Skip to main content
SpringerLink
Log in

Pheromones of two arctiid moths (Creatonotos transiens andC. gangis)

Chiral components from both sexes and achiral female components

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

The two major components of the female sex pheromones of twoCreatonotos species have been identified as an achiral C21 triene, (Z,Z,Z)-3,6,9-heneicosatriene, and a chiral epoxide, (Z,Z)-2(2,5-octadienyl)-3-undecyloxirane. The ratios of these components in the two species fall into nonoverlapping ranges. Two additional achiral minor components, (Z,Z)-6,9-heneicosadiene and (Z,Z,Z)-3,6,9-tricosatriene, were also identified in the female sex gland extracts. The male pheromone of both species consists of hydroxydanaidal, a chiral dihydropyrrolizine derived from pyrrolizidine alkaloids in the larval diet.Creatonotos transiens was found to convert dietary heliotrine into (R)-(−)-hydroxydanaidal, with inversion at the single asymmetric carbon atom. The possible biological and biosynthetic significance of the chiral pheromone components are discussed, and they are compared with known examples of chiral lepidopteran pheromones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Attenburrow, J., Cameron, A.F.B., Chapman, J.H., Evans, R.M., Herns, B.A., Jansen, A.B.A., andWalker, T. 1952. A synthesis of vitamin A from cyclohexanone.J. Chem. Soc. 1952: 1094–1111.

    Google Scholar 

  • Baker, R., andBradshaw, J.W.S. 1981. Insect pheromones and related behavior-modifying chemicals.Aliphatic Relat. Nat. Prod. Chem. 2:46–75.

    Google Scholar 

  • Baker, R., andBradshaw, J.W.S. 1983. Insect pheromones and related natural products.Aliphatic Relat. Nat. Product Chem. 3:66–106.

    Google Scholar 

  • Baker, R., andEvans, D.A., 1979. Insect pheromones are related behavior-modifying chemicalsAliphatic Relat.Nat. Prod. Chem. 1:102–127.

    Google Scholar 

  • Baker, R., andHerbert, R.H. 1984. Insect pheromones and related natural products.Nat. Prod. Rep. 1:299–318.

    Google Scholar 

  • Baker, T.C., Nishida, R., andRoelofs, W.L. 1981. Close-range attraction of female oriental fruit moths to herbal scent of male hairpencils.Science 214:1359–1360.

    Google Scholar 

  • Bell, T.W., Boppŕe, M., Schneider, D., andMeinwald, J. 1984. Stereochemical course of pheromone biosynthesis in an artiid moth,Creatonotos transiens.Experientia 40:713–714.

    Google Scholar 

  • Beroza, M., Bierl, B.A., Knipling, E.F., andTardif, J.G.R. 1971. The activity of the gypsy moth sex attractant disparlure vs. that of the live female moth.J. Econ. Entomol. 64:1527–1529.

    Google Scholar 

  • Bierl, B.A., Beroza, M., andCollier, C.W. 1970. Potent sex attractant of the gypsy moth: Its isolation, identification, and synthesis.Science 170:87–89.

    Google Scholar 

  • Bierl, B.A., Beroza, M., andCollier, C.W. 1972. Isolation, identification and synthesis of the gypsy moth sex attactant.J. Econ. Entomol. 65:659–664.

    Google Scholar 

  • Bierl, B.A., Beroza, M., Adler, V.E., Kasang, G., Schroter, H., andSchneider, D. 1975. The presence of disparlure, the sex pheromone of the gypsy moth, in the female nun moth.Z. Naturforsch. 30C: 672–675.

    Google Scholar 

  • Birch, M. 1974. Aphrodisiac pheromones in insects, pp. 115–134,in M.C. Birch (ed.). Pheromones. American Elsevier, New York.

    Google Scholar 

  • Boppŕe, M. 1984. Chemically mediated interactions between butterflies, pp. 259–275,in R.I. Vane-Wright and P.R. Ackery (eds.). The Biology of Butterflies. Academic Press, London.

    Google Scholar 

  • Connor, W.E., Eisner, T., Vander Meer, R.K., Guerrero, A., Ghiringelli, D., andMeinwald, J. 1980. Sex attractant of an arctiid moth (Utetheisa ornatrix): A pulsed chemical signal.Behav. Ecol. Sociobiol. 7:55–63.

    Google Scholar 

  • Connor, W.E., Eisner, T., vander Meer, R.K., Guerrero, A., andMeinwald, J. 1981. Precopulatory sexual interaction in an arctiid moth (Utetheisa ornatrix): Role of a pheromone derived from dietary alkaloids.Behav. Ecol. Sociobiol. 9:277–235.

