Tetrangomycin
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| Category | Antibiotics |
| Catalog number | BBF-03110 |
| CAS | 7351-08-8 |
| Molecular Weight | 322.31 |
| Molecular Formula | C19H14O5 |
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Description
Tetrangomycin is a quinone antibiotic produced by Str. rimosus var. sp. NRRL 3016. It has activity against gram-positive bacteria, but has no protective effect on mice infected with the Smith strain of golden staphylococcus aureus.
Specification
| Synonyms | (+)-3,4-dihydro-3,8-dihydroxy-3-methylbenz(a)anthracene-1,7,12(2H)-trione; (-)-tetrangomycin; Benzanthramycin |
| IUPAC Name | (3R)-3,8-dihydroxy-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=C4O)O |
| InChI | InChI=1S/C19H14O5/c1-19(24)7-9-5-6-11-16(14(9)13(21)8-19)18(23)10-3-2-4-12(20)15(10)17(11)22/h2-6,20,24H,7-8H2,1H3/t19-/m1/s1 |
| InChI Key | UGEKKXLEYACFTD-LJQANCHMSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 615.2°C at 760 mmHg |
| Melting Point | 182-184°C |
| Density | 1.49 g/cm3 |
Reference Reading
1. Characterization of Bioactivities and Biosynthesis of Angucycline/Angucyclinone Derivatives Derived from Gephyromycinifex aptenodytis gen. nov., sp. nov
Wen-Zhuo Zhu, Shu-Heng Wang, Hui-Min Gao, Ya-Ming Ge, Jun Dai, Xiao-Ling Zhang, Qiao Yang Mar Drugs. 2021 Dec 29;20(1):34. doi: 10.3390/md20010034.
Strain NJES-13T is the type strain and currently the only species of the newly established actinobacteria genera Aptenodytes in the family Dermatophilaceae isolated from the gut microbiota of the Antarctic emperor penguin. This strain demonstrated excellent bioflocculation activity with bacteria-derived exopolysaccharides (EPSs). Moreover, it produced bioactive angucycline/angucyclinone derivatives (ADs) and contained one type III polyketide synthase (T3PKS), thus demonstrating great potential to produce novel bioactive compounds. However, the low productivity of the potential new AD metabolite was the main obstacle for its chemical structure elucidation. In this study, to increase the concentration of targeted metabolites, the influence of cellular morphology on AD metabolism in strain NJES-13T was determined using glass bead-enhanced fermentation. Based on the cellular ultra-structural observation driven by bacterial EPSs, and quantitative analysis of the targeted metabolites, the successful increasing of the productivity of three AD metabolites was achieved. Afterward, a new frigocyclinone analogue was isolated and then identified as 2-hydroxy-frigocyclinone, as well as two other known ADs named 2-hydroxy-tetrangomycin (2-HT) and gephyromycin (GPM). Three AD metabolites were found to demonstrate different bioactivities. Both C-2 hydroxyl substitutes, 2-hydroxy-tetrangomycin and 2-hydroxy-frigocyclinone, exhibited variable inhibitory activities against Staphylococcus aureus, Bacillus subtilis and Candida albicans. Moreover, the newly identified 2-hydroxy-frigocyclinone also showed significant cytotoxicity against three tested human-derived cancerous cell lines (HL-60, Bel-7402 and A549), with all obtained IC50 values less than 10 µM. Based on the genetic analysis after genomic mining, the plausible biogenetic pathway of the three bioactive ADs in strain NJES-13T was also proposed.
2. Structure-activity relationships and mechanism of action of tetragomycin derivatives as inhibitors of Staphylococcus aureus staphyloxanthin biosynthesis
L M B C Ribeiro, F Fumagalli, R B Mello, T Q Froes, M V S da Silva, S M Villamizar Gómez, T F Barros, F S Emery, M S Castilho Microb Pathog. 2020 Jul;144:104127. doi: 10.1016/j.micpath.2020.104127. Epub 2020 Mar 10.
Despite the main strategy to overcome bacterial resistance has focused on the development of more potent antimicrobial agents, the evolutionary pressure caused by such drugs makes this strategy limited. Molecules that interfere with virulence factors appear as a promising alternative though, as they cause reduced selective pressure. As a matter of fact, staphyloxanthin biosynthesis inhibition (STXBI) has been pursued as promising strategy to reduce S. aureus virulence. Herein, we report the inhibitory profile of 27 tetrangomycin derivatives over staphyloxanthin production. The experimental result showed that naphthoquinone dehydro-α-lapachone (25 - EC50 = 57.29 ± 1.15 μM) and 2-Isopropylnaphtho[2,3-b]furan-4,9-dione (26 EC50 = 82.10 ± 1.09 μM) are the most potent compounds and suggest that hydrogen acceptor groups and lipophilic moieties decorating the naphthoquinone ring are crucial for STXBI. In addition, we present an in situ analysis, through RAMAN spectroscopy, that is inexpensive and might be employed to probe the mechanism of action of staphyloxanthin biosynthesis inhibitors. Therefore, our molecular simplification strategies afforded promising lead compounds for the development of drugs that modulate S. aureus staphyloxanthin biosynthesis.
3. Streptomyces globosus DK15 and Streptomyces ederensis ST13 as new producers of factumycin and tetrangomycin antibiotics
Ivana Charousová, Juraj Medo, Lukáš Hleba, Soňa Javoreková Braz J Microbiol. 2018 Oct-Dec;49(4):816-822. doi: 10.1016/j.bjm.2017.12.007. Epub 2018 Mar 1.
Fifty seven soil-borne actinomycete strains were assessed for the antibiotic production. Two of the most active isolates, designed as Streptomyces ST-13 and DK-15 exhibited a broad range of antimicrobial activity and therefore they were selected for HPLC fractionation against the most suppressed bacteria Staphylococcus aureus (ST-13) and Chromobacterium violaceum (DK-15). LC/MS analysis of extracts showed the presence of polyketides factumycin (DK15) and tetrangomycin (ST13). The taxonomic position of the antibiotic-producing actinomycetes was determined using a polyphasic approach. Phenotypic characterization and 16S rRNA gene sequence analysis of the isolates matched those described for members of the genus Streptomyces. DK-15 strain exhibited the highest 16S rRNA gene sequence similarity to Streptomyces globosus DSM-40815 (T) and Streptomyces toxytricini DSM-40178 (T) and ST-13 strain to Streptomyces ederensis DSM-40741 (T) and Streptomyces phaeochromogenes DSM-40073 (T). For the proper identification, MALDI-TOF/MS profile of whole-cell proteins led to the identification of S. globosus DK-15 (accession number: KX527570) and S. ederensis ST13 (accession number: KX527568). To our knowledge, there is no report about the production of these antibiotics by S.globosus and S. ederensis, thus isolates DK15 and ST13 identified as S. globosus DK-15 and S.ederensis ST-13 can be considered as new sources of these unique antibacterial metabolites.
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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 ╳
