Journal of Chemical Ecology

, Volume 18, Issue 1, pp 27–37 | Cite as

Mandibular gland secretions of the male beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher (Hymenoptera: Sphecidae)

  • C. A. McDaniel
  • J. O. Schmidt
  • R. W. Howard


The composition of the territorial marking pheromones from mandibular glands of males of the beewolvesPhilanthus crabroniformis, P. barbatus, andP. pulcher have been determined. The structures of the components were elucidated by gas chromatography-mass spectrometry and gas chromatography-Fourier transform infrared spectroscopy. The major compound ofP. crabroniformis is isopropyl tetradecanoate, with somewhat lesser amounts of 2-tridecanone, 3-methyl-3-butenyl tetradecanoate, and 92∶8 (Z)∶(E)-11-eicosen-1-ol. The major compounds ofP. barbatus are ethyl tetradecanoate and hexadecanal, which are present in approximately a 60∶40 ratio. These two compounds comprise over 95% of the neutral lipids. Also present in lesser amounts are ethyl dodecanoate, tetradecanal, hexadecan-1-ol, a Δ x -octadecen-1-ol, and octadecan-1-ol. The major compounds ofP. pulcher are ethyl (Z)-7-hexadecenoate and geranylgeraniol acetate, which comprise nearly 90% of the neutral lipid fraction, with smaller amounts of tetradecanal, pentadecanal, and ethyl hexadecanoate; trace amounts of Δ x hexadecenal, hexadecanal, and octadecanal are also present.

