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Cuticular Hydrocarbons and Pheromones of Arthropods

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Hydrocarbons, Oils and Lipids: Diversity, Origin, Chemistry and Fate

Abstract

Cuticular hydrocarbons and pheromones of insects are often derived from fatty acids and terpenoid lipid components. This chapter describes the chemistry and biochemistry of insect hydrocarbons and pheromones and emphasizes recent work. Cuticular hydrocarbons consist of complex mixtures of straight chain, unsaturated, and methyl-branched components with 21 to 40+ carbon atoms. They function both to restrict water loss to prevent a lethal rate of desiccation and serve in chemical communication in many species. The major volatile insect pheromones consist of modified fatty acids and terpenoids. Many of the lepidopteran pheromones arise from fatty acid precursors, are modified with desaturases, and undergo limited chain shortening or elongation followed by modification of the carboxyl group to produce acetate esters, aldehydes, alcohols, and hydrocarbons. Many coleopteran pheromones are terpenoids, while still other insects use a variety of other compounds. The volatile, long range pheromones produced by insects are often produced in specific glands, and pheromone glands on the abdomen of many lepidopterans produce 10–21 carbon atom pheromone components. In some coleopterans, midgut tissue produces terpenoid pheromones. Recent work on hydrocarbon and pheromone production is taking advantage of the tools of molecular biology to better understand hydrocarbon and pheromone biosynthesis, and this information is summarized.

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References

  • Ando T, Hase T, Arima R, Uchiyama M (1988) Biosynthetic pathway of bombykol, the sex pheromone of the female silkworm moth. Agric Biol Chem 52:473–478

    CAS  Google Scholar 

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

    CAS  PubMed  Google Scholar 

  • Antony B, Fujii T, Moto K, Matsumoto S, Fukuzawa M, Nakano R, Tatsuki S, Ishikawa Y (2009) Pheromone-gland-specific fatty-acyl reductase in the adzuki bean borer, Ostrinia scapulalis (Lepidoptera: Crambidae). Insect Biochem Mol Biol 39:90–95

    CAS  PubMed  Google Scholar 

  • Antony B, Soffan A, Jakše J, Alfaifi S, Sutanto KD, Aldosari SA, Aldawood AS, Pain A (2015) Genes involved in sex pheromone biosynthesis of Ephestia cautella, an important food storage pest, are determined by transcriptome sequencing. BMC Genomics 16:532

    PubMed  PubMed Central  Google Scholar 

  • Arsequell G, Fabriàs G, Camps F (1990) Sex pheromone biosynthesis in the processionary moth Thaumetopoea pityocampa by delta-13 desaturation. Arch Insect Biochem Physiol 14:47–56

    CAS  PubMed  Google Scholar 

  • Aw T, Schlauch K, Keeling CI, Young S, Bearfield JC, Blomquist GJ, Tittiger C (2010) Functional genomics of the mountain pine beetle (Dendrotonus ponderosae) midguts and fat bodies. BMC Genomics 11:215

    PubMed  PubMed Central  Google Scholar 

  • Baker GL, Vroman HE, Padmore J (1963) Hydrocarbons of the American cockroach. Biochem Biophys Res Commun 13:360–365

    CAS  Google Scholar 

  • Balabanidou EA, Kampouraki MacLean M, Blomquist GJ, Tittiger C, Juarez MP, Mijailovsky SJ, Chalepakis G, Anthousi A, Lynd A, Antoine S, Memingway J, Ranson H, Lycett G, Vontas J (2016) Cytochromes P450 associated with insecticide resistance catalyze cuticular hydrocarbon production in Anopheles gambiae. Proc Natl Acad Sci U S A 113:9268–9273

    CAS  PubMed  PubMed Central  Google Scholar 

  • Barbier J, Lederer E (1960) Structure chémique de la substance royale de la reine d’abeille (Apis mellifica L.). C R Acad Sci Paris 251:1131–1135

    Google Scholar 

  • Barkawi LS, Francke W, Blomquist GJ, Seybold SJ (2003) Frontalin: de novo synthesis of an aggregation pheromone component by Dendroctonus spp. bark beetles (Coleoptera: Scolytidae). Insect Biochem Mol Biol 33:773–788

    CAS  PubMed  Google Scholar 

  • Bartelt RJ (1999) Sap beetles. In: Hardie J, Minks AK (eds) Pheromones of non-lepidopteran insects associated with agricultural plants. CAB International, Wallingford, pp 69–89

    Google Scholar 

  • Bartelt RJ (2010) Volatile hydrocarbon pheromones from beetles. In: Blomquist GJ, Bagneres A-G (eds) Insect hydrocarbons biology, biochemistry and chemical ecology. Cambridge University Press, Cambridge, pp 448–476

    Google Scholar 

  • Bartelt RJ, Weisleder D, Dowd PF, Plattner RD (1992) Male-specific tetraene and triene hydrocarbons of Carpophilus hemipterus: structure and pheromonal activity. J Chem Ecol 18:379–402

    CAS  PubMed  Google Scholar 

  • Beale MH, Birkett MA, Bruce TJA, Chamberlain K, Field LM, Huttly AK, Martin JL, Parker R, Phillips AL, Pickett JA (2006) Aphid alarm pheromone produced by transgenic plants affects aphid and parasitoid behavior. Proc Natl Acad Sci USA 103:10509–10513

    CAS  PubMed  Google Scholar 

  • Bello JE, McElfresh S, Millar JG (2015) Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons. Proc Natl Acad Sci USA 112:1077–1082

    CAS  PubMed  Google Scholar 

  • Berger RS (1966) Isolation, identification, and synthesis of the sex attractant of the cabbage looper, Trichoplusia ni. Ann Entomol Soc Am 59:767–771

    CAS  Google Scholar 

  • Bestmann HJ, Herrig M, Attygalle AB (1987) Terminal acetylation in pheromone biosynthesis by Mamestra brassicae L. (Lepidoptera: Noctuidae). Experientia 43:1033–1034

