Acetosyringone

Last updated
Acetosyringone
Acetosyringone.svg
Names
Preferred IUPAC name
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethan-1-one
Other names
Acetosyringenin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.017.828 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3 Yes check.svgY
    Key: OJOBTAOGJIWAGB-UHFFFAOYSA-N Yes check.svgY
  • CC(=O)C1=CC(=C(C(=C1)OC)O)OC
  • O=C(c1cc(OC)c(O)c(OC)c1)C
Properties
C10H12O4
Molar mass 196.202 g·mol−1
Melting point 125.5 °C (257.9 °F; 398.6 K)
Boiling point 335 °C (635 °F; 608 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Acetosyringone is a phenolic natural product and 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.

Contents

Occurrence and biological role

Historically, this substance has been best known for its involvement in plant-pathogen recognition, [1] especially its role as a signal attracting and transforming unique, oncogenic bacteria in genus Agrobacterium . The virA gene on the Ti plasmid of Agrobacterium tumefaciens 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. [2] 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. [3]

Acetosyringone can also be found in Posidonia oceanica [4] and a wide variety of other plants. It is secreted at wounded sites of dicotyledons. This compound enhances the Agrobacterium-mediated gene transformation in dicots. Monocotyledons lack this wound response, which is considered the limiting factor in Agrobacterium-mediated gene transformation in monocots. [5]

The compound is also produced by the male leaffooted bug ( Leptoglossus phyllopus ) and used in its communication system. [6] [7] [8]

In vitro studies show that acetosyringone increases mycorrhizae formation in the fungus Glomus intraradices . [9]

A total synthesis of this simple natural product was performed by Crawford et al. in 1956, [10] 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.

See also

Related Research Articles

<span class="mw-page-title-main">Bacterial conjugation</span> Method of bacterial gene transfer

Bacterial conjugation is the transfer of genetic material between bacterial cells by direct cell-to-cell contact or by a bridge-like connection between two cells. This takes place through a pilus. It is a parasexual mode of reproduction in bacteria.

<span class="mw-page-title-main">Transformation (genetics)</span> Genetic alteration of a cell by uptake of genetic material from the environment

In molecular biology and genetics, transformation is the genetic alteration of a cell resulting from the direct uptake and incorporation of exogenous genetic material from its surroundings through the cell membrane(s). For transformation to take place, the recipient bacterium must be in a state of competence, which might occur in nature as a time-limited response to environmental conditions such as starvation and cell density, and may also be induced in a laboratory.

<i>Agrobacterium tumefaciens</i> Bacterium, genetic engineering tool

Agrobacterium radiobacter is the causal agent of crown gall disease in over 140 species of eudicots. It is a rod-shaped, Gram-negative soil bacterium. Symptoms are caused by the insertion of a small segment of DNA, from a plasmid into the plant cell, which is incorporated at a semi-random location into the plant genome. Plant genomes can be engineered by use of Agrobacterium for the delivery of sequences hosted in T-DNA binary vectors.

<i>Agrobacterium</i> Genus of bacteria

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 is well known for its ability to transfer DNA between itself and plants, and for this reason it has become an important tool for genetic engineering.

<span class="mw-page-title-main">Transfer DNA</span>

The transfer DNA is the transferred DNA of the tumor-inducing (Ti) plasmid of some species of bacteria such as Agrobacterium tumefaciens and Agrobacterium rhizogenes . The T-DNA is transferred from bacterium into the host plant's nuclear DNA genome. The capability of this specialized tumor-inducing (Ti) plasmid is attributed to two essential regions required for DNA transfer to the host cell. The T-DNA is bordered by 25-base-pair repeats on each end. Transfer is initiated at the right border and terminated at the left border and requires the vir genes of the Ti plasmid.

<i>Leptoglossus phyllopus</i> Species of true bug

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 Florida to California, through Mexico, and as far south as Costa Rica.

