Coleoptera pheromones

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. 

Tolasch T (2004) Identifizierung und Synthese fluchtiger Inhaltsstoffe und neuer Pheromone aus Kafern (Coleoptera). Dissertation, Hamburg... 

Field bioassays with adult cerambycid beedes, Neoclytus acuminatus acumi-natus (F.) (Coleoptera Cerambycidae), revealed that males produce a pheromone that attracts both sexes. Male extracts revealed a single major male-specific compound IS, 3>S )-hexanediol. Field trials showed that a racemic blend of IS, 3S) and 2R, 3i )-hexanediols attracted both sexes and that activity was similar to enantiomerically enriched IS, 3S) hexanediol (e.e. 80.2%). However, a blend of all four stereoisomers attracted only a few beetles. ... 

The female sex pheromone of the cranberry root grub, Lichnanthe vulpina Hentz (Coleoptera Glaphyridae), was identified as ( )-7-hexade-cenol and (Z )-7-hexadecenal. Both compounds captured males although it was observed that the alcohol was slightly more effective than the aldehyde. ... 

The aggregation pheromone of the leaf beetle Diorhabda elongata Brulle (Coleoptera Chrysomelidae) have been identified as two compounds namely, (2E , 42 )-2,4-heptadienal and (2E , 42 )-2,4-heptadien-l-ol produced exclusively by males. They were also detected in trace quantities from females but the levels in males were 8—40 times higher. ... 

Males from Galerucella calmariensis and Galerucellapusilla (Coleoptera Chrysomelidae) emit an aggregation pheromone while feeding on host foliage. The compound was identified by spectrometric and other microchemical tests as the novel dimethylfuran lactone, 12,13-dimethyl-5,l4-dioxabicyclo[9.2.1]-tetradeca-l(13),ll-dien-4-one. The structure was confirmed by synthesis and the synthetic compound attracted both males and females in field tests. 

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. ... 

The sex pheromone emitted by the female yellow mealworm beetles, Tenebrio molitor L. (Coleoptera Tenebrionidae), 4-methyl-1-nonanal is well known. However, it was observed that males emit a pheromone that attracts females, which was identified as (Z )-3-dodecenyl acetate. 

Peng, C. W. and Weiss, M. J. (1992). Evidence of an aggregation pheromone in the flea beetle, Phyllotreta cruciferae (Goeze) (Coleoptera, Chrysomelidae). Journal of Chemical Ecology 18 875-884. 

Bartelt, R. J. and Weisleder, D. (1996). Polyketide origin of pheromones of Carpophilus davidsoni and C. mutilatus (Coleoptera Nitidulidae). Bioorganic and Medicinal Chemistry 4 429 138. 

Kuwahara, Y., Fukami, H., Ishii, S., Matsumura, F. and Burkholder, W. E. (1975b). Studies on the isolation and bioassay of the sex pheromone of the drugstore beetle, Stegobium paniceum (Coleoptera Anobiidae). Journal of Chemical Ecology 1 413 122. 

Chemical studies on the Anobiidae sex pheromone of the drugstore beetle, Stegobium paniceum (L) (Coleoptera). Tetrahedron 34 1769-1774. 

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. 

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. 

A small group of Coleoptera-like, mostly parasitic insects, is the Strepsiptera. The placement of these insects in a totally separate taxonomic group is controversial. A search of the literature did not show any information on their sex pheromone. 

Biemont J.-C., Chaibou, M. and Pouzat J. (1992) Localization and fine structure of the female sex pheromone-producing glands in Bruchidius atrolineatus (Pic) (Coleoptera Bruchidae). Int. J. Insect Morphol. Embryol. 21, 251-262. 

Iwabuchi K. (1986) Mating behavior of Xylotrechus pyrrhoderus Bates (Coleoptera Cerambycidae). III. Pheromone secretion by male. Appl. Entomol. Zool. 21, 606-612. 

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. 

Nardi J. B., Dowd P. F. and Bartelt R. J. (1996) Fine structure of cells specialized for secretion of aggregation pheromone in a nitidulid beetle Carpophilus freemani (Coleoptera Nitidulidae). Tissue Cell 28, 43-52. 

Noldt U., Fettkother R. and Dettner K. (1995) Structure of the sex pheromone-producing prothoracic glands of the male old house borer, Hylotrupes bajulus (L.) (Coleoptera Cerambycidae). Int. J. Insect Morphol. Embrol. 24, 223-234. 

Schneider I. and Rudinsky J. A. (1969) The site of pheromone production in Trypodendron lineatum (Coleoptera Scolytidae) bioassay and histological studies of the hindgut. Can. Entomol. 101, 1181-1186. 

Tada S. and Leal W. S. (1997) Localization and morphology of the sex pheromone glands in scarab beetles (Coleoptera Rutelinae, Melolonthinae). J. Chem. Ecol. 23, 903-915. 

Zethner-M0ller O. and Rudinsky J. A. (1967) Studies on the site of sex pheromone production in Dendroctonus pseudotsugae (Coleoptera Scolytidae). Ann. Entomol. Soc. Am. 60, 575-582. 

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

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...

Algarvio R., Teixeira C., Barata E., Pickett J., Novas P. C. and Figueiredo D. (2002) Identification of a putative aggregation pheromone from males of Platypus cylindrus (Coleoptera Platypodidae). Presented at Annu. Meet. Int. Soc. Chem. Ecol., 19th, Hamburg. 

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