Epicorazine A
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| Category | Antibiotics |
| Catalog number | BBF-01242 |
| CAS | 62256-05-7 |
| Molecular Weight | 420.46 |
| Molecular Formula | C18H16N2O6S2 |
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Description
It is produced by the strain of Epicoccum nigrum. It has activity against gram-positive bacteria, including methicillin-resistant staphylococcus aureus (MRSA) and vancomycin resistant enterococcus (VRE), MIC is 12.5-25 μg/mL. It also has effect on candida albicans with MIC of 25 μg/mL.
Specification
| Synonyms | (4S)-4,4aα,7,7aβ,11,11aα,14,14aβ-Octahydro-4α,11α-dihydroxy-8H,13H-6aβ,13aβ-epidithio-1H,6H-pyrazino[1,2-a:4,5-a']diindole-1,6,8,13-tetrone; 8H,13H-6A,13A-Epidithio-1H,6H-pyrazino(1,2-A:4,5-A')diindole-1,6,8,13-tetrone,4,4A,7,7A,11,11A,14,14A-octahydro-4,11-dihydroxy-, (4S-(4alpha,4aalpha,6abeta,7abeta,11alpha,11aalpha,13abeta,14abeta))- |
| IUPAC Name | (1R,4S,5S,9S,11R,14S,15S,19S)-5,15-dihydroxy-21,22-dithia-3,13-diazahexacyclo[9.9.2.01,13.03,11.04,9.014,19]docosa-6,16-diene-2,8,12,18-tetrone |
| Canonical SMILES | C1C2C(C(C=CC2=O)O)N3C14C(=O)N5C6C(CC5(C3=O)SS4)C(=O)C=CC6O |
| InChI | InChI=1S/C18H16N2O6S2/c21-9-1-3-11(23)13-7(9)5-17-15(25)20-14-8(10(22)2-4-12(14)24)6-18(20,28-27-17)16(26)19(13)17/h1-4,7-8,11-14,23-24H,5-6H2/t7-,8-,11+,12+,13+,14+,17-,18-/m1/s1 |
| InChI Key | RCODXLGTKJXDNC-UORGKRBOSA-N |
Properties
| Appearance | Colorless Flaky Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Yeast |
| Boiling Point | 870.7 °C at 760 mmHg |
| Melting Point | 195-198 °C |
| Density | 1.85 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Isolation, structure elucidation, and antibacterial activity of methiosetin, a tetramic acid from a tropical sooty mold (Capnodium sp.)
Kithsiri Herath, Hiranthi Jayasuriya, Deborah L Zink, Jan Sigmund, Francisca Vicente, Mercedes de la Cruz, Angela Basilio, Gerald F Bills, Jon D Polishook, Robert Donald, John Phillips, Michael Goetz, Sheo B Singh J Nat Prod. 2012 Mar 23;75(3):420-4. doi: 10.1021/np200857y. Epub 2012 Jan 30.
Drug-resistant bacteria continue to make many existing antibiotic classes ineffective. In order to avoid a future epidemic from drug-resistant bacterial infections, new antibiotics with new modes of action are needed. In an antibiotic screening program for new drug leads with new modes of action using antisense Staphylococcus aureus Fitness Test screening, we discovered a new tetramic acid, methiosetin, from a tropical sooty mold, Capnodium sp. The fungus also produced epicorazine A, a known antibiotic. The structure and relative configuration of methiosetin was elucidated by 2D NMR and ESIMS techniques. Methiosetin and epicorazine A showed weak to modest antibacterial activity against S. aureus and Haemophilus influenzae. The isolation, structure elucidation, and antibacterial activity of both compounds are described.
2. Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum
Harwoko Harwoko, Georgios Daletos, Fabian Stuhldreier, Jungho Lee, Sebastian Wesselborg, Michael Feldbrügge, Werner E G Müller, Rainer Kalscheuer, Elena Ancheeva, Peter Proksch Nat Prod Res. 2021 Jan;35(2):257-265. doi: 10.1080/14786419.2019.1627348. Epub 2019 Jun 18.
A new epidithiodiketopiperazine (ETP), pretrichodermamide G (1), along with three known (epi)dithiodiketopiparazines (2-4) were isolated from cultures of Trichoderma harzianum and Epicoccum nigrum, endophytic fungi associated with medicinal plants Zingiber officinale and Salix sp., respectively. The structure of the new compound (1) was established on the basis of spectroscopic data, including 1D/2D NMR and HRESIMS. The isolated compounds were investigated for their antifungal, antibacterial and cytotoxic potential against a panel of microorganisms and cell lines. Pretrichodermamide A (2) displayed antimicrobial activity towards the plant pathogenic fungus Ustilago maydis and the human pathogenic bacterium Mycobacterium tuberculosis with MIC values of 1 mg/mL (2 mM) and 25 µg/mL (50 µM), respectively. Meanwhile, epicorazine A (3) exhibited strong to moderate cytotoxicity against L5178Y, Ramos, and Jurkat J16 cell lines with IC50 values ranging from 1.3 to 28 µM. Further mechanistic studies indicated that 3 induces apoptotic cell death.
3. Azacoccones F-H, new flavipin-derived alkaloids from an endophytic fungus Epicoccum nigrum MK214079
Harwoko Harwoko, Jungho Lee, Rudolf Hartmann, Attila Mándi, Tibor Kurtán, Werner E G Müller, Michael Feldbrügge, Rainer Kalscheuer, Elena Ancheeva, Georgios Daletos, Marian Frank, Zhen Liu, Peter Proksch Fitoterapia. 2020 Oct;146:104698. doi: 10.1016/j.fitote.2020.104698. Epub 2020 Jul 31.
Three new flavipin-derived alkaloids, azacoccones F-H (1-3), along with six known compounds (4-9) were isolated from the endophytic fungus Epicoccum nigrum MK214079 associated with leaves of Salix sp. The structures of the new compounds were established by analysis of their 1D/2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectroscopy (HRESIMS) data. The absolute configuration of azacoccones F-H (1-3) was determined by comparison of experimental electronic circular dichroism (ECD) data with reported ones and biogenetic considerations. Epicocconigrone A (4), epipyrone A (5), and epicoccolide B (6) exhibited moderate antibacterial activity against Staphylococcus aureus ATCC 29213 with minimal inhibitory concentration (MIC) values ranging from 25 to 50 μM. Furthermore, epipyrone A (5) and epicoccamide A (7) displayed mild antifungal activity against Ustilago maydis AB33 with MIC values of 1.6 and 1.8 mM, respectively. Epicorazine A (8) showed pronounced cytotoxicity against the L5178Y mouse lymphoma cell line with an IC50 value of 1.3 μM.
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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 ╳