    CAS  Google Scholar 

  • Billen J, Morgan ED (1998) Pheromone communication in social insects: sources and secretions. In: Vander Meer RK, Breed MD, Winston ML, Espelie KE (eds) Pheromone communication in social insects. Westview Press, Boulder, pp 3–33

    Google Scholar 

  • Birgersson G, Byers JA, Bergstrom G, Lofqvist J (1990) Production of pheromone components, chalcogran and methyl (E,Z)-2,4-decadienoate, in the spruce engraver Pityogenes chalcographus. J Insect Physiol 36:391–395

    CAS  Google Scholar 

  • Bjostad LB, Roelofs WL (1983) Sex pheromone biosynthesis in Trichoplusia ni: key steps involve delta-11 desaturation and chain-shortening. Science 220:1387–1389

    CAS  PubMed  Google Scholar 

  • Bjostad LB, Roelofs WL (1984) Biosynthesis of sex pheromone components and glycerolipid precursors from sodium [1-14C]acetate in redbanded leafroller moth. J Chem Ecol 10:681–691

    CAS  PubMed  Google Scholar 

  • Bjostad LB, Wolf WA, Roelofs WL (1987) Pheromone biosynthesis in lepidopterans: desaturation and chain shortening. In: Prestwich GD, Blomquist GJ (eds) Pheromone biochemistry. Academic Press, New York, pp 77–120

    Google Scholar 

  • Blailock TT, Blomquist GJ, Jackson LL (1976) Biosynthesis of 2-methylalkanes in the cricket Nemobius fasciatus and Gryllus pennsylvanicus. Biochem Biophys Res Commun 68:841–849

    CAS  PubMed  Google Scholar 

  • Blomquist GJ (2003) Biosynthesis and ecdysteroid regulation of housefly sex pheromone production. In: Blomquist GJ, Vogt RG (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 131–252

    Google Scholar 

  • Blomquist GJ (2010) Structure and analysis of insect hydrocarbons. In: Blomquist GJ, Bagnères A-G (eds) Insect hydrocarbons: biology biochemistry and chemical ecology. Cambridge University Press, Cambridge, pp 19–34

    Google Scholar 

  • Blomquist GJ, Bagnères A-G (2010) Insect hydrocarbons: biology, biochemistry, and chemical ecology. Cambridge University Press, Cambridge

    Google Scholar 

  • Blomquist GJ, Howard RW (2003) Pheromone biosynthesis in social insects. In: Blomquist GJ, Vogt RG (eds) Insect pheromone biochemistry and molecular biology. Elsevier, New York, pp 323–340

    Google Scholar 

  • Blomquist GJ, Kearney GP (1976) Biosynthesis of the internally branched monomethylalkanes in the cockroach Periplaneta fulliginosa. Arch Biochem Biophys 173:546–553

    CAS  PubMed  Google Scholar 

  • Blomquist GJ, Major MA, Lok JB (1975) Biosynthesis of 3-methylpentacosane in the cockroach Periplaneta americana. Biochem Biophys Res Commun 64:43–50

    CAS  PubMed  Google Scholar 

  • Blomquist GJ, Howard RW, McDaniel CA, Remaley S, Dwyer LA, Nelson DR (1980) Application of methoxymercuration-demercuration followed by mass spectrometry as a convenient microanalytical technique for double-bond location in insect-derived alkenes. J Chem Ecol 6:257–269

    CAS  Google Scholar 

  • Blomquist GJ, Guo L, Gu P, Blomquist C, Reitz RC, Reed JR (1994) Methyl-branched fatty acids and their biosynthesis in the housefly, Musca domestica L. (Diptera: Muscidae). Insect Biochem Mol Biol 24:803–810

    CAS  Google Scholar 

  • Blomquist GJ, Figueroa-Teran R, Aw M, Song M, Gorzalski A, Abbot A, Chang E, Tittiger C (2010) Pheromone production in bark beetles. Insect Biochem Mol Biol 40:699–712

    CAS  PubMed  Google Scholar 

  • Blount BK, Chibnall AC, Mangouri EI (1937) The wax of the white pine chermes. Biochem J 31:1375–1378

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bordon JH (1985) Aggregation pheromones. In: Kerkut GA, Gilbert LI (eds) Comprehensive insect physiology, biochemistry, and pharmacology, vol 9. Pergamon Press, Oxford, pp 257–285

    Google Scholar 

  • Braga MV, Pinto ZT, de Carvatho Queiroz MM, Matsumoto N, Blomquist GJ (2013) Cuticular hydrocarbons as a tool for the identification of insect species: puparial cases from Sarcophagidae. Acta Trop 128:479–485

    CAS  PubMed  Google Scholar 

  • Buček A, Matoušková P, Vogel H, Šebesta P, Jahn U, Weissflog J, Svatos A, Pichová I (2015) Evolution of moth sex pheromone composition by a single amino acid substitution in a fatty acid desaturase. Proc Natl Acad Sci USA 112:12586–12591

    PubMed  Google Scholar 

  • Buckner JS (2010) Oxygenated derivatives of hydrocarbons. In: Blomquist GJ, Bagnères A-G (eds) Insect hydrocarbons: biology, biochemistry, and chemical ecology. Cambridge University Press, Cambridge, pp 187–203

    Google Scholar 

  • Butenandt A, Beckmann R, Stamm D, Hecker E (1959) U¨berdem sexual-lockstoff des seidenspinners Bombyx mori: Reindarstellung und konstitution. Z Naturforsch A 14:283–284

    Google Scholar 

  • Callow RK, Johnston NC (1960) The chemical constitution and synthesis of queen substance of honeybees (Apis mellifera L.). Bee World 41:152–153

    CAS  Google Scholar 

  • Carlson DA, Nelson DR, Langley PA, Coates TW, Leegwater-Vander Linden ME (1984) Contact sex pheromone in the tsetse fly Glossina pallidipes (Austen): identification and synthesis. J Chem Ecol 10:429–450

    CAS  PubMed  Google Scholar 

  • Carlson DA, Roan C-S, Yost RA (1989) Dimethyl disulfide derivatives of long chain alkenes, alkadienes, and alkatrienes for gas chromatography/mass spectrometry. Anal Chem 61:1564–1571

