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HomeProduct name listpyoluteorin

pyoluteorin

pyoluteorin Structural

What is pyoluteorin?

The Uses of pyoluteorin

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.

What are the applications of Application

Pyoluteorin is a small chlorinated pyrrol with a broad bioprofile

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].

Safety Profile

A poison by ingestion and intraperitoneal routes. A flammable liquid. When heated to decomposition it emits toxic vapors of NOx and Cl-.

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.

Properties of pyoluteorin

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

Safety information for pyoluteorin

Computed Descriptors for pyoluteorin

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