K. Dettner et al., CHEMICAL DEFENSE OF GIANT SPRINGTAIL TETRODONTOPHORA-BIELANENSIS (WAGA) (INSECTA, COLLEMBOLA), Journal of chemical ecology, 22(5), 1996, pp. 1051-1074
The giant springtail, Tetrodontophora bielanensis (Waga), is character
ized by integumental openings (pseudocells) from which small droplets
of a sticky defensive fluid are secreted after molestation. The secret
ion originates initially from secretory cells below the pseudocellae;
subsequent irritations result in release of hemolymph, which was ident
ified by both chemical and microscopical methods as well as by scannin
g electron microscopy. Bioassays with topically treated ground beetles
Nebria brevicollis showed that the pseudocellular quid evokes a total
disorientation and cleansing behavior of the beetle. The main constit
uents were identified as the following pyrido-pyrazines: 2.3-dimethoxp
yrido[2.3-b]pyrazine (1), 3-isopropyl-2-methoxy pyrido[2,3-b] pyrazine
(2), and 2-methoxy-4H-pyrido[2,3-b]pyrazine-3-one (3). These alkaloid
s are mainly present in the pseudocellar quids of female and male spri
ngtails but are absent in their food or feces. Minor amounts are found
in the hemolymph of adults, while larvae contain traces of 2 only. Al
l compounds were synthesized and tested for activity. In natural conce
ntrations, the synthetic alkaloids elicited the same effects from the
ground beetles as the pseudocellar fluid.