    Google Scholar 

  • Culvenor, C.C.J., Edgar, I.A., Smith, L.W., andTweedale, H.J. 1970. Dihydropyrrolizidines. IV. Manganese dioxide oxidation of 1,2,-dehydropyrrolizidines.Aust. J. Chem. 23:1869–1879.

    Google Scholar 

  • Culvenor, C.C.J., andEdgar, J.A. 1972. Dihydropyrrolizidine secretions associated with coremata ofUtetheisa moths (family Arctiidae).Experientia 23:627–628.

    Google Scholar 

  • Edgar, J.A. 1975. Danainae (Lep.) and 1,2,-dehydropyrrolizidine alkaloid-containing plantswith reference to observations made in the New Hebrides.Phil. Trans. R. Soc. London Ser. B 272:467–476.

    Google Scholar 

  • Edgar, J.A. 1982. Pyrrolizidine alkaloids sequestered by Solomon Island Danainae butterflies. The feeding preferences of the Danainae and Ithomiinae.J. Zool. 196:385–399.

    Google Scholar 

  • Edgar, J.A., Culvenor, C.C.J., andPliske, T.E. 1976. Isolation of a lactone, structurally related to the esterifying acids of pyrrolizidine alkaloids, from the costal fringes of male Ithomiinae.J. Chem. Ecol. 3:263–270.

    Google Scholar 

  • Einhorn, J., Lallemand, J.-Y., Zagatti, P., Gallois, M., Virelizier, H., Riom, J., andMenassieu, P. 1982. Isolement et identification de la phéromone sexuelle attractive deHyphantria cunea (Drury) (Lépidoptère, Arctiidae).C. R. Acad. Sci. Paris, Ser. C. 249:41–44.

    Google Scholar 

  • Einhorn, J., Boniface, B., Renou, M., andMilat, M.-L. 1984. Etude de la phéromone sexuelle deArctia villica L. (Lépidoptère, Arctiidae).C. R. Acad. Sci. Paris, Ser. C. 298:573–576.

    Google Scholar 

  • Francke, W., Mackenroth, W., Schroeder, W., Schulz, S., Tengoe, J., Engels, E., Engels, W., Kittmann, R., andSchneider, D., 1985. Identification of cyclic enolethers from insects: Alkyldihydropyranes from bees and alkyldihydro-4H-pyran-4-ones from a male moth.Z. Naturforsch. 40C: 145–147.

    Google Scholar 

  • Grula, J.W., McChesney, J.D., andTaylor, O.R., Jr. 1980. Aphrodisiac pheromones of the sulfur butterfliesColias Eurytheme andC. philodice (Lepidoptera, Pieridae).J. Chem. Ecol. 6:241–256.

    Google Scholar 

  • Hansen, K., 1984. Discrimination and production of disparlure enantiomers by the gypsy moth and nun moth.Physiol. Entomol. 9:9–18.

    Google Scholar 

  • Hill, A.S., Anoroelofs, W.L. 1981. Sex pheromone of the saltmarsh caterpillar moth,Estigmene acrea.J. Chem. Ecol. 7:655–668.

    Google Scholar 

  • Hill, A.S., Kovalev, B.G., Nikolaeva, L.N., andRoelofs, W.L. 1982. Sex pheromone of the fall webworm moth,Hyphantria cunea.J. Chem. Ecol. 8:383–396.

    Google Scholar 

  • Jacobson, M., Beroza, M., andJones, W.A. 1960. Isolation, identification, and synthesis of the sex attractant of the gypsy moth.Science 132:1011–1012.

    Google Scholar 

  • Jacobson, M., Beroza, M., andJones, W.A. 1961. Insect sex attractants. I. The isolation, identification, and synthesis of the sex attractant of the gypsy moth.J. Am. Chem. Soc. 83:4819–4824.

    Google Scholar 

  • Jacobson, M., Green, N., Warthen, D., Harding, C., andToba, H.H. 1970. Sex pheromones of the lepidoptera, recent progress and structure-activity relationships, pp. 3–20,in M. Beroza (ed.). Chemicals Controlling Insect Behavior. Academic Press, New York.

    Google Scholar 

  • Jain, S.C., Doussard, D.E., Connor, W.E., Eisner, T., Guerrero, andMeinwald, J. 1983. Polyene pheromone components from an arctiid moth (Utetheisa ornatrix): characterization and synthesis.J. Org. Chem. 48:2266–2270.

