Abscisic acid

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Abscisic acid
Stereo, skeletal formula of abscisic acid
Names
Systematic 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[citation needed]
Identifiers
21293-29-8 YesY
3DMet B00898
Abbreviations ABA
2698956
ChEBI CHEBI:2635 N
ChEMBL ChEMBL288040 YesY
ChemSpider 4444418 YesY
EC Number 244-319-5
Jmol 3D model Interactive image
MeSH Abscisic+Acid
PubChem 5280896
RTECS number RZ2475100
  • InChI=1S/C15H20O4/c1-10(7-13(17)18)5-6-15(19)11(2)8-12(16)9-14(15,3)4/h5-8,19H,9H2,1-4H3,(H,17,18)/b6-5+,10-7-/t15-/m1/s1 YesY
    Key: JLIDBLDQVAYHNE-YKALOCIXSA-N YesY
  • OC(=O)\C=C(\C)/C=C/[C@@]1(O)C(C)=CC(=O)CC1(C)C
Properties
C15H20O4
Molar mass 264.32 g·mol−1
Appearance Colorless crystals
Density 1.193 g/mL
Melting point 163 °C (325 °F; 436 K)[2]
Boiling point 458.7 °C (857.7 °F; 731.8 K)[3] sublimes
log P 1.896
Acidity (pKa) 4.868
Basicity (pKb) 9.129
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Abscisic acid (ABA), also known as abscisin II and dormin, is best known as a plant hormone. ABA functions in many plant developmental processes, including bud dormancy. It is degraded by the enzyme (+)-abscisic acid 8'-hydroxylase into phaseic acid.

In Plants

Function

ABA was originally believed to be involved in abscission. 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.[4][5] The plant genes for ABA biosynthesis and sequence of the pathway have been elucidated.[6][7] ABA is also produced by some plant pathogenic fungi via a biosynthetic route different from ABA biosynthesis in plants.[8]

Abscisic acid owes its names to its role in the abscission of plant leaves. In preparation for winter, ABA is produced in terminal buds.[citation needed] 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.[citation needed]

Abscisic acid is also produced in the roots in response to decreased soil water potential 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, 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.[9]

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.[10] It is the first agonist of the ABA pathway that is not structurally related to ABA.[citation needed]

Homeostasis

Biosynthesis

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.[6]

Xanthtoaba.svg

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.[11]

Location and timing of ABA biosynthesis

  • Released during desiccation of the vegetative tissues and when roots encounter soil compaction.[12]
  • 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 roots to the leaves by the transpiration stream in the xylem
  • Produced in response to environmental stress, such as heat stress, water stress, salt stress
  • Synthesized in all plant parts, e.g., roots, flowers, leaves and stems

Inactivation

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 AOG. 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.[13] In soil bacteria, an alternative catabolic pathway leading to dehydrovomifoliol via the enzyme vomifoliol dehydrogenase has been reported.

Effects

In Fungi

Like plants, some fungal species (for example Cercospora rosicola, Botrytis cinerea [18] 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.

In Animals

ABA has also been found to be present in metazoans, from sponges up to mammals including humans.[19] Currently, its biosynthesis and biological role in animals is poorly known. ABA has recently been shown to elicit potent anti-inflammatory and anti-diabetic effects in mouse models of diabetes/obesity, inflammatory bowel disease, atherosclerosis and influenza infection.[20] 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. Whlile ABA clearly has beneficial biological activities 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. Its anti-cancer properties are, for example, poorly supported at this moment but not completely dismissed. [1] [2][3]. 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).[21] Interestingly, LANCL2 is conserved in plants and was originally suggested to be an ABA receptor also in plants, which was later challenged [4].

An aquatic herbicide, fluridone, has been found to act as an anti-inflammatory drug in humans. Fluridone inhibits photosynthesis by disruption of ABA, killing plants systemically. This same inhibition of ABA in humans leads to an anti-inflammatory response.[22][23]

Oral ABA at 0.5–1 µg/kg significantly lowered glycemia and insulinemia in rats and in humans. So, low-dose ABA intake may be proposed as an aid to improving glucose tolerance in patients with diabetes who are deficient in or resistant to insulin.[24][25][26]

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 GC, and ELISA. Recently, 2 independent FRET probes have been developed that can measure intracellular ABA concentrations in real time in vivo [5] [6].

References

  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found. The melting point is decided by experimental data by Tokyo Chemical Industry Ltd.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found. The boiling point is reported there to be predicted by ACD/Labs
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.[citation needed]
  10. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Abscisic acid biosynthesis inhibitor, Shigeo Yoshida et al US 7098365 
  12. ↑ DeJong-Hughes, J., et al. (2001) Soil Compaction: causes, effects and control. University of Minnesota extension service
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  22. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ Magnone, M., Ameri, P., Salis, A., Andraghetti, G., Emionite, L., Murialdo, G., ... & Zocchi, E. (2015). Microgram amounts of abscisic acid in fruit extracts improve glucose tolerance and reduce insulinemia in rats and in humans. The FASEB Journal, 29(12), 4783-4793 doi:10.1096/fj.15-277731
  25. ↑ Bruzzone, S., Ameri, P., Sturla, L., Guida, L., De Flora, A., & Zocchi, E. (2012). Abscisic acid: a new mammalian hormone regulating glucose homeostasis. Messenger, 1(2), 141-149 DOI: http://dx.doi.org/10.1166/msr.2012.1012
  26. ↑ De Flora, A., Bruzzone, S., Guida, L., Sturla, L., Magnone, M., Fresia, C., ... & Zocchi, E. (2014). Toward a Medicine-Oriented Use of the Human Hormone/Nutritional Supplement Abscisic Acid. Messenger, 3(1-2), 86-97 DOI: http://dx.doi.org/10.1166/msr.2014.1029
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