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

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• 作者：Qi Yan (1)
  Akiko Kanegae (1)
  Takashi Miyachi (1)
  Hideshi Naka (2)
  Haruki Tatsuta (3)
  Tetsu Ando (1)
  
  1. Graduate School of Bio-Applications and Systems Engineering ; Tokyo University of Agriculture and Technology ; Koganei ; Tokyo ; 184-8588 ; Japan
  2. Laboratory of Applied Entomology ; Faculty of Agriculture ; Tottori University ; 4-101 Koyama-minami ; Tottori ; 680-8553 ; Japan
  3. Department of Subtropical Agro-Environmental Sciences ; Faculty of Agriculture ; University of the Ryukyus ; Nishihara-cho ; Nakagami-gun ; Okinawa ; 903-0213 ; Japan
  
• 关键词：Female sex pheromone ; Structure determination ; E6 ; Z11 ; 16 ; Ald ; E4 ; Z9 ; 14 ; OAc ; Pellucid silk moth ; Male attractant
• 刊名：Journal of Chemical Ecology
• 出版年：2015
• 出版时间：January 2015
• 年：2015
• 卷：41
• 期：1
• 页码：1-8
• 全文大小：544 KB
• 参考文献：1. Ando T (2014) Internet database: http://www.tuat.ac.jp/~antetsu/LepiPheroList.htm
  2. Ando T, Yamakawa R (2011) Analyses of lepidopteran sex pheromones by mass spectrometry. Trends Anal Chem 30:990鈥?002. doi:10.1016/j.trac.2011.03.010 CrossRef
  3. 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鈥?36
  4. 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鈥?914. doi:10.1016/S0040-4039(00)99156-1 56-1" target="_blank" title="It opens in new window">CrossRef
  5. El-Sayed AM (2014) Internet database: http://www.pherobase.com/
  6. 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鈥?272. doi:10.1007/s10886-013-0349-1 CrossRef
  7. 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鈥?270. doi:10.1021/jo00161a024 CrossRef
  8. Kochansky J, Tette J, Taschenberg EF, Card茅 RT, Kaissling KE, Roelofs W (1975) Sex pheromone of the moth / Antheraea polyphemus. J Insect Physiol 21:1977鈥?983. doi:10.1016/0022-1910(75)90230-9 5)90230-9" target="_blank" title="It opens in new window">CrossRef
  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鈥?124. doi:10.1007/s10886-008-9521-4 521-4" target="_blank" title="It opens in new window">CrossRef
  10. 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鈥?06. doi:10.1023/A:1010310204552 552" target="_blank" title="It opens in new window">CrossRef
  11. McElfresh JS, Hammond AM, Millar JG (2001b) Sex pheromone components of the buck moth / Hemileuca maia. J Chem Ecol 27:1409鈥?422. doi:10.1023/A:1010369326866 CrossRef
  12. 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鈥?32. doi:10.1007/s10886-010-9831-1 CrossRef
  13. Mitamura T (2003) Mating behavior and oviposition of wild silkmoth, / Rhodinia fugax Butler (Lepidoptera: Saturniidae). Int J Wild Silkmoth Silk 8:73鈥?0
  14. Pattison FLM, Dear REA (1963) Toxic fluorine compounds xix. 蠅-Fluoroalkynes. Can J Chem 41:2600鈥?606. doi:10.1139/v63-380 CrossRef
  15. R Development Core Team (2014) R: a language and environment for statistical computing. R Foundation for Statistical Computing, Vienna. http://www.R-project.org
  16. 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鈥?57. doi:10.1007/s10886-013-0253-8 53-8" target="_blank" title="It opens in new window">CrossRef
  17. Wang HL, Lienard MA, Zhao CH, Wang CZ, L枚fstedt C (2010) Neofunctionalization in an ancestral insect desaturase lineage led to rare 螖⁶ pheromone signals in the Chinese tussah silkworm. Insect Biochem Mol Biol 40:742鈥?51. doi:10.1016/j.ibmb.2010.07.009 CrossRef
  
• 刊物主题：Ecology; Biochemistry, general; Entomology; Biological Microscopy; Agriculture;
• 出版者：Springer US
• ISSN：1573-1561

文摘

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.