Skip to main content
SpringerLink
Log in

Chemistry of Abscisic Acid, Abscisic Acid Catabolites and Analogs

  • Thematic Article
  • Published:
Journal of Plant Growth Regulation Aims and scope Submit manuscript

Abstract

Recently there have been breakthroughs on a number of fronts in abscisic acid (ABA) biology research that have advanced the field significantly, including discovery of genes involved in ABA metabolism, along with progress in understanding of ABA signaling (Finkelstein and others 2002; Kushiro and others 2004; Lim and others 2005; Saito and others 2004). At the same time, the chemistry of ABA has advanced. New analytical methods have been developed for profiling ABA and catabolites (Ross and others 2004; Zaharia and others 2005). Novel bioactive catabolites have been discovered from feeding studies with deuterated ABA and catabolites (Zaharia and others 2004; Zhou and others 2004). This review covers recent advances and prospects in natural products chemistry, analysis of ABA catabolism, and applications of ABA analogs for biochemical studies and horticultural uses.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9

Similar content being viewed by others

References

  • Abrams SR, Reaney MJT, Abrams GD, Mazurek T, Shaw AC, others. 1989. Ratio of (S)- to (R)-abscisic acid from plant cell cultures supplied with racemic ABA. Phytochemistry 28:2885–2889

    Article  CAS  Google Scholar 

  • Abrams SR, Gusta LV, Ewan BE, Reaney MJT. 1993. ABA related plant growth regulators - germination promoters. US patent 5,201,931

  • Abrams SR, Rose PA, Cutler AJ, Balsevich JJ, Lei B, others. 1997. 8′-Methylene abscisic acid. An effective and persistent analog of abscisic acid. Plant Physiol 114:89–97

    PubMed  CAS  Google Scholar 

  • Abrams SR, Nelson K, Ambrose SJ. 2003. Deuterated abscisic acid analogs for mass spectrometry and metabolism studies. J Label Compd Radiopharm 46:273–283

    Article  CAS  Google Scholar 

  • Birkemeyer C, Kolasa A, Kopka J. 2003. Comprehensive chemical derivatization for gas chromatography-mass spectrometry-based multi-targeted profiling of the major phytohormones. J Chromatogr A 993:89–102

    Article  PubMed  CAS  Google Scholar 

  • Boyer GL, Zeevaart JAD. 1982. Isolation and quantitation of b-D-glucopyranosyl abscisate from leaves of Xanthium and spinach. Plant Physiol 70:227-231

    CAS  PubMed  Google Scholar 

  • Calis I, Kuruuzum-Uz A, Lorenzetto PA, Ruedi P. 2002. (6S)-Hydroxy-3-oxo-a-ionol glucosides from Capparis spinosa fruits. Phytochemistry 59:451–457

    Article  PubMed  CAS  Google Scholar 

  • Chiwocha SDS, Abrams SR, Ambrose SJ, Cutler AJ, Loewen M, others. 2003. A method for profiling classes of plant hormones and their metabolites using liquid chromatography-electrospray ionization tandem mass spectrometry: an analysis of hormone regulation of thermodormancy of lettuce (Lactuca sativa L.) seeds. Plant J 35:405–417

    Article  PubMed  CAS  Google Scholar 

  • Cutler AJ, Krochko JE. 1999. Formation and breakdown of ABA. Trends Plant Sci 4:472–478

    Article  PubMed  Google Scholar 

  • Cutler AJ, Rose PA, Squires TM, Loewen MK, Shaw AC, others. 2000. Inhibitors of abscisic acid 8′-hydroxylase. Biochemistry 39:13614–13624

    Article  PubMed  CAS  Google Scholar 

  • Dewitte W, Van Onckelen H. 2001. Probing the distribution of plant hormones by immunocytochemistry. Plant Growth Regul 33:67–74

    Article  CAS  Google Scholar 

  • Feurtado JA, Ambrose SJ, Cutler AJ, Ross ARS, Abrams SR, others. 2004. Dormancy termination of western white pine (Pinus monticola Dougl. Ex D. Don) seeds is associated with changes in abscisic acid metabolism. Planta 218:630–639

