Scolytidae pheromone components

Seybold S. J., Quilici D. R., Tillman J. A., Vanderwel D., Wood D. L. and Blomquist G. J. (1995) De novo biosynthesis of the aggregation pheromone components ipsenol and ipsdienol by the pine bark beetles Ips paraconfusus Lanier and Ipspini (Say) (Coleoptera Scolytidae). Proc. Natl. Acad. Sci. USA 92, 8393-8397. 

Figure 6.9 Examples of pheromone components of bark beetles (Scolytidae) and ambrosia beetles (Scolytidae and Platypodidae) classified by likely biosynthetic origin (based on Francke and Schulz, 1999). (A) References for identification and/or behavioral activity of isoprenoid pheromone compounds are as follows-. 2-methyl-3-buten-2-ol (Bakke efa/., 1977 Giesen etal., 1984 Klimetzek etal., 1989a Lanne etal., 1989), 3-methyl-3-buten-1-ol (Stoakley etal., 1978 Bowers and Borden, 1990 Bowers etal, 1991 Zhang efa/., 2000), 3-methyl-1-butanol (Renw ick etal, 1977), 3-hydroxy-3-methylbutan-2-one (Francke and Heeman, 1974 Francke etal 1974), ipsenol and ipsdienol...

Figure 6.10 De novo biosynthesis of isoprenoid pheromone components by bark and ambrosia beetles through the mevalonate biosynthetic pathway. The end products are hemiterpenoid and monoterpenoid pheromone products common throughout the Scolytidae and Platypodidae (Figure 6.9A). The biosynthesis is regulated by juvenile hormone III (JH III), which is a sesquiterpenoid product of the same pathway. The stereochemistry of JH III is indicated as described in Schooley and Baker (1985). Although insects do not biosynthesize sterols de novo, they do produce a variety of derivatives of isopentenyl diphosphate, geranyl diphosphate, and farnesyl diphosphate. Figure adapted from Seybold and Tittiger (2003).

Figure 6.11 Biosyntheses of isoprenoid pheromone components by bark and ambrosia beetles from host conifer monoterpenes. (A) Conversion by the male California fivespined ips, Ips paraconfusus Lanier (Coleoptera Scolytidae), of myrcene from the xylem and phloem oleoresin of ponderosa pine, Pinus ponderosa Laws., to (4S)-(+)-ipsdienol and (4S)-(-)-ipsenol, components of the aggregation pheromone (Hendry et al., 1980). (B) Conversion by male and female I. paraconfusus of (1 S,5S)-(-)-a-pinene (2,6,6-trimethyl-bicyclo[3.1,1]hept-2-ene) from the xylem and phloem oleoresin of P. ponderosa to (1 S,2S,5S)-(+)-c/s-verbenol (c/s-4,6,6-trimethyl-bicyclo[3.1,1]hept-3-en-2-ol), an aggregation pheromone synergist and of (1 R,5R)-(+)-a-pinene to (1 fl,2S,5fl)-(+)-frans-verbenol (frans-4,6,6-trimethyl-bicyclo[3.1,1]hept-3-en-2-ol), a compound of unknown behavioral activity for /. paraconfusus. Male and female western pine beetle, Dendroctonus brevicomis LeConte (Coleoptera Scolytidae), convert (1 S,5S)-(-)-a-pinene to (1S,2ft,5S)-(-)-frans-verbenol, an aggregation pheromone interruptant and (1R,5R)-(+)-a-pinene to (1 R,2S,5R)-(+)-frans-verbenol, a compound of...

Barkawi L. S., Francke W., Blomquist G. J. and Seybold S. J. (2003) Frontalin de novo biosynthesis of an aggregation pheromone component by Dendroctonus spp. bark beetles (Coleoptera Scolytidae). Insect Biochem. Mol. Biol. 33, 773-788. 

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. 

Teale S. A., Webster F. X., Zhang A. and Lanier G. N. (1991) Lanierone a new pheromone component from Ips pini (Coleoptera Scolytidae) in New York. J. Chem. Ecol. 17, 1159-1176. 

A second example is the spruce beetle, Dendroctonus rufipennis (Kirby) (Coleoptera Scolytidae), a major cause of mortality in mature spruce stands. Gries et al. (1992) found that the terpene verbenene (31 in Figure 19.5), was emitted from the beetles, predominantly from females, and concluded that it is a pheromone component. The oxygenated compounds seudenol, frontalin, and l-methyl-cyclohex-2-en-l-ol, were previously identified as pheromone components in this species. Attraction to verbenene alone was demonstrated in field traps, and it enhanced captures to the other pheromone components. The absolute configuration of verbenene has not been investigated. 

One of the best understood pheromone systems in bark beetles is from the pine engraver, Ips pini (Say) (Coleoptera Scolytidae). This species is broadly distributed across North America, and populations can be divided into three distinct groups based on the enantiomeric composition of ipsdienol. Ipsdienol is the major pheromone component produced by pioneer males. Eastern populations synthesize and respond to mostly (+) ipsdienol, while western populations rely on the (-)... 

QUILICI, D.R., De novo biosynthesis of aggregation pheromone components by the pine bark beetles, Ips paraconfusus (Lanier) and Ips pini (Say) (Coleoptera Scolytidae), and identification of an interruptant and a synergist produced by Ips pini., Ph.D., 1997, University of Nevada, Reno. 

Lanier G. N., Gore W. E., Pearce G. T., Peacock J. W. and Silverstein R. M. (1977) Response of the European elm bark beetle, Scolytus multistriatus (Coleoptera Scolytidae) to isomers and components of its pheromone. J. Chem. Ecol. 3, 1-8. 

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