    Google Scholar 

  • Kafka, W.A., Ohloff, G., Schneider, D., andVareschi, E. 1973. Olfactory discrimination of two enantiomers of 4-methylhexenoic acid by the migratory locust and honeybee.J. Comp. Physiol. 87:277–284.

    Google Scholar 

  • Klun, J.A., Chapman, O.L., Mattes, K.C., Wojtkowski, P.W., Beroza, M., andSonnet, P.E. 1973. Insect sex pheromones: Minor amount of opposite geometrical isomer critical to attraction.Science 181:661–663.

    Google Scholar 

  • Komae, H., Nishi, A., Tanaka, T., Hayashi, N., Wesou, C., andKuwahara, Y. 1982. Major components in the hairpencil secretions of danaid butterflies from far East Asia.Biochem. Syst. Ecol. 10:181–183.

    Google Scholar 

  • Komae, H., Nishi, A., Hayashi, N., Wesou, C., andKuwahara, Y. 1983. Components of the sex brand secretions of some danaid butterflies.Agric. Biol. Chem. 47:157–158.

    Google Scholar 

  • Kubo, I., Matsumoto, T., Wagner, D.L. andShoolery, J.N. 1985. Isolation and structure of hepialone: Principal component from male sex scales ofHepialus californicus (Lepidoptera).Tetrahedron Lett. 26:563–566.

    Google Scholar 

  • Kunesch, G., Zagatti, P., Lallemand, J.Y., Debal, A., Vigneron, J.P. 1981. Structure and synthesis of the wing gland pheromone of the male African sugar-cane borer:Eldana saccharina (Wlk.) (Lepidoptera, Pyralidae).Tetrahedron Lett. 22:5271–5274.

    Google Scholar 

  • Meyer, W. 1984. MS thesis, Cornell University.

  • Mori, K. 1984. The significance of chirality: Method for determining absolute configuration and optical purity of pheromones and related compounds, p. 323–370,in H.E. Hummel and T.A. Miller, (eds.). Techniques in Pheromone Research, Springer-Verlag, New York.

    Google Scholar 

  • Mori, K., andEbata, T. 1981. Synthesis of optically active pheromones with an epoxy ring, (+)- disparlure and the saltmarsh caterpiller moth pheromone [(Z, Z)-3,6-cis-9,10-epoxyheneico-sadiene].Tetrahedron Lett. 43:4281–4282.

    Google Scholar 

  • Myerson, J., Haddon, W.F., andSoderstrom, E.L. 1982.sec-Butyl (Z)-7-tetradecanoate. A novel sex pheromone component from the Western grapeleaf skeletonizer,Harrisina brillians.Tetrahedron Lett. 23:2757–2760.

    Google Scholar 

  • Roelofs, W. 1979. Production and perception of lepidopterous pheromone blends, pp. 159–168, F.J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier/North Holland Biomedical Press, New York.

    Google Scholar 

  • Roelofs, W., andBjostad, L. 1984. Biosynthesis of lepidopteran pheromones.Bioorg. Chem. 12:279–298.

    Google Scholar 

  • Roelofs, W., andCardé, R.T., 1974. Sex pheromones in the reproductive isolation of lepidopterous species, pp. 96–114,in M.C. Birch (ed.) Pheromones. American Elsevier, New York.

    Google Scholar 

  • Roelofs W.L., Hill, A., andCardé, R. 1975. Sex pheromone components of the red-banded leafroller,Argyrotaenia velutinana (Lepodoptera: Tortricidae).J. Chem. Ecol. 1:83–89.

    Google Scholar 

  • Schneider, D. 1984a. Pheromone biology in the Lepidoptera: Overview, some recent findings and some generalizations, pp. 301–313,in L. Bolis, R.D. Keynes, and S.H.P. Maddrell (eds.). Comparative Physiology of Sensory Systems. Cambridge University Press, London.

    Google Scholar 

  • Schneider, D. 1984b. Insect olfaction-our research endeavor, pp. 381–418, W.W. Dawson and J.M., Enoch, (eds.). Foundations of Sensory Science. Springer-Verlag, New York.

    Google Scholar 

  • Schneider, D., Boppŕe, M., Schneider, H., Thompson, W.R., Boriack, C.J., Petty, R.L., andMeinwald, J. 1975. A pheromone precursor and its uptake in maleDanaus butterflies.J. Comp. Physiol. 97:245–256.

