Cinerubin B
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00642 |
| CAS | 35906-51-5 |
| Molecular Weight | 825.85 |
| Molecular Formula | C42H51NO16 |
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Description
It is produced by the strain of Streptomyces cinereoruber var. fructo fermentans. Cinerubin B has anti-gram-positive bacteria, mycobacterium, fungis and amoeba activity, and has strong effect on mouse adenocarcinoma E0771.
Specification
| Synonyms | Cinerubine B; Tavromycetin III; Antibiotic MA 144B2; NSC 18335 |
| IUPAC Name | methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[[(1R,3R,5S,8S,10S,12S,14S)-5,14-dimethyl-6-oxo-2,4,9,13-tetraoxatricyclo[8.4.0.03,8]tetradecan-12-yl]oxy]-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7,10-tetrahydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate |
| Canonical SMILES | CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C=CC(=C4C3=O)O)O)O)OC5CC(C(C(O5)C)OC6CC7C(C(O6)C)OC8C(O7)CC(=O)C(O8)C)N(C)C)O |
| InChI | InChI=1S/C42H51NO16/c1-8-42(51)15-27(30-19(34(42)40(50)52-7)11-20-31(36(30)48)37(49)33-23(45)10-9-22(44)32(33)35(20)47)57-28-12-21(43(5)6)38(17(3)53-28)58-29-14-25-39(18(4)54-29)59-41-26(56-25)13-24(46)16(2)55-41/h9-11,16-18,21,25-29,34,38-39,41,44-45,48,51H,8,12-15H2,1-7H3/t16-,17-,18-,21-,25-,26-,27-,28-,29-,34-,38+,39+,41-,42+/m0/s1 |
| InChI Key | ZBDDFHXUDIPRSM-DQCCILMQSA-N |
Properties
| Appearance | Orange Red Crystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria; fungi; parasites |
| Melting Point | 180-181 °C |
Reference Reading
1. Actinobacteria from Antarctica as a source for anticancer discovery
Ana Lucia Tasca Gois Ruiz,Eduardo José Crevelin,Valeria Maia de Oliveira,Leonardo Jose Silva,Danilo Tosta Souza,Luiz Henrique Rosa,Luiz Alberto Beraldo Moraes,Itamar Soares Melo,Gileno Vieira Lacerda-Júnior Sci Rep . 2020 Aug 17;10(1):13870. doi: 10.1038/s41598-020-69786-2.
Although many advances have been achieved to treat aggressive tumours, cancer remains a leading cause of death and a public health problem worldwide. Among the main approaches for the discovery of new bioactive agents, the prospect of microbial secondary metabolites represents an effective source for the development of drug leads. In this study, we investigated the actinobacterial diversity associated with an endemic Antarctic species, Deschampsia antarctica, by integrated culture-dependent and culture-independent methods and acknowledged this niche as a reservoir of bioactive strains for the production of antitumour compounds. The 16S rRNA-based analysis showed the predominance of the Actinomycetales order, a well-known group of bioactive metabolite producers belonging to the Actinobacteria phylum. Cultivation techniques were applied, and 72 psychrotolerant Actinobacteria strains belonging to the genera Actinoplanes, Arthrobacter, Kribbella, Mycobacterium, Nocardia, Pilimelia, Pseudarthrobacter, Rhodococcus, Streptacidiphilus, Streptomyces and Tsukamurella were identified. The secondary metabolites were screened, and 17 isolates were identified as promising antitumour compound producers. However, the bio-guided assay showed a pronounced antiproliferative activity for the crude extracts of Streptomyces sp. CMAA 1527 and Streptomyces sp. CMAA 1653. The TGI and LC50values revealed the potential of these natural products to control the proliferation of breast (MCF-7), glioblastoma (U251), lung/non-small (NCI-H460) and kidney (786-0) human cancer cell lines. Cinerubin B and actinomycin V were the predominant compounds identified in Streptomyces sp. CMAA 1527 and Streptomyces sp. CMAA 1653, respectively. Our results suggest that the rhizosphere of D. antarctica represents a prominent reservoir of bioactive actinobacteria strains and reveals it as an important environment for potential antitumour agents.
