyzed in harvested tumor tissues.
ADME/Pharmacokinetics
β-Elemene (CAS: 515-13-9) has a molecular weight of 204.35 g/mol and a molecular formula of C15H24. It is also known as (-)-β-Elemene or Levo-β-elemene. It is a colorless to pale yellow liquid that is insoluble in water but soluble in organic solvents. It is typically stored as a liquid and should be protected from light and heat. The compound is a natural product.
Toxicity/Toxicokinetics
β-Elemene is a natural product with a relatively low toxicity profile. It has been studied for its potential as an anticancer agent. Common side effects are not well-documented, but as a natural product, it may cause gastrointestinal irritation. It is not an FDA-approved drug. Standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Ross, S.A., and ElSohly, M.A. The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J. Nat. Prod. 59(1), 49-51 (1996).

[2]. β-elemene enhances cisplatin-induced apoptosis in bladder cancer cells through the ROS-AMPK signaling pathway.Oncol Lett. 2020 Jan;19(1):291-300.

Additional Infomation
(-)-β-elemene is the (-)-enantiomer of β-elemene, with a (1S,2S,4R)-configuration. It is an antitumor drug. β-elemene has been reported in Calypogeia muelleriana, Neolitsea aciculata, and other organisms with relevant data. β-elemene is one of the isomers of elemene, a lipid-soluble sesquiterpene, the active ingredient isolated from the traditional Chinese medicine Rhizoma zedoariae, possessing potential antitumor and chemopreventive activities. Although the exact mechanism of action of β-elemene is not fully elucidated, the drug appears to induce apoptosis through different mechanisms and, depending on the type of tumor cells involved, induce cell cycle arrest at different stages. β-elemene may make cancer cells more sensitive to other chemotherapeutic drugs. See also: Top of Cannabis indicum (partial).
β-Elemene is a natural sesquiterpene isolated from Curcuma aromatica. It has anticancer, anti-inflammatory, and antioxidant properties and can induce apoptosis in cancer cells. It has shown promise in enhancing the efficacy of other chemotherapy drugs. It is not an approved drug and is intended for research use only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C₁₅H₂₄
Molecular Weight
204.35
Exact Mass
204.188
CAS #
515-13-9
Related CAS #
515-13-9
PubChem CID
6918391
Appearance
Colorless to light yellow liquid
Density
0.862g/cm3
Boiling Point
252.1ºC at 760mmHg
Flash Point
98.3ºC
Index of Refraction
1.501
LogP
4.747
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
0
Rotatable Bond Count
3
Heavy Atom Count
15
Complexity
284
Defined Atom Stereocenter Count
3
SMILES
C=C[C@]1(C)CC[C@H](C[C@H]1C(=C)C)C(=C)C
InChi Key
OPFTUNCRGUEPRZ-QLFBSQMISA-N
InChi Code
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
Chemical Name
(1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(prop-1-en-2-yl)cyclohexane
Synonyms
β-Elemene; (-)-β-Elemene; Levo-β-elemene
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
Ethanol: ~50 mg/mL (~244.68 mM)
DMSO: ~50 mg/mL (~244.68 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (12.23 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.8936 mL 24.4678 mL 48.9356 mL
5 mM 0.9787 mL 4.8936 mL 9.7871 mL
10 mM 0.4894 mL 2.4468 mL 4.8936 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
Title:A Study on β-elemene as Maintain Treatment for Newly Diagnosed Malignant Gliomas
Status:Unknown status
updateDate:2018-02-23
Ctid:NCT02629757

Link: https://clinicaltrials.gov/ct2/show/NCT02629757

Conditions:Anaplastic Oligoastrocytoma|Anaplastic Astrocytoma|Glioblastoma
Interventions:β-elemene
Phase:Phase 3
Title:β-elemene Combine With EGFR-TKI for Advanced EGFR-TKI-resistant NSCLC
Status:Unknown status
updateDate:2017-04-21
Ctid:NCT03123484

Link: https://clinicaltrials.gov/ct2/show/NCT03123484

Conditions:Non Small Cell Lung Cancer
Interventions:EGFR-TKIs(Erlotinib, Gefitinib and Icotinib)
Phase:Phase 2
Biological Data
  • β-elemene (ELE) facilitates cisplatin-induced apoptosis by activating the AMPK signaling pathway. Oncol Lett . 2020 Jan;19(1):291-300.
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