TY - JOUR
T1 - Metabolic transformations of acquired lucibufagins by firefly "femmes fatales"
AU - González, Andrés
AU - Schroeder, Frank C.
AU - Attygalle, Athula B.
AU - Svatoš, Aleš
AU - Meinwald, Jerrold
AU - Eisner, Thomas
PY - 1999
Y1 - 1999
N2 - 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.
AB - 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.
KW - Chemical defense
KW - Coleoptera: Lampyridae
KW - Glycosylation
KW - Lucibufagins
KW - Oxidation
KW - Photinus ignitus
KW - Photuris
KW - Steroidal pyrones
UR - http://www.scopus.com/inward/record.url?scp=9444259116&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=9444259116&partnerID=8YFLogxK
U2 - 10.1007/s000490050040
DO - 10.1007/s000490050040
M3 - Article
AN - SCOPUS:9444259116
SN - 0937-7409
VL - 9
SP - 105
EP - 112
JO - Chemoecology
JF - Chemoecology
IS - 3
ER -