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Chemical Divergences in the Sex Pheromone Communication Systems in Moths

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Insect Sex Pheromone Research and Beyond

Part of the book series: Entomology Monographs ((ENTMON))

Abstract

Moth female sex pheromones have been classified into type I, type II, and miscellaneous, the former two of which are defined by the presence and absence of a terminal functional group, respectively. The classification of moth female sex pheromones is subject to refinement with the increase in our knowledge on the chemical structures of the pheromone molecules and biosynthetic pathways that underlie the formation of chemical structure. Recently, the addition of type 0 and type III to the classification has been proposed. Type-0 pheromones are short-chain secondary alcohols and their corresponding methyl ketones, which have been found from some primitive moths. Type-III pheromones are those containing one or more methyl branches in their carbon chain. In this chapter, we review the chemical structure and classification of moth female sex pheromones, and discuss scenarios for the evolution of different types of sex pheromones.

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References

  • Ando T, Yamamoto M (2019) Internet database: https://lepipheromone.sakura.ne.jp/pdb_top.html. Cited 15 Nov 2019

  • Ando T, Inomata S, Yamamoto M (2004) Lepidopteran sex pheromones. Top Curr Chem 239:51–96

    Article  CAS  PubMed  Google Scholar 

  • Butenandt A, Beckmann R, Stamm D, Hecker E (1959) Ãœber den Sexuallockstoff des Seidenspinners. Bombyx mori: Reindarstellung und Konstitution. Z Naturforsch 14:283–284

    Google Scholar 

  • Butenandt A, Beckmann R, Hecker E (1961a) Ãœber den Sexuallockstoff des Seidenspinners, I. Der biologische Test und die Isolierung des reinen Sexuallockstoffes Bombykol. Hoppe-Seyler Z Physiolog Chemie 324:71

    Article  CAS  Google Scholar 

  • Butenandt A, Beckmann R, Hecker E (1961b) Ãœber den Sexuallockstoff des Seidenspinners. II Konstitution und Konfiguration des Bombykols. Hoppe-Seyler Z Physiolog Chemie 324:84–87

    Article  CAS  Google Scholar 

  • Cabrera A, Eiras AE, Gries G, Gries R, Urdaneta N, Mirás B, Badji C, Jafee K (2001) Sex pheromone of tomato fruit borer, Neoleucinodes elegantalis. J Chem Ecol 27:2097–2107

    Article  CAS  PubMed  Google Scholar 

  • Charlton RE, Roelofs WL (1991) Biosynthesis of a volatile, methyl-branched hydrocarbon sex pheromone from leucine by arctiid moths (Holomelina spp.). Arch Insect Biochem 18:81–97

    Article  CAS  Google Scholar 

  • Chino H (1985) Lipid transport: biochemistry of hemolymph lipophorin. In: Kerkut GA, Gilbert LI (eds) Comprehensive insect physiology, biochemistry and pharmacology, vol 10. Pergamon Press, New York, pp 115–135

    Google Scholar 

  • Einhorn J, Lallemand J-Y, Zagatti P, Gallois M, Virelizier H, Riom J, Menassieu P (1982) Isolation and identification of the sex pheromone blend of Hyphantria cunea (Drury) (Lepidoptera, Arctiidae). C R Acad Sci Ser 2(294):41–44

    Google Scholar 

  • El-Sayed AM (2019) Pherobase: http://www.pherobase.com/. Cited 15 Nov 2019

  • El-Sayed AM, Gibb AR, Mitchell VJ, Manning LAM, Revell J, Thistleton B, Suckling DM (2013) Identification of the sex pheromone of Conogethes pluto: a pest of Alpinia. Chemoecology 23:93–101

    Article  CAS  Google Scholar 

  • Fabre JH (1913) The great peacock moth. In: Teale EW (ed) The Insect World of J. Henri Fabre, 1964. Dodd, Mead & Co., New York

    Google Scholar 

  • Foster SP (2016) Toward a quantitative paradigm for sex pheromone production in moths. In: Allison FD, Carde RT (eds) Pheromone communication in moths. University of California Press, Berkeley, pp 113–126

