Pyrrolnitrin
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| Category | Antibiotics |
| Catalog number | BBF-02594 |
| CAS | 1018-71-9 |
| Molecular Weight | 257.07 |
| Molecular Formula | C10H6Cl2N2O2 |
| Purity | 98% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-02594 | 1 mg | $299 | In stock | |
| BBF-02594 | 10 mg | $524 | In stock |
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Add to cartDescription
Pyrrolnitrin is a nitrogen-containing heterocyclic antibiotic produced by Pseudomonas pyrrocinia 2327. It has antifungal effect and weak anti-Gram-positive bacteria activity.
Specification
| Synonyms | Pyrrolnitrine; Pyroace |
| IUPAC Name | 3-chloro-4-(3-chloro-2-nitrophenyl)-1H-pyrrole |
| Canonical SMILES | C1=CC(=C(C(=C1)Cl)[N+](=O)[O-])C2=CNC=C2Cl |
| InChI | InChI=1S/C10H6Cl2N2O2/c11-8-3-1-2-6(10(8)14(15)16)7-4-13-5-9(7)12/h1-5,13H |
| InChI Key | QJBZDBLBQWFTPZ-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Boiling Point | 410.5°C at 760 mmHg |
| Melting Point | 125°C |
| Density | 1.523 g/cm3 |
Reference Reading
1. Pyrrolnitrin is more essential than phenazines for Pseudomonas chlororaphis G05 in its suppression of Fusarium graminearum
Zhibin Feng, Ruiyang Lu, Yihe Ge, Xiaoqiang Sun, Wangtai Luo, Baoshen Zhang, Yanhua Wang, Xiaoyan Chi, Run Huang, Jing Miao, Yang Lu Microbiol Res . 2018 Oct;215:55-64. doi: 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.
2. Effects of pesticides on the bacterial production of pyrrolnitrin
Hye Ri Lee, Jeong-Han Kim, Young Soo Keum J Agric Food Chem . 2010 May 12;58(9):5531-7. doi: 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.
3. Microbial Pyrrolnitrin: Natural Metabolite with Immense Practical Utility
Shraddha Pawar, Ratna Prabha, Dhananjaya P Singh, Renu Shukla, Ambalal Chaudhari Biomolecules . 2019 Sep 3;9(9):443. doi: 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,SerratiaandBurkholderia. 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 ofSerratiaandBurkholderia, 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.
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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 ╳
