Ergosterol Peroxide
(Synonyms: 过氧麦角甾醇) 目录号 : GC47302
An oxidized sterol with diverse biological activities
Cas No.:2061-64-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Ergosterol peroxide is an oxidized sterol and derivative of ergosterol that has been found in S. aspratus and has diverse biological activities.1,2,3,4,5 It is active against the P. falciparum chloroquine-sensitive strain FCA 20/GHA with an IC50 value of 8.2 µM.2 Ergosterol peroxide (6.25-50 µM) induces apoptosis in LNCaP and DU145 prostate cancer cells.3 It inhibits growth of SNU-1 gastric, SNU-354 hepatoma, and SNU-C4 colorectal cancer cells (IC50s = 18.7, 158.2, and 84.6 µM, respectively).6 Ergosterol peroxide (60 µM) inhibits LPS-induced NF-kB DNA-binding activity and production of TNF-α in RAW 264.7 cells.4 Topical application of ergosterol peroxide reduces ear edema in a mouse model of inflammation induced by phorbol 12-myristate 13-acetate with an ID50 value of 0.2 mg/ear.5
1.Nielson, J.R., Fredrickson, E.K., Waller, T.C., et al.Sterol oxidation mediates stress-responsive Vms1 translocation to mitochondriaMol. Cell68(4)673-685(2017) 2.Kuria, K.A.M., Chepkwony, H., Govaerts, C., et al.The antiplasmodial activity of isolates from Ajuga remotaJ. Nat. Prod.65(5)789-793(2002) 3.Russo, A., Cardile, V., Piovano, M., et al.Pro-apoptotic activity of ergosterol peroxide and (22E)-ergosta-7,22-dien-5α-hydroxy-3,6-dione in human prostate cancer cellsChem. Biol. Interact.184(3)352-358(2010) 4.Kobori, M., Yoshida, M., Ohnishi-Kameyama, M., et al.Ergosterol peroxide from an edible mushroom suppresses inflammatory responses in RAW264.7 macrophages and growth of HT29 colon adenocarcinoma cellsBr. J. Pharmacol.150(2)209-219(2007) 5.Yasukawa, K., Aoki, T., Takido, M., et al.Inhibitory effects of ergosterol isolated from the edible mushroom Hypsizigus marmoreus on TPA‐induced inflammatory ear oedema and tumour promotion in micePhytother. Res.8(1)10-13(1994) 6.Nam, K.S., Jo, Y.S., Kim, Y.H., et al.Cytotoxic activities of acetoxyscirpenediol and ergosterol peroxide from Paecilomyces tenuipesLife Sci.69(2)229-237(2001)
| Cas No. | 2061-64-5 | SDF | |
| 别名 | 过氧麦角甾醇 | ||
| Canonical SMILES | CC(C)[C@@H](C)/C=C/[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@@]3(OO4)C=C[C@@]54C[C@@H](O)CC[C@]5(C)[C@@]3([H])CC[C@@]21C | ||
| 分子式 | C28H44O3 | 分子量 | 428.7 |
| 溶解度 | DMSO : 11.11 mg/mL (25.92 mM; Need ultrasonic and warming) | 储存条件 | Store at -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。 |
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| 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 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.3326 mL | 11.6632 mL | 23.3263 mL |
| 5 mM | 0.4665 mL | 2.3326 mL | 4.6653 mL |
| 10 mM | 0.2333 mL | 1.1663 mL | 2.3326 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。
Ergosterol Peroxide: A Mushroom-Derived Compound with Promising Biological Activities-A Review
Int J Med Mushrooms 2017;19(2):93-105.PMID:28436318DOI:10.1615/IntJMedMushrooms.v19.i2.10.
Ergosterol Peroxide (EP; 5α,8α-epidioxy-22E-ergosta-6,22-dien-3β-ol) is a C28-sterol and a component of many medicinal mushrooms. Since its discovery nearly a century ago, many sources and biological effects of this compound have been described. Effects range from antimicrobial to cytotoxic to immunosuppressive and other activities. This review covers biological investigations of EP, its activities, and possible mechanisms of action. EP is a promising candidate for drug development and contributes to the health-promoting effects of medicinal mushrooms.
Insights into Ergosterol Peroxide's Trypanocidal Activity
Biomolecules 2019 Sep 12;9(9):484.PMID:31547423DOI:10.3390/biom9090484.