    Google Scholar 

  • Fujii T, Suzuki MG, Katsuma S, Ito K, Rong Y, Matsumoto S, Ando T, Ishikawa Y (2013) Discovery of a disused desaturase gene from the pheromone gland of the moth Ascotis selenaria, which secretes an epoxyalkenyl sex pheromone. Biochem Biophys Res Commun 441:849–855

    Article  CAS  PubMed  Google Scholar 

  • Fujii T, Yamamoto M, Nakano R, Nirazawa T, Rong Y, Dong S-L, Ishikawa Y (2015) Alkenyl sex pheromone analogs in the hemolymph of an arctiid Eilema japonica and several non-arctiid moths. J Insect Physiol 82:109–113

    Article  CAS  PubMed  Google Scholar 

  • Gibb AR, Pinese B, Tenakanai D, Kawi AP, Bunn B, Ramankutty P, Suckling DM (2007) (Z)-11-Hexadecenal and (3Z,6Z,9Z)-tricosatriene: sex pheromone components of the red banded mango caterpillar Deanolis sublimbalis. J Chem Ecol 33:579–589

    Article  CAS  PubMed  Google Scholar 

  • Grant GG, Frech D, MacDonald L, Slessor KN, King GGS (1987) Copulation releaser pheromone in body scales of female whitemarked tussock moth, Orgyia leucostigma (Lepidoptera: Lymantriidae): identification and behavioral role. J Chem Ecol 13:345–356

    Article  CAS  PubMed  Google Scholar 

  • Hall DR, Farman D, Dominguez JC, Pajares JA (2017) Female sex pheromone of the cone moth, Dioryctria mendacella: investigation of synergism between Type I and Type II pheromone components. J Chem Ecol 43:433–442

    Article  CAS  PubMed  Google Scholar 

  • Hill AS, Roelofs WL (1981) Sex pheromone of the saltmarsh caterpillar moth, Estigmene acrea. J Chem Ecol 7:655–668

    Article  CAS  PubMed  Google Scholar 

  • Hill AS, Kovalev BG, Nikolaeva LN, Roelofs RL (1982) Sex pheromone of the fall webworm moth, Hyphantria cunea. J Chem Ecol 8:383–396

    Article  CAS  PubMed  Google Scholar 

  • Honda H, Yamasaki R, Sumiuchi Y, Uehara T, Matsuyama S, Ando T, Naka H (2015) Hybrid sex pheromones of the hibiscus flower-bud borer, Rehimena surusalis. J Chem Ecol 41:1043–1049

    Article  CAS  PubMed  Google Scholar 

  • Ishiwata K, Sasaki G, Ogawa J, Miyata T, Su Z-H (2011) Phylogenetic relationships among insect orders based on three nuclear protein-coding gene sequences. Mol Phylogenet Evol 58:169–180

    Article  CAS  PubMed  Google Scholar 

  • Jurenka R (2004) Insect pheromone biosynthesis. Top Curr Chem 239:97–132

    Article  CAS  PubMed  Google Scholar 

  • Karlson P, Lüscher M (1959) ‘Pheromones’: a new term for a class of biologically active substances. Nature 183:55–56

    Article  CAS  PubMed  Google Scholar 

  • Kiyota R, Arakawa M, Yamakawa R, Yasmin A, Ando T (2011) Biosynthetic pathways of the sex pheromone components and substrate selectivity of the oxidation enzymes working in pheromone glands of the fall webworm, Hyphantria cunea. Insect Biochem Mol Biol 41:362–369

    Article  CAS  PubMed  Google Scholar 

  • Komai F (2011) Phylogeny above superfamilies and higher classification: history. In: Komai F, Yoshiyasu Y, Nasu Y, Saito T (eds) A guide to the Lepidoptera of Japan. Tokai University Press, Hiratsuka, pp 59–64. (in Japanese)

    Google Scholar 

  • Kozlov MV, Zhu J, Philipp P, Francke W, Zvereva EL, Hannson BS, Löfstedt C (1996) Pheromone specificity in Eriocrania semipurpurella (Stephens) and E. sangii (Wood) (Lepidoptera: Eriocraniidae) based on chirality of semiochemicals. J Chem Ecol 22:431–454

