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Female Sex Pheromones of Two Japanese Saturniid Species, Rhodinia fugax and Loepa sakaei: Identification, Synthesis, and Field Evaluation

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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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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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Correspondence to Tetsu Ando.

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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

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