Β-Aminobutyric acid

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β-Aminobutyric acid
Beta-aminobutyric acid.svg
Names
IUPAC name
3-Aminobutanoic acid
Other names
3-Aminobutyric acid
β-Aminobutanoic acid
Carbocreatine
3-Azaniumylbutanoate
3-Methyl-β-alanine
β-Methyl-β-alanine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.986 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H9NO2/c1-3(5)2-4(6)7/h3H,2,5H2,1H3,(H,6,7)
    Key: OQEBBZSWEGYTPG-UHFFFAOYSA-N
  • InChI=1/C4H9NO2/c1-3(5)2-4(6)7/h3H,2,5H2,1H3,(H,6,7)
    Key: OQEBBZSWEGYTPG-UHFFFAOYAG
  • O=C(O)CC(N)C
Properties
C4H9NO2
Molar mass 103.121 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

β-Aminobutyric acid (BABA) is an isomer of the amino acid aminobutyric acid with the chemical formula C4H9NO2. It has two isomers, α-aminobutyric acid and γ-aminobutyric acid (GABA), a neurotransmitter in animals that is also found in plants, where it may play a role in signalling. [1] [2] All three are non-proteinogenic amino acids, not being found in proteins. BABA is known for its ability to induce plant disease resistance, as well as increased resistance to abiotic stresses, when applied to plants.

Contents

Synthesis

Methods to synthesise BABA are known from at least 1857. Early methods to produce BABA included from ammonia and crotonic acid under pressure; from the acetoacetic ester phenylhydrazone; or from malonic acid, acetaldehyde, and ammonia. In 1957, Zilkha reported a new simpler method based on adding amines to crotonic acid and then catalytically hydrogenolysing the product to produce BABA. [3] [4] Since 2000, methods to produce only the S  stereoisomer of BABA have also been reported. [5] [6]

Plant disease resistance

BABA was first found to increase the resistance of plants to disease in 1960, when it was observed that it decreased late blight of tomato. [7] Further tests were made in the 1960s, but it was not until the 1990s that interest in the compound was renewed. [8] Since then, it has been shown to be effective in many different pathosystems under controlled conditions. Both perennial and annual plants have been shown to respond, as well as both monocot and dicot plants in the Solanaceae, Cucurbitaceae, Compositae, Fabaceae, Brassicaceae, Graminae, Malvaceae, Rosaceae, and Vitaceae families. Pathogen groups that have shown a response include viruses, bacteria, nematodes, fungi and oomycetes. [8] It has also been shown to be effective in the field at protecting potato and tomato plants from late blight, grape vines from Plasmopara viticola and melons from Monosporascus cannonballus . [8] [9]

Rather than having a direct effect on plant pathogens, it activates plant immune systems enabling them to resist infection more effectively. The effects that it has been studied extensively using the model plant Arabidopsis thaliana . [8]

Mode of action

BABA induces defense responses in plants by both physical and biochemical means. The precise mechanism depends on the plant and pathogen species (the pathosystem). [8] It is unknown how BABA interacts with plant tissues to increase disease resistance. It does not directly activate defensive genes in isolation, but in combination with an infection, BABA treated plants respond more quickly and strongly to the pathogen. [10]

In some pathosystems, enhanced callose and lignin deposition is seen around the point of infection, which act as a physical barrier preventing disease. Pathogenesis-related proteins (PR proteins) which perform many different functions that help to prevent disease accumulate in some BABA treated plants, regardless of whether they are inoculated with a pathogen or not. If infected however, the level of PR proteins tends to increase further. PR proteins are not the only mechanism of preventing infection however, as soil drenches of BABA that do not induce PR protein production, still confer resistance. This may be due to differences between plant families, as the Solanaceae (potato, tomato, pepper) respond by producing PR proteins without any pathogen present, whereas crucifers (Arabidopsis, cauliflower) require a pathogen to induce PR proteins. In other pathosystems, phytoalexins (anti-microbial compounds) accumulate to higher levels in BABA treated plants when they are infected by pathogens, but not when the pathogen is not present. Foliar sprays of BABA can cause small necrotic spots to form on leaves 1 or 2 days after application. This has been suggested to be due to BABA inducing the hypersensitive response which plants normally use to kill infected cells to limit the spread of infection. [8]