    Article  CAS  PubMed  Google Scholar 

  • Krishnakumari B, Prasuna AL, Jyothi KN, Valli MY, Sighamony S, Prasad AR, Yadav JS (1998) Behavioural and electrophysiological responses of Achaea janata Linn. (Lepidoptera: Noctuidae) males to synthetic female-produced sex pheromone components. J Entomol Res 22:197–202

    CAS  Google Scholar 

  • Kristensen NP, Scoble MJ, Karsholt O (2007) Lepidoptera phylogeny and systematics: the state of inventorying moth and butterfly diversity. Zootaxa 1668:699–747

    Article  Google Scholar 

  • Kuenen LPS, McElfresh JS, Millar JG (2010) Identification of critical secondary components of the sex pheromone of the navel orangeworm (Lepidoptera: Pyralidae). J Econ Entomol 103:314–330

    Article  CAS  PubMed  Google Scholar 

  • Leal WS, Parra-Pedrazzoli AL, Kaissling K-E, Morgan TI, Zalom FG, Pesak DJ, Dundulis EA, Burks CS, Higbee BS (2005) Unusual pheromone chemistry in the navel orangeworm: novel sex attractants and a behavioral antagonist. Naturwissenschaften 92:139–146

    Article  CAS  PubMed  Google Scholar 

  • Liu W, Rooney AP, Xue B, Roelofs WL (2004) Desaturases from the spotted fireworm moth (Choristoneura parallela) shed light on the evolutionary origins of novel moth sex pheromone desaturases. Gene 342:303–311

    Article  CAS  PubMed  Google Scholar 

  • Löfstedt C, Zhu J, Kozlov MV, Buda V, Jirle EV, Hellqvist S, Löfqvist J, Plass E, Franke S, Francke W (2004) Identification of the sex pheromone of the currant shoot borer Lampronia capitella. J Chem Ecol 30:643–658

    Article  PubMed  Google Scholar 

  • Löfstedt C, Bergmann J, Francke W, Jirle E, Hannson BS, Ivanov VD (2008) Identification of a sex pheromone produced by sternal glands in females of the caddisfly Molanna angustata Curtis. J Chem Ecol 34:220–228

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  • Löfstedt C, Svensson GP, Jirle EV, Rosenberg O, Roques A, Millar JG (2012) (3Z,6Z,9Z,12Z,15Z)-pentacosapentaene and (9Z,11E)-tetradecadienyl acetate: sex pheromone of the spruce coneworm Dioryctria abietella (Lepidoptera: Pyralidae). J Appl Entomol 136:70–78

    Article  CAS  Google Scholar 

  • Löfstedt C, Wahlberg N, Millar JG (2016) Evolutionary pattern of pheromone diversity in Lepidoptera. In: Allison FD, Carde RT (eds) Pheromone communication in moths. University of California Press, Berkeley, pp 43–78

    Google Scholar 

  • Melnitsky SI, Deev RV (2009) The fine structure of sternal pheromone glands in the two caddisfly species from the Rhyacophilidae and Limnephilidae families (Insecta: Trichoptera). Russ Entomol 18:107–116

    Google Scholar 

  • Millar JG (2000) Polyene hydrocarbons and epoxides: a second major class of lepidopteran sex attractant pheromones. Annu Rev Entomol 45:575–604

    Article  CAS  PubMed  Google Scholar 

  • Millar JG, Grant GG, McElfresh JS, Strong W, Rudolph C, Stein JD, Moreira JA (2005) (3Z,6Z,9Z,12Z,15Z)-Pentacosapentaene, a key pheromone component of the fir coneworm moth, Dioryctria abietivorella. J Chem Ecol 31:1229–1234

    Article  CAS  PubMed  Google Scholar 

  • Miller DR, Millar JG, Mangini A, Crowe CM, Grant GG (2010) (3Z,6Z,9Z,12Z,15Z)-Pentacosapentaene and (Z)-11-hexadecenyl acetate: sex attractant blend for Dioryctria amatella (Lepidoptera: Pyralidae). J Econ Entomol 103:1216–1221

    Article  CAS  PubMed  Google Scholar 

  • Molnár BP, Tröger A, Toshova TB, Subchev M, van Nieukerken EJ, (Sjaak) Koster JC, Szöcs G, Tóth M, Francke W (2012) Identification of the female-produced sex pheromone of Tischeria ekebladella, an oak leafmining moth. J Chem Ecol 38:1298–1305

