Moths, arctiid

The sex attractant of the female arctiid moth contains among other components a com pound of molecular formula C21H40 that yields... 

Several families of moths utilize hydrocarbons or epoxides of hydrocarbons as their sex pheromone. Oenocyte cells produce hydrocarbons that are transported through the hemolymph by lipophorin [71]. In a study using arctiid moths it was shown that sex pheromone hydrocarbons are transported on the same lipophorin particle as the hydrocarbons destined for the cuticular surface [ 17]. Therefore, specific uptake of the sex pheromone hydrocarbon occurred in pheromone glands [17]. Similar findings have been found with other moths [72-74]. The mechanism behind this specific uptake of one hydrocarbon from a potential pool of other hydrocarbons is unknown. 

Some male arctiid moths produce their courtship pheromone from dietary pyrrolizidine alkaloids acquired during feeding by the larvae [ 126]. Conversion of monocrotaline to hydroxydanaidal by males is accomplished by aromatiza-tion, ester hydrolysis and oxidation of an alcohol to the aldehyde [7]. In the case of Utetheisa ornatirx the stereo-configuration at C7 of the dietary alkaloid is the same as the pheromone released (R). In contrast, another arctiid, Creatono-tos transiens, can convert a dietary precursor alkaloid with the (S) configuration at C7 (heliotrine) to (l )-hydroxydanaidal. The biosynthesis occurs by first oxidation-reduction at C7 to convert the stereochemistry and then proceeds through aromatization, hydrolysis, and oxidation [7]. 

FIGURE 1 Female arctiid moth in a wind tunnel. Pheromone emission as a visible stream of liquid droplets is shown. Photo by S. Krasnoff. 

A further finding concerns the stereochemistry of HD and its derivation from PA. Both HD and the primary PAs (monocrotaline, usaramine) that we know to be available to Utetheisa in the field are of the same (7R) stereochemical configuration. It was therefore not surprising to find that Utetheisa is unable to convert a PA of opposite (7S) stereochemistry (heliotrine) into HD. However, we found another arctiid moth, the Asian species Creatonotus transiens, which also produces HD in its coremata, to be able to use 7R and 7S PAs interchangeably for HD production (31). We are tempted to conclude that Creatonotus, unlike Utetheisa, has dietary access to PAs of both stereochemical configurations in its environment. 

Acharya, L. and Fenton, M. B. (1992). Echolocation behavior of vespertillionid bats (Lasiurus cinereus and Lasiurus borealis) attacking aerial targets including arctiid moths. Canadian Journal of Zoology IQ 1292-1298. 

Bell, T. W. and Meinwald, J. (1986). Pheromones of two arctiid moths (Creatonotos transiens and C. gangis) chiral components from both sexes and achiral female components. Journal of Chemical Ecology 12 385 109. 

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. 

Conner, W. E. (1987). Ultrasound its role in the courtship of the arctiid moth, Cycnia tenera. Experientia 43 1029-1031. 

Conner, W. E., Eisner T., Vander Meer, R. K., Guerrero, A. and Meinwald, J. (1981). Precopulatory sexual interactions in an arctiid moth (Utetheisa ornatrix) role of pheromone derived from alkaloids. Behavioral Ecology and Sociobiology 9 227-235. 

Conner, W. E. Roach, B., Benedict, E., Meinwald, J. and Eisner, T. (1990). Courtship pheromone production and body size as correlates of larval diet in males of the arctiid moth, Utetheisa ornatrix. Journal of Chemical Ecology 16 543-551. 

Dunning, D. C Acharya, L., Merriman, . B. and Ferro, L. D. (1992). Interactions between bats and arctiid moths. Canadian Journal of Zoology 70 2218-2223. 

Egalhaaf, A., Coelln, K., Schmitz, B Buck, M Wink, M. and Schneider, D. (1990). Organ specific storage of dietary pyrrolizidine alkaloids in the arctiid moth Creatonotus transiens. Zeitschrift fur Naturforschung 45c 172-177. 

