8-Hydroxycoumarin
(Synonyms: 8-羟基-2H-苯并吡喃-2-酮) 目录号 : GC61451
8-Hydroxycoumarin是喹诺酮类药物微生物转化的中间产物。
Cas No.:2442-31-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
8-Hydroxycoumarin is an intermediate in the microbial transformation of quinolone[1].
[1]. Gao Y, et al. Enhanced degradation of quinoline by coupling microbial electrolysis cell with anaerobic digestion simultaneous [published online ahead of print, 2020 Feb 28]. Bioresour Technol. 2020;306:123077.
| Cas No. | 2442-31-1 | SDF | |
| 别名 | 8-羟基-2H-苯并吡喃-2-酮 | ||
| Canonical SMILES | O=C1C=CC2=CC=CC(O)=C2O1 | ||
| 分子式 | C9H6O3 | 分子量 | 162.14 |
| 溶解度 | 储存条件 | Store at -20°C | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.1675 mL | 30.8375 mL | 61.6751 mL |
| 5 mM | 1.2335 mL | 6.1675 mL | 12.335 mL |
| 10 mM | 0.6168 mL | 3.0838 mL | 6.1675 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Xenobiotic reductase A in the degradation of quinoline by Pseudomonas putida 86: physiological function, structure and mechanism of 8-Hydroxycoumarin reduction
J Mol Biol 2006 Aug 4;361(1):140-52.PMID:16822524DOI:10.1016/j.jmb.2006.06.007.
A continuous evolutionary pressure of the biotic and abiotic world has led to the development of a diversity of microbial pathways to degrade and biomineralize aromatic and heteroaromatic compounds. The heterogeneity of compounds metabolized by bacteria like Pseudomonas putida indicates the large variety of enzymes necessary to catalyse the required reactions. Quinoline, a N-heterocyclic aromatic compound, can be degraded by microbes along different pathways. For P. putida 86 quinoline degradation by the 8-Hydroxycoumarin pathway has been described and several intermediates were identified. To select enzymes catalysing the later stages of the 8-Hydroxycoumarin pathway P. putida 86 was grown with quinoline. The FMN-containing enzyme xenobiotic reductase A (XenA) was isolated and analysed for its reactivity with intermediates of the 8-Hydroxycoumarin pathway. XenA catalyses the NADPH-dependent reduction of 8-Hydroxycoumarin and coumarin to produce 8-hydroxy-3,4-dihydrocoumarin and 3,4-dihydrocoumarin, respectively. Crystallographic analysis of XenA alone and in complex with the two substrates revealed insights into the mechanism. XenA shows a dimeric arrangement of two (beta/alpha)(8) barrel domains each binding one FMN cofactor. High resolution crystal structures of complexes with 8-Hydroxycoumarin and coumarin show different modes of binding for these molecules in the active site. While coumarin is ideally positioned for hydride transfer from N-5 of the isoalloxazine ring to C-4 of coumarin, 8-Hydroxycoumarin forms a non-productive complex with oxidised XenA. Orientation of 8-Hydroxycoumarin in the active site appears to be dependent on the electronic state of the flavin. We postulate that XenA catalyses the last step of the 8-Hydroxycoumarin pathway before the heterocyclic ring is hydrolysed to yield 3-(2,3-dihydroxyphenyl)-propionic acid. As XenA is also found in P. putida strains unable to degrade quinoline, it appears to have more than one physiological function and is an example of how enzymes with low substrate specificity can help to explain the variety of degradation pathways possible.
Biodegradation of Quinoline by a Newly Isolated Salt-Tolerating Bacterium Rhodococcus gordoniae Strain JH145
Microorganisms 2022 Apr 9;10(4):797.PMID:35456847DOI:10.3390/microorganisms10040797.
Quinoline is a typical nitrogen-heterocyclic compound with high toxicity and carcinogenicity which exists ubiquitously in industrial wastewater. In this study, a new quinoline-degrading bacterial strain Rhodococcus sp. JH145 was isolated from oil-contaminated soil. Strain JH145 could grow with quinoline as the sole carbon source. The optimum growth temperature, pH, and salt concentration were 30 °C, 8.0, and 1%, respectively. 100 mg/L quinoline could be completely removed within 28 h. Particularly, strain JH145 showed excellent quinoline biodegradation ability under a high-salt concentration of 7.5%. Two different quinoline degradation pathways, a typical 8-Hydroxycoumarin pathway, and a unique anthranilate pathway were proposed based on the intermediates identified by liquid chromatography-time of flight mass spectrometry. Our present results provided new candidates for industrial application in quinoline-contaminated wastewater treatment even under high-salt conditions.
