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Names | |
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Preferred IUPAC name (2Z,4E)-5-[(1S)-1-Hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid [1] | |
Other names (2Z,4E)-(S)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-2,4-pentanedienoic acid; Dormic acid;[ citation needed ] Dormin [2] [3] | |
Identifiers | |
3D model (JSmol) | |
3DMet | |
Abbreviations | ABA |
2698956 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.040.275 |
EC Number |
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MeSH | Abscisic+Acid |
PubChem CID | |
RTECS number |
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UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C15H20O4 | |
Molar mass | 264.321 g·mol−1 |
Appearance | Colorless crystals |
Density | 1.193 g/mL |
Melting point | 163 °C (325 °F; 436 K) [4] |
log P | 1.896 |
Acidity (pKa) | 4.868 |
Basicity (pKb) | 9.129 |
Hazards | |
GHS labelling: | |
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Warning | |
H315, H319, H335 | |
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Abscisic acid (ABA or abscisin II [5] ) is a plant hormone. ABA functions in many plant developmental processes, including seed and bud dormancy, the control of organ size and stomatal closure. It is especially important for plants in the response to environmental stresses, including drought, soil salinity, cold tolerance, freezing tolerance, heat stress and heavy metal ion tolerance. [6]
In the 1940s, Torsten Hemberg, while working at the University of Stockholm, found evidence that a positive correlation exists between the rest period and the occurrence of an acidic ether soluble growth inhibitor in potato tubers. [7] [8]
In 1963, abscisic acid was first identified and characterized as a plant hormone by Frederick T. Addicott and Larry A. Davis. They were studying compounds that cause abscission (shedding) of cotton fruits (bolls). Two compounds were isolated and called abscisin I and abscisin II. Abscisin II is presently called abscisic acid (ABA). [5]
ABA was originally believed to be involved in abscission, which is how it received its name. This is now known to be the case only in a small number of plants. ABA-mediated signaling also plays an important part in plant responses to environmental stress and plant pathogens. [9] [10] The plant genes for ABA biosynthesis and sequence of the pathway have been elucidated. [11] [12] ABA is also produced by some plant pathogenic fungi via a biosynthetic route different from ABA biosynthesis in plants. [13]
In preparation for winter, ABA is produced in terminal buds. [14] This slows plant growth and directs leaf primordia to develop scales to protect the dormant buds during the cold season. ABA also inhibits the division of cells in the vascular cambium, adjusting to cold conditions in the winter by suspending primary and secondary growth.
Abscisic acid is also produced in the roots in response to decreased soil water potential (which is associated with dry soil) and other situations in which the plant may be under stress. ABA then translocates to the leaves, where it rapidly alters the osmotic potential of stomatal guard cells, causing them to shrink and stomata to close. The ABA-induced stomatal closure reduces transpiration (evaporation of water out of the stomata), thus preventing further water loss from the leaves in times of low water availability. A close linear correlation was found between the ABA content of the leaves and their conductance (stomatal resistance) on a leaf area basis. [15]
Seed germination is inhibited by ABA in antagonism with gibberellin. ABA also prevents loss of seed dormancy.[ citation needed ]
Several ABA-mutant Arabidopsis thaliana plants have been identified and are available from the Nottingham Arabidopsis Stock Centre - both those deficient in ABA production and those with altered sensitivity to its action. Plants that are hypersensitive or insensitive to ABA show phenotypes in seed dormancy, germination, stomatal regulation, and some mutants show stunted growth and brown/yellow leaves. These mutants reflect the importance of ABA in seed germination and early embryo development.[ citation needed ]
Pyrabactin (a pyridyl containing ABA activator) is a naphthalene sulfonamide hypocotyl cell expansion inhibitor, which is an agonist of the seed ABA signaling pathway. [16] It is the first agonist of the ABA pathway that is not structurally related to ABA.[ citation needed ]
