| Identification | Back Directory | [Name]
pyoluteorin | [CAS]
25683-07-2 | [Synonyms]
pyoluteorin
4,5-Dichloro-1H-pyrrol-2-yl 2,6-dihydroxyphenyl ketone
(4,5-Dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)methanone
Methanone, (4,5-dichloro-1H-pyrrol-2-yl)(2,6-dihydroxyphenyl)- | [Molecular Formula]
C11H7Cl2NO3 | [MDL Number]
MFCD01716546 | [MOL File]
25683-07-2.mol | [Molecular Weight]
272.08 |
| Chemical Properties | Back Directory | [Melting point ]
174-175 °C (decomp) | [Boiling point ]
436.9±45.0 °C(Predicted) | [density ]
1.4931 (rough estimate) | [refractive index ]
1.6140 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
solid | [pka]
6.97±0.35(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Uses]
Pyoluteorin is a small chlorinated pyrrol produced by several species of Pseudomonas, first reported in 1958. Pyoluteorin exhibits a broad bioprofile, demonstrating antibiotic, antifungal and herbicidal activity. More recently, pyoluteorin has been investigated as bio-pesticide and has been shown to modulate the levels of metabolites in Pseudomonas. | [Uses]
Pyoluteorin is a small chlorinated pyrrol produced by several species of Pseudomonas, first reported in 1958. Pyoluteorin has a broad bioprofile, demonstrating antibiotic, antifungal and herbicidal activity. More recently, pyoluteorin has been investigated as a bio-pesticide and has been shown to modulate the levels of metabolites in Pseudomonas. | [Definition]
ChEBI: Pyoluteorin is a member of the class of resorcinols that is resorcinol in which the hydrogen at position 2 is replaced by a 4,5-dichloro-1H-pyrrole-2-carbonyl group. It is a natural product found in Pseudomonas fluorescens which exhibits antibacterial properties and is a strong inducer of caspase-3-dependent apoptosis. It has a role as a bacterial metabolite, an apoptosis inducer, an antifungal agent, a marine metabolite and an antibacterial agent. It is a member of resorcinols, a member of pyrroles, an organochlorine compound, a diol, a beta-hydroxy ketone, a polyketide, an aromatic ketone and an organochlorine pesticide. | [Biological Activity]
pyoluteorin is a secondary metabolite produced by the biological control organism pseudomonas fluorescens pf-5, a rhizosphere bacterium. pyoluteorin shows no toxicity to seed- and root-rotting plant pathogens. pyoluteorin production is influenced by positive autoregulation. addition of pyoluteorin to liquid cultures of pf-5 enhanced pyoluteorin production.pyoluteorin functions as a signal molecule negatively regulating additional secondary metabolites produced by pseudomonas [1]. the pyoluteorin contributes to the biological control of soilborne plant diseases by some strains of pseudomonas fluorescens, including pf-5. pyoluteorin induces its own productionand represses the other’s production [2]. depending on the plant, pyoluteorin production plays an important role in the suppression of damping-off by strain cha0 without being a major mechanism in disease suppression [3]. | [References]
[1] brodhagen m, henkels m d, loper j e. positive autoregulation and signaling properties of pyoluteorin, an antibiotic produced by the biological control organism pseudomonas fluorescens pf-5[j]. applied and environmental microbiology, 2004, 70(3): 1758-1766.
[2] kidarsa t a, goebel n c, zabriskie t m, et al. phloroglucinol mediates cross‐talk between the pyoluteorin and 2, 4‐diacetylphloroglucinol biosynthetic pathways in pseudomonas fluorescens pf‐5[j]. molecular microbiology, 2011, 81(2): 395-414.
[3] maurhofer m, keel c, haas d, et al. pyoluteorin production bypseudomonas fluorescens strain cha0 is involved in the suppression ofpythium damping-off of cress but not of cucumber[j]. european journal of plant pathology, 1994, 100(3): 221-232. |
| Safety Data | Back Directory | [Safety Profile]
A poison by ingestion and intraperitoneal routes. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx and Cl-. |
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