    Google Scholar 

  • Schneider, D., Boppŕe, M., Zweig, J., Horsley, S.B., Bell, T.W., Meinwald, J., Hansen, K., andDiehl, E.W. 1982. Scent organ development inCreatonotos moths: Regulation by pyrrolizidine alkaloids.Science 215:1264–1265.

    Google Scholar 

  • Silverstein, R.M. 1979. Enantiomeric composition and bioactivity of chiral semiochemicals in insects, pp. 133–146,in F.J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier/North Holland Biomedical Press, New York.

    Google Scholar 

  • Silverstein, R.M. 1982. Chemical communication in insects: Background and application.Pure Appl. Chem. 54:2479–2488.

    Google Scholar 

  • Sinnwell, V., Schulz, S., Francke, W., Kittmann, R., andSchneider, D. 1985. Identification of pheromones from the male swift mothHepialus hecta L.Tetrahedron Lett. 26:1707–1710.

    Google Scholar 

  • Tamaki, Y. 1979. Multi-component sex pheromone of Lepidoptera with special reference toAdoxophyes sp., pp. 169–180,in F.J. Ritter (ed.). Chemical Ecology: Odour Communication in Animals. Elsevier/North Holland Biomedical Press, New York.

    Google Scholar 

  • Tamaki, Y., Noguchi, H., Sugie, H., Sato, R., andKariya, A. 1979. Minor components of the female sex-attractant pheromone of the smaller tea tortrix moth (Lepidoptera: Tortricidae): Isolation and identification.Appl. Entomol. Zool. 14:101–113.

    Google Scholar 

  • Tamaki, Y., Sugie, H., Osakabe, M., andSonnet, P. 1983. Biological activities of (R)- and (S)-10-methyldodecyl acetates, the chiral component of the sex pheromone of the smaller tea tortrix moth (Adoxophyes sp., Lepidoptera: Tortricidae).Appl. Entomol. Zool. 18:292–294.

    Google Scholar 

  • Tamaki, Y., Noguchi, H., Horiike, M., andHirano, C. 1984. Biological activities of analogs of 10-methyldodecyl acetate, a sex-pheromonal component of the smaller tea tortrix moth (Adoxophyes sp., Lepidoptera: Tortricidae).Appl. Entomol. Zool. 19:245–251.

    Google Scholar 

  • Tumlinson, J.H., Heath, R.R., andTeal, P.E.A. 1982. Analysis of chemical communications systems of Lepidoptera, pp. 1–25,in B.A. Leonhardt and M. Beroza (eds.). Insect Pheromone Technology: Chemistry and Applications. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Uchino, K., Yamagawa, Y., Kamikawa, T., andKubo, I. 1985. Synthesis of hepialone; principal component from male sex cells ofHepialus californicns (Lepidoptera).Tetrahedron Lett. 26:1319–1320.

    Google Scholar 

  • Vigneron, J.P., Méric, R., Larcheveque, M., Debal, A., Kunesch, G., Zagatti, P., andGallois, M. 1982. Absolute configuration of eldanolide, the wing gland pheromone of the male African sugar cane borer,Eldana saccharina (Wlk.) Synthesis of its (+) and (−) enantiomers.Tetrahedron Lett. 23:5051–5054.

    Google Scholar 

  • Vité, J.P., Klimetzek, D., Loskant, G., Hedden, R., andMori, K. 1976. Chirality of insect pheromones: Response interruption by inactive antipodes.Naturwissenschaften 63:582–583.

    Google Scholar 

  • Wunderer, H.,Hansen, K.,Bell, T. W.,Schneider, D.,and Meinwald, J. 1986. Pheromones of males and females of two Asian moths (Creatonotos transiens, C. gangis; Lepidoptera: Arctiidae): Behavior, Morphology, Chemistry and Electrophysiology.Experimental Biology 45: Submitted.

  • Zaretskii, Z.V. 1976. Mass Spectrometry of Steroids. Wiley, New York.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Departments of Chemistry, State University of New York at Stony Brook, 11794, Stony Brook, New York

    Thomas W. Bell

  2. Departments of Chemistry, Cornell University, 14853, Ithaca, New York

    Jerrold Meinwald

Authors
  1. Thomas W. Bell
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jerrold Meinwald
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bell, T.W., Meinwald, J. Pheromones of two arctiid moths (Creatonotos transiens andC. gangis). J Chem Ecol 12, 385–409 (1986). https://doi.org/10.1007/BF01020563

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01020563

Key words

Search

Navigation