Emestrin
目录号 : GC46137
A mycotoxin
Cas No.:97816-62-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Emestrin is a mycotoxin originally isolated from E. striata that has antimicrobial, immunomodulatory, and cytotoxic activities.1,2,3,4,5 It is active against the fungi C. albicans and C. neoformans, as well as the bacteria E. coli, S. aureus, and methicillin-resistant S. aureus (MRSA; IC50s = 3.94, 0.6, 2.21, 4.55, and 2.21 μg/ml, respectively).2 Emestrin is a chemokine (C-C motif) receptor 2 (CCR2) antagonist (IC50 = 5.4 μM in a radioligand binding assay using isolated human monocytes).3 Emestrin (0.1 μg/ml) induces apoptosis in HL-60 cells.4 It induces heart, thymus, and liver tissue necrosis in mice when administered at doses ranging from 18 to 30 mg/kg.5
|1. Seya, H., Nakajima, S., Kawai, K.-i., et al. Structure and absolute configuration of emestrin, a new macrocyclic epidithiodioxopiperazine from Emericella striata. J. Chem. Soc. Chem. Commun. 10, 657-658 (1985).|2. Herath, H.M.T.B., Jacob, M., Wilson, A.D., et al. New secondary metabolites from bioactive extracts of the fungus Armillaria tabescens. Nat. Prod. Res. 27(17), 1562-1568 (2013).|3. Herath, K.B., Jayasuriya, H., Ondeyka, J.G., et al. Isolation and structures of novel fungal metabolites as chemokine receptor (CCR2) antagonists. J. Antibiot. (Tokyo) 58(11), 686-694 (2005).|4. Ueno, Y., Umemori, K., Niimi, E.-c., et al. Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells. Nat. Toxins 3(3), 129-137 (1995).|5. Terao, K., Ito, E., Kawai, K.-i., et al. Experimental acute poisoning in mice induced by emestrin, a new mycotoxin isolated from Emericella species. Mycopathologia 112(2), 71-79 (1990).
| Cas No. | 97816-62-1 | SDF | |
| Canonical SMILES | OC(C=CC([C@@H]([C@]1(SS2)N(C)C([C@]2([C@H](O)C3=COC=CC(OC4=O)[C@]35[H])N5C1=O)=O)O)=C6)=C6OC7=CC4=CC=C7OC | ||
| 分子式 | C27H22N2O10S2 | 分子量 | 598.6 |
| 溶解度 | DMF: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 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 | 1.6706 mL | 8.3528 mL | 16.7056 mL |
| 5 mM | 0.3341 mL | 1.6706 mL | 3.3411 mL |
| 10 mM | 0.1671 mL | 0.8353 mL | 1.6706 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。
Asperemestrins A-D, Emestrin Hybrid Polymers with Bridged Skeletons from the Endophytic Fungus Aspergillus nidulans
Org Lett 2022 Sep 23;24(37):6800-6804.PMID:36074729DOI:10.1021/acs.orglett.2c02701.
Four Emestrin hybrid polymers, asperemestrins A-D (1-4, respectively), were isolated from the fungus Aspergillus nidulans. Asperemestrins A-C are the first examples of emestrin-sterigmatocystin heterodimers bearing a 7/5/6/6/5/5/6/6/6 nonacyclic system with a 2,5-diazabicyclo[2.2.2]octane-3,6-dione core, while asperemestrin D features an unprecedented 2,15-dithia-17,19-diazabicyclo[14.2.2]icosa-4,8-diene-12,18,20-trione core skeleton. Their structures were determined by extensive spectroscopic data, electronic circular dichroism calculations, and single-crystal X-ray diffraction. Asperemestrin B showed moderate cytotoxicity against cancer cell lines, including SU-DHL-2, HEPG2, and HL-60.
Endophytic Akanthomyces sp. LN303 from Edelweiss Produces Emestrin and Two New 2-Hydroxy-4 Pyridone Alkaloids
ACS Omega 2021 Jan 15;6(3):2184-2191.PMID:33521458DOI:10.1021/acsomega.0c05472.
