Abstract
Wheat (Triticum aestivum L.) embryo germination is inhibited by natural (S)-(+)-abscisic acid (ABA). In this report we have determined critical structural features of the ABA molecule, particularly the methyl and ketone groups of the ABA ring, required for inhibitory activity. To examine the ring residues a series of new optically active ABA analogs have been synthesized in which the 4[prime]-keto, 7[prime]-, 8[prime]-, or 8[prime]- and 9[prime]-carbons have been replaced with hydrogen atoms. Each of the analogs was tested over a range of concentrations as a germination inhibitor. Enantiomers of the analogs altered at the 4[prime]-keto or 8[prime]- and 9[prime]-methyl groups were active, but less so than ABA. Both enantiomers of 7[prime]-demethylABA were inactive as germination inhibitors. The results show that the 7[prime]-methyl group is absolutely required for activity, but that the other residues are less critical for hormone recognition.
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Selected References
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- Allan A. C., Trewavas A. J. Abscisic Acid and Gibberellin Perception: Inside or Out? Plant Physiol. 1994 Apr;104(4):1107–1108. [PMC free article] [PubMed] [Google Scholar]
- Anderson B. E., Ward J. M., Schroeder J. I. Evidence for an Extracellular Reception Site for Abscisic Acid in Commelina Guard Cells. Plant Physiol. 1994 Apr;104(4):1177–1183. doi: 10.1104/pp.104.4.1177. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Gilroy S., Jones R. L. Perception of Gibberellin and Abscisic Acid at the External Face of the Plasma Membrane of Barley (Hordeum vulgare L.) Aleurone Protoplasts. Plant Physiol. 1994 Apr;104(4):1185–1192. doi: 10.1104/pp.104.4.1185. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Mousseron-Canet M., Mani J. C., Durand B., Nitsch J., Dornand J., Bonnafous J. C. Analogues de l'acide abscisique (plus or minus) hormone de dormance. Relations structure-activité. C R Acad Sci Hebd Seances Acad Sci D. 1970 Apr 13;270(15):1936–1939. [PubMed] [Google Scholar]
- Sondheimer E., Galson E. C., Chang Y. P., Walton D. C. Asymmetry, its importance to the action and metabolism of abscisic Acid. Science. 1971 Nov 19;174(4011):829–831. doi: 10.1126/science.174.4011.829. [DOI] [PubMed] [Google Scholar]
- Walker-Simmons M. K., Reaney M. J., Quarrie S. A., Perata P., Vernieri P., Abrams S. R. Monoclonal antibody recognition of abscisic Acid analogs. Plant Physiol. 1991 Jan;95(1):46–51. doi: 10.1104/pp.95.1.46. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Wilen R. W., Hays D. B., Mandel R. M., Abrams S. R., Moloney M. M. Competitive Inhibition of Abscisic Acid-Regulated Gene Expression by Stereoisomeric Acetylenic Analogs of Abscisic Acid. Plant Physiol. 1993 Feb;101(2):469–476. doi: 10.1104/pp.101.2.469. [DOI] [PMC free article] [PubMed] [Google Scholar]