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Camphor and Borneol as the Male-Produced Sex Pheromone of the Shield Bug, Orsilochides leucoptera (Hemiptera: Scutelleridae)

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Abstract

The ability of stink bugs to release high amounts of strong-smelling and irritating defensive compounds is related to their metathoracic gland (MTG), which is an exocrine gland with defensive, sexual, alarm and aggregation signal functions. Orsilochides leucoptera (Scutelleridae) is a widespread species in the Neotropical region that feeds on plants of the families Malvaceae, Poaceae and Euphorbiaceae. A series of compounds (ketones, alcohols and esters) have been identified in the MTGs among the three species of Scutelleridae whose MTG secretions have been investigated thus far; however, no sex pheromone compounds have been described for any scutellerid species. The aim of this work was to study sex pheromone communication within this family of stink bugs, and identify the compounds present in the MTG of O. leucoptera. Analysis by gas chromatography/mass spectrometry (GC/MS) revealed two male specific compounds identified as (R)-camphor (1) and (R)-borneol (2), which were attractive to females in Y-tube olfactometer bioassays. Also, GC/MS analysis of secretions from MTG of males and females of O. leucoptera, identified eight additional compounds: 2-(E)-hexenal (3), (E)-4-oxo-2-hexenal (4), (E)-hex-2-enyl acetate (5), (R)-linalool (6), (R)-α-terpineol (7), dodecane (8), 1-tridecene (9) and n-tridecane (10). From these, (R)-α-terpineol was detected only in the gland of males, and is probably a biosynthetic intermediate of the pheromone components. Most of the MTG compounds identified in O. leucoptera have been identified in other heteropteran species. Camphor is often a toxic and repellent compound for insects. However, we report it, for the first time, as a sex pheromone component of an insect.

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References

  • Abad RFP, Azhari S, Djozan D, Hejazi MJ (2012) Compounds in abdominal and metathoracic scent glands of nymphs and adults of Graphosoma lineatum (Linnaeus, 1758) (Het., Scutelleridae) under laboratory conditions. Mun Ent Zool 7:870–880

    Google Scholar 

  • Acosta LG, Jahnke SM, Redaelli LR, Pires PRS (2017) Insect diversity in organic rice fields under two management systems of levees vegetation. Braz J Biol 77:731–744

    Article  CAS  Google Scholar 

  • Aldrich JR, Lusby R, Kochansky WP, Abrams JC (1984) Volatile compounds from the predatory insect Podisus maculiventris (Hemiptera: Pentatomidae): Male and female metathoracic scent gland and female dorsal abdominal gland secretions. J Chem Ecol 10:561–568

    Article  CAS  Google Scholar 

  • Aldrich JR (1988) Chemical ecology of the Heteroptera. Annu Rev Entomol 33:211–238

    Article  Google Scholar 

  • Aldrich JR, Leal WS, Nishida R, Khrimian AP, Lee CJ, Sakuratani Y (1997) Semiochemistry of aposematic seed bugs. Entomol Exp Appl 84:127–135

    Article  CAS  Google Scholar 

  • Aldrich JR, Oliver JE, Taghizadeh T, Ferreira JTB, Liewehr D (1999) Pheromones and colonization: Reassessment of the milkweed bug migration model (Heteroptera: Lygaeidae: Lygaeinae). Chemoecol 9:63–71

    Article  CAS  Google Scholar 

  • Aldrich JR, Zhang A, Oliver JE (2000) Attractant pheromone and allomone from the metathoracic scent gland of a broad-headed bug (Hemiptera: Alydidae). Can Entomol 132:915–923

    Article  Google Scholar 

  • Ambrogi BG, Zarbin PHG (2008) Aggregation pheromone in Sternechus subsignatus (Coleoptera: Curculionidae): olfactory behavior and temporal pattern of emission. J Appl Entomol 132:54–58

    Article  CAS  Google Scholar 

  • Arakaki N, Shimoji Y, Wakamura S (2009) Camphor: An attractant for the cupreous polished chafer, Protaetia pryeri pryeri (Janson) (Coleoptera: Scarabaeidae). Appl Entomol Zool 44:621–625

    Article  CAS  Google Scholar 

  • Banthorpe DV, Charlwood BV, Francis MJO (1972) The biosynthesis of monoterpenes. Chem Rev 72:115–155

