Acetosyringone
Encyclopedia
Acetosyringone is a phenolic
natural product
, and is a chemical compound related to acetophenone
and 2,6-dimethoxyphenol
. It was first described in relation to lignan
/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.
Historically, this substance has been best known for its involvement in plant-pathogen recognition, especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus Agrobacterium
. The virA gene on the Ti plasmid
in the genome of Agrobacterium tumefaciens
and Agrobacterium rhizogenes
is used by these soil bacteria to infect plants, via its encoding for a receptor for acetosyringone and other phenolic phytochemicals exuded by plant wounds. This compound also allows higher transformation efficiency in plants, in A. tumefaciens mediated transformation procedures, and so is of importance in plant biotechnology.
Acetosyringone can also be found in Posidonia oceanica
and a wide variety of other plants. The compound is also produced by the male leaffooted bug (Leptoglossus phyllopus
) and used in its communication system.
In vitro studies show that acetosyringone increases mycorrhiza
e formation in the fungus Glomus intraradices
.
Total synthesis of this simple natural product performed by Crawford et al in 1956, but is of limited contemporary synthetic interest. A variety of acetosyringone analogs are available, including some which are covalent inactivators of cellular processes that involve acetosyringone.
Phenolic
Phenolic is an adjective and a substantive that may apply to :* Natural phenolics and polyphenols, two related classes of natural compounds found in plants* Phenol , a colorless crystalline solid and aromatic compound...
natural product
Natural product
A natural product is a chemical compound or substance produced by a living organism - found in nature that usually has a pharmacological or biological activity for use in pharmaceutical drug discovery and drug design...
, and is a chemical compound related to acetophenone
Acetophenone
Acetophenone is the organic compound with the formula C6H5CCH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.-Production:Acetophenone can be obtained by a variety of methods...
and 2,6-dimethoxyphenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
. It was first described in relation to lignan
Lignan
The lignans are a group of chemical compounds found in plants. Lignans are one of the major classes of phytoestrogens, which are estrogen-like chemicals and also act as antioxidants. The other classes of phytoestrogens are the isoflavones and coumestans...
/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.
Historically, this substance has been best known for its involvement in plant-pathogen recognition, especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus Agrobacterium
Agrobacterium
Agrobacterium is a genus of Gram-negative bacteria established by H. J. Conn that uses horizontal gene transfer to cause tumors in plants. Agrobacterium tumefaciens is the most commonly studied species in this genus...
. The virA gene on the Ti plasmid
Ti plasmid
Ti plasmid is a circular plasmid that often, but not always, is a part of the genetic equipment that Agrobacterium tumefaciens and Agrobacterium rhizogenes use to transduce its genetic material to plants. Ti stands for tumor inducing. The Ti plasmid is lost when Agrobacterium is grown above 28°C....
in the genome of Agrobacterium tumefaciens
Agrobacterium tumefaciens
Agrobacterium tumefaciens is the causal agent of crown gall disease in over 140 species of dicot. It is a rod shaped, Gram negative soil bacterium...
and Agrobacterium rhizogenes
Agrobacterium rhizogenes
Agrobacterium rhizogenes is a Gram negative soil bacterium that produces hairy root disease in dicotyledonous plants.A...
is used by these soil bacteria to infect plants, via its encoding for a receptor for acetosyringone and other phenolic phytochemicals exuded by plant wounds. This compound also allows higher transformation efficiency in plants, in A. tumefaciens mediated transformation procedures, and so is of importance in plant biotechnology.
Acetosyringone can also be found in Posidonia oceanica
Posidonia oceanica
Posidonia oceanica is a seagrass species that is endemic to the Mediterranean Sea. It forms large underwater meadows that are an important part of the ecosystem. The fruit is free floating and known in Italy as 'the olive of the sea'...
and a wide variety of other plants. The compound is also produced by the male leaffooted bug (Leptoglossus phyllopus
Leptoglossus phyllopus
Leptoglossus phyllopus or Florida leaf-footed bug is a species of leaf-footed bug in the same genus as the western conifer seed bug ....
) and used in its communication system.
In vitro studies show that acetosyringone increases mycorrhiza
Mycorrhiza
A mycorrhiza is a symbiotic association between a fungus and the roots of a vascular plant....
e formation in the fungus Glomus intraradices
Glomus intraradices
Glomus intraradices is an arbuscular mycorrhizal fungus used as a soil inoculant in agriculture and horticulture. In addition, it is one of the best mycorrhizal varieties of fungi available to mycoforestry, but it "has virtually no market value as an edible or medicinal mushroom" Glomus ...
.
Total synthesis of this simple natural product performed by Crawford et al in 1956, but is of limited contemporary synthetic interest. A variety of acetosyringone analogs are available, including some which are covalent inactivators of cellular processes that involve acetosyringone.