Cuticular hydrocarbons

Workers are often cited as the source of nestmate or kin recognition cues (e.g., [115]). Many GC analysis studies have shown that the cuticular hydrocarbon profiles are different between nestmates and non-nestmates. However, only recently have specific hydrocarbons, 7-methylnonacosane 73,11-methyl-nonacosane 74, (llZ)-nonacos-ll-ene 75, (llZ)-hentriacont-ll-ene 76, and (9Z)-nonacos-9-ene 77, been shown to mediate nestmate recognition in the paper wasp, Polistes dominulus [116]. 

The female produced sex pheromone of Aleochara curtula has been described to consist of a mixture of (Z)-7-henicosene and (Z)-7-tricosene [114]. The same compounds are reported to be used by young males as a kind of camouflage to avoid aggression from older males. Similarly, chemical camouflage by using hydrocarbons plays a role in the relations between the myrme-cophilous staphylinid beetle Zyras cones and the ant Lasius fuliginosus. The host worker ants never attack these beetles which show the same profiles of cuticular hydrocarbons as the ants [115]. 

Recently, two new facets have been added to scarab chemistry. A suite of unusual A9 10-allenic hydrocarbons like 86 has been identified among the cutic-ular hydrocarbons from several Australian melolonthine scarab beetles [184]. Though very low-level components in the related cane beetle Antitrogus parvu-luSy the major cuticular hydrocarbons in this species proved to be oligomethyl-docosanes like 87. Only the relative configurations of these compounds could be determined [185]. Whether these interesting hydrocarbons have a function as pheromones needs to be established. 

Attractive Compounds. While the defence chemistry of ladybird beetles has been extensively investigated, little is known about intraspecific communication. The role of chemical and behavioural cues has been described in mate recognition in Adalia bipunctata. Cuticular hydrocarbons, especially 7- and 9-methyltri-cosane seem to play an important role [301]. In Coccinella septempunctata, 2-isopropyl-3-methoxypyrazine 158 (see Scheme 17) accounting for the dis-... 

It has been suggested that the ethers, compounds unique to spiders, may provide reliable signals for pattern recognition and species determination. In contrast, a pattern of hydrocarbons, as used in several insect species, might be susceptible to contamination from cuticular hydrocarbons from insect prey remnants, which might alter the blends produced by the spiders and deposited on the webs (Schulz, 1997a, 1999). 

Jurenka, R. A., Schal, C Burns, E., Chase, J. and Blomquist, G. J. (1989). Structural correlation between cuticular hydrocarbons and female contact sex pheromone of German cockroach Blattella germanica (L.). Journal of Chemical Ecology 15 939-949. 

Jurenka R. A. and Subchev M. (2000) Identification of cuticular hydrocarbons and alkene precursor to the pheromone in hemolymph of the female gypsy moth, Lymantria dispar. Arch. Insect Biochem. Physiol. 43, 108-115. 

Subchev M. and Jurenka R. A. (2001) Identification of the pheromone in the hemolymph and cuticular hydrocarbons from the moth Scoliopteryx libatrix L. (Lepidoptera Noctuidae). Arch. Insect Biochem. Physiol. 47, 35 -3. 

Coyne J. A., Wicker-Thomas C. and Jallon J.-M. (1999) A gene responsible for a cuticular hydrocarbon polymorphism in Drosophila melanogaster. Genet. Res. Camb. 73, 189— 203. 

Pennanec h M., Bricard L., Kunesh G. and Jallon J.-M. (1997) Incorporation of fatty acids into cuticular hydrocarbons of male and female Drosophila melanogaster. J. Insect Physiol. 43, 111 1-1116. 

Takahashi A., Tsaur S.-C., Coyne J. A., and Wu C. I. (2001) The nucleotide changes governing cuticular hydrocarbon variation and their evolution in Drosophila melanogaster. Proc. Natl. Acad. Sci. USA 98, 3920-3925. 

Bartelt R. J., Arnold M. T., Schaner A. M. and Jackson L. L. (1986) Comparative analysis of cuticular hydrocarbons of the Drosophila virilis group. Comp. Biochem. Physiol. 83B, 731-742. 