    Article  CAS  Google Scholar 

  • Calam DH, Youdeowei A (1968) Identification and functions of secretion from the posterior scent gland of fifth instar larva of the bug Dysdercus intermedius. J Insect Physiol 14:1147–1158

    Article  CAS  Google Scholar 

  • Donkin RA (1999) Dragon’s Brain Perfume – An Historical Geography of Camphor. Brill, Leiden, p 307

    Google Scholar 

  • Durak D, Kalender Y (2007) Fine structure and chemical analysis of the metathoracic scent gland of Eurygaster maura (Linnaeus, 1758) (Heteroptera: Scutelleridae). Folia Biol 55:133–141

    Article  CAS  Google Scholar 

  • Eger JE, Barcellos A, Weiler L (2015) Shield bugs (Scutelleridae). In: Panizzi AR, Grazia J (eds) True bugs (Heteroptera) of the Neotropics. Springer-Dordrecht, pp 757–788

  • Fávaro CF, Rodrigues MACM, Aldrich JR, Zarbin PHG (2011) Identification of semiochemicals in sdults and symphs of the stink bug Pallantia macunaima Grazia (Hemiptera: Pentatomidae). J Braz Chem Soc 22:58–64

    Article  Google Scholar 

  • Fávaro CF, Santos TB, Zarbin PHG (2012) Defensive compounds and male-specific sex pheromone of the stink bug, Agroecus griseus. J Chem Ecol 38:1124–1132

    Article  Google Scholar 

  • Fávaro CF, Zarbin PHG (2013) Identification of (Z)-4- and 1-Tridecene in the metathoracic gland secretions of stink bugs employing the GC/FT-IR technique. J Chem Ecol 39:1182–1185

    Article  Google Scholar 

  • Feldlaufer MF, Domingue MJ, Chauhan KR, Aldrich JR (2010) 4-oxo-Aldehydes from the dorsal abdominal glands of the bed bug (Hemiptera: Cimicidae). J Med Entomol 47:140–143

    CAS  PubMed  Google Scholar 

  • Hassani H, Abad RFP, Djozan D, Fazel MM (2010) Compounds in metathoracic glands of adults of the sunn pest, Eurygaster integriceps (Puton) (Heteroptera: Scutelleridae). Mun. Ent Zool 5:232–239

    Google Scholar 

  • Inoue KM, Vidal DM, Saad EB, Martins CBC, Zarbin PHG (2019) Identification of the alarm and sex pheromones of the leaf-footed bug, Leptoglossus zonatus (Heteroptera: Coreidae). J Braz Chem Soc 30:939–947

    CAS  Google Scholar 

  • Javahery MCW, Schaefer JDL (2000) Shield bugs (Scutelleridae). In: Schaefer CW, Panizzi AR (eds) Heteroptera of Economic Importance. CRC, Boca Raton, pp 475–503

    Google Scholar 

  • Leal WS, Higughi H, Mizutani N, Nakamori H, Kadosawa T, Ono M (1995) Multifunctional communication in Riptortus clavatus (Heteroptera: Alydidae): Conspecific nymphs and egg parasitoid Ooencyrtus nezarae use the same adult attractant pheromone as chemical cue. J Chem Ecol 21:973–985

    Article  CAS  Google Scholar 

  • Leal WS, Ueda Y, Ono M (1996) Attractant pheromone for male rice bug, Leptocorisa chinensis: Semiochemicals produced by both male and female. J Chem Ecol 22:1429–1437

    Article  CAS  Google Scholar 

  • Leal WS, Zarbin PHG, Wojtasek H, Ferreira JT (1999) Biosynthesis of scarab beetle pheromones – Enantioselective 8-hydroxylation of fatty acids. Eur J Biochem 259:175–180

    Article  CAS  Google Scholar 

  • Martins CBC, Zarbin PHG (2013) Volatile organic compounds of conspecific-damaged Eucalyptus benthamii influence responses of mated females of Thaumastocoris peregrinus. J Chem Ecol 39:602–611

    Article  CAS  Google Scholar 

  • Millar JG, Rice RE, Wang Q (1997) Sex pheromone of the mirid bug Phytocoris relativus. J Chem Ecol 23:1743–1754

    Article  CAS  Google Scholar 

  • Millar JG, McBrien HL, Ho HY, Rice RE, Cullen E, Zalom FG, Uokl A (2002) Pentatomid bug pheromones in IPM: possible applications and limitations. IOBC Bull 25:1–11