    Article  PubMed  CAS  Google Scholar 

  • MozÅ«raitis R, Karalius V (2007) Identification of minor sex pheromone components of the poplar clearwing moth Paranthrene tabaniformis (Lepidoptera, Sesiidae). Zeit Naturforsch C 62:138–142

    Article  Google Scholar 

  • Naka H, Horie Y, Mochizuki F, Vang LV, Yamamoto M, Saito T, Watrai T, Tsuchida K, Arita Y, Ando T (2008) Identification of the sex pheromone secreted by Synanthedon hector (Lepidoptera: Sesiidae). Appl Entomol Zool 43:467–474

    Article  CAS  Google Scholar 

  • Nuss M, Landry B, Mally R, Vegliante F, Trankner A, Bauer F, Hayden J, Segerer A, Schouten R, Li H, Trofimova T, Solis MA, De Prins J, Speidel W (2018) Global Information System on Pyraloidea: www.pyraloidea.org. Cited 2 Nov 2018

  • Ozaki M, Wada-Katsumata A, Fujikawa K, Iwasaki M, Yokohari F, Satoji Y, Nisimura T, Yamaoka R (2005) Ant nestmate and non-nestmate discrimination by a chemosensory sensillum. Science 309:311–314

    Article  CAS  PubMed  Google Scholar 

  • Percy-Cunningham JE, MacDonald JA (1987) Biology and ultrastructure of sex pheromone-producing glands. In: Prestwich GD, Blomquist GJ (eds) Pheromone biochemistry. Academic, Orlando, FL, pp 27–75

    Google Scholar 

  • Persoons CJ, Vos JD, Yadav JS, Prasad AR, Sighomony S, Jyothi KN, Prasuna AL (1993) Indo-Dutch cooperation on pheromones of Indian agricultural pest insects: sex pheromone components of Diacrisia obliqua (Arctiidae), Achaea janata (Noctuidae) and Amsacta albistriga (Arctiidae). Bulletin Oilb Srop 16:136–140

    Google Scholar 

  • Regier JC, Mitter C, Zwick A, Bazinet AL, Cummings MP, Kawahara AY, Sohn J-C, Zwickl DJ, Cho S, Davis DR, Baixeras J, Brown J, Parr C, Weller S, Lees DC, Mitter K (2013) A large-scale, higher-level, molecular phylogenetic study of the insect order Lepidoptera (moths and butterflies). PLoS One 8:e58568

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Roelofs WL, Hill AS, Cardé RT, Baker TC (1974) Two sex pheromone components of tobacco budworm moth, Heliothis virescens. Life Sci 14:1555–1562

    Article  CAS  PubMed  Google Scholar 

  • Rong Y, Fujii T, Katsuma S, Yamamoto M, Ando T, Ishikawa Y (2014) CYP341B14: a cytochrome P450 involved in the specific epoxidation of pheromone precursors in the fall webworm Hyphantria cunea. Insect Biochem Mol Biol 54:122–128

    Article  CAS  PubMed  Google Scholar 

  • Rule GS, Roelofs RL (1989) Biosynthesis of sex pheromone components from linolenic acid in arctiid moths. Arch Insect Biochem 12:89–97

    Article  CAS  Google Scholar 

  • Schal C, Sevala V (1998) Novel and highly specific transport of a volatile sex pheromone by hemolymph lipophorin in moths. Naturwissenschaften 85:339–342

    Article  CAS  Google Scholar 

  • Silk PJ, Eveleigh E, Roscoe L, Burgess K, Weatherby S, Leclair G, Mayo P, Brophy M (2017) Unsaturated cuticular hydrocarbons enhance responses to sex pheromone in spruce budwork, Choristoneura fumiferana. J Chem Ecol 43:753–762

    Article  CAS  PubMed  Google Scholar 

  • Tóth M, Szöcs G, van Nieukerken EJ, Philipp P, Schmidt F, Francke W (1995) Novel type of sex pheromone structure identified from Stigmella malella (Stainton) (Lepidoptera: Nepticulidae). J Chem Ecol 21:13–27