In the search for new antibiotics, several fungal endophytes were isolated from the medicinal plant Leontopodium nivale subsp. alpinum (Edelweiss). The extract from one of these fungi classified as Akanthomyces sp. displayed broad-spectrum antibiotic activity against gram-negative bacteria and fungi. Further investigation into the composition of this extract using bioactivity-guided fractionation, HRMS, and nuclear magnetic resonance revealed two new 4-hydroxy-2-pyridone alkaloids (1, 2) and Emestrin (3), an epidithiodioxopiperazine not previously known to be produced by a member of Cordycipitaceae. Further testing of purified compounds 1 and 2 proved that they are devoid of antibiotic activity, and all the activities observed in the crude extract could be assigned to Emestrin (3), whose configuration was confirmed by crystallographic data. This study demonstrates, for the first time, that endophytic fungi from Edelweiss can produce new compounds, prompting further investigation into them for drug discovery.
Toxicity of Emestrin, a new macrocyclic dithiodioxopiperazine mycotoxin, to mitochondrial function
Mycotoxin Res 1989 Mar;5(1):2-8.PMID:23605226DOI:10.1007/BF03192110.
The effect of Emestrin, a new macrocyclic epidithiodioxopiperazine mycotoxin from severalEmericella species, on mitochondrial reactions was studied using isolated rat liver mitochondria to gain insight into the molecular mechanism for itsin vivo toxicity to rat and mouse. Emestrin was found to inhibit ATP synthesis in mitochondria causing an uncoupling of oxidative phosphorylation and a depression of respiration in isolated mitochondria. In addition to these effects on mitochondrial respiration, Emestrin elicited a dratsic structural alteration (swelling) of mitochondria as observed in thein vivo system. The mitochondrial swelling was significantly enhanced by the subsequent addition of calcium ion. Emestrin B, in which dithio group is replaced by trithio group, exerted an uncoupling effect on oxidative phosphorylation without accompanying such depressive effect on state 3 respiration as observed for Emestrin.
Induction of apoptosis by Emestrin from the plant endophytic fungus Emericella nidulans ATCC 38163 in Huh-7 human hepatocellular carcinoma cells
Nat Prod Res 2023 Feb 10;1-7.PMID:36772803DOI:10.1080/14786419.2023.2176489.
This research aimed to investigate the anticancer properties of Emestrin, a major constituent of Emericella nidulans ATCC 38163 through the induction of apoptosis in Huh-7 human hepatocellular carcinoma cells. In this study, this fungus was isolated from the fresh leaves of Ruprechtia salicifolia (Cham. & Schltdl.) C.A. Mey, and identified by morphology and 18S rDNA followed by large-scale fermentation in liquid biomalt broth medium. Epidithiodioxopiperazine derivative Emestrin along with ten known metabolites were isolated and identified from the fungal extract. The cytotoxic assay revealed that Emestrin had the strongest cytotoxicity against Huh-7 and A-549 cells with IC50 values of 4.89 and 6.3 μM, respectively. Using annexin V-FITC assay, treatment of Huh-7 cells with 4.89 µM for 24 h resulted in a significant increase in the percentage of early and late apoptosis (3.16% and 22.84%, respectively) compared to untreated cells. Additionally, Bax and bcl-2 protein levels were regulated, which induced apoptosis in treated cells. These results indicate that Emestrin induces mitochondrial pathway to stimulate apoptosis and inhibits cell proliferation in hepatocellular carcinoma.
New secondary metabolites from bioactive extracts of the fungus Armillaria tabescens
Nat Prod Res 2013;27(17):1562-8.PMID:23140424DOI:10.1080/14786419.2012.738206.
Ethyl acetate extracts of Armillaria tabescens (strain JNB-OZ344) showed significant fungistatic and bacteristatic activities against several major human pathogens including Candida albicans, Cryptococcus neoformans, Escherichia coli and Mycobacterium intracellulare. Chemical analysis of these extracts led to the isolation and identification of four new compounds, emestrin-F (1), emestrin-G (2), 6-O-(4-O-methyl-β-D-glucopyranosyl)-8-hydroxy-2,7-dimethyl-4H-benzopyran-4-one (3) and cephalosporolide-J (4), along with five other previously known compounds, Emestrin (5), cephalosporolide-E (6), decarestrictine-C2 (7), ergosterol and brassicasterol. Structural elucidation of all compounds was carried out by NMR and MS analyses. Antimicrobial assays revealed that compounds 1 and 5 were responsible for the observed growth inhibitory activities of the fungal extracts against the human pathogens tested.