Molecular modelling, synthesis and biological activity of methyl 3-methyljasmonate and related derivatives

J L Ward, P Gaskin, M H Beale, R Sessions, Y Koda, C Wasternack

Research output: Contribution to journalArticle (Academic Journal)peer-review

17 Citations (Scopus)

Abstract

Methyl 3-methyljasmonate was synthesised from methyl jasmonate via methyl 3,7-dehydrojasmonate. Molecular modelling predicted an increase in the proportion of cis-orientated sidechains for equilibrated 3-methyl-substituted jasmonate. The synthetic 3-methyljasmonate was shown by gc-ms analysis to equilibrate to a 2:1 ratio of isomers, which appeared from the NMR spectra to comprise mainly the cis-isomer. Surprisingly, both 3,7-dehydro- and 3-methyl-derivatives were inactive in four well established jasmonate bioassays. Methyl-2-methyljasmonate was synthesised and also found to be inactive. Methyl 4,5-dehydrojasmonate was prepared, via the 5-diazo derivative. Both of these compounds have low activity. Our results are discussed with reference to previous knowledge of jasmonate structure-activity relationships and indicate that there are stringent steric demands in jasmonate-receptor interactions. (C) 1997 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8181-8194
Number of pages14
JournalTetrahedron
Volume53
Issue number24
Publication statusPublished - 16 Jun 1997

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