    Article  PubMed  CAS  Google Scholar 

  • Finkelstein RR, Gampala SSL, Rock CD. 2002. Abscisic acid signaling in seeds and seedlings. Plant Cell 14:S15–S45

    PubMed  CAS  Google Scholar 

  • Gomez-Cadenas A, Pozo OJ, Garcia-Augustin P, Sancho JV. 2002. Direct analysis of abscisic acid in crude plant extracts by liquid chromatography-electrospray/tandem mass spectrometry. Phytochem Anal 13:228–234

    PubMed  CAS  Google Scholar 

  • Harrison MA, Walton DC. 1975. Abscisic acid metabolism in water-stressed bean leaves. Plant Physiol 56:250–254

    CAS  PubMed  Google Scholar 

  • Hill RD, Liu J-H, Durnin D, Lamb N, Shaw A, others. 1995. Abscisic acid structure–activity relationships in barley aleurone layers and protoplasts. Biological activity of optically active, oxygenated abscisic acid analogs. Plant Physiol 108:573–579

    PubMed  CAS  Google Scholar 

  • Hirai N, Kondo S, Ohigashi H. 2003. Deuterium-labeled phaseic acid and dihydrophaseic acids for internal standards. Biosci Biotechnol Biochem 67:2408–2415

    Article  PubMed  CAS  Google Scholar 

  • Hogge LR, Balsevich JJ, Olson DJH, Abrams GD, Jacques SL. 1993. Improved methodology for liquid chromatography/continuous flow secondary-ion mass spectrometry: quantitation of abscisic acid glucose ester using reaction monitoring. Rapid Commun Mass Spectrom 7:6–11

    Article  CAS  Google Scholar 

  • Kikuzaki H, Kayano S, Fukutsuka N, Aoki A, Kasamatsu K, others. 2004. Abscisic acid related compounds and lignans in prunes (Prunus domestica L.) and their oxygen radical absorbance capacity (ORAC). J Agric Food Chem 52:344–349

    Article  PubMed  CAS  Google Scholar 

  • Krochko JE, Abrams GD, Loewen MK, Abrams SR, Cutler AJ. 1998. (+)-Abscisic acid 8′-hydroxylase is a cytochrome P450 monooxygenase. Plant Physiol 118:849–860

    Article  PubMed  CAS  Google Scholar 

  • Kushiro T, Okamoto M, Nakabayashi K, Yamagishi K, Kitamura S, others. 2004. The Arabidopsis cytochrome P450 CYP707A encodes ABA 8′-hydroxylases: key enzymes in ABA catabolism. EMBO J 23:1647–1656

    Article  PubMed  CAS  Google Scholar 

  • Lamb N, Wahab N, Rose PA, Shaw AC, Abrams SR, others. 1996. Synthesis, metabolism and biological activity of a deuterated analog of the plant hormone S-(+)-abscisic acid. Phytochemistry 41:23–28

    Article  CAS  Google Scholar 

  • Lin B-L, Wang H-J, Wang J-S, Zaharia LI, Abrams SR. 2005. Abscisic acid regulation of heterophylly in Marsilea guadrifolia: Effects of R-(−) and S-(+)isomers. J Exp Bot 56:2935–2948

    Article  PubMed  CAS  Google Scholar 

  • Lim E-K, Doucet CJ, Hou B, Jackson RG, Abrams SR, others. 2005. Resolution of (+)-abscisic acid using an Arabidopsis glycosyltransferase. Tetrahedron Asymmetry 16:143–147

    Article  CAS  Google Scholar 

  • Lin B-L, Wang H-J, Wang J-S, Zaharia LI, Abrams SR. 2005, submitted. Abscisic acid regulation of heterophylly in Marsilea quadrifolia.: Effects of R-(-) and S-(+) isomers. J Exp Bot

  • Macias FA, Lopez A, Varela RM, Torres A, Molinillo JMG. 2004. Bioactive apocarotenoids, annuionones F and G: structural revision of annuionones A, B and E. Phytochemistry 65:3057–3063

    Article  PubMed  CAS  Google Scholar 

  • Muller A, Duchting P, Weiler EW. 2002. A multiplex GC-MS/MS technique for the sensitive and quantitative single-run analysis of acidic phytohormones and related compounds, and its application to Arabidopsis thaliana. Planta 216:44–56

