Pheromones precursors

Iwata T., Umezawa K., Toyoda F., Takahashi N., et al. (1999). Molecular cloning of newt sex pheromone precursor cDNAs evidence for the existence of species-specific forms of pheromones. FEBS Lett 457, 400-404. 

Although proteinuria is often considered to be a pathological event, we demonstrated that this is not the case for the domestic cat. Male cat urine contains a large amount of the mammalian carboxylesterase family member termed cauxin. Cauxin is excreted in a species-, sex-, and age-dependent manner and regulates the production of felinine, a putative pheromone precursor. This finding provides an example of a previously unknown type of proteinuria involved in chemical communication. 

Miyazaki, M., Yamashita, T., Suzuki, Y., Soeta, S., Taira, H. and Suzuki, A. (2006b) A major urinary protein of the domestic cat regulates the production of felinine, a putative pheromone precursor. Chem. Biol. 13, 1071-1079. 

A unique semi synthetic pathway in which a genetically modified plant with the ability to produce moth sex pheromones precursors was used to synthesize sex pheromones of the cabbage moth. ... 

Schaffer, W.R., et al. Euzymalic Coupling of Cholesterol Intenuedialesto a Mating Pheromone Precursor and to the Ras Protein, Science, 1133 (September 7, 1990). Sikoiski, ZE. Chemical and Functional Properties of Food Proteins, CRC Press, LLC., Boca Raton, FL, 2001. 

The site of hydrocarbon pheromone production in the nitidulid beetles has been identified as very large, round abdominal cells, connected to the tracheal system by fine ducts (Dowd and Bartelt, 1993 Nardi et al., 1996). The secretory cells contain several lipid spheres (presumably pheromone and pheromone precursors), and are dramatically larger in beetles that are actively emitting pheromone (Nardi et al., 1996). Pheromone apparently diffuses from the cells,... 

Ivarsson P., Tittiger C., Blomquist C., Borgeson C. E., Seybold S. J., Blomquist G. J. and Hogberg H.-E. (1998) Pheromone precursor synthesis is localized in the metathorax of Ips paraconfusus Lanier (Coleoptera Scolytidae). Naturwissenschaften 85, 507-511. 

The CM of fatty acids and derived compounds also has been used for the production of fine chemicals that are difficult to obtain by other synthetic approaches. Some examples include the synthesis of a plant growth stimulant, an insect pheromone precursor, the sex pheromone of the peach twig borer moth, and others [28]. Furthermore, the conjugation of fatty acid derivatives, sugars, and amino acids via CM was shown by Vemall and Abell [41]. C4 with a catalyst loading of 20 mol% was used to perform the CM of either Ai-Boc-L-ly sine or N-Boc-L-cysteine bearing a 10-undecenoic chain with methyl 10-undecenoate or a sugar olefin. 

One of the most striking examples of specificity in the deposition of hydrocarbons occurs in several lepidopterans, in which shorter-chain pheromone or pheromone precursor... 

Further evidence that oenocytes are the cell type involved in hydrocarbon production was obtained by Wicker-Thomas et al. (unpublished data). The enzyme involved in the final step in hydrocarbon production, a cytochrome P450 that oxidatively decarbonylates aldehydes, was RNAi silenced specifically in oenocytes of both male and female D. melanogaster, resulting in marked inhibition of hydrocarbon production. The RNAi-silenced insects produced less than 10% of the hydrocarbon compared to control insects. Thus, the available evidence overwhelmingly supports oenocytes, whether associated with epidermal tissue or present in the peripheral fat body, as the site of cuticular hydrocarbon production. In some cases, even the shorter-chain hydrocarbon pheromones and pheromone precursors (see below) are produced in oenocytes. 

Schafer, W.R., et al. (1990). Enzymatic coupling of cholesterol intermediates to a mating pheromone precursor and to the ras protein. Science 249 1133-1139. 

Kim, H., Metzenberg, R.L., and Nelson, M.A. (2002). Multiple functions of mfa-1, a putative pheromone precursor gene of Neurospora crassa. Eukaryot Cell 1 987-999. 

Host plants play a key role in the production and use of sex pheromones by herbivorous insects through larval or adult sequestration of chemically active compounds and pheromone precursors [210]. One of the best examples of sequestration of plant chemicals by larvae and their subsequent use by adult males in sex attraction or courtship interactions is shown in Utetheisa ornatrix (Arctiidae), whose courtship pheromone derives from pyrrolizidine alkaloids (PAs) ingested at the larval stage from the host plant Crotalaria spectabilis [211]. U. omatrix larvae sequester PAs (e.g. monocrotaline) and retain the alkaloids through metamorphosis into the adult stage to provide egg protection for the next generation. 

Hydrogen transfer occurs in a highly diastereoselective fashion, giving nearly exclusively the cA-product, as shown in the hydrogenation of pheromone precursor l9-10. 

Thus the fact that living females produce a higher pheromone activity than can be calculated from the female release rates, suggests the involvement of pheromone potentiators or pheromone precursors in the biological response (Steinbrecht, 1964 Shorey and Gaston, 1965 1967). 

Cross-metathesis reactions are useful for the production of fine chemicals such as synthetic perfumes, prostaglandin intermediates, and insect pheromones. An example of the last is the cross-metathesis of ethyl oleate with 5-decene in the presence of a MoCl5/Si02/Me4Sn catalyst at 90 °C [14], or a Mo03/Si02/cyclopropane catalyst at 50 °C [16], resulting in a cisitrans mixture of ethyl 9-tetradecenoate, an insect pheromone precursor (Eq. 12). 

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