Abscisic acid
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[3] | |
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[1][2]
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Identifiers | |
3D model (
JSmol ) |
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3DMet | |
Abbreviations | ABA |
2698956 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.040.275 |
EC Number |
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MeSH | Abscisic+Acid |
PubChem CID
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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: | |
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).
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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]
Discovery
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]
In plants
Function
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
Abscisic acid is also produced in the
Seed germination is inhibited by ABA in antagonism with gibberellin. ABA also prevents loss of seed dormancy.[citation needed]
Several ABA-
Homeostasis
Biosynthesis
Abscisic acid (ABA) is an
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]
Locations and timing of ABA biosynthesis
- Synthesized in nearly all plant tissues, e.g., roots, flowers, leaves and stems
- Stored in chlorenchyma) cells where it is conjugated to glucose via uridine diphosphate-glucosyltransferase resulting in the inactivated form, ABA-glucose-ester [18]
- Activated and released from the chlorenchyma in response to environmental stress, such as heat stress, water stress, salt stress[18]
- Released during desiccation of the vegetative tissues and when roots encounter soil compaction.[19]
- Synthesized in green fruits at the beginning of the winter period
- Synthesized in maturing seeds, establishing dormancy
- Mobile within the leaf and can be rapidly translocated from the leaves to the roots (opposite of previous belief) in the phloem
- Accumulation in the roots modifies lateral root development, improving the stress response
- ABA is synthesized in almost all cells that contain chloroplasts or amyloplasts
Inactivation
ABA can be catabolized to
Effects
- stomatal closure, decreasing transpiration to prevent water loss.[21]
- Promotes root growth during periods of low humidity.[22]
- Inhibits fruit ripening
- Responsible for seed dormancy by inhibiting cell growth – inhibits seed germination
- Inhibits the synthesis of Kinetin nucleotide[23]
- Downregulates enzymes needed for photosynthesis.[24]
- Acts on endodermis to prevent growth of roots when exposed to salty conditions[25]
- Promotion of plant antiviral immunity[26][27]
Signal cascade
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]
In fungi
Like plants, some fungal species (for example
In animals
ABA has also been found to be present in
Measurement of ABA concentration
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. Recently, 2 independent FRET probes have been developed that can measure intracellular ABA concentrations in real time in vivo.[34][35]
References
- ^ O'Neil, Maryadele J; Heckelman, PE; Koch, CB; Roman, KJ (2006). The Merck Index, 14th.
- ^ 21293-29-8
- ^ "Abscisic Acid - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 22 October 2011.
- ^ "ChemSpider database - Abscisic acid - Properties". Retrieved 27 December 2012. The melting point is decided by experimental data by Tokyo Chemical Industry Ltd.
- ^ PMID 16658017.
- ^ PMID 24273463.
- ISSN 0031-9317.
- S2CID 253856375.
- PMID 12221975.
- PMID 11804826.
- ^ PMID 15862093.
- PMID 11432933.
- PMID 15240257.
- PMID 26793222.
- S2CID 30298332.[citation needed]
- PMID 19407142.
- ^ US 7098365, Yoshida, Shigeo & Asami, Tadao, "Abscisic acid biosynthesis inhibitor", published 2006-08-29, assigned to Riken
- ^ a b Zhang, Y., et al. (2021) ABA homeostasis and long-distance translocation are redundantly regulated by ABCG ABA importers. Science Advances.[1]
- ^ DeJong-Hughes, J., et al. (2001) Soil Compaction: causes, effects and control. University of Minnesota extension service
- PMID 24273463.
- .
- ^ Ralls, Eric (2023-06-27). "Plant leaves send signals to their roots on dry days telling them to keep digging deeper for water". www.msn.com/. Retrieved October 4, 2023.
- .
- .
- PMID 23341337.
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- PMID 20015036. Archived from the originalon 2012-04-01. Retrieved 2018-09-30.
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- PMID 24737862.