25 years of natural product R&D with New South Wales agriculture.

Following recent NSW Government restructuring, the Department of Agriculture now exists in a composite form along with Forestry, Fisheries and Minerals in the new NSW Department of Primary Industries. This paper outlines some of the highlights of secondary metabolite R&D accomplished in the 25 years since the essential oil research unit was transferred from the Museum of Applied Arts & Sciences, Sydney to NSW Agriculture's Wollongbar Agricultural Institute on the NSW north coast. The essential oil survey was continued, typing the Australian flora as a suitable source of isolates such as myrtenal (Astartea), myrtenol (Agonis), methyl chavicol(Ochrosperma), alpha-phellandren-8-ol (Prostanthera), methyl myrtenate (Darwinia), methyl geranate (Darwinia), kessane (Acacia), cis-dihydroagarofuran (Prosthanthera), protoanemonin (Clematis), isoamyl isovalerate (Micromyrtus), methyl cinnamate (Eucalyptus) and bornyl acetate (Boronia). Many of these components are used, or have potential use in the fragrance, flavour, medicinal plant or insect attraction fields. Two weeds toxic to livestock in the Central West of the State are also harvested commercially as medicinal plants. Measurement of hypericin concentrations in the various plant parts of St John's Wort (Hypericum perforatum) over two seasons has shown that the weed can be effectively managed by grazing sheep during the winter months when toxin levels are low. Syntheses of beta-carbolines tribulusterine and perlolyrine have shown that the former alkaloid was misidentified in the literature and hence not the toxic principle responsible for Tribulus staggers in sheep. Poor quality (high 1,8-cineole - low terpinen-4-ol) oil bearing tea tree (Melaleuca alternifolia) plantations have been established to the detriment of many a tea tree farmer. Analytical methods developed to check leaf quality at an early age indicated precursor sabinene constituents that convert to the active terpinen-4-ol both as the leaf matures or as the precursors are distilled for oil production. Tea tree's major insect pest, pyrgo beetle (Paropsisterna tigrina), was seen to selectively metabolize only 1,8-cineole from it's monoterpenoid-rich diet. Characterization of these and other metabolites from myrtaceous herbivores showed a species specific production of predominately ring hydroxylated products, some of which were attractive when bioassayed against adult beetles.