Steffimycin B
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| Category | Antibiotics |
| Catalog number | BBF-03485 |
| CAS | 54526-94-2 |
| Molecular Weight | 588.56 |
| Molecular Formula | C29H32O13 |
| Purity | >98% |
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Description
Steffimycin B is an anthracycline antibiotic produced by Str. steffisburgensis var. steffisburgensis NRRL 3193. Activity against gram-positive bacteria.
Specification
| Synonyms | 1,6,11(2H)-Naphthacenetrione, 4-((6-deoxy-2,4-di-O-methyl-alpha-L-mannopyranosyl)oxy)-3,4-dihydro-2,5,7-trihydroxy-3,9-dimethoxy-2-methyl- |
| Storage | Store at -20°C |
| IUPAC Name | 2,5,7-trihydroxy-4-(4-hydroxy-3,5-dimethoxy-6-methyloxan-2-yl)oxy-3,9-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione |
| Canonical SMILES | CC1C(C(C(C(O1)OC2C(C(C(=O)C3=CC4=C(C(=C23)O)C(=O)C5=C(C4=O)C=C(C=C5O)OC)(C)O)OC)OC)O)OC |
| InChI | InChI=1S/C29H32O13/c1-10-23(38-4)22(34)25(39-5)28(41-10)42-24-18-14(26(35)29(2,36)27(24)40-6)9-13-17(21(18)33)20(32)16-12(19(13)31)7-11(37-3)8-15(16)30/h7-10,22-25,27-28,30,33-34,36H,1-6H3 |
| InChI Key | VHJWDTPKSIFZBV-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Orange Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 801.2±65.0°C at 760 mmHg |
| Melting Point | 240-246°C |
| Density | 1.5±0.1 g/cm3 |
| Solubility | Soluble in Methanol, Chloroform |
Reference Reading
1. Antimycobacterial activity of an anthracycline produced by an endophyte isolated from Amphipterygium adstringens
Clara I Espitia-Pinzón, José F Rivero-Cruz, Sergio Sánchez, Karol Rodríguez-Peña, Miriam Trenado-Uribe, Mayra Silva-Miranda, Romina Rodríguez-Sanoja Mol Biol Rep . 2018 Dec;45(6):2563-2570. doi: 10.1007/s11033-018-4424-0.
The search for new compounds effective against Mycobacterium tuberculosis is still a priority in medicine. The evaluation of microorganisms isolated from non-conventional locations offers an alternative to look for new compounds with antimicrobial activity. Endophytes have been successfully explored as source of bioactive compounds. In the present work we studied the nature and antimycobacterial activity of a compound produced by Streptomyces scabrisporus, an endophyte isolated from the medicinal plant Amphipterygium adstringens. The active compound was detected as the main secondary metabolite present in organic extracts of the streptomycete and identified by NMR spectroscopic data as steffimycin B (StefB). This anthracycline displayed a good activity against M. tuberculosis H37Rv ATCC 27294 strain, with MIC100and SI values of 7.8 µg/mL and 6.42, respectively. When tested against the rifampin mono resistant M. tuberculosis Mtb-209 pathogen strain, a better activity was observed (MIC100of 3.9 µg/mL), suggesting a different action mechanism of StefB from that of rifampin. Our results supported the endophyte Streptomyces scabrisporus as a good source of StefB for tuberculosis treatment, as this anthracycline displayed a strong bactericidal effect against M. tuberculosis, one of the oldest and more dangerous human pathogens causing human mortality.
2. Synthesis and Cytotoxic Evaluation of Arimetamycin A and Its Daunorubicin and Doxorubicin Hybrids
Jo Ann W Byl, Nathan D Schley, Neil Osheroff, Eric D Huseman, Scott M Chapp, Steven D Townsend ACS Cent Sci . 2021 Aug 25;7(8):1327-1337. doi: 10.1021/acscentsci.1c00040.
The arimetamycin A glycan governs the compound's cytotoxicity (IC50). To study this branched, deoxy-amino disaccharide, we designed and synthesized a modified acyl donor that underwent glycosylation with three anthracycline aglycones: steffimycinone, daunorubicinone, and doxorubicinone. The result of the approach was a synthesis of arimetamycin A and two novel hybrid anthracyclines. Each molecule exhibited enhanced cytotoxicity in comparison to the parent anthracyclines, steffimycin B, daunorubicin, and doxorubicin. An orienting mechanistic evaluation revealed that the daunorubicin hybrid inhibits the ability of human topoisomerase IIα to relax negatively and positively supercoiled DNA.
3. Microbial conversion of steffimycin and steffimycin B to 10-dihydrosteffimycin and 10-dihydrosteffimycin B
J M Slavicek, P F Wiley, V P Marshall, D W Elrod J Antibiot (Tokyo) . 1980 Aug;33(8):819-23. doi: 10.7164/antibiotics.33.819.
It has been shown that steffimycin (1) and steffmycin B (2) are reduced at the C-10 carbonyl by Actinoplanes utahensis, UC-5885 and Chaetomium sp., UC-4634, respectively. Using cell-free extracts of the latter organism, the optimum conversion time, pH, and enzyme concentration have been determined for the conversion of 2 to 4. The biochemical conversion of 2 has been found to be TPNH linked.
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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 ╳
