Coleoptera pheromone biosynthesis

Coleoptera comprise the largest order of insects and accordingly pheromone structures and biochemical pathways are diverse [98, 99]. Beetle pheromone biosynthesis involves fatty acid, amino acid, or isoprenoid types of pathways. In some cases dietary host compounds can be converted to pheromones, but it is becoming apparent that most beetle pheromones are synthesized de novo. 

In contrast to the rutelines, the melolonthine scarabs generally use terpenoid-and amino acid-derived pheromones (reviewed in Leal, 1999). For example, the female large black chafer, Holotrichia parallela Motschulsky, produces methyl (2.S, 3. Sj - 2 - am ino-3-methy lpcn tanoatc (L-isoleucine methyl ester) as an amino acid-derived sex pheromone (Leal et al., 1992 Leal, 1997). There is no direct evidence that the chafer beetles or any other Coleoptera use the shikimic acid pathway for de novo pheromone biosynthesis, but some scarabs and scolytids (see section 6.6.4.2) may convert amino acids such as tyrosine, phenylalanine, or tryptophan to aromatic pheromone components (Leal, 1997,1999). In another melolonthine species, the female grass grab beetle, Costelytra zealandica (White), the phenol sex pheromone is produced by symbiotic bacteria (Henzell and Lowe, 1970 Hoyt et al. 1971). 

Bacala R. (2000) In vitro studies of sex pheromone biosynthesis in the yellow mealworm beetle, Tenebrio molitor (Coleoptera Tenebrionidae). MSc thesis. Univ. of Manitoba, 133 pp. 

Hedin P. A., Lindig O. H. and Wiygul G. (1982) Enhancement of boll weevil Anthonomus grandis Boh. (Coleoptera Curculionidae) pheromone biosynthesis with JH III. Experientia 38, 375-376. 

Ivarsson P., Schlyter F. and Birgersson G. (1993) Demonstration of de novo pheromone biosynthesis in Ips duplicatus (Coleoptera Scolytidae) inhibition of ipsdienol and E-myrcenol production by compactin. Insect Biochem. Molec. Biol. 23, 655-662. 

Lu F. (1999) Origin and endocrine regulation of pheromone biosynthesis in the pine bark beetles, Ips pini (Say) and Ips paraconfusus Lanier (Coleoptera Scolytidae). PhD thesis. Univ. of Reno, Nevada, 152 pp. 

Tillman J. A., Holbrook G. L., Dallara P. L., Schal C., Wood D. L., Blomquist G. J. and Seybold S. J. (1998) Endocrine regulation of de novo aggregation pheromone biosynthesis in the pine engraver, Ips pini (Say) (Coleoptera Scolytidae). Insect Biochem. Molec. Biol. 28, 705-715. 

Tittiger C., Blomquist G. J., Ivarsson P., Borgeson C. E. and Seybold S. J. (1999) Juvenile hormone regulation of HMG-R gene expression in the bark beetle, Ips paraconfusus (Coleoptera Scolytidae) implications for male aggregation pheromone biosynthesis. Cell. Mol. Life Sci. 55, 121-127. 

Coleoptera Scolytidae) implications for male aggregation pheromone biosynthesis. Cell. Mol. Life Sci. 55, 121-127. 

Evidence accumulated for and against the paradigm that bark beetle pheromone biosynthesis involved direct modification of host precursor monoterpenes. For 1. pini, the issue was laid to rest with the demonstration that male tissues incorporate radio-labeled acetate into ipsdienol in a manner consistent with pheromone production. Similar experiments proved the de novo biosynthesis of frontalin, an important isoprenoid-derived semiochemical produced by male Dendroctonus jeffreyi It is probable that other Coleoptera can also synthesize monoterpenes, either as pheromone components " or defensive compounds. Despite the capacity for de novo biosynthesis, plant precursor modification is likely an important source of pheromone components for some species. In these cases, plant chemicals could enter the pheromone biosynthetic pathway at later steps. 

TILLMAN, J.A., LU, F., STAEHLE, L., DONALDSON, Z DWINELL, S.C., TITTIGER, C., HALL, G.M., STORER, A.J., BLOMQUIST, G.J., SEYBOLD, S.J., Juvenile hormone regulates de novo isoprenoid aggregation pheromone biosynthesis in pine bark beetles, Ips spp. (Coleoptera Scolytidae), through transcriptional control of HMG-CoA reductase, J. Chem. Ecol, 2004,30, 2335-2358. 

KEELING, C.I., BLOMQUIST, G.J., TITTIGER, C., Coordinated gene expression for pheromone biosynthesis in the pine engraver beetle, Ips pini (Coleoptera Scolytidae). Naturwissenschaften, 2004, 91, 324-328. 

Vanderwel D. and Oehlschlager A. C. (1987) Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera. In Pheromone Biochemistry, eds G. J. Blomquist and G. D. Prestwich, pp. 175-215. Academic Press, Orlando, FL. Villet R. H. (1974) Involvement of amino and sylfhydryl groups in olfactory transduction in silkmoths. Nature 248, 707-709. 

Biosynthesis and endocrine regulation of pheromone production in the Coleoptera... 

Ivarsson P. and Birgersson G. (1995) Regulation and biosynthesis of pheromone components in the double spined bark beetle Ips duplicatus (Coleoptera Scolytidae). J. Insect Physiol. 41, 843-849. 

LanneB. S., IvarssonP., Johnson P., Bergstrom G. and Wassgren A. B. (1989) Biosynthesis of 2-methyl-3-buten-2-ol, a pheromone component of Ips typographus (Coleoptera Scolytidae). Insect Biochem. 19, 163-168. 

Petroski R. J., Bartelt R. J. and Weisleder D. (1994) Biosynthesis of (2 ,4 ,6 )-5-ethyl-3-methyl-2,4,6-nonatriene the aggregation pheromone of Carpophilus freemani (Coleoptera Nitidulidae). Insect Biochem. Molec. Biol. 24, 69-78. 

SEYBOLD, S.J., QUILICI, D.R., TILLMAN, J.A., VANDERWEL, D., WOOD, D.L., BLOMQUIST, G.J., De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ips pini (Say) (Coleoptera Scolytidae), Proc. Natl. Acad. Sci. USA, 1995, 92, 8393-8397. 

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