Skip to main content
PMC home page
Plant Physiology logoLink to Plant Physiology
. 1997 Jun;114(2):419–428. doi: 10.1104/pp.114.2.419

Importance of the Chiral Centers of Jasmonic Acid in the Responses of Plants (Activities and Antagonism between Natural and Synthetic Analogs).

L Holbrook 1, P Tung 1, K Ward 1, D M Reid 1, S Abrams 1, N Lamb 1, J W Quail 1, M M Moloney 1
PMCID: PMC158321  PMID: 12223716

Abstract

The importance of the two chiral centers at C-3 and C-7 in the molecular structure of jasmonic acid in plant responses was investigated. We separated methyl jasmonate (MeJA) into (3R)- and (3S)-isomers with a fixed stereochemistry at C-3, but epimerization at C-7 is possible. The four isomers of the nonepimerizable analog 7-methyl MeJA were synthesized. These six esters and their corresponding acids were tested in three bioassays: (a) senescence in sunflower (Helianthus annuus) cotyledons; (b) proteinase inhibitor II gene expression in transgenic tobacco (Nicotiana tabacum) with [beta]-glucuronidase as a biochemical reporter; and (c) seed germination in Brassica napus and wheat (Triticum aestivum). The esters and acids had similar activities in the three assays, with the ester being more effective than its acid. The (3R)-stereochemistry was critical for jasmonate activity. Although activity was reduced after substituting the C-7 proton with a methyl group, the analogs with (3R,7R)- or (3R,7S)-stereochemistry were active in some of the assays. Although the four isomers of 7-methyl MeJA were inactive or only weakly active in the senescence assay, they could overcome the senescence-promoting effect of (3R)-MeJA. The strongest antagonistic effect was observed with the (3R,7S)-isomer.

Full Text

The Full Text of this article is available as a PDF (1.7 MB).

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Farmer E. E., Johnson R. R., Ryan C. A. Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic Acid. Plant Physiol. 1992 Mar;98(3):995–1002. doi: 10.1104/pp.98.3.995. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Farmer E. E., Ryan C. A. Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc Natl Acad Sci U S A. 1990 Oct;87(19):7713–7716. doi: 10.1073/pnas.87.19.7713. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Farmer E. E., Ryan C. A. Octadecanoid Precursors of Jasmonic Acid Activate the Synthesis of Wound-Inducible Proteinase Inhibitors. Plant Cell. 1992 Feb;4(2):129–134. doi: 10.1105/tpc.4.2.129. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Gundlach H., Müller M. J., Kutchan T. M., Zenk M. H. Jasmonic acid is a signal transducer in elicitor-induced plant cell cultures. Proc Natl Acad Sci U S A. 1992 Mar 15;89(6):2389–2393. doi: 10.1073/pnas.89.6.2389. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Hildmann T., Ebneth M., Peña-Cortés H., Sánchez-Serrano J. J., Willmitzer L., Prat S. General roles of abscisic and jasmonic acids in gene activation as a result of mechanical wounding. Plant Cell. 1992 Sep;4(9):1157–1170. doi: 10.1105/tpc.4.9.1157. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Holbrook L. A., van Rooijen G. J., Wilen R. W., Moloney M. M. Oilbody Proteins in Microspore-Derived Embryos of Brassica napus: Hormonal, Osmotic, and Developmental Regulation of Synthesis. Plant Physiol. 1991 Nov;97(3):1051–1058. doi: 10.1104/pp.97.3.1051. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Mason H. S., DeWald D. B., Mullet J. E. Identification of a methyl jasmonate-responsive domain in the soybean vspB promoter. Plant Cell. 1993 Mar;5(3):241–251. doi: 10.1105/tpc.5.3.241. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Reinbothe S., Mollenhauer B., Reinbothe C. JIPs and RIPs: the regulation of plant gene expression by jasmonates in response to environmental cues and pathogens. Plant Cell. 1994 Sep;6(9):1197–1209. doi: 10.1105/tpc.6.9.1197. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Staswick P. E., Huang J. F., Rhee Y. Nitrogen and methyl jasmonate induction of soybean vegetative storage protein genes. Plant Physiol. 1991 May;96(1):130–136. doi: 10.1104/pp.96.1.130. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Staswick P. E. Jasmonate, genes, and fragrant signals. Plant Physiol. 1992 Jul;99(3):804–807. doi: 10.1104/pp.99.3.804. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Thornburg R. W., An G., Cleveland T. E., Johnson R., Ryan C. A. Wound-inducible expression of a potato inhibitor II-chloramphenicol acetyltransferase gene fusion in transgenic tobacco plants. Proc Natl Acad Sci U S A. 1987 Feb;84(3):744–748. doi: 10.1073/pnas.84.3.744. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Ueda J., Kato J. Isolation and Identification of a Senescence-promoting Substance from Wormwood (Artemisia absinthium L.). Plant Physiol. 1980 Aug;66(2):246–249. doi: 10.1104/pp.66.2.246. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Vick B. A., Zimmerman D. C. Biosynthesis of jasmonic Acid by several plant species. Plant Physiol. 1984 Jun;75(2):458–461. doi: 10.1104/pp.75.2.458. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Wilen R. W., van Rooijen G. J., Pearce D. W., Pharis R. P., Holbrook L. A., Moloney M. M. Effects of jasmonic Acid on embryo-specific processes in brassica and linum oilseeds. Plant Physiol. 1991 Feb;95(2):399–405. doi: 10.1104/pp.95.2.399. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Xu Y., Chang PFL., Liu D., Narasimhan M. L., Raghothama K. G., Hasegawa P. M., Bressan R. A. Plant Defense Genes Are Synergistically Induced by Ethylene and Methyl Jasmonate. Plant Cell. 1994 Aug;6(8):1077–1085. doi: 10.1105/tpc.6.8.1077. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Plant Physiology are provided here courtesy of Oxford University Press

RESOURCES