Abscisic acid (ABA) is an isoprenoid plant hormone, which is synthesized in the plastidal 2-C-methyl-D-erythritol-4-phosphate (MEP) pathway; unlike the structurally related sesquiterpenes, which are formed from the mevalonic acid-derived precursor farnesyl diphosphate (FDP), the C15 backbone of ABA is formed after cleavage of C40 carotenoids in MEP. Zeaxanthin is the first committed ABA precursor; a series of enzyme-catalyzed epoxidations and isomerizations via violaxanthin, and final cleavage of the C40 carotenoid by a dioxygenation reaction yields the proximal ABA precursor, xanthoxin, which is then further oxidized to ABA. via abscisic aldehyde. [11]
Abamine has been designed, synthesized, developed and then patented as the first specific ABA biosynthesis inhibitor, which makes it possible to regulate endogenous levels of ABA. [17]
ABA can be catabolized to phaseic acid via CYP707A (a group of P450 enzymes) or inactivated by glucose conjugation (ABA-glucose ester) via the enzyme uridine diphosphate-glucosyltransferase (UDP-glucosyltransferase). Catabolism via the CYP707As is very important for ABA homeostasis, and mutants in those genes generally accumulate higher levels of ABA than lines overexpressing ABA biosynthetic genes. [20] In soil bacteria, an alternative catabolic pathway leading to dehydrovomifoliol via the enzyme vomifoliol dehydrogenase has been reported.
In the absence of ABA, the phosphatase ABI1-INSENSITIVE1 (ABI1) inhibits the action of SNF1-related protein kinases (subfamily 2) (SnRK2s). ABA is perceived by the PYRABACTIN RESISTANCE 1 (PYR1) and PYR1-like membrane proteins. On ABA binding, PYR1 binds to and inhibits ABI1. When SnRK2s are released from inhibition, they activate several transcription factors from the ABA RESPONSIVE ELEMENT-BINDING FACTOR (ABF) family. ABFs then go on to cause changes in the expression of a large number of genes. [6] Around 10% of plant genes are thought to be regulated by ABA.[ citation needed ]
Like plants, some fungal species (for example Cercospora rosicola , Botrytis cinerea [28] and Magnaporthe oryzae ) have an endogenous biosynthesis pathway for ABA. In fungi, it seems to be the MVA biosynthetic pathway that is predominant (rather than the MEP pathway that is responsible for ABA biosynthesis in plants). One role of ABA produced by these pathogens seems to be to suppress the plant immune responses. [29]
ABA has also been found to be present in metazoans, from sponges up to mammals including humans. [30] Currently, its biosynthesis and biological role in animals is poorly known. ABA elicits potent anti-inflammatory and anti-diabetic effects in mouse models of diabetes/obesity, inflammatory bowel disease, atherosclerosis and influenza infection. [31] Many biological effects in animals have been studied using ABA as a nutraceutical or pharmacognostic drug, but ABA is also generated endogenously by some cells (like macrophages) when stimulated. There are also conflicting conclusions from different studies, where some claim that ABA is essential for pro-inflammatory responses whereas other show anti-inflammatory effects. Like with many natural substances with medical properties, ABA has become popular also in naturopathy. While ABA clearly has beneficial biological activities[ citation needed ] and many naturopathic remedies will contain high levels of ABA (such as wheatgrass juice, fruits and vegetables), some of the health claims made may be exaggerated or overly optimistic. In mammalian cells ABA targets a protein known as lanthionine synthetase C-like 2 (LANCL2), triggering an alternative mechanism of activation of peroxisome proliferator-activated receptor gamma (PPAR gamma). [32] LANCL2 is conserved in plants and was originally suggested to be an ABA receptor also in plants, which was later challenged. [33]
Several methods can help to quantify the concentration of abscisic acid in a variety of plant tissue. The quantitative methods used are based on HPLC and ELISA. Two independent FRET probes can measure intracellular ABA concentrations in real time in vivo. [34] [35]
Germination is the process by which an organism grows from a seed or spore. The term is applied to the sprouting of a seedling from a seed of an angiosperm or gymnosperm, the growth of a sporeling from a spore, such as the spores of fungi, ferns, bacteria, and the growth of the pollen tube from the pollen grain of a seed plant.