BABA applied as a foliar spray causes the plant hormone salicylic acid (SA) to accumulate, which is a key hormone in controlling systemic acquired resistance (SAR). Genetically modified tobacco plants that are unable to accumulate SA are still protected by BABA against some pathogens, but not others, indicating pathosystem-specific mechanisms by which BABA confers resistance. Arabidopsis unable to produce SA, jasmonic acid or ethylene (other hormones involved in defence) were still protected from the oomycete Peronospora parasitica but plants unable to produce SA were susceptible to the bacteria Pseudomonas syringae . This variation in the hormones required for BABA to confer resistance makes it differ from other synthetic activators of plant defence, which only operate through the SAR pathway of PR proteins. [8]

Related Research Articles

<i>Arabidopsis thaliana</i> Model plant species in the family Brassicaceae

Arabidopsis thaliana, the thale cress, mouse-ear cress or arabidopsis, is a small plant from the mustard family (Brassicaceae), native to Eurasia and Africa. Commonly found along the shoulders of roads and in disturbed land, it is generally considered a weed.

γ-Aminobutyric acid Main inhibitory neurotransmitter in the mammalian brain

γ-Aminobutyric acid, or GABA, is the chief inhibitory neurotransmitter in the developmentally mature mammalian central nervous system. Its principal role is reducing neuronal excitability throughout the nervous system.

<span class="mw-page-title-main">Calmodulin</span> Calcium Modulated Regulatory Protein

Calmodulin (CaM) (an abbreviation for calcium-modulated protein) is a multifunctional intermediate calcium-binding messenger protein expressed in all eukaryotic cells. It is an intracellular target of the secondary messenger Ca2+, and the binding of Ca2+ is required for the activation of calmodulin. Once bound to Ca2+, calmodulin acts as part of a calcium signal transduction pathway by modifying its interactions with various target proteins such as kinases or phosphatases.

<span class="mw-page-title-main">Plant hormone</span> Chemical compounds that regulate plant growth and development

Plant hormones are signal molecules, produced within plants, that occur in extremely low concentrations. Plant hormones control all aspects of plant growth and development, including embryogenesis, the regulation of organ size, pathogen defense, stress tolerance and reproductive development. Unlike in animals each plant cell is capable of producing hormones. Went and Thimann coined the term "phytohormone" and used it in the title of their 1937 book.

α-Aminobutyric acid Chemical compound

α-Aminobutyric acid (AABA), also known as homoalanine in biochemistry, is a non-proteinogenic alpha amino acid with chemical formula C4H9NO2. The straight two carbon side chain is one carbon longer than alanine, hence the prefix homo-.

<span class="mw-page-title-main">Jasmonate</span> Lipid-based plant hormones

Jasmonate (JA) and its derivatives are lipid-based plant hormones that regulate a wide range of processes in plants, ranging from growth and photosynthesis to reproductive development. In particular, JAs are critical for plant defense against herbivory and plant responses to poor environmental conditions and other kinds of abiotic and biotic challenges. Some JAs can also be released as volatile organic compounds (VOCs) to permit communication between plants in anticipation of mutual dangers.

Systemic acquired resistance (SAR) is a "whole-plant" resistance response that occurs following an earlier localized exposure to a pathogen. SAR is analogous to the innate immune system found in animals, and although there are many shared aspects between the two systems, it is thought to be a result of convergent evolution. The systemic acquired resistance response is dependent on the plant hormone, salicylic acid.