Key Words

Philanthus crabroniformis Philanthus barbatus Philanthus pulcher Hymenoptera Sphecidae beewolf mandibular glands pheromones semiochemicals mass spectrometry infrared spectroscopy 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Ahlquist, L., Bergström, G., andLiljenberg, C. 1978. Acyclic diterpene alcohols: occurrence and synthesis of geranylcitronellol, phytol and geranylgeraniol.Prog. Chem. Fats Other Lipids 16:231–255.Google Scholar
  2. Alcock, J. 1974. The behavior ofPhilanthus crabroniformis (Hymenoptera: Sphecidae).J. Zool., London 173:233–246.Google Scholar
  3. Alcock, J. 1975. Territorial behavior by males ofPhilanthus multimaculatus (Hymenoptera: Sphecidae) with a review of territoriality in male sphecids.Anim. Behav. 23: 889–895.Google Scholar
  4. Blum, M.S. 1981. Chemical Defenses of Arthropods. Academic Press, New York. 562 pp.Google Scholar
  5. Borg-Karlson, A.-K., andTengo, J. 1980. Pyrazines as marking volatiles in philanthine and nyssonine wasps (Hymenoptera; Sphecidae).J. Chem. Ecol. 6(4):827–835.Google Scholar
  6. Buser, H.-R., Arn, H., Guerin, P., andRauscher, S. 1983. Determination of double bond positions in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts.Anal. Chem. 55:818–822.Google Scholar
  7. Cavill, G.W.K., andHoughton, E. 1974. Volatile constituents of the Argentine ant,Iridomyrmex humilis.J. Insect Physiol. 20:2048–2059.Google Scholar
  8. Dettner, K. 1984. Isopropyl esters as wetting agents from the defensive secretion of the rove beetleCoprophilus striatulus F. (Coleoptera, Staphylinidae).Insect Biochem. 14:383–390.Google Scholar
  9. Duffield, R.M., Laberge, W.E., Cane, J.H., andWheeler, J.W. 1982. Exocrine secretions of bees IV: Macrocyclic lactones and isopentenyl esters in DuFour's gland secretions ofNomia bees (Hymenoptera: Halictidae).J. Chem. Ecol. 8:535–543.Google Scholar
  10. Dunkelblum, E., Tan, S.H., andSilk, P.J. 1985. Double-bond location in monounsaturated fatty acids by dimethyl disulfide derivatization and mass spectrometry: application to analysis of fatty acids in pheromone glands of four lepidoptere.J. Chem. Ecol. 11(3):265–277.Google Scholar
  11. Evans, H.E. 1982. Nesting and territorial behavior ofPhilanthus barbatus Smith (Hymenoptera: Sphecidae).J. Kans. Entomol. Soc. 55:571–576.Google Scholar
  12. Evans, H.E., andO'Neill, K.M. 1988. The Natural History and Behavior of North American Beewolves. Cornell University Press, Ithica, New York. 278 pp.Google Scholar
  13. Francis, G.W., andVeland, K. 1981. Alkylthiolation for the determination of double-bond positions in linear alkenes.J. Chromatogr. 219:379–384.Google Scholar
  14. Francke, W., Levinson, A.R., Jen, T.-L., andLevinson, H.Z. 1979. Carbonsäure-isopropylester—ein neue klasse von insektenpheromonen.Angew. Chem. 91:843–844.Google Scholar
  15. Free, J.B., Williams, I.H., Pickett, J.A., Ferguson, A.W., andMartin, A.P. 1982. Attractiveness of (Z)-11-eicosen-1-ol to foraging honeybees.J. Apic. Res. 21:151–156.Google Scholar
  16. Gwynne, D.T. 1978. Male territoriality in the bumblebee wolf,Philanthus bicinctus (Mickel) (Hymenoptera: Sphecidae): Observations on the behaviour of individual males. Z.Tierpsychol. 47:89–103.Google Scholar
  17. Hedin, P.A., Davis, F.M., Dickens, J.C., Burks, M.L., Bird, T.G., andKnutson, A.E. 1986. Identification of the sex attractant pheromone of the southwestern corn borerDiatraea grandiosella Dyar.J. Chem. Ecol. 12:2051–2063.Google Scholar
  18. McDaniel, C.A., andHoward, R.W. 1985. Mass spectral determination of aldehydes, ketones, and carboxylic acids using 1,1-dimethylhydrazine.J. Chem, Ecol. 11:303–310.Google Scholar
  19. McDaniel, C.A., Howard, R.W., O'Neill, K.M., andSchmidt, J.O. 1987. Chemistry of male mandibular secretions ofPhilanthus basilaris Cresson andPhilanthus bicinctus (Mickel) (Hymenoptera: Sphecidae).J. Chem. Ecol. 13:227–235.Google Scholar
  20. O'Neill, K.M. 1979. Territorial behavior in males ofPhilanthus psyche (Hymenoptera, Sphecidae).Psyche 86:19–43.Google Scholar
  21. O'Neill, K.M. 1983. Territoriality, body size, and spacing in males of the beewolfPhilanthus basilaris (Hymenoptera; Sphicidae).Behaviour 86:295–321.Google Scholar
  22. Opdyke, D.L.J. 1976. Isopropylmyristate.Food Cosmet. Toxicol. 14:323–326.Google Scholar
  23. Schmidt, J.O., O'Neill, K.M., Fales, H.M., McDaniel, C.A., andHoward, R.W. 1985. Volatiles from mandibular glands of male beewolves (Hymenoptera: Sphecidae,Philanthus) and their possible roles.J. Chem. Ecol. 11:895–901.Google Scholar
  24. Schmidt, J.O., McDaniel, C.A., andSimon Thomas, R.T. 1990. Chemistry of male mandibular gland secretions ofPhilanthus triangulum.J. Chem. Ecol. 16:2135–2143.Google Scholar
  25. Schwartz, D.P., Brewington, C.R., andWeidhranch, J.T. 1972. Methods for the isolation and characterization of constituents of natural products. XVII. A simple microhydrogenation technique.Microchem. J. 17:677–681.Google Scholar
  26. Scribe, P., Guezennec, J.D., Pepe, C., andSaliot, A. 1988. Identification of the position and stereochemistry of the double bond in monounsaturated fatty acid methyl esters by gas chromatography/mass spectrometry of dimethyl disulfide derivatives.Anal. Chem. 60:928–931.Google Scholar
  27. Simon Thomas, R.T., andPoorter, E.P.R. 1972. Notes on the behaviour of males ofPhilanthus triangulum (F.) (Hymenoptera, Sphecidae).Tijdschrifi Etomol. Deel. 115:141–151.Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • C. A. McDaniel
    • 1
  • J. O. Schmidt
    • 2
  • R. W. Howard
    • 3
  1. 1.Forestry Sciences LaboratoryUSDA-Forest ServiceGulfport
  2. 2.Carl Hayden Bee Research CenterTucson
  3. 3.U.S. Grain Marketing Research LaboratoryManhattan

Personalised recommendations