    CAS  Google Scholar 

  • Carlson DA, Offor II, El Messoussi S, Matsyyama K, Mori K, Jallon JM (1998) Sex pheromone of Glossinatachioides: isolation, identification and synthesis. J Chem Ecol 24:1563–1575

    CAS  Google Scholar 

  • Carot-Sans G, Muñoz L, Piulachs MD, Guerrero A, Rosell G (2015) Identification and characterization of a fatty acyl reductase from a Spodoptera littoralis female gland involved in pheromone biosynthesis. Insect Mol Biol 24:82–92

    CAS  PubMed  Google Scholar 

  • Chase J, Jurenka RA, Schal C, Halarnkar PP, Blomquist GJ (1990) Biosynthesis of methyl branched hydrocarbons in the German cockroach Blattella germanica (L.) (Orthoptera, Blattellidae). Insect Mol Biol 20:149–156

    CAS  Google Scholar 

  • Chertemps T, Duportets L, Labeur C, Udeda R, Takahashi K, Saigo K, Wicker-Thomas C (2007) A female-biased expressed elongase involved in long-chain hydrocarbon biosynthesis and courtship behavior in Drosophila melanogaster. Proc Natl Acad Sci USA 104:4273–4278

    CAS  PubMed  Google Scholar 

  • Chibnall AC, Piper SH, Pollard A, Willimas EF, Sahai PN (1934) The constitution of the primary alcohols, fatty acids and paraffins present in plant and insect waxes. Biochem J 28:2189–2208

    CAS  PubMed  PubMed Central  Google Scholar 

  • Choi M-Y, Lim H, Park K-C, Adlof R, Wang S, Zhang A, Jurenka R (2007) Identification and biosynthetic studies of the hydrocarbon sex pheromone in Utetheisa ornatrix (Lepidoptera: Arctiidae). J Chem Ecol 33:1336–1345

    CAS  PubMed  Google Scholar 

  • Chung H, Loehlin DW, Dufour HD, Vaccarro K, Millar JG, Carroll SB (2014) A single gene affects both ecological divergence and mate choice in Drosophila. Science 343:148–151

    Google Scholar 

  • Dallerac R, Labeur C, Jallon J-M, Knipple DC, Roelofs WL, Wicker-Thomas C (2000) A 9 desaturase gene with a different substrate specificity is responsible for the cuticular diene hydrocarbon polymorphism in Drosophila melanogaster. Proc Natl Acad Sci USA 97:9449–9454

    CAS  PubMed  Google Scholar 

  • Dillwith JW, Nelson JH, Pomonis JG, Nelson DR, Blomquist GJ (1982) A 13C NMR study of methyl-branched hydrocarbon biosynthesis in the housefly. J Biol Chem 257:11305–11314

    CAS  PubMed  Google Scholar 

  • Ding B-J, Löfstedt C (2015) Analysis of the agrotis segetum pheromone gland transcriptome in the light of sex pheromone biosynthesis. BMC Genomics 16:711

    PubMed  PubMed Central  Google Scholar 

  • Ding B-J, Liénard MA, Wang H-L, Zhao C-H, Löfstedt C (2011) Terminal fatty-acyl-CoA desaturase involved in sex pheromone biosynthesis in the winter moth (Operophtera brumata). Insect Biochem Mol Biol 41:715–722

    CAS  PubMed  Google Scholar 

  • Ding B-J, Hofvander P, Wang H-L, Durrett TP, Stymne S, Löfstedt C (2014) A plant factory for moth pheromone production. Nature Comm 5:3353

    Google Scholar 

  • Drijfhout FK (2010) Cuticular hydrocarbons: a new tool in forensic entomology? In: Amendt J, Lee Goff M, Campobasso CP, Grassberger M (eds) Current concepts in forensic entomology. Springer, New York, pp 179–203

    Google Scholar 

  • Dwyer LA, Blomquist GJ, Nelson JH, Pomonis JG (1981) A 13C-NMR study of the biosynthesis of 3-methylpentacosane in the American cockroach. Biochim Biophys Acta 663:536–544

    CAS  PubMed  Google Scholar 

  • Eliyahu D, Applebaum S, Rafaeli A (2003) Moth sex-pheromone biosynthesis is inhibited by the herbicide diclofop. Pestic Biochem Physiol 77:75–81

    CAS  Google Scholar 

  • Fang N, Teal PEA, Doolittle RE, Tumlinson JH (1995a) Biosynthesis of conjugated olefinic systems in the sex pheromone gland of female tobacco hornworm moths, Manduca sexta (L.). Insect Biochem Mol Biol 25:39–48

    Google Scholar 

  • Fang N, Teal PEA, Tumlinson JH (1995b) Characterization of oxidase(s) associated with the sex pheromone gland in Manduca sexta (L.) females. Arch Insect Biochem Physiol 29:243–257

    CAS  Google Scholar 

  • Figueroa-Teran R, Welch WH, Blomquist GJ, Tittiger C (2012) Ipsdienol dehydrogenase (IDOLDH): a novel oxidoreductase important for Ips pini pheromone production. Insect Biochem Mol Biol 42:81–90

    CAS  PubMed  Google Scholar 

  • Figueroa-Terany R, Pak H, Blomquist GJ, Tittiger C (2016) High substrate specificity of ipsdienol dehydrogenase (IDOLDH), a short-chain dehydrogenase from Ips pini bark beetles. J Biochem 160:141–151

    Google Scholar 

  • Foster SP, Roelofs WL (1988) Sex pheromone biosynthesis in the leafroller moth Planotortrix excessana by Δ10 desaturation. Arch Insect Biochem Physiol 8:1–9

    CAS  Google Scholar 

  • Foster SP, Roelofs WL (1990) Biosynthesis of a monoene and a conjugated diene sex pheromone component of the light brown apple moth by E11-desaturation. Experientia 46:269–273

