Chrysomelid beetles

Fig. 12 Structures of oleanane glycosides from chrysomelid beetles...

Compound 150, one of two isoxazolinones first found in the defensive secretion of chrysomelid beetles, Chrysomela tremulae, shows a UV spectrum... 

Interestingly, Lepidoptera and aphids seem to avoid already infested plants, whereas Coleoptera are in general attracted to volatiles emitted by plants that are under attack by conspecifics. This has been shown for scarabaeid (Domek and Johnson, 1988 Harari etal., 1994 Loughrin etal., 1995b) and chrysomelid beetles (Peng and Weiss, 1992 Bolter et al., 1997 Kalberer et al., 2001). The Colorado... 

Southwell, I. A. and Stiff, I. A. (1989). Presence of long-chain dialkyl ethers in cuticular wax of the Australian chrysomelid beetle Monolepta australis. J. Chem. Ecol., 15, 255-263. 

Another unusual structure is represented by the male-produced pheromone of the chrysomelid beetles, Galerucella calmariensis and Galerucella pusilla. The compound, 12,13-dimethyl-5,14-dioxabicyclo[9.2.1]tetra-deca-l(13),ll-dien-4-one, (09) is a lactone including a 3,4-dimethylfuran substructure.943 Similar... 

Figure 3. Association of trans-epoxide hydrolase with arthropod herbivory. Trans/cis ratios of epoxide hydrolase in midguts of adult chrysomelid beetles are plotted relative to number of plant families ( ) or genera ( A) found within the host range of each species. See Figure 2 for details.

Monarch butterflies t.g., Danaus plexipus) combine two sets of natural compounds. Larvae feed on plants rich in cardiac glycosides and use them as chemical defense compounds. Adult butterflies visit plants with PAs, where they collect PAs that are converted to pheromones or transferred to their eggs 4,17,31,33,361,515). A similar PA utilization scheme was observed with larvae of the moth Utetheisa ornatrix 367,516), where the compounds were shown to be deterrent for spiders and birds 225, 525). The chrysomelid beetle Oreina feeds on PA-containing plants, such as Adenostyles, and stores the dieUuy PAs in the defense fluid 463,524). 

Rowell-Rahier, M., Witte, L., Ehmke, A. and Hartmann, T. (1991) Sesquestration of plant pyrrolizidine alkaloids by chrysomelid beetles and selective transfer into the defensive secretions. Chemoecology, 2, 41-8. 

Figure 46 3-Nitropropanoic acid esters (193-195) from chrysomelid beetles and pinoresinol (35) from caterpillars of the cabbage butterfly, Pieris rapae.

In summary, the Delphinium diterpene alkaloids cardiopetamine (30) and 15-acetylcardiopetamine (27) are potent insect antifeedants active on two insect species with different feeding adaptations (a polyphagous Lepidopteran and an oligophagous Chrysomelid beetle), suggesting a potential broad range of antifeedant action for this class of compounds [20]. 

Pasteels, j. M., S. Duffey, and M. Rowell-Rahier, Toxins in chrysomelid beetles, J. Chem. Ecol., 16, 211-222 (1990). 

Pasteels, J. M., M. Rowell-Rahier, and M. J. Raupp, Plant-derived defense in Chrysomelid beetles, in Novel Aspects of In-... 

Fig. 16.18. Isoxazolinone glucosides from chrysomelid beetle eggs and defensive glands.

The larvae of a number of chrysomelid beetles synthesize and accumulate cardiac glycosides (Pasteels et al., 1988, 1989). In this instance, the beetles do not take the compounds from the host plants (many of which lack cardenolides) but biosynthesize them from cholesterol. 

Larvae of the chrysomelid beetle Oreina cacaliae produce seniciphylline A -oxide (12) as a part of their defensive secretions. This pyrrolizidine alkaloid probably is derived from the alkaloids of the host plant Adenostyles leucophylla (Asteraceae Senecioneae) (Pasteels et al., 1988). 

Pasteels, J.M., and D. Daloze Cardiac Glycosides in the Defensive Secretion of Chrysomelid Beetles Evidence for their Production by the Insects. Science 197, 70-72 (1977). 

Daloze, D., and J.M. Pasteels Production of Cardiac Glycosides by Chrysomelid Beetles and Larvae. J. Chem. Ecol. 5, 63-77 (1979). 

Synthesized in certain chrysomelid beetles, feeding deterrent... 

Little evidence is available for the de novo synthesis of toxins in insects. Pasteels and Daloze (1977) have presented evidence for the production of cardiac glycosides in the defensive secretion in chrysomelid beetles. The situation is very difficult to define and involves the detection limits of our chemistry. If cardiac glycosides were to be detected in a butterfly but not in... 

Pasteels, J. M. and Daloze, D. (1977) Cardiac glycosides in the defensive secretion of chrysomelid beetles evidence for their production by the insects. Science, 197, 70-2. 

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