    Google Scholar 

  • Millar JG (2005) Pheromones of true bugs. Top Curr Chem 240:37–84

    Article  CAS  Google Scholar 

  • Moraes MCB, Pareja M, Laumann RA, Borges M (2008) The chemical volatiles (Semiochemicals) produced by neotropical stink bugs (Hemiptera: Pentatomidae). Neotrop Entomol 37:489–505

    Article  CAS  Google Scholar 

  • Nasipuri D, Samaddar AK, Gupta MD (1993) Asymmetric reduction of carbonyl compounds with chiral alkoxyaluminium and alkoxymagnesium halides: an overview. Proc. Indian Acad. Sci. 93(4):601–614

  • Pattenden G, Staddon BW (1970) Observations of the metasternal scent glands of Lethocerus spp. (Hem: Het: Belostomatidae) Ann Entomol Soc Amer 63:900–901

    Article  Google Scholar 

  • Prudic KL, Noge K, Becerra JX (2008) Adults and nymphs do not smell the same: The different defensive compounds of the giant mesquite bug (Thasus neocalifornicus: Coreidae). J Chem Ecol 34:734–741

    Article  CAS  Google Scholar 

  • Smith RF, Pierce JR, Borden HD JH (1991) Sex pheromone of the mullein bug, Campylomma verbasci (Meyer) (Heteroptera: Miridae). J Chem Ecol 17:1437–1447

  • Staddon BW (1979) The scent glands of Heteroptera. Adv Insect Physiol 14:351–418

    Article  CAS  Google Scholar 

  • Soldi RA, Rodrigues MACD, Aldrich JR, Zarbin PHG (2012) The sex pheromone of the true bug Phthia picta (Heteroptera: Coreidae) is an unusual hydrocarbon. J Chem Ecol 38:814–824

    Article  CAS  Google Scholar 

  • Vandendool H, Kratz PD (1963) A generalization of retention index system including linear temperature programmed gas-liquid partition chromatography. J Chromatogr A 11:463–471

    Article  CAS  Google Scholar 

  • Watanabe K, Shimizu N (2017) Identification of a sex pheromone of the chrysanthemum lace bug Corythucha marmorata (Hemiptera: Tingidae). Sci Rep 7:7302

    Article  Google Scholar 

  • Zarbin PHG, Ferreira JTB, Leal WS (1999) Metodologias gerais empregadas no isolamento e identificação estrutural de feromônios de insetos. Quím Nova 22:263–268

    Article  CAS  Google Scholar 

  • Zarbin PHG, Borges M, Santos AA, Oliveira ARM, Simonelli F, Marques FA (2000) Alarm Pheromone system of stink bug Piezodorus guildinii (Heteroptera: Pentatomidae). J Braz Chem Soc 11:424–428

    Article  CAS  Google Scholar 

  • Zhang QH, Aldrich JR (2003) Pheromones of milkweed bugs (Heteroptera: Lygaeidae) attract wayward plant bugs: Phytocoris mirid sex pheromone. J Chem Ecol 29:1835–1851

    Article  CAS  Google Scholar 

  • Zhang QH, Aldrich JR (2008) Sex pheromone of the plant bug. Phytocoris calli Knight J Chem Ecol 34:719–724

Download references

Acknowledgements

Financial support from Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Instituto Nacional de Ciência e Tecnologia (INCT) de Semioquímicos na Agricultura.

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  1. Departamento de Química, Universidade Federal do Paraná, Caixa Postal 19081, Curitiba, PR, 81531-990, Brazil

    Douglas José de Melo, Maycon Roberto da Silva, Antonioni Acácio Campos Moliterno & Paulo Henrique Gorgatti Zarbin

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  1. Douglas José de Melo
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  2. Maycon Roberto da Silva
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  3. Antonioni Acácio Campos Moliterno
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  4. Paulo Henrique Gorgatti Zarbin
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Correspondence to Paulo Henrique Gorgatti Zarbin.

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de Melo, D.J., da Silva, M.R., Moliterno, A.A.C. et al. Camphor and Borneol as the Male-Produced Sex Pheromone of the Shield Bug, Orsilochides leucoptera (Hemiptera: Scutelleridae). J Chem Ecol 46, 490–496 (2020). https://doi.org/10.1007/s10886-020-01189-z

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