Ehmke, A., Witte, L., Biller, A. and Hartmann, T. (1990). Sequestration, A-oxidation, and transformation of plant pyrrolizidine alkaloids by the arctiid moth Tyria jacobaeae... 

Fullard, J. H. and Heller, B. (1990). Functional organization of the arctiid moth tymbal (Insecta, Lepidoptera). Journal of Morphology 204 57-65. 

Iyengar, V. K. and Eisner, T. (1999a). Heritability of body mass, a sexually selected trait, in an arctiid moth (Utetheisa ornatrix). Proceedings of the National Academy of Sciences, USA 96 9169-9171. 

Krasnoff, S. B. and Dussourd, D. E. (1989). Dihydropyrrolizidine attractants for arctiid moths that visit plants containing pyrrolizidine alkaloids. Journal of Chemical Ecology 15 47-60. 

Evolutionary trends in the male pheromone systems of arctiid moths evidence from studies of courtship in Phragmatobia fuliginosa and Pyrrharctia isabella (Lepidoptera Arctiidae). Zoological Journal of the Linnaean Society 99 319-338. 

Krasnoff, S. B. and Yager, D. D. (1988). Acoustic response to a pheromonal cue in the arctiid moth Pyrrharctia isabella. Physiological Entomology 13 433 140. 

LaMunyon, C. W. (1997). Increased fecundity, as a function of mutiple mating, in an arctiid moth, Utetheisa ornatrix. Ecological Entomology 22 69-73. 

L Empereur, . M., Li, Y. and Stermitz, F. R. (1989). Pyrrolizidine alkaloids from Hackelia californica and Gnophaela latipennis, an H. califomica-hosted arctiid moth. Journal of Natural Products 52 360-366. 

Meyer, W. (1984). Sex pheromone chemistry and biology of some arctiid moths... 

Miller, L. (1991). Arctiid moth clicks can degrade the accuracy of range difference discrimination in echolocating big brown bats, Eptesicus fuscus. Journal of Comparative Physiology A 168 571-579. 

Alkaloid content of the pupal parasitoids of an alkaloid sequestering arctiid moth (Utetheisa ornatrix). Entomological News 111 287-290. 

Rothschild, M., Aplin, R. T., Cockrum, P. A., Edgar, J. A., Fairweather, P. and Lees, R. (1979). Pyrrolizidine alkaloids in arctiid moths (Lep.) with a discussion on host plant... 

Stoneman, M. G. and Fenton, M. B. (1988). Disrupting foraging bats the clicks of arctiid moth. In NATO ASI Series A, Life Sciences, vol. 156, Animal Sonar Processes and Performance, eds. P. E. Nachtigall and P. W. B. Moore, pp. 635-638. Brussels NATO. 

Tougaard, J., Casseday, J. H. and Covey, E. (1998). Arctiid moths and bat echolocation broad band clicks interfere with neural responses to auditory stimuli in the nuclei of the lateral lemniscus of the big brown bat. Journal of Comparative Physiology A 182 203-215. 

Willis, M. A. and Birch, M. C. (1982). Male lek formation and female calling in a population of the arctiid moth, Estigmene acrea. Science 218 168-170. 

Wink, M. L Schneider, D. and Witte, L. (1988). Biosynthesis of pyrrolizidine alkaloid-derived pheromones in the arctiid moth, Creatonotos transiens stereochemical conversion of heliotrine. Zeitschrift fiir Naturforschung 43c 737-741. 

Since HCCH2CH is one of the products of its ozonolysis, the sex attractant of the arctiid moth must contain the unit =CHCH2CH=. This unit must be bonded to an unbranched 12-carbon unit at one end and an unbranched 6-carbon unit at the other in order to give CH3(CH2)10CH=O and CH3(CH2)4CH=0 on ozonolysis. 

Sex attractant of arctiid moth (wavy lines show positions of cleavage on ozonolysis)... 

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