    CAS  Google Scholar 

  • Foster SP, Roelofs WL (1996) Sex pheromone biosynthesis in the tortricid moth, Ctenopseustis herana (Felder & Rogenhofer). Arch Insect Biochem Physiol 33:135–147

    CAS  Google Scholar 

  • Francke W, Bartels J, Meyer H, Schroder F, Kohnle U, Baader E, Vite JP (1995) Semiochemicals from bark beetles: new results, remarks, and reflections. J Chem Ecol 21:1043–1063

    CAS  PubMed  Google Scholar 

  • Fukui H, Matsumura F, Barak AV, Burkholder WE (1977) Isolation and identification of a major sexattracting component of Attagenus elongatus (Casey) (Coleoptera: Dermestidae). J Chem Ecol 3:539–548

    CAS  Google Scholar 

  • Gilg AB, Bearfield JC, Tittiger C, Welch WH, Blomquist GJ (2005) Isolation and functional expression of the first animal geranyl diphosphate synthase and its role in bark beetle pheromone biosynthesis. Proc Natl Acad Sci USA 102:9760–9765

    CAS  PubMed  Google Scholar 

  • Gilg AB, Tittiger C, Blomquist GJ (2009) Unique animal prenyltransferase with monoterpene synthase activity. Naturwissenschaften 96:731–735

    CAS  PubMed  Google Scholar 

  • Ginzel MD, Blomquist GJ (2016) Insect hydrocarbons: biochemistry and chemical ecology. In: Cohen E, Moussian B (eds) Extracellular matrices in arthropods. Springer, Switzerland, pp 221–252

    Google Scholar 

  • Goller S, Szöcs G, Francke W, Schulz S (2007) Biosynthesis of (3Z,6Z,9Z)-3,6,9-octadecatriene: the main component of the pheromone blend of Erannis bajaria. J Chem Ecol 33:1505–1509

    CAS  PubMed  Google Scholar 

  • Gu X, Quilici D, Juarez P, Blomquist GJ, Schal C (1995) Biosynthesis of hydrocarbons and contact sex pheromone and their transport by lipophorin in females of the German cockroach (Blattella germanica). J Insect Physiol 41:257–267

    CAS  Google Scholar 

  • Gu S-H, Wu K-M, Guo Y-Y, Pickett JA, Field LM, Zhou J-J, Zhang Y-J (2013) Identification of genes expressed in the sex pheromone gland of the black cutworm Agrotis ipsilon with putative roles in sex pheromone biosynthesis and transport. BMC Genomics 14:636

    CAS  PubMed  PubMed Central  Google Scholar 

  • Hagström ÅK, Liénard MA, Groot AT, Hedenström E, Löfstedt C (2012) Semi–selective fatty acyl reductases from four heliothine moths influence the specific pheromone composition. PLoS One 7:e37230

    PubMed  PubMed Central  Google Scholar 

  • Hagström ÅK, Albre J, Tooman LK, Thirmawithana AH, Corcoran J, Löfstedt C, Newcomb RD (2013a) A novel fatty acyl desaturase from the pheromone glands of Ctenopseustis obliquana and C. herana with specific Z5-desaturase activity on myristic acid. J Chem Ecol 40:63–70

    Google Scholar 

  • Hagström ÅK, Walther A, Wendland J, Löfstedt C (2013b) Subcellular localization of the fatty acyl reductase involved in pheromone biosynthesis in the tobacco budworm, Heliothis virescens (Noctuidae: Lepidoptera). Insect Biochem Mol Biol 43:510–521

    PubMed  Google Scholar 

  • Hagström ÅK, Wang H-L, Liénard MA, Lassance J-M, Johansson T, Löfstedt C (2013c) A moth pheromone brewery: production of (Z)-11-hexadecenol by heterologous co-expression of two biosynthetic genes from a noctuid moth in a yeast cell factory. Microb Cell Factories 12:125

    Google Scholar 

  • Hashimoto T (1996) Peroxisomal b-oxidation: enzymology and molecular biology. Ann N Y Acad Sci 804:86–98

    CAS  PubMed  Google Scholar 

  • Howard RW (1993) Cuticular hydrocarbons and chemical communication. In: Stanley-Samuelson DW, Nelson DR (eds) Insect lipids: chemistry, biochemistry and biology. University of Nebraska Press, Lincoln, pp 179–226

    Google Scholar 

  • Howard RW, Blomquist GJ (2005) Ecological, behavioral, and biochemical aspects of insect hydrocarbons. Annu Rev Entomol 50:371–393

    CAS  PubMed  Google Scholar 

  • Islam N, Bacala R, Moore A, Vanderwel D (1999) Biosynthesis of 4-methyl-1-nonanol: female-produced sex pheromone of the yellow mealworm beetle, Tenebrio molitor (Coleoptera: Tenebrionidae). Insect Biochem Mol Biol 29:201–208

    CAS  Google Scholar 

  • Jallon J-M, Wicker-Thomas C (2003) Genetic studies on pheromone production in Drosophila. In: Blomquist GJ, Vogt RG (eds) Insect sex pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 253–281

    Google Scholar 

  • Juarez P, Chase J, Blomquist GJ (1992) A microsomal fatty acid synthetase from the integument of Blattella germanica synthesizes methyl-branched fatty acids, precursors to hydrocarbon and contact sex pheromone. Arch Biochem Biophys 293:333–341

    CAS  PubMed  Google Scholar 

  • Jung CR, Kim Y (2014) Comparative transcriptome analysis of sex pheromone glands of two sympatric lepidopteran congener species. Genomics 103:308–315

    CAS  PubMed  Google Scholar 

  • Jurenka RA (1997) Biosynthetic pathway for producing the sex pheromone component (Z,E)-9,12-tetradecadienyl acetate in moths involves a Δ12 desaturase. Cell Mol Life Sci 53:501–505

    CAS  PubMed  Google Scholar 

  • Jurenka RA (2003) Biochemistry of female moth sex pheromones. In: Blomquist GJ, Vogt R (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 53–80

    Google Scholar 

  • Jurenka RA, Roelofs WL (1989) Characterization of the acetyltransferase involved in pheromone biosynthesis in moths: specificity for the Z isomer in Tortricidae. Insect Biochem 19:639–644