    PubMed  CAS  Google Scholar 

  • Nambara E, Suzuki M, Abrams S, McCarty DR, Kamiya Y, others. 2002. A screen for genes that function in abscisic acid signaling in Arabidopsis thaliana. Genetics 161:1247–1255

    PubMed  CAS  Google Scholar 

  • Neill SJ, Horgan R, Heald JK. 1983. Determination of the levels of abscisic acid-glucose ester in plants. Planta 157:371–375

    Article  CAS  Google Scholar 

  • Netting AG, Milborrow BV, Duffield AM. 1982. Determination of abscisic acid in Eucalyptus haemastoma leaves using gas chromatography/mass spectrometry and deuterated internal standards. Phytochemistry (Elsevier) 21:385–389

    CAS  Google Scholar 

  • Nyangulu JM, Galka MM, Jadhav AS, Gai Y, Graham CM, others. 2005. An affinity probe for isolation of abscisic acid-binding proteins. J Am Chem Soc 127:1662–1664

    Article  PubMed  CAS  Google Scholar 

  • Oritani T, Kiyota H. 2003. Biosynthesis and metabolism of abscisic acid and related compounds. Nat Prod Rep 20:414–425

    Article  PubMed  CAS  Google Scholar 

  • Pedron J, Brault M, Nake C, Miginiac E. 1998. Detection of abscisic-acid-binding proteins in the microsomal protein fraction of Arabidopsis thaliana with abscisic-acid-protein conjugates used as affinity probes. Eur J Biochem 252:385–390

    Article  PubMed  CAS  Google Scholar 

  • Perata P, Vernieri P, Armellini D, Bugnoli M, Presentini R, others. 1990. A monoclonal antibody for the detection of conjugated forms of abscisic acid in plant tissues. J Plant Growth Regul 9:1–6

    Article  CAS  Google Scholar 

  • Priest DM, Jackson RG, Ashford DA, Abrams SR, Bowles DJ. 2005. The use of abscicic acid to analyse the substrate selectivity of UGT71B6, a UDP-glycosyl-transferase of Arabidopsis thaliana. FEBS Lett 579:4454–4458

    Article  PubMed  CAS  Google Scholar 

  • Ramos MR, Jerz G, Villanueva S, Lopez-Dellamary F, Waibel R, others. 2004. Two glucosylated abscisic acid derivatives from avocado seeds (Persea americana Mill. Lauraceaea cv. Haas). Phytochemistry 65:955–962

    Google Scholar 

  • Razem FA, Luo M, Liu J-H, Abrams SR, Hill RD. 2004. Purification and characterization of a barley aleurone abscisic acid-binding protein. J Biol Chem 279: 9922–9929

    PubMed  CAS  Google Scholar 

  • Rose PA, Cutler AJ, Irvine NM, Shaw AC, Squires TM, others. 1997. 8′-Acetylene ABA: an irreversible inhibitor of ABA 8′-hydroxylase. Bioorg Med Chem Lett 7:2543–2546

    Article  CAS  Google Scholar 

  • Ross ARS, Ambrose SJ, Cutler AJ, Feurtado JA, Kermode AR, others. 2004. Determination of endogenous and supplied deuterated abscisic acid in plant tissues by high performance liquid chromatography-electrospray ionization tandem mass spectrometry with multiple reaction monitoring. Anal Biochem 392:24–333

    Google Scholar 

  • Saito S, Hirai N, Matsumoto C, Ohigashi H, Ohta D, others. 2004. Arabidopsis CYP707As encode (+)-abscisic acid 8′-hydroxylase, a key enzyme in the oxidative catabolism of abscisic acid. Plant Physiol 134:1439–1449

    Article  PubMed  CAS  Google Scholar 

  • Sauter A, Abrams SR, Hartung W. 2002. Structural requirements of abscisic acid (ABA) and its impact on water flow during radial transport of ABA analogues through maize roots. J Plant Growth Regul 21:50–59

    Article  PubMed  CAS  Google Scholar 

  • Schmelz EA, Engelberth J, Alborn HT, O’Donnell P, Sammons M, others. 2003. Simultaneous analysis of phytohormones, phytotoxins, and volatile organic compounds in plants. Proc Natl Acad Sci USA 100:10552–10557

