Phytochemistry Reviews

, Volume 5, Issue 1, pp 143–178 | Cite as

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

  • Steven J. SeyboldEmail author
  • Dezene P. W. Huber
  • Jana C. Lee
  • Andrew D. Graves
  • Jörg Bohlmann


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 monoterpenoid (ipsdienol) and a hemiterpenoid (2-methyl-3-buten-2-ol) in its pheromone blend. The stereospecificity of the response of O. erosus to the monoterpenoid appears to be the key factor to the improved potency of the attractant bait for this invasive species.


Aggregation pheromone Behavior Biosynthesis Coleoptera Host colonization Ipsdienol Ips paraconfusus Kairomone 2-Methyl-3-buten-2-ol Monoterpene Myrcene Orthotomicus erosus Pinus P450 Scolytidae 


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We gratefully acknowledge the Human Frontier Science Program (Grant #RGY0382) for support of collaborative research conducted by the Seybold and Bohlmann Laboratories. We also thank three anonymous reviewers for their critical contributions to the manuscript; C. Leutenegger and T. Olineka, Lucy Whittier Molecular and Diagnostic Core Facility at UC-Davis, and M. Erickson, USDA Forest Service, PSW, for assistance with molecular expression analyses; K. Daane, University of California at Berkeley, F. Schurr and S. Rambeau, University of California Blodgett Forest Research Station, R. West, Valley Oaks Golf Course, Visalia, California, and E. Espiritu, K. Gandhi, S. Hamud, P. Jiros, J. Lacsina, and O. Singh (all USDA Forest Service, PSW) for assistance with field studies; and J.A. Tillman for assistance with graphics.


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Copyright information

© Springer Science+Business Media B.V. 2006

Authors and Affiliations

  • Steven J. Seybold
    • 1
    Email author
  • Dezene P. W. Huber
    • 1
    • 2
    • 3
  • Jana C. Lee
    • 1
    • 2
  • Andrew D. Graves
    • 4
  • Jörg Bohlmann
    • 5
  1. 1.Chemical Ecology of Forest InsectsUSDA Forest Service, Pacific Southwest Research StationDavisUSA
  2. 2.Department of EntomologyUniversity of California, DavisDavisUSA
  3. 3.Ecosystem Science and Management ProgramUniversity of Northern British ColumbiaPrince GeorgeCanada
  4. 4.Department of EntomologyUniversity of MinnesotaSt. PaulUSA
  5. 5.Michael Smith LaboratoriesUniversity of British ColumbiaVancouverCanada

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