Abstract
A study was undertaken to assess the potency of 1-methylcyclopropene (1-MCP) analogues to block the ethylene receptor and thereby inhibit ethylene action. Eight structural analogues of 1-MCP with substitution in the 1-position and a side chain containing 2–10 carbons were synthesized and their potency to inhibit ethylene-induced plant processes was tested on climacteric fruit like avocado, and tomato, on ethylene-induced growth modification in etiolated pea seedlings and on abscission in citrus leaf explants. High concentrations of ethylene were used under conditions which hasten ethylene-induced processes. The results showed differences in the responses of the various tissues tested as related to the concentrations of the inhibitors. Some required much higher concentration to exert the same effect, while some, when applied at the same concentration, blocked the receptor for a longer period of time than the others. Fruits responded differently than other plant organs to the same inhibitor, indicating possible differences in characteristics and availability of the ethylene receptors in the various tissues. The potency of the inhibitors was greatly affected by their molecular structure and size. The highest potency of a given inhibitor was obtained when the treatment was applied before the onset of ethylene action. The relationship between ethylene and the inhibitors was found to be of an apparent non-competitive nature. All the fruits treated with the various inhibitors resumed normal ripening after recovery from the inhibition which is crucial when considering the putative inhibitors for practical use.
Similar content being viewed by others
Abbreviations
- CP:
-
Cyclopropene
- 1-MCP:
-
1-Methylcyclopropene
- 1-ECP:
-
1-Ethylcyclopropene
- 1-PCP:
-
1-Propylcycloprpene
- 1-BCP:
-
1-Butylcyclopropene
- 1-pentCP:
-
Pentylcyclopropene
- 1-HCP:
-
Hexylcyclopropene
- 1-HeptCP:
-
1-Heptylcyclopropene
- 1-ocp:
-
Oectylcyclopropene
- 1-DCP:
-
Decatylcyclopropene
- EG:
-
Endo-1,4-β-glucanase
- PG:
-
Polygalacturonase
References
Abeles FB, Morgan P, Saltveit ME Jr (1992) Ethylene in plant biology, 2nd edn. Academic Press, New york, pp 414
Al Dulayymi JR, Baird MS, Simpson MJ, Nyman S (1996) Structure based interference with insect behaviour-cyclopropenes analogues of pheromones containing Z-Alkenes. Tetrahedron 52:12509–12520
Al Dulayymi AR, Al Dulayymi JR, Baird MS, Koza G (1997) Simple four and five carbon cyclopropane and cyclopropene synthetic intermediates. Russian Jour Org Chem 33:798–816
Apelbaum A (1990) Interrelationship between polyamines and ethylene and its implication for plant growth and fruit ripening. In: Flores HE, Arteca RN, Shannon JC (eds) Biochemistry, physiology and interactions. American Society of Plant Physiologists. Rockville MD, pp 278–294
Apelbaum A, Burg SP (1972a) Effect of ethylene on cell division and DNA synthesis in Pisum sativum. Plant Physiol 50:117–124
Apelbaum A, Burg SP (1972b) Effect of ethylene and 2,4-D on cellular expansion in Pisum sativum. Plant Physiol 50:125–131
Bakhanashvili M, Barkai-Golan R, Kopeliovitch E, Apelbaum A (1987) Polyamine biosynthesis in Rhisopus-infected tomato fruits; possible interaction with ethylene. Physiol Mol Plant Pathol 31:41–50
Beyer EM Jr (1979) Effect of silver ion, carbon dioxide, and oxygen on ethylene action and metabolism. Plant Physiol 60:169–173
Burg SP, Burg EA (1967) Molecular requirements for the biological activity of ethylene. Plant Physiol 42:144–152
Feng X, Apelbaum A, Sisler EC, Goren R (2000) Control of ethylene responses in avocado fruit with 1-methylcyclopropene. Postharvest Biol Technol 20:143–150
Feng X, Apelbaum A, Sisler E, Goren R (2004) Control of ethylene activity in various plant systems by structural analogues of 1-methylecyclopropene. Plant Growth Regul 42:29–38
Goren R (1993) Anatomical, physiological and hormonal aspects of abscission in citrus. In: Jules J (ed) Horticultural reviews, vol 15. John Wiley & Sons Inc, Hoboken, NJ, USA, pp 145–182
Goren R, Zhong GY, Huberman M, Feng X, Holland D, Sisler EC (2003) Effect of 1-methylcyclopropene on ethylene-induced abscission of citrus sinensis leaves. In: Vendrell M, Klee, Pech JC, Romojaro F (eds) Biology and Biotechnology of the Plant Hormone Ethylene III. pp 198–204