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.
Gibberellins (GAs) are plant hormones that regulate various developmental processes, including stem elongation, germination, dormancy, flowering, flower development, and leaf and fruit senescence. GAs are one of the longest-known classes of plant hormone. It is thought that the selective breeding of crop strains that were deficient in GA synthesis was one of the key drivers of the "green revolution" in the 1960s, a revolution that is credited to have saved over a billion lives worldwide.
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.
The apoplast is the extracellular space outside of plant cell membranes, especially the fluid-filled cell walls of adjacent cells where water and dissolved material can flow and diffuse freely. Fluid and material flows occurring in any extracellular space are called apoplastic flow or apoplastic transport. The apoplastic pathway is one route by which water and solutes are transported and distributed to different places through tissues and organs, contrasting with the symplastic pathway.
Hydrotropism is a plant's growth response in which the direction of growth is determined by a stimulus or gradient in water concentration. A common example is a plant root growing in humid air bending toward a higher relative humidity level.
Plant senescence is the process of aging in plants. Plants have both stress-induced and age-related developmental aging. Chlorophyll degradation during leaf senescence reveals the carotenoids, such as anthocyanin and xanthophylls, which are the cause of autumn leaf color in deciduous trees. Leaf senescence has the important function of recycling nutrients, mostly nitrogen, to growing and storage organs of the plant. Unlike animals, plants continually form new organs and older organs undergo a highly regulated senescence program to maximize nutrient export.
Guard cells are specialized plant cells in the epidermis of leaves, stems and other organs that are used to control gas exchange. They are produced in pairs with a gap between them that forms a stomatal pore. The stomatal pores are largest when water is freely available and the guard cells become turgid, and closed when water availability is critically low and the guard cells become flaccid. Photosynthesis depends on the diffusion of carbon dioxide (CO2) from the air through the stomata into the mesophyll tissues. Oxygen (O2), produced as a byproduct of photosynthesis, exits the plant via the stomata. When the stomata are open, water is lost by evaporation and must be replaced via the transpiration stream, with water taken up by the roots. Plants must balance the amount of CO2 absorbed from the air with the water loss through the stomatal pores, and this is achieved by both active and passive control of guard cell turgor pressure and stomatal pore size.
In botany, drought tolerance is the ability by which a plant maintains its biomass production during arid or drought conditions. Some plants are naturally adapted to dry conditions, surviving with protection mechanisms such as desiccation tolerance, detoxification, or repair of xylem embolism. Other plants, specifically crops like corn, wheat, and rice, have become increasingly tolerant to drought with new varieties created via genetic engineering. From an evolutionary perspective, the type of mycorrhizal associations formed in the roots of plants can determine how fast plants can adapt to drought.
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.
Phaseic acid is a terpenoid catabolite of abscisic acid. Like abscisic acid, it is a plant hormone associated with photosynthesis arrest and abscission.
9-cis-epoxycarotenoid dioxygenase (EC 1.13.11.51, nine-cis-epoxycarotenoid dioxygenase, NCED, AtNCED3, PvNCED1, VP14) is an enzyme in the biosynthesis of abscisic acid (ABA), with systematic name 9-cis-epoxycarotenoid 11,12-dioxygenase. This enzyme catalyses the following chemical reaction
Feronia, also known as FER or protein Sirene, is a recognition receptor kinase found in plants. FER plays a significant part in the plant immune system as a receptor kinase which assists in immune signaling within plants, plant growth, and plant reproduction. FER is regulated by the Rapid Alkalinization Factor (RALF). FER regulates growth in normal environments but it is most beneficial in stressful environments as it helps to initiate immune signaling. FER can also play a role in reproduction in plants by participating in the communication between the female and male cells. FER is found in and can be studied in the organism Arabidopsis thaliana.
