Umbelliprenin
(Synonyms: 7-Farnesyloxycoumarin) 目录号 : GC48659
A prenylated coumarin with diverse biological activities
Cas No.:532-16-1
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Umbelliprenin is a prenylated coumarin that has been found in Ferula and has diverse biological activities.1,2 It inhibits 5-lipoxygenase (5-LO) in a cell-free assay (IC50 = 72.5 nM).1 Umbelliprenin is active against L. major promastigotes (IC50 = 13.3 µM) and lethal to A. albopictus fourth instar larvae (LC50 = 194.96 ppm). It induces cell cycle arrest at the G1 phase in, as well as inhibits the growth of (IC50 = 12.5 µM), M4Beu metastatic pigmented melanoma cells and reduces tumor volume in a mouse Lewis lung carcinoma model. It reduces tumor growth and the number of metastases in a 4T1 mouse allograft model.2 Umbelliprenin (0.01 mmol/kg) reduces carrageenan-induced paw edema in mice.1
1.Shakeri, A., Iranshahy, M., and Iranshahi, M.Biological properties and molecular targets of umbelliprenin--a mini-reviewJ. Asian Nat. Prod. Res.16(8)884-889(2014) 2.Rashidi, M., Khalilnezhad, A., Amani, D., et al.Umbelliprenin shows antitumor, antiangiogenesis, antimetastatic, anti-inflammatory, and immunostimulatory activities in 4T1 tumor-bearing Balb/c miceJ. Cell. Physiol.233(11)8908-8918(2018)
| Cas No. | 532-16-1 | SDF | |
| 别名 | 7-Farnesyloxycoumarin | ||
| Canonical SMILES | C/C(C)=C/CC/C(C)=C/CC/C(C)=C/COC1=CC=C(C=CC(O2)=O)C2=C1 | ||
| 分子式 | C24H30O3 | 分子量 | 366.5 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 5 mg/ml | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
||
| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 2.7285 mL | 13.6426 mL | 27.2851 mL |
| 5 mM | 0.5457 mL | 2.7285 mL | 5.457 mL |
| 10 mM | 0.2729 mL | 1.3643 mL | 2.7285 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Umbelliprenin relieves paclitaxel-induced neuropathy
J Pharm Pharmacol 2020 Dec;72(12):1822-1829.PMID:32930406DOI:10.1111/jphp.13365.
Objectives: Umbelliprenin (UMB) is a prenylated coumarin that acts as an in vitro antioxidant and inhibits lipoxygenase managing the inflammation pathways, while in vivo it exerts anti-inflammatory activities. Methods: In this study, neuropathic pain was induced by four intraperitoneal doses of 2 mg/kg per day of paclitaxel (PTX) on days 1, 3, 5 and 7. Here, 49 male mice were randomly divided in the following groups: sham (not treated animals), negative control (PTX-treated receiving normal saline), single-dose UMB 6.25, 12.5 and 25 mg/kg groups (PTX-treated receiving UMB 6.25, 12.5 and 25 mg/kg, respectively), prevention (PTX-treated receiving PTX along with UMB 12.5 mg/kg on days 1, 3, 5 and 7) and positive control group (PTX-treated receiving imipramine 10 mg/kg as acute treatment). Hot-plate test was done to assess response to heat. Finally, interleukin (IL)-6 levels in the sciatic nerve and lipid peroxidation in sera were assessed. Key findings: Umbelliprenin was found equally effective for acute treatment with imipramine, when comparing the prevention group and the positive control group. Single, 25 mg/kg UMB effectively attenuated hyperalgesia, lipid peroxidation and IL-6 levels. Conclusions: Umbelliprenin alleviated neuropathic pain, and decreased serum IL-6 levels and oxidative stress. UMB deserves further investigations, especially in clinical settings.
Umbelliprenin induced both anti-inflammatory and regulatory cytokines in C57/BL6 mice
Iran J Basic Med Sci 2017 Jul;20(7):829-834.PMID:28852449DOI:10.22038/IJBMS.2017.9021.
Objectives: Umbelliprenin is a prenyloxy-coumarin with pharmacologically polyvalent activity. Several studies have shown Several studies have been shown its anti-inflammatory, anti-tumor, antioxidant, and antigenotoxic activities. However, the exact mechanism of action of this compound on the immune response has not yet been shown. Here, we investigated Umbelliprenin effects on the predominance of Th1 and Th2 responses in normal C57/BL6 mice. Materials and methods: Umbelliprenin (2.5 mg/200 µl IP) were administered to six C57/BL6 mice every other day for 8 days. Paraffin and PBS-injected mice were enrolled as solvent and control groups, respectively (n=6 mice/group). IL-10, IFN-γ, and IL-4 levels were determined in sera and also in splenocytes culture supernatants in the presence of Con A (3 µg/ml) after 72 hr. H&E staining of paraffin embedded blocks was performed for lung and liver tissues of mice. Results: Umbelliprenin could significantly increase the secretion of IFN-γ and IL-4 in sera and IL-10 in splenocytes cultures. Comparison of IFN-γ/IL-4 in the sera and splenocytes culture supernatants showed lower ratios in Umbelliprenin treated mice than in solvent and untreated groups. Conclusion: The in vivo study showed that Umbelliprenin could induce anti-inflammatory responses via the predominance of Th2 cells and some regulatory responses in C57/BL6 mice.