2. Effect of pamamycin-607 on secondary metabolite production by Streptomyces spp
Risako Kato,Hiroshi Kawaide,Masahiro Natsume,Makoto Hashimoto,Hirotaka Katsura Biosci Biotechnol Biochem . 2011;75(9):1722-6. doi: 10.1271/bbb.110251.
The effect of the aerial mycelium-inducing compound, pamamycin-607, on antibiotic production by several Streptomyces spp. was examined. Exposure to 6.6 µM pamamycin-607 stimulated by 2.7 fold the puromycin production by Streptomyces alboniger NBRC 12738, in which pamamycin-607 had first been isolated, and restored aerial mycelium formation. Pamamycin-607 also stimulated the respective production of streptomycin by S. griseus NBRC 12875 and that of cinerubins A and B by S. tauricus JCM 4837 by approximately 1.5, 1.7 and 1.9 fold. The antibiotic produced by Streptomyces sp. 91-a was identified as virginiamycin M(1), and its synthesis was enhanced 2.6 fold by pamamycin-607. These results demonstrate that pamamycin-607 not only restored or stimulated aerial mycelium formation, but also stimulated secondary metabolite production.
3. Production of cinerubins by a Streptomyces griseorubiginosus strain
T Staron,G Kergomard,M Duteurtre,A Kergomard,E Scanzi,L David J Antibiot (Tokyo) . 1980 Jan;33(1):49-53. doi: 10.7164/antibiotics.33.49.
Streptomyces No. 4915 was isolated and revealed to produce cinerubins A and B. This strain was different from other cinerubins-producing strains. Production of cinerubins is reported. Assignments of the signals of the 13C-NMR spectrum of cinerubin A, the major product, have been made.
4. Anthracycline Shunt Metabolites From Philippine Marine Sediment-Derived Streptomyces Destroy Cell Membrane Integrity of Multidrug-Resistant Staphylococcus aureus
Edna M Sabido,Doralyn S Dalisay,Jonel P Saludes,Melissa June V Paderog,Angelica Faith L Suarez,Zhen Jie Low Front Microbiol . 2020 Apr 24;11:743. doi: 10.3389/fmicb.2020.00743.
The rise of antibiotic resistance (ABR) and the drying up of the pipeline for the development of new antibiotics demands an urgent search for new antibiotic leads. While the majority of clinically available antibiotics were discovered from terrestrialStreptomyces, related species from marine sediments as a source of antibiotics remain underexplored. Here, we utilized culture-dependent isolation of thirty-five marine sediment-derived actinobacterial isolates followed by a screening of their antibacterial activity against multidrug-resistantS. aureusATCC BAA-44. Our results revealed that the crude extract ofStreptomyces griseorubensstrain DSD069 isolated from marine sediments collected in Romblon, Philippines displays the highest antibacterial activity, with 96.4% growth inhibition. TheS. aureusATCC BAA-44 cells treated with crude extract ofStreptomyces griseorubensstrain DSD069 showed cell membrane damage as demonstrated by (a) leakage and loss of vital cell constituents, including DNA and proteins, (b) irregular shrinkage of cells, and (c) increase membrane permeability. The antibiotic compounds were identified as Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone with MIC value of 6.25 μg/mL and 50.00 μg/mL, respectively. Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone are shunt metabolites in the biosynthesis of anticancer anthracycline derivatives namely doxorubicin, daunorubicin, and cinerubins. It is rare, however, that shunt metabolites are accumulated during fermentation of marine sediment-derivedStreptomycesstrain without genetic modification. Thus, our study provides evidence that natural bacterial strain can produce Bisanhydroaklavinone and 1-Hydroxybisanhydroaklavinone as antibiotic leads to combat ABR.
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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 ╳
