Pyrrolnitrin
(Synonyms: 硝吡咯菌素) 目录号 : GC63287
A pyrrole with diverse biological activities
Cas No.:1018-71-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Pyrrolnitrin is pyrrole that has been found in B. cepacia and has diverse biological activities.1,2,3 It is active against isolates of the fungi C. albicans, C. neoformans, B. dermatitidis, S. schenckii, and H. capsulatum (MICs = <0.78-12.5 ?g/ml).1 Pyrrolnitrin is also active against a variety of Gram-positive bacteria, including S. antibioticus, B. subtilis, and S. aureus (MICs = 0.2, 6.25, and 12.5 ?g/ml, respectively).2 It reduces spore germination, germ-tube length, and sporulation in isolates of the phytopathogenic fungus B. cinerea (EC50s = 2.3-31.8 ?g/L).3 Pyrrolnitrin (50 mg/kg) reduces C. albicans levels by 74% in the kidney of infected mice.1
1.Gordee, R.S., and Matthews, T.R.Systemic antifungal activity of pyrrolnitrinAppl. Microbiol.17(5)690-694(1969) 2.El-Banna, N., and Winkelmann, G.Pyrrolnitrin from Burkholderia cepacia: Antibiotic activity against fungi and novel activities against streptomycetesJ. Appl. Microbiol.85(1)69-78(1998) 3.Ajouz, S., Walker, A.S., Fabre, F., et al.Variability of Botrytis cinerea sensitivity to pyrrolnitrin, an antibiotic produced by biological control agentsBioControl56(3)353-363(2011)
| Cas No. | 1018-71-9 | SDF | |
| 别名 | 硝吡咯菌素 | ||
| 分子式 | C10H6Cl2N2O2 | 分子量 | 257.07 |
| 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 | 3.89 mL | 19.45 mL | 38.8999 mL |
| 5 mM | 0.778 mL | 3.89 mL | 7.78 mL |
| 10 mM | 0.389 mL | 1.945 mL | 3.89 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。
Microbial Pyrrolnitrin: Natural Metabolite with Immense Practical Utility
Biomolecules 2019 Sep 3;9(9):443.PMID:31484394DOI:10.3390/biom9090443.
Pyrrolnitrin (PRN) is a microbial pyrrole halometabolite of immense antimicrobial significance for agricultural, pharmaceutical and industrial implications. The compound and its derivatives have been isolated from rhizospheric fluorescent or non-fluorescent pseudomonads, Serratia and Burkholderia. They are known to confer biological control against a wide range of phytopathogenic fungi, and thus offer strong plant protection prospects against soil and seed-borne phytopathogenic diseases. Although chemical synthesis of PRN has been obtained using different steps, microbial production is still the most useful option for producing this metabolite. In many of the plant-associated isolates of Serratia and Burkholderia, production of PRN is dependent on the quorum-sensing regulation that usually involves N-acylhomoserine lactone (AHL) autoinducer signals. When applied on the organisms as antimicrobial agent, the molecule impedes synthesis of key biomolecules (DNA, RNA and protein), uncouples with oxidative phosphorylation, inhibits mitotic division and hampers several biological mechanisms. With its potential broad-spectrum activities, low phototoxicity, non-toxic nature and specificity for impacts on non-target organisms, the metabolite has emerged as a lead molecule of industrial importance, which has led to developing cost-effective methods for the biosynthesis of PRN using microbial fermentation. Quantum of work narrating focused research efforts in the emergence of this potential microbial metabolite is summarized here to present a consolidated, sequential and updated insight into the chemistry, biology and applicability of this natural molecule.
Effects of pesticides on the bacterial production of Pyrrolnitrin
J Agric Food Chem 2010 May 12;58(9):5531-7.PMID:20373823DOI:10.1021/jf904195j.
Pyrrolnitrin is a halogenated bacterial metabolite with antifungal and antibacterial activities which served as a lead structure of synthetic fungicides. Several pyrrolnitrin-producing bacteria are considered to be promising biopesticides. However, the application of these microorganisms is not straightforward since many synthetic pesticides usually coexist in agricultural fields and inevitably affect the efficacy of biocontrol agents. In this regard, effects of 25 xenobiotics, including 18 pesticides, were investigated for Pyrrolnitrin biosynthesis by Burkholderia sp. O33 and Pseudomonas fluorescens Pf-5. Strong inhibition of Pyrrolnitrin synthesis was observed in 9 chemicals, including 6 pesticides, while glyphosate and validamycin enhance biosynthesis. Fenpiclonil and fludioxonil strongly inhibit the oxidative transformation of aminopyrrolnitrin to Pyrrolnitrin. Halogenation reaction to aminopyrrolnitrin was reduced by methimazole, a well-known flavin-dependent monooxygenase inhibitor. Most pesticides gave moderate growth inhibitory effects. The results suggested that synthetic chemicals can modulate the efficacy of Pyrrolnitrin producing bacteria, through the inhibition of cell growth or Pyrrolnitrin biosynthesis. Pathway specific inhibition by fenpiclonil, fludioxonil, and methimazole will give structural insights of corresponding enzymes.
