Echinosporin
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| Category | Antibiotics |
| Catalog number | BBF-01196 |
| CAS | 79127-35-8 |
| Molecular Weight | 223.18 |
| Molecular Formula | C10H9NO5 |
| Purity | >98% |
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Description
It is produced by the strain of Bacillus brevis Vm4, Streptomyces echinos porus MK-213. It has weak anti-gram-positive bacteria and tumor activity.
Specification
| Synonyms | (1S,4aS,5S,7aS)-1,4a,5,7a-Tetrahydro-5-hydroxy-8-oxo-1,5-(epoxymethano)cyclopenta[c]pyran-3-carboxamide; (-)-Echinosporin; Antibiotic XK 213; NSC 357683; XK 213; [1S-(1α,4aβ,5β,7aβ)]-1,4a,5,7a-Tetrahydro-5-hydroxy-8-oxo-1,5-(epoxymethano)cyclopenta[c]pyran-3-carboxamide |
| IUPAC Name | (1R,4S,7R,8S)-4-hydroxy-3-oxo-2,11-dioxatricyclo[5.4.0.04,8]undeca-5,9-diene-10-carboxamide |
| Canonical SMILES | C1=CC2(C3C1C(OC(=C3)C(=O)N)OC2=O)O |
| InChI | InChI=1S/C10H9NO5/c11-7(12)6-3-5-4-1-2-10(5,14)9(13)16-8(4)15-6/h1-5,8,14H,(H2,11,12)/t4-,5+,8-,10+/m1/s1 |
| InChI Key | OXSZHYWOGQJUST-OFCCZVAHSA-N |
Properties
| Appearance | White Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Neoplastics (Tumor) |
| Boiling Point | 635.1±55.0 °C (Predicted) |
| Melting Point | 260 °C (dec.) |
| Density | 1.709±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Water, Chloroform |
Reference Reading
1. Oligomycins and pamamycin homologs impair motility and induce lysis of zoospores of the grapevine downy mildew pathogen, Plasmopara viticola
Zerihun T Dame, M Tofazzal Islam, Elisabeth Helmke, Andreas von Tiedemann, Hartmut Laatsch FEMS Microbiol Lett. 2016 Aug;363(16):fnw167. doi: 10.1093/femsle/fnw167. Epub 2016 Jun 27.
Four antibiotics (pamamycin, oligomycin A, oligomycin B and echinosporin) were isolated and characterized from the fermentation broth of the marine Streptomyces strains B8496 and B8739. Bioassays revealed that each of these compounds impaired motility and caused subsequent lysis of P. viticola zoospores in a dose- and time-dependent manner. Pamamycin displayed the strongest motility inhibitory and lytic activities (IC50 0.1 μg mL(-1)) followed by oligomycin B (IC50 0.15 and 0.2 μg mL(-1)) and oligomycin F (IC50 0.3 and 0.5 μg mL(-1)). Oligomycin A and echinosporin also showed motility inhibitory activities against the zoospores with IC50 values of 3.0 and 10.0 μg mL(-1), respectively. This is the first report of motility inhibitory and lytic activities of these antibiotics against zoospores of a phytopathogenic peronosporomycete. Structures of all the isolated compounds were determined based on detailed spectroscopic analysis.
2. Echinosporin antibiotics isolated from Amycolatopsis strain and their antifungal activity against root-rot pathogens of the Panax notoginseng
Xindong Xu, Li Han, Lixing Zhao, Xiao Chen, Cuiping Miao, Linfang Hu, Xueshi Huang, Youwei Chen, Yiqing Li Folia Microbiol (Praha). 2019 Mar;64(2):171-175. doi: 10.1007/s12223-018-0642-z. Epub 2018 Aug 16.
Actinomycete strain YIM PH20520, isolated from the rhizosphere soil sample of Panax notoginseng collected in Wenshang, Yunnan Province, China, exhibited antifungal activity against root-rot pathogens of the Panax notoginseng. The structures of bioactive molecules, isolated from the ethyl acetate extract of the fermentation broth of the strain, were identified as echinosporin (1) and 7-deoxyechinosporin (2) based on extensive spectroscopic analyses. 1 exhibited antifungal activity against four tested root-rot pathogens of Panax notoginseng include Fusarium oxysporum, Fusarium solani, Alternaria panax, and Phoma herbarum with the MIC value at 64, 64, 32, and 64 μg/mL, respectively. 2 exhibited antifungal activities against F. oxysporum, F. solani, A. panax, and P. herbarum with the MIC value at 128, 128, 64, and 128 μg/mL, respectively. Based on the phylogenetic analyses, the closest phylogenetic relative of strain YIM PH20520 is Amycolatopsis speibonae JS72T (97.69%), so strain YIM PH20520 was identified as Amycolatopsis strain. To the best of our knowledge, this is the first report of echinosporin antibiotics isolated from Amycolatopsis strain besides Streptomyces strain and their antifungal activity against four tested root-rot pathogens of the Panax notoginseng. The results provide a reliable evidence for the following related biosynthetic investigations on Amycolatopsis strain YIM PH20520 due to echinosporins antibiotics' unique tricyclic acetal-lactone structures.
3. Amycolasporins and Dibenzoyls from Lichen-Associated Amycolatopsis hippodromi and Their Antibacterial and Anti-inflammatory Activities
Ying Jin, Nuerbiye Aobulikasimu, Zengguang Zhang, Chengbin Liu, Bixuan Cao, Bin Lin, Peipei Guan, Yu Mu, Yi Jiang, Li Han, Xueshi Huang J Nat Prod. 2020 Dec 24;83(12):3545-3553. doi: 10.1021/acs.jnatprod.0c00547. Epub 2020 Nov 20.
Eleven metabolites, six echinosporins (1-6), four dibenzoyls (7-10), and an aromatic compound (11), were isolated from the fermentation broth of lichen-associated Amycolatopsis hippodromi. The structures of the new compounds (1-5, 8-11) were elucidated by comprehensive spectroscopic analysis including data from experimental and calculated ECD spectra. Amycolasporins A-C (1-3) demonstrated antibacterial activities against Bacillus subtilis, Staphylococcus aureus, and Escherichia coli with MIC values of 25 or 100 μg/mL. Amycolasporin C (3) and the known dibenzoyl (7) attenuated the production of NO due to the suppression of the expression of nitric oxide synthase (iNOS) in LPS-induced RAW 264.7 cells in a dose-dependent manner.
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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 ╳
