Acetosyringone is a phenolic

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...

and a chemical compound related to

acetophenone Acetophenone is the organic compound with the chemical formula, formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byprodu ...

and

2,6-dimethoxyphenol Syringol is the organic compound with the formula HO(CH3O)2C6H3. The molecule is a phenol, with methoxy groups in the flanking (2 and 6) positions. It is the symmetrically dimethylated derivative of pyrogallol. It is a colorless solid, althoug ...

. It was first described in relation to

lignan The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role ...

/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.

Occurrence and biological role

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'' 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. ''Agrobacterium ...

''. The ''virA'' gene on the

Ti plasmid A tumour inducing (Ti) plasmid is a plasmid found in pathogenic species of ''Agrobacterium'', including ''A. tumefaciens, ''A. rhizogenes'', ''A. rubi'' and ''A. vitis''. Evolutionarily, the Ti plasmid is part of a family of plasmids carried b ...

of ''

Agrobacterium tumefaciens ''Agrobacterium radiobacter'' (more commonly known as ''Agrobacterium tumefaciens'') is the causal agent of crown gall disease (the formation of tumours) in over 140 species of eudicots. It is a rod-shaped, Gram-negative soil bacterium. Symptom ...

'' and the Ri plasmid of '' 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, as shown in ''A. tumefaciens''-mediated transformation procedures, and so is of importance in plant biotechnology. Acetosyringone can also be found in ''

Posidonia oceanica ''Posidonia oceanica'', commonly known as Neptune grass or Mediterranean tapeweed, 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 f ...

'' and a wide variety of other plants. It is secreted at wounded sites of

dicotyledon The dicotyledons, also known as dicots (or, more rarely, dicotyls), are one of the two groups into which all the flowering plants (angiosperms) were formerly divided. The name refers to one of the typical characteristics of the group: namely, t ...

s. This compound enhances the ''Agrobacterium''-mediated gene transformation in dicots.

Monocotyledon Monocotyledons (), commonly referred to as monocots, ( Lilianae '' sensu'' Chase & Reveal) are grass and grass-like flowering plants (angiosperms), the seeds of which typically contain only one embryonic leaf, or cotyledon. They constitute one ...

s lack this wound response, which is considered the limiting factor in ''Agrobacterium''-mediated gene transformation in monocots. The compound is also produced by the male leaffooted bug (''

Leptoglossus phyllopus ''Leptoglossus phyllopus'' or Eastern leaf-footed bug is a species of leaf-footed bugs in the same genus as the western conifer seed bug (''L. occidentalis''. The Eastern leaf-footed bug is found throughout the southern United States, from Flori ...

'') and used in its communication system. In vitro studies show that acetosyringone increases

mycorrhiza A mycorrhiza (from Greek μύκης ', "fungus", and ῥίζα ', "root"; pl. mycorrhizae, mycorrhiza or mycorrhizas) is a symbiotic association between a fungus and a plant. The term mycorrhiza refers to the role of the fungus in the plan ...

e formation in the fungus '' Glomus intraradices''. A

total synthesis Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes i ...

of this simple natural product was performed by Crawford et al. in 1956, but is of limited contemporary synthetic interest. A variety of acetosyringone analogues are available, including some which are covalent inactivators of cellular processes that involve acetosyringone.

Chemical characteristics

Acetosyringone does not dissolve well in water. Although it has a melting point of about 125 degree Celsius, it is not wise to autoclave acetosyringone along with the medium used for (for example) plant infiltration by microbes.

References

{{reflist, 30em O-methylated natural phenols Insect pheromones Vanilloids Aromatic ketones

Occurrence and biological role

Chemical characteristics

See also

References