<span class="mw-page-title-main">Systemin</span> Plant peptide hormone

Systemin is a plant peptide hormone involved in the wound response in the family Solanaceae. It was the first plant hormone that was proven to be a peptide having been isolated from tomato leaves in 1991 by a group led by Clarence A. Ryan. Since then, other peptides with similar functions have been identified in tomato and outside of the Solanaceae. Hydroxyproline-rich glycopeptides were found in tobacco in 2001 and AtPeps were found in Arabidopsis thaliana in 2006. Their precursors are found both in the cytoplasm and cell walls of plant cells, upon insect damage, the precursors are processed to produce one or more mature peptides. The receptor for systemin was first thought to be the same as the brassinolide receptor but this is now uncertain. The signal transduction processes that occur after the peptides bind are similar to the cytokine-mediated inflammatory immune response in animals. Early experiments showed that systemin travelled around the plant after insects had damaged the plant, activating systemic acquired resistance, now it is thought that it increases the production of jasmonic acid causing the same result. The main function of systemins is to coordinate defensive responses against insect herbivores but they also affect plant development. Systemin induces the production of protease inhibitors which protect against insect herbivores, other peptides activate defensins and modify root growth. They have also been shown to affect plants' responses to salt stress and UV radiation. AtPEPs have been shown to affect resistance against oomycetes and may allow A. thaliana to distinguish between different pathogens. In Nicotiana attenuata, some of the peptides have stopped being involved in defensive roles and instead affect flower morphology.

The gene-for-gene relationship is a concept in plant pathology that plants and their diseases each have single genes that interact with each other during an infection. It was proposed by Harold Henry Flor who was working with rust (Melampsora lini) of flax (Linum usitatissimum). Flor showed that the inheritance of both resistance in the host and parasite ability to cause disease is controlled by pairs of matching genes. One is a plant gene called the resistance (R) gene. The other is a parasite gene called the avirulence (Avr) gene. Plants producing a specific R gene product are resistant towards a pathogen that produces the corresponding Avr gene product. Gene-for-gene relationships are a widespread and very important aspect of plant disease resistance. Another example can be seen with Lactuca serriola versus Bremia lactucae.

Leptosphaeria maculans is a fungal pathogen of the phylum Ascomycota that is the causal agent of blackleg disease on Brassica crops. Its genome has been sequenced, and L. maculans is a well-studied model phytopathogenic fungus. Symptoms of blackleg generally include basal stem cankers, small grey lesions on leaves, and root rot. The major yield loss is due to stem canker. The fungus is dispersed by the wind as ascospores or rain splash in the case of the conidia. L. maculans grows best in wet conditions and a temperature range of 5–20 degrees Celsius. Rotation of crops, removal of stubble, application of fungicide, and crop resistance are all used to manage blackleg. The fungus is an important pathogen of Brassica napus (canola) crops.

<span class="mw-page-title-main">Powdery scab</span> Disease of potatoes

Powdery scab is a disease of potato tubers. It is caused by the cercozoan Spongospora subterranea f. sp. subterranea and is widespread in potato growing countries. Symptoms of powdery scab include small lesions in the early stages of the disease, progressing to raised pustules containing a powdery mass. These can eventually rupture within the tuber periderm. The powdery pustules contain resting spores that release anisokont zoospores to infect the root hairs of potatoes or tomatoes. Powdery scab is a cosmetic defect on tubers, which can result in the rejection of these potatoes. Potatoes which have been infected can be peeled to remove the infected skin and the remaining inside of the potato can be cooked and eaten.

<span class="mw-page-title-main">Halo blight</span> Bacterial plant disease

Halo blight of bean is a bacterial disease caused by Pseudomonas syringae pv. phaseolicola. Halo blight’s pathogen is a gram-negative, aerobic, polar-flagellated and non-spore forming bacteria. This bacterial disease was first discovered in the early 1920s, and rapidly became the major disease of beans throughout the world. The disease favors the places where temperatures are moderate and plentiful inoculum is available.

<i>gamma</i>-Amino-<i>beta</i>-hydroxybutyric acid Anticonvulsant drug

γ-Amino-β-hydroxybutyric acid (GABOB), also known as β-hydroxy-γ-aminobutyric acid (β-hydroxy-GABA), and sold under the brand name Gamibetal among others, is an anticonvulsant which is used for the treatment of epilepsy in Europe, Japan, and Mexico. It is a GABA analogue, or an analogue of the neurotransmitter γ-aminobutyric acid (GABA), and has been found to be an endogenous metabolite of GABA.

