CHEMOECOLOGY

, Volume 9, Issue 3, pp 105–112

Metabolic transformations of acquired lucibufagins by firefly “femmes fatales”

  • Andrés González
  • Frank C. Schroeder
  • Athula B. Attygalle
  • Aleš Svatoš
  • Jerrold Meinwald
  • Thomas Eisner
Article

DOI: 10.1007/s000490050040

Cite this article as:
González, A., Schroeder, F., Attygalle, A. et al. Chemoecology (1999) 9: 105. doi:10.1007/s000490050040

Summary.

Female Photuris fireflies sequester defensive steroidal pyrones (lucibufagins) from male fireflies of the genus Photinus. Lucibufagin analyses of Photuris females and Photinus ignitus males show that the lucibufagin mixtures of predator and prey differ in their composition. Analyses of whole body extracts showed that P. ignitus males contain a mixture of eight non-glycosylated lucibufagins, composed mostly of compounds with two oxygenated positions in the steroidal A-ring (C-3, C-5). After feeding on P. ignitus males, Photuris females contain six major lucibufagins. Three of these compounds are not present in the prey, including the novel lucibufagin glycoside 5β,11α-dihydroxy-12-oxo-3β-O-β-D-xylopyranosylbufalin, and two other lucibufagins with a trioxygenated A-ring (C-2, C-3, C-5). These results indicate that Photuris females transform the sequestered lucibufagins both by glycosylation and oxidation, which could affect the systemic transportability of these compounds due to an increase in their polarity.

Key words.Photuris—Photinus ignitus— Coleoptera: Lampyridae — lucibufagins — steroidal pyrones — chemical defense — oxidation — glycosylation 

Copyright information

© Birkhäuser Verlag Basel, 1999

Authors and Affiliations

  • Andrés González
    • 1
  • Frank C. Schroeder
    • 2
  • Athula B. Attygalle
    • 2
  • Aleš Svatoš
    • 2
  • Jerrold Meinwald
    • 2
  • Thomas Eisner
    • 1
  1. 1.Section of Neurobiology and Behavior, Cornell University, Ithaca, NY 14853, USAUSA
  2. 2.Department of Chemistry and Chemical Biology, Cornell University, Ithaca, NY 14853, USAUSA
  3. 3.Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, CZ-166 10 Prague 6, Czech RepublicCzech Republic