Journal of Chemical Ecology

, Volume 37, Issue 4, pp 360–363 | Cite as

The Biosynthesis of Hexahydrofarnesylacetone in the Butterfly Pieris brassicae

  • Stefan Schulz
  • Selma Yildizhan
  • Joop J. A. van Loon
Rapid Communication


Hexahydrofarnesylacetone (6,10,14-trimethylpentadecan-2-one, 1) is a widespread ketone occurring in plants and insects. Several species use this compound or the respective alcohol as part of their pheromone bouquet. Here, we showed by using deuterium labeled phytol (3) and GC-MS experiments that the Large Cabbage White butterfly Pieris brassicae can take up phytol in the larval stage and transforms it into 1 by oxidative degradation.

Key Words

Biosynthesis Pheromone Labeled compounds Terpenes 



We thank the Deutsche Forschungsgemeinschaft for funding part of this research.


  1. Eltz, T., Hedenström, E., Bång, J., Wallin, E., and Andersson, J. 2010. (6R,10R)-6,10,14-Trimethylpentadecan-2-one, a dominant and behaviorally active component in male orchid bee fragrances. J. Chem. Ecol. 36:1322–1326PubMedCrossRefGoogle Scholar
  2. Kalinova, B., Kindl, J., Jiros, P., Zacek, P., Vasickova, S., Budesinsky, M., and Valterova, I. 2009. Composition and electrophysiological activity of constituents identified in male wing gland secretion of the bumblebee parasite Aphomia sociella. J. Nat. Prod. 72:8–13PubMedCrossRefGoogle Scholar
  3. Matile, P., Hörtensteiner, S., and Thomas, H. 1999. Chlorophyll degradation. Annu. Rev. Plant. Physiol. Plant. Mol. Biol. 50:67–95PubMedCrossRefGoogle Scholar
  4. Mori, K., Harada, H., Zagatti, P., Cork, A., and Hall, D.R. 1991. Pheromone synthesis, CXXVI. Synthesis and biological activity of four stereoisomers of 6,10,14-trimethyl-2-pentadecanol, the female-produced sex pheromone of rice moth (Corcyra cephalonica). Liebigs Ann. Chem. 1991:259–267CrossRefGoogle Scholar
  5. Nieberding, C.M., Vos, H. D., Schneider, M.V., Lassance, J.-M., Estramil, N., Andersson, J., Bâng, J., Hedenström, E., Löfstedt, C., and Brakefield, P.M. 2008. The male sex pheromone of the butterfly Bicyclus anynana: Towards an evolutionary analysis. PLoS One 3:e2751PubMedCrossRefGoogle Scholar
  6. Sasaerila, Y., Gries, R., Gries, G., Khaskin, G., King, S., Takács, S., and Hardi 2003. Sex pheromone components of male Tirathaba mundella; (Lepidoptera: Pyralidae). Chemoecology 13:89–93Google Scholar
  7. Schulz, S. and Nishida, R. 1996. The pheromone system of the male danaine butterfly, Idea leuconoe. Bioorg. Med. Chem. 4:341–349PubMedCrossRefGoogle Scholar
  8. Schulz, S., Boppré, M., and Vane-Wright, R.I. 1993. Specific mixtures of secretions from male scent organs of african milkweed butterflies (Danainae). Phil. Trans. R. Soc. Lond. B 342:161–181CrossRefGoogle Scholar
  9. Vendilo, N.V., Lebedeva, K.V., Ponomarev, V.L., and Pletnev, V.A. 1998. Identification of the pheromone of the male of the greater wax moth Galleria mellonella (Lepidoptera: Galleriinae). Agrokhimiya 12:52–56Google Scholar
  10. Vogel, J.T., Tan, B.-C., McCarty, D.R., and Klee, H.J. 2008. The carotenoid cleavage dioxygenase 1 enzyme has broad substrate specificity, cleaving multiple carotenoids at two different bond positions. J. Biol. Chem. 283:11364–11373PubMedCrossRefGoogle Scholar
  11. Yildizhan, S., van Loon, J.J.A., Sramkova, A., Ayasse, M., Arsene, C., Broeke, C.T., and Schulz, S. 2009. Aphrodisiac pheromones from the wings of the small cabbage white and large cabbage white butterflies, Pieris rapae and Pieris brassicae. ChemBioChem 10:1666–1677PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Stefan Schulz
    • 1
  • Selma Yildizhan
    • 1
  • Joop J. A. van Loon
    • 2
  1. 1.Institut für Organische ChemieTechnische Universität BraunschweigBraunschweigGermany
  2. 2.Laboratory of EntomologyWageningen UniversityWageningenThe Netherlands

Personalised recommendations