Trypanosoma cruzi, which causes Chagas disease, is a significant health threat in many countries and affects millions of people. Given the magnitude of this disease, a broader understanding of trypanocidal mechanisms is needed to prevent and treat infection. Natural endoperoxides, such as Ergosterol Peroxide, have been shown to be toxic to parasites without causing harm to human cells or tissues. Although prior studies have demonstrated the trypanocidal activity of Ergosterol Peroxide, the cellular and molecular mechanisms remain unknown. The results of this study indicate that a free-radical reaction occurs in T. cruzi following Ergosterol Peroxide exposure, leading to cell death. Using a combination of biochemical, microscopic and in silico experimental approaches, we have identified, for the first time, the cellular and molecular cytotoxic mechanism of an Ergosterol Peroxide obtained from Pleurotus ostreatus (Jacq) P. Kumm. f. sp. Florida.
Ergosterol Peroxide: an effect-directed detecting method from Anoectochilus elwesii and evaluation of anticancer activity
Nat Prod Res 2022 Jun;36(12):3177-3182.PMID:34254867DOI:10.1080/14786419.2021.1949593.
Ergosterol Peroxide (EP) in Anoectochilus elwesii possesses antioxidant and anticancer properties, yet few studies have been focused on its mechanisms and directed detecting. By practicing HPTLC-DPPH coupled with UHPLC-ESI-TOF MS, EP was located and the cytotoxic activity of EP was performed by MTT method. The apoptosis studies were conducted on SGC-7901cells by AO/EB and Annex V/PI staining method, PI flow cytometric assay, reactive oxygen species detection and mitochondrial membrane potential assay. An effect-directed detecting method of HPTLC-DPPH/UHPLC/ESI-TOF-MS was developed for EP rapidly and precisely, providing an option for identifying oxidative compounds. EP exhibits high cytotoxic activity against SGC-7901 gastric cancer cells and the morphological apoptosis suggested that EP induced apoptosis and cell cycle arrest in G0/G1 phase. It could enhance the ROS level and cause a decrease in the mitochondrial membrane potential. Its antiproliferative mechanism is G0/G1 phase arrest and might be traced through ROS-mediated mitochondrial dysfunction pathways.
Ergosterol Peroxide suppresses influenza A virus-induced pro-inflammatory response and apoptosis by blocking RIG-I signaling
Eur J Pharmacol 2019 Oct 5;860:172543.PMID:31323223DOI:10.1016/j.ejphar.2019.172543.
Ergosterol Peroxide has been shown to exhibit anti-tumor, antioxidant and anti-bacterial properties. However, the effects of Ergosterol Peroxide isolated from the herbal Baphicacanthus cusia root on influenza virus infection remain poorly understood. In the present study, Ergosterol Peroxide (compound 22) was obtained from the B. cusia root and subjected to investigation regarding its immunoregulatory effect on influenza A virus (IAV)-induced inflammation in A549 human alveolar epithelial cells. The structure of compound 22 isolated from B. cusia root. was elucidated by NMR analyses. Structure determination showed that the chemical structure of compound 22 closely resembles that of Ergosterol Peroxide. We observed that Ergosterol Peroxide treatment significantly suppressed IAV-induced upregulation of RIG-I expression. Additionally, Ergosterol Peroxide inhibited the activation of RIG-I downstream signaling pathways, including p38 MAP kinase and NF-κB, which ultimately resulted in the reduced production of an array of pro-inflammatory mediators and interferons (IFN-β and IFN-λ1). Interestingly, inhibitory effects of Ergosterol Peroxide on the expression of IFNs did not affect the expression of antiviral effectors or enhance viral replication. On the other hand, Ergosterol Peroxide effectively abolished the amplified production of pro-inflammatory mediators in cells pretreated with IFN-β (500 ng/ml) prior to IAV infection. Moreover, Annexin V and Hoechst 33258 staining revealed that increased apoptosis of IAV-infected cells was reversed by the presence of Ergosterol Peroxide. Our findings suggest that Ergosterol Peroxide from the B. cusia root suppressed IAV-associated inflammation and apoptosis via blocking RIG-I signaling, which may serve as a supplementary approach to the treatment of influenza.
Development of Ergosterol Peroxide probes for cellular localisation studies
Org Biomol Chem 2019 May 29;17(21):5223-5229.PMID:31025693DOI:10.1039/c9ob00145j.
Ergosterol Peroxide selectively exhibits biological activity against a wide range of diseases; however, its mode of action remains unknown. Here, we present an efficient synthesis of Ergosterol Peroxide chemical probes for in vitro anticancer evaluation, live cell studies and proteomic profiling. Ergosterol Peroxide analogues show promising anti-proliferation activity against triple negative breast cancer cellular models, revealing information on the structure-activity relationship of this natural product in order to develop superior analogues. The combined cellular studies demonstrate that Ergosterol Peroxide is distributed across the cytosol with significant accumulation in the endoplasmic reticulum (ER). These chemical probes support our efforts towards uncovering the potential target(s) of Ergosterol Peroxide against triple negative breast cancer cell lines.