    Article  PubMed  CAS  Google Scholar 

  • Schmelz EA, Engelberth J, Tumlinson JH, Block A, Alborn HT. 2004. The use of vapor phase extraction in metabolic profiling of phytohormones and other metabolites. Plant J 39:790–808

    Article  PubMed  CAS  Google Scholar 

  • Schneider G, Ziethe F, Schmidt J. 1997. Liquid chromatography/electrospray ionization-tandem mass spectrometry. A tool for the identification and quantification of abscisic acid glucosyl ester. Chromatographia 45:78–80

    CAS  Google Scholar 

  • Sharma N. 2002. Use of abscisic acid (ABA) analogs to improve performance of horticultural crops. University of Saskatchewan, Saskatoon, SK, Canada, p. 153

  • Sharma N, Abrams SR, Waterer DR. 2005. Uptake, movement, activity and persistence of an ABA analog (8′ acetylene ABA methyl ester) in marigold and tomato. J Plant Growth Regul, in press

    Article  CAS  Google Scholar 

  • Todoroki Y, Hirai N, Koshimizu K. 1995. 8′,8′-Difluoro- and 8′,8′,8′-trifluoroabscisic acids as highly potent, long-lasting analogs of abscisic acid. Phytochemistry 38:561–568

    Article  CAS  Google Scholar 

  • Todoroki Y, Nakano S-I, Arai S, Hirai N, Ohigashi H. 1997. Synthesis and biological activities of 8′-methylene- and 8′-methylidyneabscisic acids. Biosci Biotechnol Biochem 61:2043–2045

    CAS  Google Scholar 

  • Todoroki Y, Nakano S-I, Hirai N, Mitsui T, Ohigashi H. 1997. Synthesis, biological activity, and metabolism of 8′,8′,8′-trideuteroabscisic acid. Biosci Biotechnol Biochem 61:1872–1876

    CAS  Google Scholar 

  • Todoroki Y, Hirai N. 2002. Abscisic acid analogs for probing the mechanism of abscisic acid reception and inactivation. Stud Nat Prod Chem 27:321–360

    CAS  Google Scholar 

  • Ueno K, Araki Y, Hirai N, Saito S, Mizutani M, others. 2005. Differences between the structural requirements for ABA 8′-hydroxylase inhibition and for ABA activity. Bioorg Med Chem 13:3359–3370

    PubMed  CAS  Google Scholar 

  • Walker-Simmons MK, Reaney MJT, Quarrie SA, Perata P, Vernieri P, others. 1991. Monoclonal antibody recognition of abscisic acid analogs. Plant Physiol 95:46–51

    CAS  PubMed  Google Scholar 

  • Walker-Simmons MK, Anderberg RJ, Rose PA, Abrams SR. 1992. Optically pure abscisic acid analogs. Tools for relating germination inhibition and gene expression in wheat embryos. Plant Physiol 99:501–507

    Article  CAS  PubMed  Google Scholar 

  • Walton DC. 1983. Structure–activity relationships of abscisic acid analogs and metabolites. In: Addicott FT (ed), Abscisic acid. New York, USA, Praeger. pp 113–146

    Google Scholar 

  • Weiler EW. 1979. Use of immunoassay in plant science. Part VII. Radioimmunoassay for the determination of free and conjugated abscisic acid. Planta 144:255–263

    Article  CAS  Google Scholar 

  • Weiler EW. 1980. Use of immunoassay in plant science Part 11 Radioimmunoassays for the differential and direct analysis of free and conjugated abscisic acid in plant extracts. Planta 148:262–272

    Article  CAS  Google Scholar 

  • Wilen RW, Hays DB, Mandel RM, Abrams SR, Moloney MM. 1993. Competitive inhibition of abscisic acid-regulated gene expression by stereoisomeric acetylenic analogs of abscisic acid. Plant Physiol 101:469–476

    PubMed  CAS  Google Scholar 

  • Windsor ML, Zeevaart JAD. 1997. Induction of ABA 8′-hydroxylase by (+)-S-, (–)-R- and 8′,8′,8′-trifluoro-S-abscisic acid in suspension cultures of potato and Arabidopsis. Phytochemistry 45:931–934