Umbelliprenin Increases the M1/M2 Ratio of Macrophage Polarization and Improves the M1 Macrophage Activity in THP-1 Cells Cocultured with AGS Cells
Evid Based Complement Alternat Med 2021 Jul 13;2021:9927747.PMID:34335844DOI:10.1155/2021/9927747.
Background: Gastric adenocarcinoma is the fifth most diagnosed malignancy in the world. The immune system consists of a heterogeneous mixture of macrophages that defense the body through phagocytosis and the production of different cytokines and chemokines. Tumors cause macrophages to polarize differently in the manner of their favorite growth and angiogenesis. Umbelliprenin, a natural sesquiterpene coumarin, has been shown to have anticancer properties against some tumors, including gastric adenocarcinoma. The aim of our study was to investigate the effect of Umbelliprenin on the polarization of macrophages in addition to the measurement of some of the soluble factors they produce. Method: The values of IC5 and IC50 for Umbelliprenin in the AGS and THP-1 cells were estimated using the MTT assay. THP-1 cells were treated with 10 μM Umbelliprenin, either alone or cocultured with AGS cells. Flow cytometry analysis of treated THP-1 cells was performed for CD68, CD86, and CD206 markers to evaluate M0, M1, and M2 macrophages polarization, respectively. AGS cells were assessed for apoptosis and necrosis by flow cytometry after labeling with Annexin V-FITC and propidium iodide. Interleukin- (IL-) 10 and IL-12 contents were measured in the supernatant by the ELISA method. Griess Reaction assay technique was used to determine nitric oxide (NO) concentration. Results: The results of the MTT showed lower toxicity of Umbelliprenin in THP-1 (IC50 = 75.79) compared to the AGS cell line (IC50 = 48.81). Umbelliprenin significantly increased the M1/M2 ratio. IL-10 content decreased significantly in the supernatant of M1 and M2 cells after Umbelliprenin treatment, while IL-12 increased in the supernatant of M1 cells and decreased in the supernatant of the M2 cells. Umbelliprenin caused an increase in the NO in the supernatant of the M1 cells. Conclusion: Umbelliprenin alters the macrophage's secretions and its phenotypes in favor of tumor suppression.
Antitumor Effects of Umbelliprenin in a Mouse Model of Colorectal Cancer
Iran J Pharm Res 2018 Summer;17(3):976-985.PMID:30127820doi
Umbelliprenin is a sesquiterpene coumarin with vitro anti-carcinogenic activities. The aim of this study was to investigate the antitumor effects of Umbelliprenin in animal models of colorectal cancer. The cytotoxic effects of Umbelliprenin were explored on CT26 and L929by MTT assay. In this study, colorectal tumors developed in mice by intradermal injection of CT26 cell line. Tumor size, serum levels of IFN-γ and IL-4 by ELISA, and Ki-67, MMP2, MMP9, VEGF and E-cadherin markers by IHC method were evaluated. The results showed that Umbelliprenin inhibited the cancer cells in a concentration-dependent manner. IC50 Evaluation showed that L929 cells were more resistant to Umbelliprenin than CT26 cells. Umbelliprenin treatment in both tumor-bearing mice and control normal mice showed significantly increased IFN-γ and decreased IL-4(P < 0.05). The pathologic findings had shown that the E-cadherin marker in the Umbelliprenin treated cancerous mice were significantly higher compared to the control group (P < 0.05) while the expression of Ki-67 marker was reduced significantly (P < 0.05). Markers involved in angiogenesis including VEGF, MMP2, and MMP-9 in the cancerous mice group treated with Umbelliprenin showed a significant decrease compared to the control group (P < 0.05). Metastasis to lung and liver was reduced in Umbelliprenin treated group. Our results showed that Umbelliprenin inhibited CT26 tumor cells in-vitro. The in-vivo reduction of tumor size, angiogenesis, and proliferation markers and the absence of metastasis represents the antitumor effects of Umbelliprenin on colorectal cancer. The results showed that Umbelliprenin can be considered as a good candidate for the treatment of colorectal cancer.
Assessment of the Antitumor Potential of Umbelliprenin, a Naturally Occurring Sesquiterpene Coumarin
Biomedicines 2020 May 18;8(5):126.PMID:32443431DOI:10.3390/biomedicines8050126.
Cancer is one of the greatest causes of mortality worldwide. The prevalence rates of different types of cancer is increasing around the world as well. Limitations in chemotherapy and radiotherapy, owing to multiple side effects including cytotoxic effects of antitumor compounds on normal cells as well as the development of resistance to these treatment options in patients, create a serious threat to successful treatment of cancer. The use of natural compounds to prevent and treat cancers has been found to be quite effective, with fewer adverse effects found in patients. Umbelliprenin (UMB) is a naturally occurring sesquiterpene compound found in Ferula species and recently in Artemisia absinthium. Many studies have highlighted the antitumor potential of UMB in different cancer cell lines as well as in animal models. UMB exerts its anticancer actions by regulating extrinsic and intrinsic apoptotic pathways; causing inhibition of the cell cycle at the G0/G1 phase; and attenuating migration and invasion by modulating the Wnt signaling, NF-ĸB, TGFβ, and Fox3 signaling pathways. UMB also affects the key hallmarks of tumor cells by attenuating tumor growth, angiogenesis, and metastasis. This review provides an insight into the role of UMB as a potential antitumor drug for different malignancies and highlights the signaling cascades affected by UMB treatment in diverse tumor cell lines and preclinical models.