Analysis pheromones

In the late 1950s, the first sexual attractant pheromone, bombykol, of the female silk moth Bomhyx, was chemically identified. The identification of bombykol was widely accepted as a model for the search for the atlractants of insect pest species and the BAG (electroantennogram) [23] was the simple biotest. Over the years, with rapidly improving methods for chemical analysis, pheromones of the major pest insects became... 

The insect pheromone lineatin (21) contains a four-membered ring it also contains an acetal and disconnection of this reveals the carbon skeleton (22). Lineatin analysis... 

The chemoreceptive mechanisms in amphibia are undoubtedly worthy of further analysis, not only for their own sake, but to provide clues as to the origination of advanced chemosignal systems. As noted above, a pheromonal signal from the mental gland acts as a courtship/ receptivity inducer. The plethodontid receptivity factor (PRF) (Chap. 3) despite its size (22 kD), seems to have been converted from its internal role as an inter-cellular cytokine, to an inter-individual coordinator of reproductive activity (Rollmann et al., 1999). Endocrine or... 

Feldhoff R.C., Rollman S.M. and Houck L.D. (1999). Chemical analysis of courtship pheromones in a Plethodontid Salamander. In Advances in Chemical Signals in Vertebrates (Johnston R.E., Miiller-Schwarze D. and Sorenson P., eds.). Kluwer, New York, pp. 117-126. 

Keil W. and von Stralendorff E (1990). A behavioral bioassay for analysis of rabbit nipple-search pheromone. Physiol Behav 47, 525-530. 

Robertson D., Benyon R.L. and Evershed R. (1993). Extraction, characterization and binding analysis of two pheromonally active ligands associated with major urinary proteins of house mouse (Mus musculus). J Chem Ecol 19, 1405-1416. 

The aggregation pheromone of the broad-horned flour beetle (Gnatocerus cornutus) was reported to be (lJR,4i, 5S)-(+)-acoradiene (33) by Tebayashi et al. [72]. Scheme 47 shows Mori s synthesis of (lRy4Ry5S)-33 [73]. The key-step was the ring-closing olefin metathesis of A to give B. An X-ray analysis of C confirmed the structure shown. The product (lJR,4JR,5S)-33, however, was different... 

The extract, which is prepared with pheromoneglands severed exclusively from abdomens, can be directly analyzed by GC-MSwithout any purification. El at 70 eV is widely used for this analysis, and are liable spectrum is recorded with a sample at least at a level of several ng. The gland of a large insect such as a Noctuidae species contains around 10-100 ng of the sex pheromone [21], and,... 

Fig. 9A,B GC-MS analysis of the pheromone extract of Anadevidia peponis (Noctuidae, 1 FE) treated with DMDS A TIC B mass chromatograms [141]. The mass chromatograms, which are multiplied by indicated factors, monitor the M+ of DMDS adducts derived from C10 to C16 monoenyl acetates (m/z 292,320,348, and 376) and some diagnostic fragment ions (m/z 89,117,145,173,175,203,231, and 259) to determine their double-bond position. Peaks I-VI indicate the DMDS adducts of the following components in the pheromone gland Z5-10 OAc (I),Z5-12 OAc (II),Z7-12 OAc (III), ll-12 OAc (IV),Z9-14 OAc (V), and Zll-16 OAc (VI)...

Fig. 10A-D Diagnostic fragment ions for the GC-MS analysis of Type II pheromones A Z6,29-dienes and Z3,Z6,Z9-trienes B monoepoxy derivatives of Z3,Z6-dienes C monoepoxy derivatives of Z3,Z6,Z9-trienes D diepoxy derivatives of Z3,Z6,Z9-trienes...

Currently, LC-MS is widely used for the analysis of polar compounds, such as medicinal metabolites and bioactive peptides, since the interface has been improved and several new ionization methods have been developed. The sensitivity and reproducibility are sufficient for a daily quantitative analysis. The usefulness of the LC-MS has been demonstrated for studies on Type II pheromones using a time-of-flight MS with electrospray ionization (ESI) [180]. Each epoxydiene derived from the (Z3,Z6,Z9)-triene shows three ion series of [M+NHJ+, [M+H]+, and [M-OH]+ with high resolution and good sensitivity, indicating its molecular formula. In addition to these, characteristic fragment... 

Flowers of some orchids mimic both the appearance and sex pheromone of virgin females of certain species of bees or wasps. This sexual deception results in pollination by male hymenoptera that would not normally visit flowers. Japanese honey bee drones (Apis cerana japonica) cluster on the oriental orchid (Cymbidiumpumilum) while on their mating flights [ 134]. By comparing volatile profiles of orchids and the female hymenoptera they mimic, or by GC-EAD and GC-MS analysis of orchid volatiles, several compounds have been identified that may mediate this attraction for the solitary bee Andrena nigroaenea [135, 136] and the scoliid wasp Campsoscolia ciliata [135]. 

MacKay, V. L., Li, X., Flory, M. R., Turcott, E., and Law, G. L. (2004). Gene expression analyzed by high-resolution state array analysis and quantitative proteomics Response of yeast to mating pheromone. Mol. Cell Proteomics 3, 478—489. 

Wittemyer, G., Douglas-Hamilton, I. and Getz, W.M. (2005) The socioecology of elephants analysis of the processes creating multitiered social structures. Anim. Behav. 69, 1357-1371. Wyatt, T.D. (2003) Pheromones and Animal Behaviour Communication by Smell and Taste. Cambridge University Press, Cambridge. 

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