<span class="mw-page-title-main">Ti plasmid</span>

A tumour inducing (Ti) plasmid is a plasmid found in pathogenic species of Agrobacterium, including A. tumefaciens, A. rhizogenes, A. rubi and A. vitis.

<span class="mw-page-title-main">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid, is an organic compound and a polyphenol with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans.

<i>Rhizobium rhizogenes</i> Disease-causing bacterium

Rhizobium rhizogenes is a Gram-negative soil bacterium that produces hairy root disease in dicotyledonous plants. R. rhizogenes induces the formation of proliferative multiple-branched adventitious roots at the site of infection, so-called 'hairy roots'. It also induces galls.

<span class="mw-page-title-main">Gene delivery</span> Introduction of foreign genetic material into host cells

Gene delivery is the process of introducing foreign genetic material, such as DNA or RNA, into host cells. Gene delivery must reach the genome of the host cell to induce gene expression. Successful gene delivery requires the foreign gene delivery to remain stable within the host cell and can either integrate into the genome or replicate independently of it. This requires foreign DNA to be synthesized as part of a vector, which is designed to enter the desired host cell and deliver the transgene to that cell's genome. Vectors utilized as the method for gene delivery can be divided into two categories, recombinant viruses and synthetic vectors.

<span class="mw-page-title-main">Jozef Schell</span> Belgian molecular biologist

Jozef Stefaan "Jeff", Baron Schell was a Belgian molecular biologist.

Plant transformation vectors are plasmids that have been specifically designed to facilitate the generation of transgenic plants. The most commonly used plant transformation vectors are termed binary vectors because of their ability to replicate in both E. coli, a common lab bacterium and Agrobacterium tumefaciens, a bacterium used to insert the recombinant (customized) DNA into plants. Plant Transformation vectors contain three key elements;

A transfer DNA (T-DNA) binary system is a pair of plasmids consisting of a T-DNA binary vector and a virhelper plasmid. The two plasmids are used together to produce genetically modified plants. They are artificial vectors that have been derived from the naturally occurring Ti plasmid found in bacterial species of the genus Agrobacterium, such as A. tumefaciens. The binary vector is a shuttle vector, so-called because it is able to replicate in multiple hosts.

VirA is a protein histidine kinase which senses certain sugars and phenolic compounds. These compounds are typically found from wounded plants, and as a result VirA is used by Agrobacterium tumefaciens to locate potential host organisms for infection. This detection is the first stage in the Ti plasmid transfer.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

EHA101 was one of the first and most widely used Agrobacterium helper plasmid for plant gene transfer. Created in 1985 in the laboratory of Mary-Dell Chilton at Washington University in St. Louis, it was named after the graduate student who constructed it. The EH stands for "Elizabeth Hood" and A for "Agrobacterium". The EHA101 helper strain is a derivative of A281, the hypervirulent A. tumefaciens strain that causes large, fast-growing tumors on solanaceous plants. This strain is used for moving genes of interest into many hundreds of species of plants all over the world.

Allorhizobium vitis is a plant pathogen that infects grapevines. The species is best known for causing a tumor known as crown gall disease. One of the virulent strains, A. vitis S4, is responsible both for crown gall on grapevines and for inducing a hypersensitive response in other plant species. Grapevines that have been affected by crown gall disease produce fewer grapes than unaffected plants. Though not all strains of A. vitis are tumorigenic, most strains can damage plant hosts.

Transient expression, more frequently referred to "transient gene expression", is the temporary expression of genes that are expressed for a short time after nucleic acid, most frequently plasmid DNA encoding an expression cassette, has been introduced into eukaryotic cells with a chemical delivery agent like calcium phosphate (CaPi) or polyethyleneimine (PEI). However, unlike "stable expression," the foreign DNA does not fuse with the host cell DNA, resulting in the inevitable loss of the vector after several cell replication cycles. The majority of transient gene expressions are done with cultivated animal cells. The technique is also used in plant cells; however, the transfer of nucleic acids into these cells requires different methods than those with animal cells. In both plants and animals, transient expression should result in a time-limited use of transferred nucleic acids, since any long-term expression would be called "stable expression."

