β-Elemene
(Synonyms: β-榄香烯; (-)-β-Elemene; Levo-β-elemene) 目录号 : GC19537β-Elemene是从天然植物温郁金(Curcuma aromatica)中提取的一种单萜类化合物,具有抗肿瘤活性。
Cas No.:515-13-9
Sample solution is provided at 25 µL, 10mM.
β-Elemene is a monoterpenoid compound extracted from the natural plant Curcuma aromatica, which has antitumor activity[1]. β-Elemene has antiproliferative effects on multiple cancer cells mainly by inducing apoptosis and blocking the cell cycle[2]. β-Elemene is a RhoA kinase inhibitor[3].
In vitro, β-Elemene (0.5, 5, 50μM) pretreated human umbilical vein endothelial cells (HUVECs) for 24h, and the inhibition rates of H2O2-induced cytotoxicity were 59.7%, 75.1% and 86.2%, respectively, reducing the production of reactive oxygen species (ROS) and preventing the activation of mitogen-activated protein kinase (MAPK) signaling pathway in cells[4]. β-Elemene (0-320μg/mL) treated A549 cells for 24-72h inhibited cell growth in a dose- and time-dependent manner, with an IC50 value of 27.5μg/mL[5]. Treatment of H460 cells with β-Elemene (0-50μg/mL) for 24h or 48h inhibited cell growth and induced cell cycle arrest and apoptosis[6].
In vivo, β-Elemene (20, 50mg/kg) was intraperitoneally injected into B16F10 cell xenograft mice, inhibiting B16F10 melanoma lung metastasis and the expression of vascular endothelial growth factor (VEGF)[7].
References:
[1] Zhang Y, Peng F, Yu C. Therapeutic potential of Curcuma oil and its terpenoids in gynecological cancers[J]. Biomedicine & Pharmacotherapy, 2023, 157: 114016.
[2] Zhai B, Zhang N, Han X, et al. Molecular targets of β-elemene, a herbal extract used in traditional Chinese medicine, and its potential role in cancer therapy: A review[J]. Biomedicine & Pharmacotherapy, 2019, 114: 108812.
[3] Wang J, Li H, Yao Y, et al. β-Elemene enhances GAP-43 expression and neurite outgrowth by inhibiting RhoA kinase activation in rats with spinal cord injury[J]. Neuroscience, 2018, 383: 12-21.
[4] Liu M, Mao L, Daoud A, et al. β-elemene inhibits monocyte–endothelial cells interactions via reactive oxygen species/MAPK/NF-κB signaling pathway in vitro[J]. European journal of pharmacology, 2015, 766: 37-45.
[5] Liu Y, Jiang Z, Zhou Y, et al. β-elemene regulates endoplasmic reticulum stress to induce the apoptosis of NSCLC cells through PERK/IRE1α/ATF6 pathway[J]. Biomedicine & Pharmacotherapy, 2017, 93: 490-497.
[6] Wang G, Li X, Huang F, et al. Antitumor effect of β-elemene in non-small-cell lung cancer cells is mediated via induction of cell cycle arrest and apoptotic cell death[J]. Cellular and Molecular Life Sciences CMLS, 2005, 62: 881-893.
[7] Chen W, Lu Y, Wu J, et al. Beta-elemene inhibits melanoma growth and metastasis via suppressing vascular endothelial growth factor-mediated angiogenesis[J]. Cancer chemotherapy and pharmacology, 2011, 67: 799-808.
