Metabolic transformations of acquired lucibufagins by firefly "femmes fatales"

Gonzalez, Andres; Schroeder, Frank C.; Attygalle, Athula B.; Svatoš, Aleš; Meinwald, Jerrold; Eisner, Thomas

doi:10.1007/s000490050040

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Metabolic transformations of acquired lucibufagins by firefly "femmes fatales"

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Gonzalez, A., Schroeder, F. C., Attygalle, A. B., Svatoš, A., Meinwald, J., & Eisner, T. (1999). Metabolic transformations of acquired lucibufagins by firefly "femmes fatales". Chemoecology, 9(3), 105-112. doi:10.1007/s000490050040.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0015-0FA0-B

Abstract

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 5 beta, 11 alpha-dihydroxy-12-oxo-3 beta-O-beta-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.