Systemic antifungal activity of Pyrrolnitrin
Appl Microbiol 1969 May;17(5):690-4.PMID:5785951DOI:10.1128/am.17.5.690-694.1969.
The antifungal activity of Pyrrolnitrin, previously shown to be effective against superficial infections, was evaluated against experimental systemic mycoses. Pyrrolnitrin was inhibitory in vitro at <0.78 to 100 mug/ml to Candida albicans, Cryptococcus neoformans, Blastomyces dermatitidis, Sporotrichum schenckii, and Histoplasma capsulatum. Pyrrolnitrin activity was reduced about 90% in sera. After multiple subcutaneous doses of Pyrrolnitrin at 20 mg/kg, activity was recovered in mouse blood and urine as well as kidney, liver, and brain homogenates. Multiple daily doses (50 mg/kg) of this antibiotic were effective in reducing by 74% the number of viable cells of C. albicans recovered from kidney homogenates. Multiple doses (15 mg/kg) resulted in a 74% reduction in the number of C. neoformans from brain homogenates. Pyrrolnitrin was ineffective in reducing the recovery of B. dermatitidis or H. capsulatum from liver or spleen homogenates of infected mice. When compared with amphotericin B, hamycin, 5-fluorocytosine, and saramycetin, this antibiotic was less effective. This study indicates that Pyrrolnitrin would have limited usefulness as a systemic antifungal agent.
Pyrrolnitrin is more essential than phenazines for Pseudomonas chlororaphis G05 in its suppression of Fusarium graminearum
Microbiol Res 2018 Oct;215:55-64.PMID:30172309DOI:10.1016/j.micres.2018.06.008.
Fusarium graminearum is the major causal agent of Fusarium head blight (FHB) disease in cereal crops worldwide. Infection with this fungal phytopathogen can regularly cause severe yield and quality losses and mycotoxin contamination in grains. In previous other studies, one research group reported that Pyrrolnitrin had an ability to suppress of mycelial growth of F. graminearum. Other groups revealed that phenazine-1-carboxamide, a derivative of phenazine-1-carboxylic acid, could also inhibit the growth of F. graminearum and showed great potentials in the bioprotection of crops from FHB disease. In our recent work with Pseudomonas chlororaphis strain G05, however, we found that although the phz operon (phenazine biosynthetic gene cluster) was knocked out, the phenazine-deficient mutant G05Δphz still exhibited effective inhibition of the mycelial growth of some fungal phytopathogens in pathogen inhibition assay, especially including F. graminearum, Colletotrichum gloeosporioides, Botrytis cinerea. With our further investigations, including deletion and complementation of the prn operon (Pyrrolnitrin biosynthetic gene cluster), purification and identification of fungal compounds, we first verified that not phenazines but Pyrrolnitrin biosynthesized in P. chlororaphis G05 plays an essential role in growth suppression of F. graminearum and the bioprotection of cereal crops against FHB disease.
Pyrrolnitrin from Rhizospheric Serratia marcescens NCIM 5696: Optimization of Process Parameters Using Statistical Tools and Seed-Applied Bioprotectants for Vigna radiata (L.) Against Fusarium oxysporum MTCC 9913
Appl Biochem Biotechnol 2020 Mar;190(3):803-825.PMID:31493159DOI:10.1007/s12010-019-03123-w.
The extensive use of chemical fungicide in the health and agriculture sectors has increased environmental concerns and promoted an extensive search for alternative bioactives from the microbial system. In the present study, two rhizospheric strains of Serratia spp. (TO-2 and TW-3) have been shown to secrete Pyrrolnitrin (PRN) in the range of 11.35 to 35.97 μg ml-1 using MSG and MSD medium after 72 h under static and shake conditions, respectively, but thereafter marginally declined in 96 to 240 h. Alternative one variable assortment at a time (OVAT) for PRN secretion by TW-3 yielded 59.27 μg ml-1 using (gl-1) glycerol (20), monosodium glutamate (14), KH2PO4 (14), NH4Cl (3), Na2HPO4 (4), and MgSO4 (0.3) at pH 7, 120 rpm within 72 h. Further, the Placket-Burman Design (PBD) identified KH2PO4, glycerol, pH, and monosodium glutamate as significant variables and optimized by centered composite design. Accordingly, 3% glycerol, 1.72% KH2PO4, 1.1% monosodium glutamate, 0.4% Na2HPO4, 0.03% MgSO4, 0.05% FeSO4, and 0.01% ZnSO4 were found to enhance the yield of PRN to 96.54 μg ml-1 by TW-3 in 72 h, 120 rpm. Thus, the statistical tool employed in the present study showed a threefold hike in PRN secretion over the OVAT approach, thereby indicating the scope for more PRN production from rhizobacteria. Further, seed application of low PRN (30 μg ml-1) concentration in treatments I and II showed > 90% germination in the initial seed germination and pot assay with the Fusarium oxysporum challenge compared to the control. Also, various growth parameters calculated during 11 days of experiment were significantly increased compared to the negative control (seed + fungus) in both treatments. Thus, the application of PRN at a low concentration to seeds of Vigna radiata (L.) offered protection against the phytopathogenic F. oxysporum MTCC 9913 challenge, suggesting biocontrol activity potential for use in agriculture soils particularly salt-affected soil.