Phaseic acid
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Names | |
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Preferred IUPAC name
(2Z,4E)-5-[(1R,5R,8S)-8-Hydroxy-1,5-dimethyl-3-oxo-6-oxabicyclo[3.2.1]octan-8-yl]-3-methylpenta-2,4-dienoic acid | |
Other names
Phaseic acid
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H20O5 | |
Molar mass | 280.31 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phaseic acid is a terpenoid catabolite of abscisic acid. Like abscisic acid, it is a plant hormone associated with photosynthesis arrest[1] and abscission.
Function
Abscisic acid (ABA) is a multifunctional plant hormone, playing roles in
Phaseic acid inhibits glutamate receptors in mouse brain.[3]
Biosynthesis
Early precursors
Phaseic acid is an
![](http://upload.wikimedia.org/wikipedia/commons/3/30/Carotene.jpg)
![](http://upload.wikimedia.org/wikipedia/commons/b/b9/Carotene2.jpg)
Carotenoid precursors
Phaseic acid is a product of abscisic acid, which is itself the product of the C40
![](http://upload.wikimedia.org/wikipedia/commons/thumb/c/c4/Violaxanthinsynth.svg/350px-Violaxanthinsynth.svg.png)
![](http://upload.wikimedia.org/wikipedia/commons/thumb/d/de/Xanthoxinsynth.svg/350px-Xanthoxinsynth.svg.png)
Modification of xanthoxin
Xanthoxin is reduced at the epoxy group and then hydroxylated at the aldehyde group, producing abscisic acid.
- The biosynthesis of phaseic acid
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Xanthoxin is converted enzymatically to abscisic acid
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Abscisic acid is oxidized to form phaseic acid
References
- ^ a b Sharkey, T.D. "Effects of Phaseic Acid and Dihydrophaseic Acid on Stomata and the Photosynthetic Apparatus". Plant Physiol. 65(2): 291--297.
- ^ Milborrow BV. (1969). "Identification of 'Metabolite C' from abscisic acid and a new structure for phaseic acid". Chem Commun 966-967.
- PMID 27864367.
- ^ Cutler and Krochko (1999). Formation and breakdown of ABA. Trends in Plant Science, 4: 472-478
- ^ a b Saito S. (2004). "Arabidopsis CYP707As encode -abscisic acid 8'-hydroxylase, a key enzyme in the catabolism of abscisic acid". Plant Physiol. 134(4):1439-49.
- ^ Kushiro T. (2004). "The arabidopsis cytochrome P450 CYP707A encodes ABA 8'-hydroxylases: key enzymes in ABA catabolism". EMBO J. 23(7):1647-56.
- ^ Milborrow B.V. "The cyclization of 8'-hydroxy abscisic acid to phaseic acid in vivo". Phytochemistry 27:757-759.