β-Elemene是从天然植物温郁金(Curcuma aromatica)中提取的一种单萜类化合物,具有抗肿瘤活性[1]。β-Elemene主要通过诱导细胞凋亡和阻滞细胞周期对多来源癌细胞具有抗增殖作用[2]。β-Elemene是一种RhoA激酶抑制剂[3]。
在体外,β-Elemene(0.5, 5, 50μM)预处理人脐静脉内皮细胞(HUVECs)24h,对H2O2诱导的细胞毒性的抑制率分别为59.7%、75.1%和86.2%,减少了活性氧(ROS)的产生,阻止了细胞中丝裂原活化蛋白激酶(MAPK)信号通路的激活[4]。β-Elemene(0-320μg/mL)处理A549细胞24-72h,以剂量和时间依赖性方式抑制了细胞的生长,IC50值为27.5μg/mL[5]。β-Elemene(0-50μg/mL)处理H460细胞24h或48h,抑制了细胞的生长,诱导了细胞周期停滞和细胞凋亡[6]。
在体内,β-Elemene(20,50mg/kg)通过腹腔注射治疗B16F10细胞异种移植小鼠,抑制了B16F10黑色素瘤肺转移,抑制了血管内皮生长因子(VEGF)的表达[7]。
Cell experiment [1]: | |
Cell lines | Human umbilical vein endothelial cells (HUVECs) |
Preparation Method | HUVECs were seeded in 96-well plates at a density of 5×103 cells/well. After 24h growth, HUVECs were pre-treated with β-Elemene (0.5, 5, 50μM) for 24h at 37°C in 5% CO2 incubator. Then, HUVECs were treated with 0.5mM H2O2 for 2h. After that MTT (0.5%, 20μL) was added to the medium and cells were further incubated for 4h. The supernatant was removed and 100μL DMSO was added to dissolve the precipitate. Finally, the absorbance was measured spectrophotometrically at 570nm. |
Reaction Conditions | 0.5, 5, 50μM; 24h |
Applications | The inhibition rates of β-Elemene (0.5, 5, and 50μM) on H2O2-induced cytotoxicity were 59.7%, 75.1%, and 86.2%, respectively, which can protect endothelial cells from H2O2-induced cytotoxicity. |
Animal experiment [2]: | |
Animal models | C57BL/6 mice |
Preparation Method | 2.5×105 B16F10 cells were injected subcutaneously into the left footpad of each 6-week-old female C57BL/6 mice. The mice were evenly divided in 4 groups (6 mice/group). Except mice of the control and untreated groups with 0.1mL of saline, other two groups were injected intraperitoneally with β-Elemene (20 and 50mg/kg) once a day, starting from the day after injection of the B16F10 cells into the footpad. This continued until the mice were killed. The length and width of the tumor were measured every day. Approximately 3 weeks later, when tumors in control group reached a diameter of 1cm3, the tumor-bearing legs were amputated along with the left popliteal lymph node. The primary melanoma was carefully separated from the legs for size analysis and then fixed with formalin for immunohistochemistry assay. After an additional 21 days, the mice were killed and autopsied to count the metastatic colonies in the bilateral lungs, and the lung of mice was stored at -80°C refrigerator for melanin measurement. In addition, the serum was prepared before the mice were killed and stored at -80°C refrigerator. |
Dosage form | 20、50mg/kg; i.p. |
Applications | β-Elemene inhibited primary melanoma growth and angiogenesis. β-Elemene inhibited B16F10 melanoma lung metastasis. β-Elemene inhibited VEGF in vivo. |
References: |
Cas No. | 515-13-9 | SDF | |
别名 | β-榄香烯; (-)-β-Elemene; Levo-β-elemene | ||
化学名 | (1S,2S,4R)-1-ethenyl-1-methyl-2,4-bis(1-methylethenyl)-cyclohexane | ||
Canonical SMILES | C=C[C@@]1(C)[C@H](C(C)=C)C[C@H](C(C)=C)CC1 | ||
分子式 | C15H24 | 分子量 | 204.4 |
溶解度 | DMF: 30 mg/mL;DMSO: 30 mg/mL;Ethanol: 30 mg/mL | 储存条件 | Store at -20°C, protect from light |
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1 mg | 5 mg | 10 mg | |
1 mM | 4.8924 mL | 24.4618 mL | 48.9237 mL |
5 mM | 0.9785 mL | 4.8924 mL | 9.7847 mL |
10 mM | 0.4892 mL | 2.4462 mL | 4.8924 mL |
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