1,4-Benzoquinones in African Millipeds

Volume: 82Start Page: 78End Page: 8

Bioactive alkaloids of frog skin: Combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source

Nearly 500 alkaloids have been detected in skin extracts from frogs of the family Dendrobatidae. All seem to have been sequestered unchanged into skin glands from alkaloid-containing arthropods. Ants, beetles, and millipedes seem to be the source of decahydroquinolines, certain izidines, coccinellines, and spiropyrrolizidine oximes. But the dietary source for a major group of frog-skin alkaloids, namely the pumiliotoxins (PTXs), alloPTXs, and homoPTXs, remained a mystery. In hopes of revealing an arthropod source for the PTX group, small arthropods were collected from eight different sites on a Panamanian island, where the dendrobatid frog (Dendrobates pumilio) was known to contain high levels of two PTXs. The mixed arthropod collections from several sites, each representing up to 20 arthropod taxa, contained PTX 307A and/or alloPTX 323B. In addition, the mixed arthropod collections from several sites contained a 5,8-disubstituted indolizidine (205A or 235B), representing another class of alkaloids previously unknown from an arthropod. An ant alkaloid, decahydroquinoline 195A, was detected in the mixed arthropod collections from several sites. Thus, “combinatorial bioprospecting” demonstrates that further collection and analysis of individual taxa of leaf-litter arthropods should reveal the taxa from which PTXs, alloPTXs, and 5,8-disubstituted indolizidines are derived

Convergent evolution of chemical defense in poison frogs and arthropod prey between Madagascar and the Neotropics

With few exceptions, aposematically colored poison frogs sequester defensive alkaloids, unchanged, from dietary arthropods. In the Neotropics, myrmicine and formicine ants and the siphonotid millipede Rhinotus purpureus are dietary sources for alkaloids in dendrobatid poison frogs, yet the arthropod sources for Mantella poison frogs in Madagascar remained unknown. We report GC-MS analyses of extracts of arthropods and microsympatric Malagasy poison frogs (Mantella) collected from Ranomafana, Madagascar. Arthropod sources for 11 “poison frog” alkaloids were discovered, 7 of which were also detected in microsympatric Mantella. These arthropod sources include three endemic Malagasy ants, Tetramorium electrum, Anochetus grandidieri, and Paratrechina amblyops (subfamilies Myrmicinae, Ponerinae, and Formicinae, respectively), and the pantropical tramp millipede R. purpureus. Two of these ant species, A. grandidieri and T. electrum, were also found in Mantella stomachs, and ants represented the dominant prey type (67.3% of 609 identified stomach arthropods). To our knowledge, detection of 5,8-disubstituted (ds) indolizidine iso-217B in T. electrum represents the first izidine having a branch point in its carbon skeleton to be identified from ants, and detection of 3,5-ds pyrrolizidine 251O in A. grandidieri represents the first ponerine ant proposed as a dietary source of poison frog alkaloids. Endemic Malagasy ants with defensive alkaloids (with the exception of Paratrechina) are not closely related to any Neotropical species sharing similar chemical defenses. Our results suggest convergent evolution for the acquisition of defensive alkaloids in these dietary ants, which may have been the critical prerequisite for subsequent convergence in poison frogs between Madagascar and the Neotropics

Arthropod alkaloids

SCOPUS: ar.jinfo:eu-repo/semantics/publishe