Relationship between chemical functional groups on Eucalyptus secondary metabolites and their effectiveness as marsupial antifeedants

Abstract

Eucalyptus displays strong intraspecific variation in resistance to browsing by marsupial folivores that can be attributed to variation in the concentration and type of diformylphloroglucinol compounds (DFPCs) in the foliage. In this study, we ask which functional groups of diformylphloroglucinol compounds determine their effectiveness in deterring feeding. We used a simple and highly deterrent compound, jensenone, as a model DFPC and compared its activity to structural variants that differ in the types of functional groups on the phloroglucinol molecule. Torquatone, a naturally occurring compound in the steam volatile fraction of Eucalyptus torquata foliage, has neither the aldehyde nor phenol groups that are believed to contribute to the antifeedant actions of jensenone. From the naturally occurring compounds we have synthesized two intermediates, a capped phenol/free aldehyde compound (acetyl-jensenone) and a free phenol/no aldehyde compound (demethyl-torquatone). Addition of jensenone and acetyl- jensenone to diets of common ringtail possums (Pseudocheirus peregrinus) substantially reduced their food intakes. Torquatone showed less activity, and there was little reduction in food intake when demethyl-torquatone was added to the diet. We conclude that at least the aldehyde groups attached to the aromatic nucleus are important in determining whether these compounds deter feeding by common ringtail possums, whereas the phenol groups may play only a minor role.