Moths pheromone biosynthesis

Sequence homology has been noted previously (17) between the N-terminus of Hez-PBAN and insulin-like growth factor II, and the C-terminus with the insect peptide leucopyrokinin (Table II) isolated from cockroach heads. The striking similarity of the first 16 residues of the melanization and reddish colorization hormone (MRCH) of B. mori (18) and Bom-PBAN has led to the suggestion by Kitamura ti 1. (17) that they are identical (Table II), thus implying a dual role for this hormone in the larvae (melanization and reddish colorization) and adult moth (pheromone biosynthesis). 

Identification of 9,12-tetradecadienyl (9,12-14) compounds began with studies on two cosmopolitan pests of stored products, the almond moth (Cadra cmtella, Pyralidae Phycitinae) and the Indian meal moth (Plodia interpunctella, Phycitinae) [38,39]. This 9,12-14 structure has been reported from another 13 Pyralidae (only in Phycitinae) species and 11 Noctuidae species (9 species in Amphipyrinae, and 1 species each in Hadeninae and Plusiinae). These two families, however, are not closely related. Most likely, the females classified in distant groups happened to produce the same chemical in the train of their perpetual evolution of modifying the original systems for pheromone biosynthesis. The 5,7-dodecadienyl (5,7-12) structure is a carbon skeleton common... 

Abstract Pheromones are utilized by many insects in a complex chemical communication system. This review will look at the biosynthesis of sex and aggregation pheromones in the model insects, moths, flies, cockroaches, and beetles. The biosynthetic pathways involve altered pathways of normal metabolism of fatty acids and isoprenoids. Endocrine regulation of the biosynthetic pathways will also be reviewed for the model insects. A neuropeptide named pheromone biosynthesis activating neuropeptide regulates sex pheromone biosynthesis in moths. Juvenile hormone regulates pheromone production in the beetles and cockroaches, while 20-hydroxyecdysone regulates pheromone production in the flies. 

Moths, beetles, flies, and cockroaches have received the most attention regarding pheromone biosynthesis because their members contain prominent pest species and in addition are typically easy to rear in the laboratory. However several other insects have been investigated regarding pheromone biosynthesis, most notably the bees and butterflies. 

Most female moths release sex pheromones in a typical calling behavior in which the pheromone gland is extruded to release pheromone during a particular time of the photoperiod. In most cases pheromone biosynthesis coincides... 

PBAN binding to a receptor results in signal transduction events to stimulate the pheromone biosynthetic pathway (Fig. 5). Receptor activation results in the influx of extracellular calcium and has been demonstrated in a number of moths [163-168]. The increase in cytosolic calcium can directly stimulate pheromone biosynthesis in some moths [165-168] or it will stimulate the production of cAMP [169,170]. So far cAMP has only been implicated in signal... 

The role of the nervous system in pheromone biosynthesis in moths is not clearly understood. Christensen and co-workers [208-211] proposed that the neurotransmitter octopamine may be involved as an intermediate messenger during the stimulation of sex pheromone production in H. virescens. These workers suggested that octopamine was involved in the regulation of pheromone production and that PBAN s role lies in the stimulation of octopamine release at nerve endings. However, contradicting results concerning octopa-mine-stimulated pheromone production were reported in the same species as well as other moth species [163,172,212-214]. 

In moths, it was discovered in Helicoverpa zea that a peptide produced in the subesophageal ganglion portion of the brain complex regulates pheromone production in female moths (19). This factor has been purified and characterized in three species, Helicoverpa zea (20), Bombyx mori (21, 22), and Lymantria dispar (23). They are all a 33- or 34-amino acid peptide (named pheromone biosynthesis activating neuropeptide, PBAN) and have in common an amidated C-terminal 5-amino acid sequence (FXPRL-amide), which is the minimum peptide fragment required for pheromon-tropic activity. In the redbanded leafroller moth, it was shown that PBAN from the brain stimulates the release of a different peptide from the bursae copulatrix that is used to stimulate pheromone production in the pheromone gland found at the posterior tip of the abdomen (24). 

Bell, T. W Boppre, M., Schneider, D. and Meinwald, J. (1984). Stereochemical course of pheromone biosynthesis in the arctiid moth, Creatonotos transiens. Experientia 40 713-714. 

Boppre, M. and Schneider, D. (1985). Pyrrolizidine alkaloids quantitatively regulate both scent organ morphogenesis and pheromone biosynthesis in male Creatonotos moths (Lepidoptera Arctiidae). Journal of Comparative Physiology A 157 569-577. 

Another technique that is utilized to help ensure that label is incorporated into the pheromone is to apply the precursor at the same time as pheromone biosynthesis activating neuropeptide (PBAN). PBAN is a peptide hormone that regulates pheromone biosynthesis in most, but not all, moths. So, first it must be demonstrated that PBAN regulates pheromone production. In the case of the cabbage looper,... 

Arsequell G., Fabrias G. and Camps F. (1990) Sex pheromone biosynthesis in the processionary moth Thaumetopoeapityocampa by delta-13 desaturation. Arch. Insect Biochem. Physiol. 14, 47-56. 

Bjostad L. B. and Roelofs W. L. (1981) Sex pheromone biosynthesis from radiolabeled fatty acids in the redbanded leafroller moth. J. Biol. Chem. 256, 7936-7940. 

Foster S. P. (2000) Fatty acyl pheromone analogue-containing lipids and their roles in sex pheromone biosynthesis in the lightbrown apple moth, Epiphyaspostvittana (Walker). J. Insect Physiol. 47, 433 443. 

Jurenka R. A. and Roelofs W. L. (1989) Characterization of the acetyltransferase involved in pheromone biosynthesis in moths specificity for the Z isomer in Tortricidae. Insect Biochem. 19, 639-644. 

Lofstedt C. and Bengtsson M. (1988) Sex pheromone biosynthesis of (E,E)-8,10-dodecadienol in codling moth Cydia pomonella involves E9 desaturation. J. Chem. Ecol. 14, 903-915. 

Teal P. E. A. and Tumlinson J. H. (1987) The role of alcohols in pheromone biosynthesis by two noctuid moths that use acetate pheromone components. Archives of Insect Biochemistry and Physiology 4, 261-269. 

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