    CAS  Google Scholar 

  • Jurenka RA, Subchev M (2000) Identification of cuticular hydrocarbons and the alkene precursor to the pheromone in hemolymph of the female gypsy moth Lymantria dispar. Arch Insect Biochem Physiol 43:108–115

    CAS  PubMed  Google Scholar 

  • Jurenka RA, Haynes KF, Adlof RO, Bengtsson M, Roelofs WL (1994) Sex pheromone component ratio in the cabbage looper moth altered by a mutation affecting the fatty acid chain-shortening reactions in the pheromone biosynthetic pathway. Insect Biochem Mol Biol 24:373–381

    CAS  Google Scholar 

  • Jurenka RA, Subchev M, Abad J-L, Choi M-Y, Fabrias G (2003) Sex pheromone biosynthetic pathway for disparlure in the gypsy moth, Lymantria dispar. Proc Natl Acad Sci USA 100:809–814

    CAS  PubMed  Google Scholar 

  • Jurenka RA, Blomquist GJ, Schal C, Tittiger C (2017) Biochemistry and molecular biology of pheromone production. Ref Mod Life Sci. https://doi.org/10.1016/B978-0-12-809633-8.04037-1

  • Kavanagh K, Jornvall H, Persson B (2008) The SDR superfamily: functional and structural diversity within a family of metabolic and regulatory enzymes. Cell Mol Life Sci 65:3895–3906

    CAS  PubMed  PubMed Central  Google Scholar 

  • Keeling CI, Slessor KN, Higo HA, Winston ML (2003) New components of the honey bee (Apis mellifera L.) queen retinue pheromone. Proc Natl Acad Sci USA 100:4486–4491

    CAS  PubMed  Google Scholar 

  • Keeling CI, Blomquist GJ, Tittiger C (2004) Coordinated gene expression for pheromone biosynthesis in the pine engraver beetle, Ips pini (Coleoptera: Scolytidae). Naturwissenschaften 91:324–328

    CAS  PubMed  Google Scholar 

  • Keeling CI, Bearfield JC, Young S, Blomquist GJ, Tittiger C (2006) Effects of juvenile hormone on gene expression in the pheromone-producing midgut of the pine engraver beetle, Ips pini. Insect Mol Biol 15:207–216

    CAS  PubMed  Google Scholar 

  • Keeling CI, Chiu CC, Aw T, Li M, Henderson H, Tittiger C, Weng H, Blomquist GJ, Bohlman J (2013) Frontaliln pheromone biosynthesis in the mountain pine beetle, Dendroctonus ponderosae, and the role of isoprenyl diphosphate synthases. Proc Natl Acad Sci USA 110:18838–18843

    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

    CAS  PubMed  Google Scholar 

  • Knipple DC, Roelofs WL (2003) Molecular biological investigations of pheromone desaturases. In: Blomquist GJ, Vogt R (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 81–106

    Google Scholar 

  • Lanne BS, Ivarrson P, Johnsson P, Bergström G, Wassgren A-B (1989) Biosynthesis of 2-methyl-3buten-2-ol, a pheromone component of Ips typographus (Coleoptera: Scolytidae). Insect Biochem 19:163–168

    CAS  Google Scholar 

  • Lassance J-M, Groot AT, Liénard MA, Antony B, Borgwardt C, Andersson F, Hedenstrom E, Heckel DG, Lofstedt C (2010) Allelic variation in a fatty-acyl reductase gene causes divergence in moth sex pheromones. Nature 466:486–489

    CAS  PubMed  Google Scholar 

  • Lassance J-M, Liénard MA, Antonya B, Qian S, Fujii T, Tabata J, Ishikawa Y, Lofstedt C (2013) Functional consequences of sequence variation in the pheromone biosynthetic gene pgFAR for Ostrinia moths. Proc Natl Acad Sci USA 110:3967–3972

    CAS  PubMed  Google Scholar 

  • Leal WS (1998) Chemical ecology of phytophagous scarab beetles. Annu Rev Entomol 43:39–61

    CAS  PubMed  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

    CAS  PubMed  Google Scholar 

  • Li Z-Q, Zhang S, Luo J-Y, Wang C-Y, Lv L-M, Dong S-L, Cui J-J (2015) Transcriptome comparison of the sex pheromone glands from two sibling Helicoverpa species with opposite sex pheromone components. Sci Rep 5:932

    Google Scholar 

  • Liénard MA, Hagström ÅK, Lassance J-M, Löfstedt C (2010) Evolution of multicomponent pheromone signals in small ermine moths involves a single fatty-acyl reductase gene. Proc Natl Acad Sci U S A 107:10955–10960

    PubMed  PubMed Central  Google Scholar 

  • Liénard MA, Wang H-L, Lassance J-M, Löfstedt C (2014) Sex pheromone biosynthetic pathways are conserved between moths and the butterfly Bicyclus anynana. Nat Commun 5:957

    Google Scholar 

  • Löfstedt C, Bengtsson M (1988) Sex pheromone biosynthesis of (E,E)-8,10-dodecadienol in codling moth Cydia pomonella involves E9 desaturation. J Chem Ecol 14:903–915

    PubMed  Google Scholar 

  • Löfstedt C, Wahlberg N, Millar JG (2017) Evolutionary patterns of pheromone diversity in Lepidoptera. In: Allison JD, Cardé RT (eds) Pheromone communication in moths: evolution, behavior, and application. University of California Press, Oakland, pp 43–78

    Google Scholar 

  • Luxova A, Svatos A (2006) Substrate specificity of membrane-bound alcohol oxidase from the tobacco hornworm moth (Manduca sexta) female pheromone glands. J Mol Catal B Enzym 38:37–42

    CAS  Google Scholar 

  • Ma PWK, Ramaswamy SB (2003) Biology and ultrastructure of sex pheromone producing tissue. In: Blomquist GJ, Vogt R (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 19–51