    Article  PubMed  CAS  Google Scholar 

  • Xu Z-J, Nakajima M, Suzuki Y, Yamaguchi I. 2002. Cloning and characterization of the abscisic acid-specific glucosyltransferase gene from Adzuki bean seedlings. Plant Physiol 129:1285–1295

    PubMed  CAS  Google Scholar 

  • Yamazaki H. 2003. Studies on the control and physiology of bulb formation and dormancy of Allium * wakegi Araki. Yasai Chagyo Kenkyusho Kenkyu Hokoku 2:139–211

    CAS  Google Scholar 

  • Zaharia LI, Gay Y, Nelson KM, Ambrose SJ, Abrams SR. 2004. Oxidation of 8′-hydroxy abscisic acid in Black Mexican Sweet maize cell suspension cultures. Phytochemistry 65:3199–3209

    PubMed  CAS  Google Scholar 

  • Zaharia LI, Galka MM, Ambrose SJ, Abrams SR. 2005. Preparation of deuterated abscisic acid metabolites for use in mass spectrometry and feeding studies. J Label Compd Radiopharm 48:435–445

    Article  CAS  Google Scholar 

  • Zeevaart JAD, Milborrow BV. 1976. Metabolism of abscisic acid and the occurrence of epidihydrophaseic acid in Phaseolus vulgaris. Phytochemistry (Elsevier) 15:493–500

    CAS  Google Scholar 

  • Zeevaart JAD, 1999. Abscisic acid metabolism and its regulation. In: Hooykaas PJJ, Hall MA, Libbenga KR (eds). Biochemistry and molecular biology of plant hormones. Amsterdam, The Netherlands, Elsevier Science, pp 189–207

    Google Scholar 

  • Zhang D-P, Wu Z-Y, Li X-Y, Zhao Z-X. 2002. Purification and identification of a 42-kilodalton abscisic acid-specific-binding protein from epidermis of broad bean leaves. Plant Physiol 128:714–725

    PubMed  CAS  Google Scholar 

  • Zhou R, Squires TM, Ambrose SJ, Abrams SR, Ross ARS, others. 2003. Rapid extraction of abscisic acid and its metabolites for liquid chromatography-tandem mass spectrometry. J Chromatogr A 1010:75–85

    Article  PubMed  CAS  Google Scholar 

  • Zhou R, Cutler AJ, Ambrose SJ, Galka MM, Nelson KM, others. 2004. A new abscisic acid catabolic pathway. Plant Physiol 134:361–369

    Article  PubMed  CAS  Google Scholar 

  • Zou J, Abrams GD, Barton DL, Taylor DC, Pomeroy MK, others. 1995. Induction of lipid and oleosin biosynthesis by (+)-abscisic acid and its metabolites in microspore-derived embryos of Brassica napus L. cv Reston. Biological responses in the presence of 8′-hydroxyabscisic acid. Plant Physiol 108:563–571

    PubMed  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank Mary Loewen and Dr. Adrian Cutler for sharing unpublished data.

Author information

Authors and Affiliations

  1. National Research Council Canada, Plant Biotechnology Institute, 110 Gymnasium Place, Saskatoon, Saskatchewan, S7N 0W9, Canada

    L. Irina Zaharia & Suzanne R. Abrams

  2. USDA Agricultural Research Service, George Washington Carver Building, 5601 Sunnyside Ave., Room 4-2210, Beltsville, Maryland, 20705-5139, USA

    Mary K. Walker-Simmon

  3. Department of Plant Physiology, University of Salamanca, 37007, Salamanca, Spain

    Carlos Nicolás Rodríguez

Authors
  1. L. Irina Zaharia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mary K. Walker-Simmon
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Carlos Nicolás Rodríguez
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Suzanne R. Abrams
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Suzanne R. Abrams.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zaharia, L.I., Walker-Simmon, M.K., Rodríguez, C.N. et al. Chemistry of Abscisic Acid, Abscisic Acid Catabolites and Analogs. J Plant Growth Regul 24, 274–284 (2005). https://doi.org/10.1007/s00344-005-0066-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00344-005-0066-2

Keywords

Search

Navigation