Strigolactones are a group of chemical compounds produced by roots of plants. Due to their mechanism of action, these molecules have been classified as plant hormones or phytohormones. So far, strigolactones have been identified to be responsible for three different physiological processes: First, they promote the germination of parasitic organisms that grow in the host plant's roots, such as Strigalutea and other plants of the genus Striga. Second, strigolactones are fundamental for the recognition of the plant by symbiotic fungi, especially arbuscular mycorrhizal fungi, because they establish a mutualistic association with these plants, and provide phosphate and other soil nutrients. Third, strigolactones have been identified as branching inhibition hormones in plants; when present, these compounds prevent excess bud growing in stem terminals, stopping the branching mechanism in plants.
Jian-Kang Zhu is a plant scientist, researcher and academic. He is a Senior Principal Investigator in the Shanghai Center for Plant Stress Biology, Chinese Academy of Sciences (CAS). He is also the Academic Director of CAS Center of Excellence in Plant Sciences.
Ethylene (CH
2=CH
2) is an unsaturated hydrocarbon gas (alkene) acting as a naturally occurring plant hormone. It is the simplest alkene gas and is the first gas known to act as hormone. It acts at trace levels throughout the life of the plant by stimulating or regulating the ripening of fruit, the opening of flowers, the abscission (or shedding) of leaves and, in aquatic and semi-aquatic species, promoting the 'escape' from submergence by means of rapid elongation of stems or leaves. This escape response is particularly important in rice farming. Commercial fruit-ripening rooms use "catalytic generators" to make ethylene gas from a liquid supply of ethanol. Typically, a gassing level of 500 to 2,000 ppm is used, for 24 to 48 hours. Care must be taken to control carbon dioxide levels in ripening rooms when gassing, as high temperature ripening (20 °C; 68 °F) has been seen to produce CO2 levels of 10% in 24 hours.
Hydraulic signals in plants are detected as changes in the organism's water potential that are caused by environmental stress like drought or wounding. The cohesion and tension properties of water allow for these water potential changes to be transmitted throughout the plant.
Cannabis (/ˈkænəbɪs/) is commonly known as marijuana or hemp and has two known strains: Cannabis sativa and Cannabis indica, both of which produce chemicals to deter herbivory. The chemical composition includes specialized terpenes and cannabinoids, mainly tetrahydrocannabinol (THC), and cannabidiol (CBD). These substances play a role in defending the plant from pathogens including insects, fungi, viruses and bacteria. THC and CBD are stored mostly in the trichomes of the plant, and can cause psychological and physical impairment in the user, via the endocannabinoid system and unique receptors. THC increases dopamine levels in the brain, which attributes to the euphoric and relaxed feelings cannabis provides. As THC is a secondary metabolite, it poses no known effects towards plant development, growth, and reproduction. However, some studies show secondary metabolites such as cannabinoids, flavonoids, and terpenes are used as defense mechanisms against biotic and abiotic environmental stressors.
Barley is known to be more environmentally-tolerant than other cereal crops, in terms of soil pH, mineral nutrient availability, and water availability. Because of this, much research is being done on barley plants in order to determine whether or not there is a genetic basis for this environmental hardiness.
Photoblasticism is a mechanism of seed dormancy. Photoblastic seeds require light in order to germinate. Once germination starts, the stored nutrients that have accumulated during maturation start to be digested which then supports cell expansion and overall growth. Within light-stimulated germination, Phytochrome B (PHYB) is the photoreceptor that is responsible for the beginning stages of germination. When red light is present, PHYB is converted to its active form and moves from the cytoplasm to the nucleus where it upregulates the degradation of PIF1. PIF1, phytochrome-interaction-factor-1, negatively regulates germination by increasing the expression of proteins that repress the synthesis of gibberellin (GA), a major hormone in the germination process. Another factor that promotes germination is HFR1 which accumulates in light in some way and forms inactive heterodimers with PIF1.