Abstract
The induction of freezing tolerance in bromegrass (Bromus inermis Leyss) cell culture was used to investigate the activity of absisic acid (ABA) analogs. Analogs were either part of an array of 32 derived from systematic alterations to four regions of the ABA molecule or related, pure optical isomers. Alterations were made to the functional group at C-1 (acid replaced with methyl ester, aldehyde, or alcohol), the configuration at C-2, C-3 (cis double bond replaced with trans double bond), the bond order at C-4, C-5 (trans double bond replaced with a triple bond), and ring saturation (C-2′, C-3′ double bond replaced with a single bond so that the C-2′ methyl and side chain were cis). All deviations in structure from ABA reduced activity. A cis C-2, C-3 double bond was the only substituent absolutely required for activity. Overall, acids and esters were more active than aldehydes and alcohols, cyclohexenones were more active than cyclohexanones, and dienoic and acetylenic analogs were equally active. The activity associated with any one substituent was, however, markedly influenced by the presence of other substituents. cis, trans analogs were more active than their corresponding acetylenic analogs unless the C-1 was an ester. Cyclohexenones were more active than cyclohexanones regardless of oxidation level at C-1. An acetylenic side chain decreased the activity of cyclohexenones but increased the activity of cyclohexanones relative to their cis, trans counterparts. Trends suggested that for activity the configuration at C-1′ has to be the same as in (S)-ABA, in dihydro analogs the C-2′-methyl and the side chain must be cis, small positional changes of the 7′-methyl are tolerable, and the C-1 has to be at the acid oxidation level.
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Chen T. H., Gusta L. V. Abscisic Acid-induced freezing resistance in cultured plant cells. Plant Physiol. 1983 Sep;73(1):71–75. doi: 10.1104/pp.73.1.71. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Reaney M. J., Gusta L. V. Factors Influencing the Induction of Freezing Tolerance by Abscisic Acid in Cell Suspension Cultures of Bromus inermis Leyss and Medicago sativa L. Plant Physiol. 1987 Feb;83(2):423–427. doi: 10.1104/pp.83.2.423. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Robertson A. J., Gusta L. V., Reaney M. J., Ishikawa M. Protein Synthesis in Bromegrass (Bromus inermis Leyss) Cultured Cells during the Induction of Frost Tolerance by Abscisic Acid or Low Temperature. Plant Physiol. 1987 Aug;84(4):1331–1336. doi: 10.1104/pp.84.4.1331. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Rock C. D., Heath T. G., Gage D. A., Zeevaart J. A. Abscisic alcohol is an intermediate in abscisic Acid biosynthesis in a shunt pathway from abscisic aldehyde. Plant Physiol. 1991 Oct;97(2):670–676. doi: 10.1104/pp.97.2.670. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Walker-Simmons M. K., Anderberg R. J., Rose P. A., Abrams S. R. Optically pure abscisic Acid analogs-tools for relating germination inhibition and gene expression in wheat embryos. Plant Physiol. 1992 Jun;99(2):501–507. doi: 10.1104/pp.99.2.501. [DOI] [PMC free article] [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]
- Walton D. C., Sondheimer E. Activity and metabolism of C-(+/-)-abscisic Acid derivatives. Plant Physiol. 1972 Mar;49(3):290–292. doi: 10.1104/pp.49.3.290. [DOI] [PMC free article] [PubMed] [Google Scholar]