Emestrin
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| Category | Antibiotics |
| Catalog number | BBF-01215 |
| CAS | 97816-62-1 |
| Molecular Weight | 598.60 |
| Molecular Formula | C27H22N2O10S2 |
| Purity | >95% |
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Description
It is produced by the strain of Mycotoxin EQ-1 Emericella sp. It has strong antifungal activity.
Specification
| Synonyms | emestrin A; Emestrine |
| IUPAC Name | (1R,3S,9S,23S,24R,32R)-19,23,32-trihydroxy-15-methoxy-28-methyl-6,10,17-trioxa-25,26-dithia-2,28-diazaheptacyclo[22.2.2.11,4.12,24.112,16.118,22.03,9]dotriaconta-4,7,12(31),13,15,18,20,22(30)-octaene-11,27,29-trione |
| Canonical SMILES | CN1C(=O)C23C(C4=COC=CC5C4N2C(=O)C1(C(C6=CC(=C(C=C6)O)OC7=C(C=CC(=C7)C(=O)O5)OC)O)SS3)O |
| InChI | InChI=1S/C27H22N2O10S2/c1-28-24(34)27-22(32)14-11-37-8-7-17-20(14)29(27)25(35)26(28,40-41-27)21(31)12-3-5-15(30)18(9-12)38-19-10-13(23(33)39-17)4-6-16(19)36-2/h3-11,17,20-22,30-32H,1-2H3/t17-,20-,21-,22+,26+,27+/m0/s1 |
| InChI Key | UWWYWUMDYAWTKK-YITDFDIYSA-N |
| Source | Emestrin is a mycotoxin produced by fungi of the genus Emericella. |
Properties
| Appearance | Crystalline Powder |
| Antibiotic Activity Spectrum | Fungi |
| Melting Point | 233-236 °C (dec.) |
| Solubility | Soluble in Chloroform, Methanol, Acetone |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Lethal Dose | LD50: 13.0 mg/kg (Intraperitoneal, Mouse). |
| Mechanism Of Toxicity | Emestrin causes degeneration of the mitochondria in both cardiac muscle cells and hepatocytes, leading to necrosis. It is also known to act as an antagonist at the chemokine receptor, reducing the inflammatory effects of autoimmune disorders including rheumatoid arthritis, multiple sclerosis, atherosclerosis. Emestrin may also cause DNA fragmentation. |
Reference Reading
1. Induction of apoptosis by emestrin from the plant endophytic fungus Emericella nidulans ATCC 38163 in Huh-7 human hepatocellular carcinoma cells
Lamia T Abou El-Kassem, Usama W Hawas, Eman F Ahmed, Najat Binothman, Rana A Alghamdi Nat Prod Res. 2023 Feb 10;1-7. doi: 10.1080/14786419.2023.2176489. Online ahead of print.
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.
2. Asperemestrins A-D, Emestrin Hybrid Polymers with Bridged Skeletons from the Endophytic Fungus Aspergillus nidulans
Qin Li, Aimin Fu, Mengsha Wei, Yang Xiao, Jie Yin, Jianzheng Huang, Xiao-Nian Li, Qingyi Tong, Chunmei Chen, Hucheng Zhu, Yonghui Zhang Org Lett. 2022 Sep 23;24(37):6800-6804. doi: 10.1021/acs.orglett.2c02701. Epub 2022 Sep 8.
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.
3. Endophytic Akanthomyces sp. LN303 from Edelweiss Produces Emestrin and Two New 2-Hydroxy-4 Pyridone Alkaloids
Martina Oberhofer, Judith Wackerlig, Martin Zehl, Havva Büyük, Jia Jian Cao, Alexander Prado-Roller, Ernst Urban, Sergey B Zotchev ACS Omega. 2021 Jan 15;6(3):2184-2191. doi: 10.1021/acsomega.0c05472. eCollection 2021 Jan 26.
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.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H22N2O10S2
Molecular Weight (Monoisotopic Mass): 598.0716 Da
Molecular Weight (Avergae Mass): 598.601 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H22N2O10S2
Molecular Weight (Monoisotopic Mass): 598.0716 Da
Molecular Weight (Avergae Mass): 598.601 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