Greenberg I, Goren R, Riov J (1975) The role of cellulase and polygalacturonase in abscission of young and mature Shamouti orange fruits. Physiol Plant 34:1–7
Hua J, Meyerowitz E (1998) Ethylene responses are negatively regulated by a receptor gene family in Arabidopsis thaliana. Cell 94:261–271
Huberman M, Goren R (1979) Exo-cellular and endo-cellular cellulase and polygalacturonase in abscission zones of developing orange fruits. Physiol Plant 45:189–196
Jacob WP (1959) What substance normally controls a given biological process? I. Foramtion of some rules. Dev Biol 1:527–533
Pesis E, Fuchs Y, Zauberman G (1978) Cellulase activity and fruit softening in avocado. Plant Physiol 61:416–419
Ratner A, Goren R, Monselise SP (1969) Activity of pectinesterase and cellulase in abscission zone of citrus leaf explants. Plant Physiol 44:1717–1723
Riov J (1974) A polygalacturonase from citrus leaf explants. Role in abscission. Plant Physiol 53:312–316
Riov J, Yang SF (1982) Stimulation of ethylene production in citrus leaf discs by mannitol. Plant Physiol 70:142–146
Sagee O, Goren R, Riov J (1980) Abscission of citrus leaf explants. Interrelationships of abscisic acid, ethylene, and hydrolytic enzymes. Plant Physiol 66:750–753
Serek M, Sisler EC, Reid MS (1995) 1-Methylcyclopropene, a novel gaseous inhibitor of ethylene action, improves the life of fruit, cut flowers and potted plants. Acta Hortic 391:337–345
Sisler EC (2006) The discovery and development of compounds counteracting ethylene at the receptor level. Biotechnol Adv 24:357–367
Sisler EC, Serek M (1997) Inhibitors of ethylene responses in plants at the receptor level: Recent developments. Physiol Plant 100:577–582
Sisler EC, Serek M (1999) Compounds controlling the ethylene receptor. Bot Bull Acad Sin 40:1–7
Sisler EC, Wood C (1988) Competition of unsaturated compounds with ethylene for binding and action in plants. Plant Growth Regul 7:181–191
Sisler EC, Goren R, Huberman M (1985) Effect of 2,5-norbornadiene on abscission and ethylene production in citrus leaf explants. Physiol Plant 63:114–120
Sisler EC, Serek M, Dupille E (1996) Comparison of cyclopropene, 1-methylcyclopropene and 3,3-dimethylcyclopropeneas an ethylene antagonist in plants. Plant Growth Reg 18:169–174
Sisler EC, Goren R, Apelbaum A (2000) Controlling ethylene responses in horticultural crops at the receptor level. Final report, United States-Israel Binational Agricultural Research and Development Fund (BARD) No. US-2786–96R
Sisler EC, Serek M, Roh KA, Goren R (2001) The effect of structure on the antagonism by Cyclopropanes of ethylene responses in banana. Plant Growth Regul 33:107–110
Sisler EC, Alwan T, Apelbaum A, Serek M, Goren R (2003) 1-substituted cyclopropenes: Effective blocking agents for the ethylene receptor in plants. Plant Growth Regul 40:223–228
Veen H, Overbeek JHM (1989) The action of silver thiosulphate in carnation petals. In: Clijsters H et al (eds) Biochemical and physiological aspects of ethylene production in lower and higher plants. Kluwer Academic Publishers, pp 109–17
Watkins CB (2006) The use of 1-Methylecyclopropene (1-MCP) on fruits and vegetables. J Biotechnol Adv 24:389–409
Wuzburger J, Goren R (1978) Abscission of citrus leaf explants. No correlation with naphthaleneacetic acid conjugation in abscission zone. Plant Phsyol 62:295–298
Zhong GY, Huberman M, Feng X, Sisler EC, Holland D, Goren R (2001) Effect of 1-methylcyclopropane on ethylene-included abscission of citrus leaves and leaf explants. Physiol Plant 113:134–141
Acknowledgments
This research was supported by Research Grant No. IS-2786-96R from BARD, the United State - Israel Binational Agricultural Research and Development Fund. The cooperation and contribution of Dr. M. Huberman to this study is greatly appreciated.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Apelbaum, A., Sisler, E.C., Feng, X. et al. Assessment of the potency of 1-substituted cyclopropenes to counteract ethylene-induced processes in plants. Plant Growth Regul 55, 101–113 (2008). https://doi.org/10.1007/s10725-008-9264-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10725-008-9264-9