7-Hydroxytropolone
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-01031 |
| CAS | |
| Molecular Weight | 138.12 |
| Molecular Formula | C7H6O3 |
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Description
7-Hydroxytropolone is an antibiotic produced by Pseudomonas sp. vV and Streptomyces neyagawaensis. It has anti-Gram-positive bacteria, negative bacteria, yeast and fungi activity, and has the effect of inhibiting 2''-O-Adenylyltransferase.
Specification
| Synonyms | 3-Hydroxytropolone |
| IUPAC Name | 2,3-dihydroxycyclohepta-2,4,6-trien-1-one |
| Canonical SMILES | C1=CC(=C(C(=O)C=C1)O)O |
| InChI | InChI=1S/C7H6O3/c8-5-3-1-2-4-6(9)7(5)10/h1-4H,(H2,8,9,10) |
| InChI Key | ABNPYUDYGCGOTK-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi; yeast |
| Boiling Point | 272.8±40.0 °C at 760 mmHg |
| Melting Point | 134-135°C |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Harnessing the genomic diversity of Pseudomonas strains against lettuce bacterial pathogens
Antoine Zboralski, Adrien Biessy, Marie Ciotola, Mélanie Cadieux, Daphné Albert, Jochen Blom, Martin Filion Front Microbiol. 2022 Dec 22;13:1038888. doi: 10.3389/fmicb.2022.1038888. eCollection 2022.
Lettuce is a major vegetable crop worldwide that is affected by numerous bacterial pathogens, including Xanthomonas hortorum pv. vitians, Pseudomonas cichorii, and Pectobacterium carotovorum. Control methods are scarce and not always effective. To develop new and sustainable approaches to contain these pathogens, we screened more than 1,200 plant-associated Pseudomonas strains retrieved from agricultural soils for their in vitro antagonistic capabilities against the three bacterial pathogens under study. Thirty-five Pseudomonas strains significantly inhibited some or all three pathogens. Their genomes were fully sequenced and annotated. These strains belong to the P. fluorescens and P. putida phylogenomic groups and are distributed in at least 27 species, including 15 validly described species. They harbor numerous genes and clusters of genes known to be involved in plant-bacteria interactions, microbial competition, and biocontrol. Strains in the P. putida group displayed on average better inhibition abilities than strains in the P. fluorescens group. They carry genes and biosynthetic clusters mostly absent in the latter strains that are involved in the production of secondary metabolites such as 7-hydroxytropolone, putisolvins, pyochelin, and xantholysin-like and pseudomonine-like compounds. The presence of genes involved in the biosynthesis of type VI secretion systems, tailocins, and hydrogen cyanide also positively correlated with the strains' overall inhibition abilities observed against the three pathogens. These results show promise for the development of biocontrol products against lettuce bacterial pathogens, provide insights on some of the potential biocontrol mechanisms involved, and contribute to public Pseudomonas genome databases, including quality genome sequences on some poorly represented species.
2. Pseudomonas species isolated via high-throughput screening significantly protect cotton plants against verticillium wilt
Xiaoyuan Tao, Hailin Zhang, Mengtao Gao, Menglin Li, Ting Zhao, Xueying Guan AMB Express. 2020 Oct 28;10(1):193. doi: 10.1186/s13568-020-01132-1.
Verticillium wilt (VW) caused by Verticillium dahliae is a devastating soil-borne disease that causes severe yield losses in cotton and other major crops worldwide. Here we conducted a high-throughput screening of isolates recovered from 886 plant rhizosphere samples taken from the three main cotton-producing areas of China. Fifteen isolates distributed in different genera of bacteria that showed inhibitory activity against V. dahliae were screened out. Of these, two Pseudomonas strains, P. protegens XY2F4 and P. donghuensis 22G5, showed significant inhibitory action against V. dahliae. Additional comparative genomic analyses and phenotypical assays confirmed that P. protegens XY2F4 and P. donghuensis 22G5 were the strains most efficient at protecting cotton plants against VW due to specific biological control products they produced. Importantly, we identified a significant efficacy of the natural tropolone compound 7-hydroxytropolone (7-HT) against VW. By phenotypical assay using the wild-type 22G5 and its mutant strain in 7-HT production, we revealed that the 7-HT produced by P. donghuensis is the major substance protecting cotton against VW. This study reveals that Pseudomonas specifically has gene clusters that allow the production of effective antipathogenic metabolites that can now be used as new agents in the biocontrol of VW.
3. Insight into the Global Negative Regulation of Iron Scavenger 7-HT Biosynthesis by the SigW/RsiW System in Pseudomonas donghuensis HYS
Shiyu Teng, Tingting Wu, Donghao Gao, Siyi Wu, Yaqian Xiao, Yan Long, Zhixiong Xie Int J Mol Sci. 2023 Jan 7;24(2):1184. doi: 10.3390/ijms24021184.
7-Hydroxytropolone (7-HT) is a unique iron scavenger synthesized by Pseudomonas donghuensis HYS that has various biological activities in addition to functioning as a siderophore. P. donghuensis HYS is more pathogenic than P. aeruginosa toward Caenorhabditis elegans, an observation that is closely linked to the biosynthesis of 7-HT. The nonfluorescent siderophore (nfs) gene cluster is responsible for the orderly biosynthesis of 7-HT and represents a competitive advantage that contributes to the increased survival of P. donghuensis HYS; however, the regulatory mechanisms of 7-HT biosynthesis remain unclear. This study is the first to propose that the ECF σ factor has a regulatory effect on 7-HT biosynthesis. In total, 20 ECF σ factors were identified through genome-wide scanning, and their responses to extracellular ferrous ions were characterized. We found that SigW was both significantly upregulated under high-iron conditions and repressed by an adjacent anti-σ factor. RNA-Seq results suggest that the SigW/RsiW system is involved in iron metabolism and 7-HT biosynthesis. Combined with the siderophore phenotype, we also found that SigW could inhibit siderophore synthesis, and this inhibition can be relieved by RsiW. EMSA assays proved that SigW, when highly expressed, can directly bind to the promoter region of five operons of the nfs cluster to inhibit the transcription of the corresponding genes and consequently suppress 7-HT biosynthesis. In addition, SigW not only directly negatively regulates structural genes related to 7-HT synthesis but also inhibits the transcription of regulatory proteins, including of the Gac/Rsm cascade system. Taken together, our results highlight that the biosynthesis of 7-HT is negatively regulated by SigW and that the SigW/RsiW system is involved in mechanisms for the regulation of iron homeostasis in P. donghuensis HYS. As a result of this work, we identified a novel mechanism for the global negative regulation of 7-HT biosynthesis, complementing our understanding of the function of ECF σ factors in Pseudomonas.
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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 ╳
