MM 47755
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03710 |
| CAS | 117620-87-8 |
| Molecular Weight | 336.34 |
| Molecular Formula | C20H16O5 |
| Purity | 95% |
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Description
MM 47755 is produced by the strain of greysporing streptomycete. It has anti-Gram-negative bacteria and fungi activity (100μg/ mL).
Specification
| Synonyms | 6-Deoxy-8-O-methylrabelomycin; (-)-3,4-Dihydro-3-hydroxy-8-methoxy-3-methylbenz(a)anthracene-1,7,12(2H)-trione; MM-47755; Benz(a)anthracene-1,7,12(2H)-trione, 3,4-dihydro-3-hydroxy-8-methoxy-3-methyl-, (-)- |
| Storage | Store at -20°C |
| IUPAC Name | 3-hydroxy-8-methoxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1(CC2=C(C(=O)C1)C3=C(C=C2)C(=O)C4=C(C3=O)C=CC=C4OC)O |
| InChI | InChI=1S/C20H16O5/c1-20(24)8-10-6-7-12-17(15(10)13(21)9-20)19(23)11-4-3-5-14(25-2)16(11)18(12)22/h3-7,24H,8-9H2,1-2H3 |
| InChI Key | XZLGWJORNHETKI-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Flake Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria; fungi |
| Boiling Point | 583.3°C at 760 mmHg |
| Melting Point | 176-177°C |
| Density | 1.39 g/cm3 |
| Solubility | Soluble in DMSO, methanol or acetone. |
Reference Reading
1. Search method for inhibitors of Staphyloxanthin production by methicillin-resistant Staphylococcus aureus
Kent Sakai, Nobuhiro Koyama, Takashi Fukuda, Yukiko Mori, Hiroyasu Onaka, Hiroshi Tomoda Biol Pharm Bull. 2012;35(1):48-53. doi: 10.1248/bpb.35.48.
Staphyloxanthin, a yellow pigment produced by methicillin-resistant Staphylococcus aureus (MRSA), is a virulent factor escaping from the host immune system. A new screening method for inhibitors of staphyloxanthin production by MRSA was established using paper disks. By this screening method, inhibitors of staphyloxanthin production were selected from the natural product library (ca. 300) and from actinomycete culture broths (ca. 1000). From the natural product library, four known inhibitors of lipid metabolism, cerulenin, dihydrobisvertinol, xanthohumol and zaragozic acid, were found to inhibit staphyloxanthin production; however, typical antibiotics used clinically, including vancomycin, had no effect on staphyloxanthin production. From actinomycete culture broths, two known anthraquinones, 6-deoxy-8-O-methylrabelomycin and tetrangomycin, were found to inhibit staphyloxanthin production by MRSA in the paper disk assay. These results suggested that this screening method is useful and effective to find compounds targeting staphyloxanthin production, leading to a new type of chemotherapeutics against MRSA infection.
2. Screening of mutant strain Streptomyces mediolani sp. AC37 for (-)-8-O-methyltetrangomycin production enhancement
Jakeline Trejos Jiménez, Maria Sturdíková, Vlasta Brezová, Emil Svajdlenka, Marta Novotová J Microbiol. 2012 Dec;50(6):1014-23. doi: 10.1007/s12275-012-2025-5. Epub 2012 Dec 30.
Streptomyces mediolani sp. AC37 was isolated from the root system of higher plant Taxus baccata and produced metabolite identified as (-)-8-O-methyltetrangomycin according to LC/MS/MS analysis. In our screening program for improvements of bioactive secondary metabolites from plant associate streptomycetes, mutation was used as a tool for the induction of genetic variations for selection of higher (-)-8-O-methyltetrangomycin producers of isolates. S. mediolani sp. AC37 was treated with UV irradiation and chemical mutagenic treatment (N-nitroso-N-methyl-urea). The radical scavenging and antioxidant capacity of (-)-8-O-methyltetrangomycin and extracts isolated from mutants were tested using EPR spin trapping technique and ABTS(·+) assay. Comparison of electron microscopic images of Streptomyces sp. AC37 and mutant strains of Streptomyces sp. AC37 revealed substantial differences in morphology and ultrastructure.
3. Isolation, purification and chemical characterization of a new angucyclinone compound produced by a new halotolerant Nocardiopsis sp. HR-4 strain
Yamina Hadj Rabia-Boukhalfa, Yannick Eveno, Solange Karama, Okba Selama, Béatrice Lauga, Robert Duran, Hocine Hacène, Véronique Eparvier World J Microbiol Biotechnol. 2017 Jun;33(6):126. doi: 10.1007/s11274-017-2292-8. Epub 2017 May 25.
A halotolerant Actinobacteria strain HR-4 was isolated from a salt lake soil sample in Algerian Sahara. Analysis of 16S rDNA gene sequence showed that strain HR-4 belonged to the genus Nocardiopsis. The similarity level ranges between 97.45 and 99.20% with Nocardiopsis species and Nocardiopsis rosea being the most closely related one. Morphological, physiological and phylogenetic characteristics comparisons showed significant differences with the nearest species. These data strongly suggest that strain HR-4 represents novel species. The antimicrobial activity of strain HR-4 showed an antibacterial activity against Gram-positive bacteria as well as an antifungal one. Two major natural products including a new one were isolated from the culture broth using various separation and purification procedures. The chemical structure established on the basis of spectroscopic studies NMR and by comparing with spectroscopic data from the literature of the two compounds affirm that they are classified in the group of Angucyclinones. This is the first report of a production of this type of molecules by the genus Nocardiopsis. The new natural compound was established as (-)-7-deoxy-8-O-methyltetrangomycin with a new configuration.
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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 ╳