    Google Scholar 

  • Martin D, Bohlmann J, Gershenzon J, Francke W, Seybold SJ (2003) A novel sex-specific and inducible monoterpene synthase activity associated with a pine bark beetle, the pine engraver, Ips pini. Naturwissenschaften 90:173–179

    CAS  PubMed  Google Scholar 

  • Martinez T, Fabria’s G, Camps F (1990) Sex pheromone biosynthetic pathway in Spodoptera littoralis and its activation by a neurohormone. J Biol Chem 265:1381–1387

    CAS  PubMed  Google Scholar 

  • Matouskova P, Pichova I, Svatos A (2007) Functional characterization of a desaturase from the tobacco hornworm moth (Manduca sexta) with bifunctional Z11- and 10,12-desaturase activity. Insect Biochem Mol Biol 37:601–610

    CAS  PubMed  Google Scholar 

  • Matsumoto S (2010) Molecular mechanisms underlying sex pheromone production in moths. Biosci Biotechnol Biochem 74:223–231

    CAS  PubMed  Google Scholar 

  • Matsumoto S, Hull J, Ohnishi A, Moto KI, Fonagy A (2007) Molecular mechanisms underlying sex pheromone production in the silkmoth, Bombyx mori: characterization of the molecular components involved in bombykol biosynthesis. J Insect Physiol 53:752–759

    CAS  PubMed  Google Scholar 

  • Millar JG (2010) Polyene hydrocarbons, epoxides, and related compounds as components of lepidopteran pheromone blends. In: Blomquist GJ, Bagnères A-G (eds) Hydrocarbon: biology biochemistry and chemical ecology. Cambridge University Press, Cambridge, pp 390–447

    Google Scholar 

  • Morse D, Meighen EA (1987a) Biosynthesis of the acetate ester precursors of the spruce budworm sex pheromone by an acetyl CoA: fatty alcohol acetyltransferase. Insect Biochem 17:53–59

    CAS  Google Scholar 

  • Morse D, Meighen EA (1987b) Pheromone biosynthesis: enzymatic studies in lepidoptera. In: Prestwich G, Blomquist GJ (eds) Pheromone biochemistry. Academic Press, Orlando, pp 121–158

    Google Scholar 

  • Moto K, Yoshiga T, Yamamoto M, Takahashi S, Okano K, Ando T, Nakata T, Matsumoto S (2003) Pheromone gland specific fatty-acyl reductase of the silk moth. Bombyx mori. Proc Natl Acad Sci USA 100:9156–9161

    CAS  PubMed  Google Scholar 

  • Nadeau J, Petereit J, Tillett RJ, Jung K, Fotoohi M, MacLean M, Young S, Schlauch K, Blomquist GJ, Tittiger C (2017) Compartive transcriptomics of mountain pine beetle heromone-biosynthetic tissues and functional analysis of CYP6DE3. BMC Genomics 18(1):1–15

    Google Scholar 

  • Nelson DR, Sukkestad DR (1970) Normal and branched aliphatic hydrocarbons from the eggs of the tobacco hornworm. Biochemist 9:4601–4610

    CAS  Google Scholar 

  • Nesnerova P, Sebek P, Macek T, Svatos A (2004) First semi-synthetic preparation of sex pheromones. Green Chem 6:305–307

    CAS  Google Scholar 

  • Ohnishi A, Hull JJ, Matsumoto S (2006) Targeted disruption of genes in the Bombyx mori sex pheromone biosynthetic pathway. Proc Natl Acad Sci USA 103:4398–4403

    CAS  PubMed  Google Scholar 

  • Ono A, Imai T, Inomata S-I, Watanabe A, Ando T (2002) Biosynthetic pathway for production of a conjugated dienyl sex pheromone of a plusiinae moth, Thysanoplusia intermixta. Insect Biochem Mol Biol 32:701–708

    CAS  PubMed  Google Scholar 

  • Payne JL, Boyer AG, Brown JH, Finnegan S, Kowalewski M, Krause RA, Lyons SK, McClain CR, McShea D, Navack-Gottshall PM (2009) Two phase increase in the maximum size of life over 3.5 billion years reflects biological innovation and environmental opportunity. Proc Natl Acad Sci USA 106:24–27

    CAS  PubMed  Google Scholar 

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

    Google Scholar 

  • Petroski RJ, Bartelt RJ, Weisleder D (1994) Biosynthesis of (2E,4E,6E)-5 ethyl-3-methyl-2,4,6-nonatriene: the aggregation pheromone of Carpophilus freemani (Coleoptera: Nitidulidae). Insect Biochem Mol Biol 24:69–78

    CAS  Google Scholar 

  • Pierce HD, Conn JE, Oehlschlager AC, Borden JH (1987) Monoterpene metabolism in female mountain pine beetles, Dendroctonus ponderosae Hopkins, attacking ponderosa pine. J Chem Ecol 13:1455–1480

    CAS  PubMed  Google Scholar 

  • Plettner E, Slessor KN, Winston ML, Oliver JE (1996) Caste-selective pheromone biosynthesis in honeybees. Science 271:1851–1853

    CAS  Google Scholar 

  • Plettner E, Slessor KN, Winston ML (1998) Biosynthesis of mandibular acids in honeybees (Apis mellifera): de novo synthesis, route of fatty acid hydroxylation and caste selective b-oxidation. Insect Biochem Mol Biol 28:31–42

    CAS  Google Scholar 

  • Prestwich GD, Blomquist GJ (1987) Pheromone biochemistry. Academic Press, Orlando

    Google Scholar 

  • Pureswaran DS, Gries R, Borden JH, Pierce HD Jr (2000) Dynamics of pheromone production and communication in the mountain pine beetle, Dendroctonus ponderosae Hopkins and the pine engraver, Ips pini (say) (Coleoptera: Scolytidae). Chemoecology 10:153–168

    CAS  Google Scholar 

  • Qiu Y, Tittiger C, Wicker-Thamas C, Le Goff G, Young S, Wajnberg E, Fricaux T, Tauet N, Blomquist GJ, Feyereisen R (2012) An insect-specific P450 oxidative decabonylase for cuticular hydrocarbon biosynthesis. Proc Natl Acad Sci USA 109:14858–14863