Biodegradation characteristics of quinoline by Pseudomonas putida
Bioresour Technol 2010 Oct;101(19):7683-6.PMID:20554200DOI:10.1016/j.biortech.2010.05.026.
A quinoline-degrading strain was isolated from activated sludge of the municipal wastewater treatment plant and identified as Pseudomonas putida on the basis of its partial 16S rRNA gene sequence analysis. The characteristics of quinoline degradation were investigated. The experimental results showed that quinoline at the concentration of 500 mg/L could be completely removed within 3h, but could not be mineralized because special pigments were observed in the process of quinoline biodegradation. The N-atom in the quinoline ring was released as NH(3); some metabolic intermediates were identified, including 2-hydroxyquinoline, 2,8-dihydroxyquinoline and 8-Hydroxycoumarin. The metabolic pathway of quinoline by P. putida was tentatively proposed, that is, via 8-Hydroxycoumarin pathway, namely, the biodegradation was initiated by hydroxylation at position 2 to form 2-oxo-1,2-dihydroquinoline (2-hydroxyquinoline), which was then oxidized to 8-hydroxy-2-oxo-1,2-dihydro-quinoline (2,8-dihydroxyquinoline) and 8-Hydroxycoumarin.
Microbial transformation of quinoline by a Pseudomonas sp
Appl Environ Microbiol 1986 Jun;51(6):1332-42.PMID:3089153DOI:10.1128/aem.51.6.1332-1342.1986.
A Pseudomonas sp. isolated from sewage by enrichment culture on quinoline metabolized this substrate by a novel pathway involving 8-Hydroxycoumarin. During early growth of the organism on quinoline, 2-hydroxyquinoline accumulated as the intermediate; 8-Hydroxycoumarin accumulated as the major metabolite on further incubation. 2,8-Dihydroxyquinoline and 2,3-dihydroxyphenylpropionic acid were identified as the other intermediates. Inhibition of quinoline metabolism by 1 mM sodium arsenite led to the accumulation of pyruvate, whereas inhibition by 5 mM arsenite resulted in the accumulation of 2-hydroxyquinoline as the major metabolite and 2,8-dihydroxyquinoline as the minor metabolite. Coumarin was not utilized as a growth substrate by this bacterium, but quinoline-grown cells converted it to 2-hydroxyphenylpropionic acid, which was not further metabolized. Quinoline, 2-hydroxyquinoline, 8-Hydroxycoumarin, and 2,3-dihydroxyphenylpropionic acid were rapidly oxidized by quinoline-adapted cells, whereas 2,8-dihydroxyquinoline was oxidized very slowly. Quinoline catabolism in this Pseudomonas sp. is therefore initiated by hydroxylation(s) of the molecule followed by cleavage of the pyridine ring to yield 8-Hydroxycoumarin, which is further metabolized via 2,3-dihydroxyphenylpropionic acid.
Enhanced degradation of quinoline by coupling microbial electrolysis cell with anaerobic digestion simultaneous
Bioresour Technol 2020 Feb 28;306:123077.PMID:32155565DOI:10.1016/j.biortech.2020.123077.
In this study, the feasibility of quinoline-wastewater treatment was investigated in a coupled microbial electrolysis cell and anaerobic digestion system (MEC-AD). Improved degradation and enhanced mineralization of quinoline were obtained, and the optimal voltage was determined to be 1.0 V. Effective removal of quinoline at relative high concentration, and a 1.5-fold increase in methane production were achieved. The results indicated that the MEC-AD could simultaneously remove carbon and nitrogen from quinoline. Gas chromatography-mass spectrometry analysis identified 2-hydroxyquinoline and 8-Hydroxycoumarin as the intermediates of quinoline. The formation and degradation of metabolites were rapid, and they did not accumulate in the MEC-AD. The results of microbial community structure analysis demonstrated that the functional species were enriched and coexisted, and that the dominant bacterial genera were SM1A02, Comamonas, Desulfovibrio, Geobacter, and Actinomarinales_norank; the dominant archaeal genera were Methanocorpusculum and Nitrosoarchaeum. Furthermore, the applied current played a selective role in the enrichment of microorganisms.