Blomquist, G. J., Tillman J. A., Mpuru S. and Seybold, S. J. (1998) The cuticle and cuticular hydrocarbons of insects structure, function and biochemistry. In Pheromone Communication in Social Insects, eds R. K. Vander Meer, M. Breed, M. Winston and C. Espelie pp. 34-54. Westview Press, Boulder, CO. 

Howard R. W. (1993) Cuticular hydrocarbons and chemical communication. In Insect Lipids Chemistry, Biochemistry and Biology, eds D. W. Stanley-Samuelson and D. R. Nelson pp. 177-226. University of Nebraska Press, Lincoln. 

Nelson D. R., Dillwith J. W. and Blomquist G. J. (1981) Cuticular hydrocarbons of the housefly, Musca domestica. Insect Biochem. 11, 187-197. 

Stoffolano J. G., Schauber E., Yin C. M., Tillman J. A. and Blomquist G. J. (1997). Cuticular hydrocarbons and then role in copulatory behavior in Phormia regina (Meigen). J. Insect Physiol. 43, 1065-1076. 

A number of studies since 1980 have concentrated on the search for a sex pheromone analogous to Muscalure, the first contact pheromone discovered in mature Musca domestica females (Carlson et al., 1971). Other hydrocarbons have been described in various Diptera (Carlson et al., 1978 Blomquist and Jackson, 1979 El Messoussi et al., 1994 Blomquist, Chapter 8, in this volume). In all cases, a cuticular hydrocarbon with low or no volatility and high abundance was necessary, but not sufficient for a response. Its action could be checked only... 

So, although a group of cuticular hydrocarbons, especially 7,11-dienes, are sex attractants, they do not seem to be the only compounds which function in this role. Although the threshold of 7,11-HD is of the order of one or a few nanograms, it has not been firmly established with accurate methods. Indeed young flies of either sex have hydrocarbon with little or no 7,11-dienes (see section 9.3), which are full of sex appeal (Jallon and Hotta, 1979 P6chin6 et al., 1988). In fact, the nature of the synergetic factor involved in sex attraction and its interaction with chemical factors is not completely clear (Savarit et al., 1999 Rouault et al., 2002). 

Parallel to studies in D. melanogaster, there have been searches for pheromones in other Drosophila species. In the sibling species D. simulans, no sexual dimorphism was found among cuticular hydrocarbons. 7-T is the major compound for both sexes in most strains, although 7-P is more abundant in a few strains living around the Benin Gulf (see section 9.2). Jallon (1984) established that synthetic (Z)-7-T applied on dummies could stimulate the wing vibration behavior of... 

The hydrocarbon systems of mature D. simulans of both sexes are very similar and mainly consist of 7-monoenes (Jallon, 1984). A geographical polymorphism concerning linear hydrocarbons with 23 and/or 25 carbons (especially 7-T and 7-P) occurs in both sexes. When 29 populations of D. simulans were compared for their cuticular hydrocarbons (Rouault et al., 2001), only flies around the Benin Gulf in Africa showed higher levels of 7-P compared to those of 7-T, while the cumulative amounts of both hydrocarbons (7-T + 7-P) were essentially constant. For example, Cameroon strain 7-T is 22.7 percent and 17.7 percent of total hydrocarbons in females and males, respectively, 7-P males up 38.5 and 37.7 percent of hydrocarbon in females and males, respectively. The Seychelles strain is typical of the general type (7-T is 55.0 and 47.6 percent in females and males, respectively and 5.4 and 7.3 percent 7-P, respectively). 

Figure 9.2 Ontogeny of cuticular hydrocarbons in D. melanogaster (Canton-S strain). Values (total quantities) are means of four groups of five flies + SEM. ...

The sexual dimorphism of cuticular hydrocarbons is completed during the first three days after imaginal eclosion. During the same period, important physiological events take place, female oocyte maturation and vitellogenesis. A number of mutations have been described which affect ovarian development or endocrine control. These mutants were used to elucidate a possible hormone control mechanism used to regulate hydrocarbon biosynthesis. 

When the feminizing tra product was overexpressed in 6 h old hsp70-GAL4 UAS-tra XX females under a 1 h heat shock treatment at 37°C, the overall production of cuticular hydrocarbons, especially linear ones, was markedly reduced (Savarit et al., 1999). A similar reduction could be induced in males (Savarit and Ferveur, unpublished). 

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