Journal of Chemical Ecology

, Volume 8, Issue 2, pp 535–543 | Cite as

Exocrine secretions of bees

IV. Macrocyclic lactones and isopentenyl esters in Dufour's gland secretions ofNomia bees (Hymenoptera: Halictidae)
  • R. M. Duffield
  • W. E. LaBerge
  • J. H. Cane
  • J. W. Wheeler


The volatile components of Dufour's gland extracts were analyzed in four species of NearcticNomia bees;Nomia (Dieunomia)heteropoda, N. (Tetrazonata)tetrazonata, N. (Epinomia)nevadensis, andN. (Epinomia)triangulifera. A homologous series of five saturated macrocyclic lactones ranging from C18 to C26 was identified. A series of esters (branched C5-alkenols and fatty acids) was also identified in all species investigated. Two of these esters are new natural products reported for bees. A discussion of the significance of the Dufour's gland secretion for halictid systematics and its function in the Halictidae is also presented.

Key words

Bees Nomia Dufour's gland exocrine products macrocyclic lactones isopentenyl esters systematics mass spectrometry 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Albans, K.R., Aplin, R.T., Brehcist, J., Moore, J.F., andO'Toole, C. 1980. Dufour's gland and its role in secretion of nest cell lining in bees of the genusColletes (Hymenoptera: Colletidae).J. Chem. Ecol. 6:549–564.Google Scholar
  2. Anderson, C.O., Bergström, G., Kullenberg, B., andStälberg-Stenhagen, S. 1966. Identification of macrocyclic lactones as odouriferous components of the scent of the solitary bee (Halictus calceatus Scop. andHalictus albipes F.Ark. Kemi. 26:191–198.Google Scholar
  3. Batra, S.W.T. 1972. Some properties of the nest-building secretions ofNomia, Anthophora, Hylaeus and other bees.J. Kans. Entomol. Soc. 45:208–218.Google Scholar
  4. Batra, S.W.T., andHefetz, A. 1979. Chemistry of the cephalic and Dufour's gland secretions ofMelissodes bees.Ann. Entomol. Soc. Am. 72:514–515.Google Scholar
  5. Bergström, G. 1974. Studies on natural odouriferous compounds X. Macrocyclic lactones in the Dufour's gland secretion of the solitary beesColletes cunicularis L. andHalictus calceatus Scop. (Hymenoptera, Apidae).Chem. Scr. 5:39–46.Google Scholar
  6. Bergström, G., andTengö, J., 1979. C24-, C22-, C20- and C18-macrocyclic lactones in halictid bees.Acta Chem. Scand. 29B:390.Google Scholar
  7. Bohart, G.E., andCross, E.A. 1955. Time relationships in the nest construction and life cycle of the alkali bee.Ann. Entomol. Soc. Am. 48:403–406.Google Scholar
  8. Cane, J.H. 1981. Dufour's gland secretion in the cell linings of bees (Hymenoptera: Apoidea).J. Chem. Ecol. 7:403–410.Google Scholar
  9. Cross, E.A., andBohart, G.E. 1960. The biology ofNomia (Epinomia) traingulifera with comparative notes on other species ofNomia.Univ. Kans. Sci. Bull. 41:761–792.Google Scholar
  10. Duffield, R.M., Fernandes, A., McKay, S., Wheeler, J.W., andSnelling, R.R. 1980. Chemistry of the exocrine secretions ofHylaeus modestus (Hymenoptera: Colletidae).Comp. Biochem. Physiol. 67B:159–162.Google Scholar
  11. Duffield, R.M., Fernandes, A., Lamb, C., Wheeler, J.W., andEickwort, G.C., 1981. Macrocyclic lactones and isopentenyl esters in the Dufour's gland secretions of halictine bees. (Hymenoptera; Halictidae).J. Chem. Ecol. 7:319–331.Google Scholar
  12. Fernandes, A., Duffield, R.M., Wheeler, J.W., andLaberge, W.E. 1981. Chemistry of the Dufour's gland secretions of North American andrenid bees (Hymenoptera: Andrenidae).J. Chem. Ecol. 7:455–465.Google Scholar
  13. Hefetz, A., Blum, M.S., Eickwort, G.C., andWheeler, J. W. 1978. Chemistry of the Dufour's gland secretions of halictine bees.Comp. Biochem. Physiol. 61B:129–132.Google Scholar
  14. Hefetz, A., Fales, H.M., andBatra, S.W.T. 1979. Natural polyesters: Dufour's gland macrocyclic lactones from brood cell laminesters inColletes bees.Science 204:415–417.Google Scholar
  15. Hurd, P.D., Jr. 1979. Apoidea, pp. 1741–2209, in K.V. Krombein, P.D. Hurd, Jr., D.R. Smith, and B.D. Burks, (eds.). Catalogue of Hymenoptera in America north of Mexico, Vol. 2, Smithsoman Institution Press, Washington, D.C.Google Scholar
  16. Lello, E. de 1971. Adnexal glands of the sting apparatus of bees: Anatomy and histology, II (Hymenoptera: Halicitidae).J. Kans. Entomol. Soc. 44:14–20.Google Scholar
  17. Malyshev, S.I. 1935. The nesting habits of solitary bees, a comparative study.Eos 11:201–309.Google Scholar
  18. Michener, C.D. 1974. The Social Behavior of the Bees. Harvard University Press, Cambridge, Massachusetts. 404pp.Google Scholar
  19. Michener, C.D. 1979. Biogeography of the bees.Ann. Mo. Bot. Gard. 66:277–347.Google Scholar
  20. Norden, B., Batra, S.W.T., Fales, H.M., Hefetz, A., andShaw, G.J. 1980.Anthophora bees: Unusual glycerides from maternal Dufour's glands serve as larval food and cell lining.Science 207:1095–1097.Google Scholar
  21. Staab, H.A. 1962. Synthesis using heterocyclic amides (Azolides).Angew. Chem. Int. Ed. 71:351–367.Google Scholar
  22. Tengö, J., andBergström, G. 1976. Odor correspondence betweenMelitta females and males of their nest parasiteNomada flabopicta K. (Hymenoptera: Apoidea).J. Chem. Ecol. 2:57–65.Google Scholar

Copyright information

© Plenum Publishing Corporation 1982

Authors and Affiliations

  • R. M. Duffield
    • 1
  • W. E. LaBerge
    • 2
  • J. H. Cane
    • 3
  • J. W. Wheeler
    • 4
  1. 1.Department of ZoologyHoward UniversityWashington, D.C.
  2. 2.Section of Faunistic Surveys and Insect IdentificationState Natural History SurveyUrbana
  3. 3.Department of EntomologyUniversity of KansasLawrence
  4. 4.Department of ChemistryHoward UniversityWashington, D.C.

Personalised recommendations