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

✍ Scribed by Jane L. Ward; Paul Gaskin; Michael H. Beale; Richard Sessions; Yasunori Koda; Claus Wasternack

• Book ID: 104207853
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 995 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00485-7

✦ Synopsis

A&r&

-Methyl 3-methyljasmonate was synthesised from methyl jasmonate via methyl 3.7dehydrojasmonate. Molecular modelling predicted an increase in the proportion of c&orientated sidechains for equilibrated 3-methyl-substituted jasmonate. The synthetic 3.methyljasmonate was shown by gc-ms analysis to equilibrate to a 2:l ratio of isomers, which appeared from the NMR spectra to comprise mainly the c&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 4,5dehydrojasmonate was prepared, viu the S-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.