Abstract
While 11 species in the family Saturniidae are found in Japan, no sex pheromones of the native species had been investigated previously. We collected larvae of Rhodinia fugax in Nagano and Tottori Prefecture, and of Loepa sakaei in Okinawa Prefecture, and extracted sex pheromones of these two species from virgin female moths. In gas chromatography-electroantennogram detection (GC-EAD) analyses, male antennae of each species responded to one component in the respective pheromone extracts of conspecific females. Chemical analyses of the extracts by GC/mass spectrometry revealed that the EAD-active compounds of R. fugax and L. sakaei were a hexadecadienal and a tetradecadienyl acetate, respectively. The two species belong to the subfamily Saturniinae, and the mass spectra of both were similar to that of the 6,11-hexadecadienyl acetate identified from Antheraea polyphemus, classified in the same subfamily, suggesting the same 6,11-dienyl structure for the C16 aldehyde and a 4,9-dienyl structure for the C14 acetate. Based on this assumption, four geometrical isomers of each dienyl compound were stereoselectively synthesized via acetylene intermediates, compared to the natural products, and tested in the field. Male catches confirmed the pheromone structures of the two Japanese saturniid species as (6E,11Z)-6,11-hexadecadienal for R. fugax and (4E,9Z)-4,9-tetradecadienyl acetate for L. sakaei. The compounds have a characteristic 1,6-dienyl motif common to the pheromones of Saturniinae species.
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Ando T (2014) Internet database: http://www.tuat.ac.jp/~antetsu/LepiPheroList.htm
Ando T, Yamakawa R (2011) Analyses of lepidopteran sex pheromones by mass spectrometry. Trends Anal Chem 30:990–1002. doi:10.1016/j.trac.2011.03.010
Bestmann HJ, Attygalle AB, Brosche T, Erler J, Platz H, Schwarz J, Vostrowsky O, Wu CH, Kaissling KE, Chen TM (1987) Identification of three sex pheromone components of the female Saturniid moth Antheraea pernyi (Lepidoptera: Saturniidae). Z Naturforsch 42c:631–636
Bestmann HJ, Attygalle AB, Schwarz J, Garbe W, Vostrowsky O, Tomida I (1989) Identification and synthesis of female sex pheromone of eri-silkworm, Samia cynthia ricini (Lepidoptera: Saturniidae). Tetrahedron Lett 30:2911–2914. doi:10.1016/S0040-4039(00)99156-1
El-Sayed AM (2014) Internet database: http://www.pherobase.com/
Gago R, Allison JD, McElfresh JS, Haynes KF, McKenney J, Guerrero A, Millar JG (2013) A tetraene aldehyde as the major sex pheromone component of the promethea moth Callosamia promethea Drury. J Chem Ecol 39:1263–1272. doi:10.1007/s10886-013-0349-1
Jain SC, Dussourd DE, Conner WE, Eisner T, Guerrero A, Meinwald J (1983) Polyene pheromone components from an arctiid moth (Utetheisa ornatrix): Characterization and synthesis. J Org Chem 48:2266–2270. doi:10.1021/jo00161a024
Kochansky J, Tette J, Taschenberg EF, Cardé RT, Kaissling KE, Roelofs W (1975) Sex pheromone of the moth Antheraea polyphemus. J Insect Physiol 21:1977–1983. doi:10.1016/0022-1910(75)90230-9
McElfresh JS, Millar JG (2008) Sex pheromone of the saturniid moth, Hemileuca burnsi, from the western Mojave Desert of California. J Chem Ecol 34:1115–1124. doi:10.1007/s10886-008-9521-4
McElfresh JS, Millar JG, Rubinoff D (2001a) (E4, Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia. J Chem Ecol 27:791–806. doi:10.1023/A:1010310204552
McElfresh JS, Hammond AM, Millar JG (2001b) Sex pheromone components of the buck moth Hemileuca maia. J Chem Ecol 27:1409–1422. doi:10.1023/A:1010369326866
Millar JG, McElfresh JS, Romero C, Vila M, Mari-Mena N, Lopez-Vaamonde C (2010) Identification of the sex pheromone of a protected species, the Spanish moon moth Graellsia isabellae. J Chem Ecol 36:923–932. doi:10.1007/s10886-010-9831-1
Mitamura T (2003) Mating behavior and oviposition of wild silkmoth, Rhodinia fugax Butler (Lepidoptera: Saturniidae). Int J Wild Silkmoth Silk 8:73–80
Pattison FLM, Dear REA (1963) Toxic fluorine compounds xix. ω-Fluoroalkynes. Can J Chem 41:2600–2606. doi:10.1139/v63-380
R Development Core Team (2014) R: a language and environment for statistical computing. R Foundation for Statistical Computing, Vienna. http://www.R-project.org
Shibasaki H, Yamamoto M, Yan Q, Naka H, Suzuki T, Ando T (2013) Identification of the sex pheromone secreted by a nettle moth, Monema flavescens, using gas chromatography/Fourier transform infrared spectroscopy. J Chem Ecol 39:350–357. doi:10.1007/s10886-013-0253-8
Wang HL, Lienard MA, Zhao CH, Wang CZ, Löfstedt C (2010) Neofunctionalization in an ancestral insect desaturase lineage led to rare Δ6 pheromone signals in the Chinese tussah silkworm. Insect Biochem Mol Biol 40:742–751. doi:10.1016/j.ibmb.2010.07.009
Acknowledgments
We thank Drs. Z. Kajiura and S. Sato in the Faculty of Textile Science and Technology, Shinshu University for supplying Rhodinia fugax. The R. fugax eggs were provided from Shinshu University according to the National Bioresource Project (NBRP) of the Ministry of Education, Culture, Sports, Science, and Technology (Japan). We also thank Mr. M. Kimura for offering Loepa sakaei livestocks. We are grateful to Mrs. R. Kiyuna, T. Shida, S. Fujita and Ms. M. Kato in Department of Ecology and Environmental Sciences, Faculty of Agriculture, University of the Ryukyus for helping field trap experiments of Loepa sakaei. Dr. T. Mitamura, Mrs. T. Yano, Y. Machijima, and A. Tamura supplied important information. The members of Faculty of Agriculture at Tottori University, especially Mr. S. Kubota and Ms. K. Ohbayashi helped with field experiments and rearing moth larvae.
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Yan, Q., Kanegae, A., Miyachi, T. et al. Female Sex Pheromones of Two Japanese Saturniid Species, Rhodinia fugax and Loepa sakaei: Identification, Synthesis, and Field Evaluation. J Chem Ecol 41, 1–8 (2015). https://doi.org/10.1007/s10886-014-0538-6
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DOI: https://doi.org/10.1007/s10886-014-0538-6