Coleoptera 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. 

MeriveeE. and Erm A. (1993) Studies on sex pheromone gland morphology and pheromone components in female elaterid beetles Agriotes obscurus L. and Agriotes lineatus L. (Coleoptera Elateridae). Proc. Estoniann Acad. Sci. Biol. 42, 108-117. 

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). 

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. 

Larsson M. C., Leal W. S. and Hansson B. S. (1999) Olfactory receptor neurons specific to chiral sex pheromone components in male and female Anomala cuprea beetles (Coleoptera Scarabaeidae). J. Comp. Physiol. A 184, 353-359. 

Fukaya, M. and Honda, H. (1995). Reproductive biology of the yellow-spotted longicom beetle, Psacothea hilaris (Pascoe) (Coleoptera Cerambycidae). 2. Evidence for two female pheromone components with different functions. Appl. Entomol. Zool., 30, 467 170. 

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. 

Over the past four decades, extensive research on insect pheromones has resulted in the chemical and/or behavioural elucidation of pheromone components from over 1500 of the estimated 875,000 described species of insects [3-5]. Research on representative species within four orders Blattodea 4000 species Coleoptera > 300,000 species Diptera -150,000 species and Lepidoptera 150,000 species [5], shows the abundance and diversity of insects. 

Cross, J.H., Byler, R.C., Cassidy, R.F. Jr, Silverstein, R.M., Greenblatt, R.E., Burkholder, W.E., Levinson, A.R. and Levinson, H.Z. (1976) Porapak-Q collection of pheromone components and isolation of (Z)- and (E)-14-methyl-8-hexadecenal, potent sex attracting components, from the frass of four species of Trogoderma (Coleoptera Dermestidae). Journal of Chemical Ecology 2, 457-468. 

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 (-)... 

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. 

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. 

Rossi, R., and A. Carpita Insect pheromones — synthesis of chiral sex pheromone components of several species of Trogoderma (Coleoptera Dermestidae). Tetrahedron 33,2447—2450(1977). 

Cross, J. H., R. C. Byler, R. M. Silverstein, R. E. Greenblatt, J. E. Gorman, and W. E. Burkholder Sex pheromone components and calling behavior of the female dermestid beetle, Trogoderma variabile Ballion (Coleoptera Dermestidae). J. Chem. Ecol. 3,115—125 (1977). 

Male Megacyllene caryae Gahan (Coleoptera Cerambycidae) respond to females only after touching them with their antennae, indicating the presence of a contact sex pheromone. The hydrocarbon, (Z )-9-nonacosene, was identified as the major component of the contact sex pheromone of the beetle. ... 

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. 

Chapter 19 by Bartelt is devoted to the pheromonal role of short-chain hydrocarbons, especially short i n etli y l/etli y I - branched and unsaturated components in beetles. The most abundant components in Carpophilus hemipterus (Coleoptera, Nitidulidae) have been identified as (2/ ,4/ ,6/ ,8/ )-3,5,7-(rimc(hyl-2,4,6,8-decatetracnc and (2E,4E,6E,SE)-3,5,7-trimethyl-2,4,6,8-undecatetraene (Bartelt et al., 1990). Later studies showed that male C. hemipterus emit nine all-E tetraene hydrocarbons and one all-E triene hydrocarbon in addition to the two previously reported pheromonally active tetraenes (Bartelt et al., 1992). In their review of biologically active compounds in beetles, Francke and Dettner (2005) fisted only a few dozen of those pheromonal compounds, most of which were identified by Bartelt. 

Hydrocarbon components in contact sex pheromone of the white-spotted longicom beetle, Anoplophora malasiaca (Thomson) (Coleoptera Cerambycidae) and pheromonal activity of synthetic hydrocarbons. Entomol. Sci., 3, 211-218. 

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