    CAS  PubMed  Google Scholar 

  • Quennedey A (1998) Insect epidermal gland cells: ultraxtructure and morphogenesis. In: Harrison FW, Locke M (eds) Microscopic anatomy of invertebrates, vol 11A. Wiley–Liss, New York, pp 177–207

    Google Scholar 

  • Rafaeli A, Jurenka RA (2003) PBAN regulation of pheromone biosynthesis in female moths. In: Blomquist GJ, Vogt R (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 107–136

    Google Scholar 

  • Reed JR, Vanderwel D, Choi S, Pomonis JG, Reitz RC, Blomquist GJ (1994) Unusual mechanism of hydrocarbon formation in the housefly: cytochrome P450 converts aldehyde to the sex pheromone component (Z)-9-tricosene and CO2. Proc Natl Acad Sci USA 91:10000–10004

    CAS  PubMed  Google Scholar 

  • Reed JR, Quilici DR, Blomquist GJ, Reitz RC (1995) Proposed mechanism for the cytochrome P450-catalyzed conversion of aldehydes to hydrocarbons in the house fly, Musca domestica. Biochemistry 34:16221–16227

    CAS  PubMed  Google Scholar 

  • Roelofs WL, Wolf WA (1988) Pheromone biosynthesis in Lepidoptera. J Chem Ecol 14:2019–2031

    CAS  PubMed  Google Scholar 

  • Romer F (1991) The oenocytes of insects: differentiation, changes during molting, and their possible involvement in the secretion of moulting hormone. In: Gupta A (ed) Morphogenetic hormones of arthropods, vol 3. Rutgers University Press. New Brunswick, NJ, pp 542–566

    Google Scholar 

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

    CAS  Google Scholar 

  • Sandstrom P, Welch WH, Blomquist GJ, Tittiger C (2006) Functional expression of a bark beetle cytochrome P450 that hydroxylates myrcene to ipsdienol. Insect Biochem Mol Biol 36:835–845

    CAS  PubMed  Google Scholar 

  • Sandstrom P, Ginzel MD, Bearfield JC, Welch WH, G J Blomquist GJ, Tittiger C (2008) Myrcene hydroxylases do not determine enantiomeric composition of pheromonal ipsdienol in Ips spp. J Chem Ecol 34:584–592

    Google Scholar 

  • Schal C, Sevala VL, Young HP, Bachmann JAS (1998) Synthesis and transport of hydrocarbons: cuticle and ovary as target tissues. Am Zool 38:382–393

    CAS  Google Scholar 

  • Schal C, Fan Y, Blomquist GJ (2003) Regulation of pheromone biosynthesis, transport and emission in cockroaches. In: Blomquist G, Vogt R (eds) Insect pheromone biochemistry and molecular biology. Elsevier, San Diego, pp 283–322

    Google Scholar 

  • Schlyter F, Birgersson GS (1999) Forest beetles. In: Hardie J, Minks AK (eds) Pheromones of non-lepidopteran insects associated with agricultural plants. CAB International, Wallingford, pp 113–148

    Google Scholar 

  • Seybold SJ, Ohtsuka T, Wood DL, Kubo I (1995) Enantiomeric composition of ipsdienol - a chemotaxonomic character for North-American populations of Ips spp in the pini subgenerec group (Coleoptera, Scolytidae). J Chem Ecol 21:995–1016

    Google Scholar 

  • Seybold SJ, Vanderwel D (2003) Biosynthesis and endocrine regulation of pheromone production in the Coleoptera. In: Blomquist GJ, Vogt R (eds) Insect pheromone biochemistry and molecular biochemistry. Elsevier, San Diego, CA, pp 137–200

    Google Scholar 

  • Seybold SJ, Bohlmann J, Raffa KF (2000) Biosynthesis of coniferophagous bark beetle pheromones and conifer isoprenoids: evolutionary perspective and synthesis. Can Entomol 132:697–753

    Google Scholar 

  • Silverstein RM, Rodin JO, Wood DL (1966) Sex attractants in frass produced by male Ips confusus in ponderosa pine. Science 154:509–510

    CAS  Google Scholar 

  • Song M, Gorzalski A, Nguyen TT, Liu X, Jeffrey C, Blomquist GJ, Tittiger C (2014) exo-Brevicomin biosynthesis in the fat body of the mountain pine beetle, Dendroctonus ponderosae. J Chem Ecol 40:181–189

    CAS  PubMed  Google Scholar 

  • Stanley-Samuelson DW, Jurenka RA, Cripps C, Blomquist GJ, deRenobales M (1988) Fatty acids in insects: composition, metabolism and biological significance. Arch Insect Biochem Physiol 9:1–33

    CAS  Google Scholar 

  • Strandh M, Johansson T, Ahren D, Löfstedt C (2008) Transcriptional analysis of the pheromone gland of the turnip moth, Agrotis segetum (Noctuidae), reveals candidate genes involved in pheromone production. Insect Mol Biol 17:73–85

    CAS  PubMed  Google Scholar 

  • Strandh M, Johansson T, Löfstedt C (2009) Global transcriptional analysis of pheromone biosynthesis-related genes in the female turnip moth, Agrotis segetum (Noctuidae) using a custom-made cDNA microarray. Insect Biochem Mol Biol 39:484–489

    CAS  PubMed  Google Scholar 

  • Subchev M, Jurenka RA (2001) Identification of the pheromone in the hemolymph and cuticular hydrocarbons from the moth Scoliopteryx libatrix L. (Lepidoptera: Noctuidae). Arch Insect Biochem Physiol 47:35–43

    CAS  PubMed  Google Scholar 

  • Tang JD, Charlton RE, Jurenka RA, Wolf WA, Phelan PL, Sreng L, Roelofs WL (1989) Regulation of pheromone biosynthesis by a brain hormone in two moth species. Proc Natl Acad Sci USA 86:1806–1810

    CAS  PubMed  Google Scholar 

  • Teal PEA, Tumlinson JH (1987) The role of alcohols in pheromone biosynthesis by two noctuid moths that use acetate pheromone components. Arch Insect Biochem Physiol 4:261–269