    Article  PubMed  Google Scholar 

  • Tumlinson JH, Yonce CE, Doolittle RE, Heath RR, Gentry CR, Mitchell ER (1974) Sex pheromones and reproductive isolation of the lesser peachtree borer and the peachtree borer. Science 185:614–616

    Article  CAS  PubMed  Google Scholar 

  • Uehara T, Naka H, Matsuyama S, Ando T, Honda H (2015) Identification of the pheromone of the diurnal halk moth, Hemaris affinis. J Chem Ecol 41:9–14

    Article  CAS  PubMed  Google Scholar 

  • Vang LV, Yan Q, Nghia NYN, Khanh CNQ, Ando T (2018) Unsaturated cuticular hydrocarbon components of the sex pheromone of eggplant fruit borer, Leucinodes orbonalis Guenee (Lepidoptera: Crambidae). J Chem Ecol 44:631–636

    Article  PubMed  CAS  Google Scholar 

  • Wang H-L, Geertsema H, van Nieukerken EJ, Löfstedt C (2015) Identification of the female-produced sex pheromone of the leafminer Holocacista capensis infesting grapevine in South Africa. J Chem Ecol 41:724–731

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wei W, Miyamoto T, Endo M, Murakawa T, Pu GQ, Ando T (2003) Polyunsaturated hydrocarbons in the hemolymph: biosynthetic precursors of epoxy pheromones of geometrid and arctiid moths. Insect Biochem Mol Biol 33:397–405

    Article  CAS  PubMed  Google Scholar 

  • Xiao W, Honda H, Matsuyama S (2011) Monoenyl hydrocarbons in female body wax of the yellow peach moth as synergists of aldehyde pheromone components. Appl Entomol Zool 46:239–246

    Article  CAS  Google Scholar 

  • Xiao W, Matsuyama S, Ando T, Millar JG, Honda H (2012) Unsaturated cuticular hydrocarbons synergize responses to sex attractant pheromone in the yellow peach moth, Conogethes punctiferalis. J Chem Ecol 38:1143–1150

    Article  CAS  PubMed  Google Scholar 

  • Yan Q, Vang LV, Nguyen C, Khanh Q, Naka H, Ando T (2014) Reexamination of the female sex pheromone of the sweet potato vine borer moth: identification and field evaluation of a tricosatriene. J Chem Ecol 40:590–598

    Article  CAS  PubMed  Google Scholar 

  • Yan Q, Li H-D, Chen Y, Ye Z-F, You X-Y, Zhou J, Mu L-F, Liu S-J, Kong X-B, Khuhro SA, Dong S-L (2018) Identification and field evaluation of the sex pheromone of Orthaga achatina (Lepidoptera: Pyralidae). J Chem Ecol 44:886–893

    Article  CAS  PubMed  Google Scholar 

  • Yasui H, Akino T, Yasuda T, Fukaya M, Ono H, Wakamura S (2003) Ketone components in the contact sex pheromone of the white-spotted longicorn beetle, Anoplophora malasiaca, and pheromonal activity of synthetic ketones. Entomol Exp Appl 107:167–176

    Article  CAS  Google Scholar 

  • Zhu J, Kozlov MV, Philipp P, Francke W, Löfstedt C (1995) Identification of a novel moth sex pheromone in Eriocrania cicatricella (Zett.) (Lepidoptera: Eriocraniidae) and its phylogenetic implications. J Chem Ecol 21:29–43

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

We thank Emeritus Prof. Yukio Ishikawa of the University of Tokyo for providing us the opportunity to write this chapter. We also thank Drs. Mei Yamaguchi and Masayuki Goshima for supplying relevant information. We gratefully acknowledge the work of all collaborators, Drs. Tetsu Ando, Hiroshi Honda, Takeshi Sakurai, Shigehiro Namiki, Rong Yu, Yoichi Seki, and Mr. Takuya Nirazawa.

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Correspondence to Hideshi Naka .

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Naka, H., Fujii, T. (2020). Chemical Divergences in the Sex Pheromone Communication Systems in Moths. In: Ishikawa, Y. (eds) Insect Sex Pheromone Research and Beyond. Entomology Monographs. Springer, Singapore. https://doi.org/10.1007/978-981-15-3082-1_1

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