<i>Peronospora hyoscyami</i> f.sp. <i>tabacina</i> Subspecies of single-celled organism

Peronospora hyoscyami f.sp. tabacina is a plant pathogen infecting tobacco that causes blue mold. It is an oomycete that is highly destructive toward seed plants. It is very prevalent in humid farming zones, like the southeastern and Eastern U.S., Canada, and countries bordering the Caribbean. The disease was first identified in 1921 in Florida and Georgia. Ten years later the same disease was found once again in the same region of the U.S. The disease began to spread into Virginia, Maryland, and North Carolina. A few years later, the disease reached Kentucky and Tennessee. In 1960, a blue mold epidemic spread in approximately eleven countries. There was approximately twenty five million dollars in losses which is nearly thirty percent of tobacco plants at the time. Each year, Peronospora hyoscyami is introduced as blue mold as windblown spores from outside the region by infected transplants.

Resistance genes (R-Genes) are genes in plant genomes that convey plant disease resistance against pathogens by producing R proteins. The main class of R-genes consist of a nucleotide binding domain (NB) and a leucine rich repeat (LRR) domain(s) and are often referred to as (NB-LRR) R-genes or NLRs. Generally, the NB domain binds either ATP/ADP or GTP/GDP. The LRR domain is often involved in protein-protein interactions as well as ligand binding. NB-LRR R-genes can be further subdivided into toll interleukin 1 receptor (TIR-NB-LRR) and coiled-coil (CC-NB-LRR).

Biotic stress is stress that occurs as a result of damage done to an organism by other living organisms, such as bacteria, viruses, fungi, parasites, beneficial and harmful insects, weeds, and cultivated or native plants. It is different from abiotic stress, which is the negative impact of non-living factors on the organisms such as temperature, sunlight, wind, salinity, flooding and drought. The types of biotic stresses imposed on an organism depend the climate where it lives as well as the species' ability to resist particular stresses. Biotic stress remains a broadly defined term and those who study it face many challenges, such as the greater difficulty in controlling biotic stresses in an experimental context compared to abiotic stress.

<span class="mw-page-title-main">Plant disease resistance</span> Ability of a plant to stand up to trouble

Plant disease resistance protects plants from pathogens in two ways: by pre-formed structures and chemicals, and by infection-induced responses of the immune system. Relative to a susceptible plant, disease resistance is the reduction of pathogen growth on or in the plant, while the term disease tolerance describes plants that exhibit little disease damage despite substantial pathogen levels. Disease outcome is determined by the three-way interaction of the pathogen, the plant and the environmental conditions.

<span class="mw-page-title-main">Leucine-rich repeat receptor like protein kinase</span>

Leucine-rich repeat receptor like protein kinase are plant cell membrane localized Leucine-rich repeat (LRR) receptor kinase that play critical roles in plant innate immunity. Plants have evolved intricate immunity mechanism to combat against pathogen infection by recognizing Pathogen Associated Molecular Patterns (PAMP) and endogenous Damage Associated Molecular Patterns (DAMP). PEPR 1 considered as the first known DAMP receptor of Arabidopsis.

Botrytis–induced kinase 1 (BIK1) is a membrane-anchored enzyme in plants. It is a kinase that provides resistance to necrotrophic and biotrophic pathogens. As its name suggests, BIK1 is only active after being induced by Botrytis infection. When Botrytis cinerea is present, the BIK1 gene is transcribed so that the kinase is present to defend the cell. BIK1 functions to regulate the amount of salicylic acid (SA) present in the cell. When Botrytis cinerea or Alternaria brassicicola or any other necrotrophic pathogen is present, BIK1 is transcribed to regulate the pathogen response mechanisms. When BIK1 is present, SA levels decrease, allowing the nectrotrophic response to take place. When nectrotrophic pathogens are not present, BIK1 is not transcribed and SA levels increase, limiting the necrotrophic resistance pathway. Only the pathogenic defense response that is initiated by BIK1 is dependent on SA levels. Non-pathogenic cellular functions occur independently. In terms of non-pathogenic cellular functions, BIK1 is described as a critical component of ET signaling and PAMP-triggered immunity to pathogens.

Plants are constantly exposed to different stresses that result in wounding. Plants have adapted to defend themselves against wounding events, like herbivore attacks or environmental stresses. There are many defense mechanisms that plants rely on to help fight off pathogens and subsequent infections. Wounding responses can be local, like the deposition of callose, and others are systemic, which involve a variety of hormones like jasmonic acid and abscisic acid.

References

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