    CAS  Google Scholar 

  • Teal PEA, Tumlinson JH (1988) Properties of cuticular oxidases used for sex pheromone biosynthesis by Heliothis zea. J Chem Ecol 14:2131–2145

    CAS  PubMed  Google Scholar 

  • Teerawanichpan P, Robertson AJ, Qiu X (2010) A fatty acyl-CoA reductase highly expressed in the head of honey bee (Apis mellifera) involves biosynthesis of a wide range of aliphatic fatty alcohols. Insect Biochem Mol Biol 40:641–649

    CAS  PubMed  Google Scholar 

  • Tillman JA, Seybold SJ, Jurenka RA, Blomquist GJ (1999) Insect pheromones: an overview of biosynthesis and endocrine regulation. Insect Biochem Mol Biol 29:481–514

    CAS  PubMed  Google Scholar 

  • Tittiger C (2003) Molecular biology of bank beetle pheromone production and endocrine regulation. In: Blomquist GJ, Vogt RG (eds) Insect biochemistry and molecular biology. Elsevier, San Diego, pp 201–230

    Google Scholar 

  • Tittiger C, Blomquist GJ (2016) Pheromone production in pine bark beetles. Adv Insect Physiol 50:235–263

    Google Scholar 

  • Tittiger C, Blomquist GJ, Ivarsson P, Borgeson CE, Seybold SJ (1999) Juvenile hormone regulation of HMG-R gene expression in the bark beetle Ips paraconfusus (Coleoptera: Scolytidae): implications for male aggregation pheromone biosynthesis. Cell Mol Life Sci 55:121–127

    CAS  PubMed  Google Scholar 

  • Vanderwel D (1994) Factors affecting pheromone production in beetles. Arch Insect Biochem Physiol 25:347–362

    CAS  Google Scholar 

  • Vanderwel D, Oehlschlager AC (1987) Biosynthesis of pheromones and endocrine regulation of pheromone production in Coleoptera. In: Prestwich GD, Blomquist GJ (eds) Pheromone biochemistry. Academic Press, Orlando, pp 175–215

    Google Scholar 

  • Vaz AH, Blomquist GJ, Reitz RC (1988) Characterization of the fatty acyl elongation reactions involved in hydrocarbon biosynthesis in the housefly, Musca domestica L. Insect Biochem 18:177–184

    CAS  Google Scholar 

  • Vioque J, Kolattukudy PE (1997) Resolultion and purification of an aldehyde-generating and an alcohol-generating fatty acyl-CoA reductase from pea leaves (Pisum sativum L). Arch Biochem Biophys 340:64–72

    CAS  PubMed  Google Scholar 

  • Vogel H, Heidel A, Heckel D, Groot A (2010) Transcriptome analysis of the sex pheromone gland of the noctuid moth Heliothis virescens. BMC Genomics 11:29

    PubMed  PubMed Central  Google Scholar 

  • Wang H-L, Liénard MA, Zhao C-H, Wang C-Z, Löfstedt C (2010a) 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

    CAS  PubMed  Google Scholar 

  • Wang H-L, Zhao C-H, Millar J, Cardé R, Löfstedt C (2010b) Biosynthesis of unusual moth pheromone components involves two different pathways in the navel orangeworm, Amyelois transitella. J Chem Ecol 36:535–547

    PubMed  PubMed Central  Google Scholar 

  • Wang H-L, Zhao C-H, Szöcs G, Chinta S, Schulz S, Löfstedt C (2013) Biosynthesis and PBAN-regulated transport of pheromone polyenes in the winter moth, Operophtera brumata. J Chem Ecol 39:790–796

    CAS  PubMed  Google Scholar 

  • Wheeler CA, Cardé RT (2014) Following in their footprints: cuticular hydrocarbons as overwintering aggregation site markers in Hippodamia convergens. J Chem Ecol 40:418–428

    CAS  PubMed  Google Scholar 

  • Wicker-Thomas C, Chertemps T (2010) Molecular biology and genetics of hydrocarbon production. In: Blomquist GJ, Bagnères A-G (eds) Insect hydrocarbons: biology biochemistry and chemical ecology. Cambridge University Press, Cambridge, pp 53–74

    Google Scholar 

  • Wicker-Thomas C, Garrido D, Bontonou G, Napal L, Mazuras N, Denis B, Rubin T, Parvy J-P, Montagne J (2015) Flexible origin of hydrocarbon/pheromone precursors in Drosophila melanogaster. J Lipid Res 56:2094–2101

    CAS  PubMed  PubMed Central  Google Scholar 

  • Xia Y-H, Zhang Y-N, Hou X-Q, Li F, Dong S-L (2015) Large number of putative chemoreception and pheromone biosynthesis genes revealed by analyzing transcriptome from ovipositor-pheromone glands of Chilo suppressalis. Sci Rep 5:7888

    CAS  PubMed  PubMed Central  Google Scholar 

  • Zhang Y-N, Xia Y-H, Zhu J-Y, Li S-Y, Dong S-L (2014) Putative pathway of sex pheromone biosynthesis and degradation by expression patterns of genes identified from female pheromone gland and adult antenna of Sesamia inferens (Walker). J Chem Ecol 40:439–451

    CAS  PubMed  Google Scholar 

  • Zhao C, Löfstedt C, Wang X (1990) Sex pheromone biosynthesis in the Asian corn borer Ostrinia furnicalis 2. Biosynthesis of (E) and (Z)-12-tetradecenyl acetate involves Δ14 desaturation. Arch Insect Biochem Physiol 15:57–65

    CAS  Google Scholar 

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  • Database of Pheromones and Semiochemicals. http://www.pherobase.com/

    Google Scholar 

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Blomquist, G.J., Tittiger, C., Jurenka, R. (2020). Cuticular Hydrocarbons and Pheromones of Arthropods. In: Wilkes, H. (eds) Hydrocarbons, Oils and Lipids: Diversity, Origin, Chemistry and Fate. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-90569-3_11

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