Pine monoterpenes and pine bark beetles: a marriage of convenience for defense and chemical communication

• Published in: Phytochemistry reviews 2006-02, Vol.5 (1), p.143-178
• Main Authors: Seybold, Steven J., Huber, Dezene P. W., Lee, Jana C., Graves, Andrew D., Bohlmann, Jörg
• Format: Article
• Language: English
• Subjects: Acetals; Agglomeration; Attractants; Baits; Bark; Beetles; Biosynthesis; Chemical communication; Coleoptera; Coniferales; Engraving; Gene expression; Insects; Introduced species; Invasive species; Ips; Ips paraconfusus; Isopentenyl diphosphate; Kairomones; Metabolites; Monoterpenes; Nexus; Oleoresins; Organic chemistry; Oxygenation; Pheromones; Physiological effects; Pinaceae; Pine; Predators; Scolytidae; Secondary metabolites; Stereospecificity; Terpenes; Tri-trophic interactions
• ISSN: 1568-7767; 1572-980X
• DOI: 10.1007/s11101-006-9002-8

Pine-feeding bark beetles (Coleoptera: Scolytidae) interact chemically with their host pines (Coniferales: Pinaceae) via the behavioral, physiological, and biochemical effects of one class of isoprenoids, the monoterpenes and their derivatives. Pine monoterpenes occur in the oleoresin and function as behaviorally active kairomones for pine bark beetles and their predators, presenting a classic example of tri-trophic chemical communication. The monoterpenes are also essential co-attractants for pine bark beetle aggregation pheromones. Ironically, pine monoterpenes are also toxic physiologically to bark beetles at high vapor concentrations and are considered an important component of the defense of pines. Research over the last 30 years has demonstrated that some bark beetle aggregation pheromones arise through oxygenation of monoterpenes, linking pheromone biosynthesis to the host pines. Over the last 10 years, however, several frequently occurring oxygenated monoterpene pheromone components (e.g., ipsenol, ipsdienol and frontalin) have also been shown to arise through highly regulated de novo pathways in the beetles (reviewed in Seybold and Tittiger, 2003). The most interesting nexus between these insects and their plant hosts involves the late-stage reactions in the monoterpenoid biosynthetic pathway, during which isomeric dimethylallyl diphosphate and isopentenyl diphosphate are ultimately elaborated to stereospecific monoterpenes in the trees and to hydroxylated monoterpenes or bicyclic acetals in the insects. There is signal stereospecificity in both production of and response to the monoterpenoid aggregation pheromones of bark beetles and in response to␣the monoterpenes of the pines. In the California fivespined ips, Ips paraconfusus, we have discovered a number of cytochome P450 genes that have expression patterns indicating that they may be involved in detoxifying monoterpene secondary metabolites and/or biosynthesizing pheromone components. Both processes result in the production of oxygenated monoterpenes, likely with varying degrees of stereospecificity. A behavioral analysis of the stereospecific response of I. paraconfusus to its pheromone is providing new insights into the development of an efficacious bait for the detection of this polyphagous insect in areas outside the western United States. In contrast, a Eurasian species that has arrived in California, the Mediterranean pine engraver, Orthotomicus (Ips) erosus, utilizes both a monoterpeno