Patricia C. Zambryski is a plant scientist known for her work on Type IV secretion and cell-to-cell transport in plants. She was an elected member of the National Academy of Sciences, the American Association for the Advancement of Science, and the American Society for Microbiology.

The root inducing (Ri) -plasmid of Rhizobium rhizogenes is a plasmid capable of undergoing horizontal gene transfer of its transfer DNA (T-DNA), upon contact with a plant host. The T-DNA of the Ri-plasmid affects the plant host in such a way, that gene expression is altered, especially in regard to phytohormonal balances, metabolism and certain phenotypical characteristics.

References

  1. Baker C. Jacyn; Mock Norton M.; Whitaker Bruce D.; Roberts Daniel P.; Rice Clifford P.; Deahl Kenneth L.; Aver'Yanov Andrey A. (2005). "Involvement of acetosyringone in plant-pathogen recognition". Biochemical and Biophysical Research Communications. 328 (1): 130–136. doi:10.1016/j.bbrc.2004.12.153. PMID   15670760.
  2. Schrammeijer, B.; Beijersbergen, A; Idler, KB; Melchers, LS; Thompson, DV; Hooykaas, PJ (2000). "Sequence analysis of the vir-region from Agrobacterium tumefaciens octopine Ti plasmid pTi15955". Journal of Experimental Botany. 51 (347): 1167–1169. doi: 10.1093/jexbot/51.347.1167 . PMID   10948245.
  3. Sheikholeslam, Shahla N.; Weeks, Donald P. (1987). "Acetosyringone promotes high efficiency transformation of Arabidopsis thaliana explants by Agrobacterium tumefaciens". Plant Molecular Biology. 8 (4): 291–298. doi:10.1007/BF00021308. PMID   24301191. S2CID   32005770.
  4. Agostini, Sylvia; Desjobert, Jean-Marie; Pergent, Gérard (1998). "Distribution of phenolic compounds in the seagrass Posidonia oceanica". Phytochemistry. 48 (4): 611–617. doi:10.1016/S0031-9422(97)01118-7.
  5. Naveed Iqbal Raja; Asghari Bano; Hamid Rashid; Zubeda Chaudry; Noshin Ilyas (2010). "Improving Agrobacterium-mediated Transformation Protocol For Integration Of XA21 Gene In Wheat (Triticum aestivum L.)" (PDF). Pak. J. Bot. 42 (5): 3613–3631.
  6. Acetosyringone on www.pherobase.com, the pheromones data base
  7. Aldrich, J.R.; Blum, M.S.; Duffey, S.S.; Fales, H.M. (1976). "Male specific natural products in the bug, Leptoglossus phyllopus: Chemistry and possible function". Journal of Insect Physiology. 22 (9): 1201–1206. doi:10.1016/0022-1910(76)90094-9.
  8. Aldrich, J. R.; Blum, M. S.; Fales, H. M. (1979). "Species-specific natural products of adult male leaf-footed bugs (Hemiptera: Heteroptera)". Journal of Chemical Ecology. 5: 53–62. doi:10.1007/BF00987687. S2CID   34346907.
  9. Estela Flores-Gómez; Lidia Gómez-Silva; Roberto Ruiz-Medrano; Beatriz Xoconostle-Cázares (2008). "Role of acetosyringone in the accumulation of a set of RNAs in the arbuscular mycorrhiza fungus Glomus intraradices". International Microbiology. 11 (4): 275–282. doi:10.2436/20.1501.01.72. PMID   19204900.
  10. L. W. Crawford; E. O. Eaton; J. M. Pepper (1956). "An Improved Synthesis of Acetosyringone". Canadian Journal of Chemistry. 34 (11): 1562–1566. doi: 10.1139/v56-204 .