Chemical defense in Platyphora kollari Baly and Leptinotarsa behrensi Harold (Coleoptera: Chrysomelidae). Hypotheses on the origin and evolution of leaf beetles toxins

Plasman, Valérie; Plehiers, M.; Braekman, Jean Claude; Daloze, Désiré; Biseau, J. C. de; Pasteels, Jacques

doi:10.1007/pl00001839

Cited by 20 publications

(12 citation statements)

References 21 publications

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“…In this species, the triterpene glycosides appear to deter predation, microbial attachment, and fouling by invertebrates and algae; in another species, Ectyoplasia ferox, they were shown to be anti-predatory and allelopathic (Kubanek et al, 2002 (Plasman et al, 2000a;Plasman et al, 2000b). These secretions are produced by glands localized on the elytra and on the pronotum of adult beetles (Plasman et al, 2001). In holothuroids, there are no data on the mode of action of saponins as a defense mechanism.…”

Section: Introductionmentioning

confidence: 99%

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

Dyck

Caulier

Todesco

et al. 2011

Journal of Experimental Biology

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SUMMARYMore than 100 triterpene glycosides (saponins) have been characterized in holothuroids in the past several decades. In particular, Holothuria forskali contains 26 saponins in its Cuvierian tubules and 12 in its body wall. This high diversity could be linked to a chemical defense mechanism, the most commonly accepted biological role for these secondary metabolites. We performed an integrated study of the body-wall saponins of H. forskali. The saponins are mainly localized in the epidermis and in the mesothelium of the body wall and appear to be released when the holothuroid is stressed. Among the saponins present in the epidermis, one (holothurinoside G) was detected in the seawater surrounding non-stressed holothuroids and three others (holohurinosides C and F, and desholothurin A) were secreted when the animals were stressed. In addition, two new congeners (detected at m/z 1301 and 1317) were also present in the immediate surroundings of stressed holothuroids. These new saponins do not originate from the epidermis and could come from an internal organ. Quantities of secreted saponins were very low compared with the body wall and Cuvierian tubules concentrations. At natural concentrations, saponins do not represent a threat to the health of predatory fish. The deterrent effect of saponins seems therefore to act as an aposematic signal, warning potential predators of the unpalatability of the holothuroid tissues.

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Section: Introductionmentioning

confidence: 99%

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

Dyck

Caulier

Todesco

et al. 2011

Journal of Experimental Biology

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“…[40,41] A similar dipeptide, g-l-glutamyl-l-(Z)-2-aminohex-3-enoic acid (24), was found in the defensive secretion of adult Platyphora kollari (Chrysomelinae). [42] A further glutamic acid derivative, gl-glutamyl-ethanolamine (25), was detected in defensive secretions of the adult Chrysomelinae Labidomera trimaculata, Zygogramma suturalis, and Chrysolina coerulans. [41,43] These compounds are structurally closely related to 1, because each contains a g-conjugated glutamic acid unit.…”

Section: Discussionmentioning

confidence: 99%

How to Spoil the Taste of Insect Prey? A Novel Feeding Deterrent against Ants Released by Larvae of the Alder Leaf Beetle, Agelastica alni

et al. 2010

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Chemical defense of leaf beetle larvae (Chrysomelidae) against enemies is provided by secretions containing a wide range of deterrent compounds or by unpalatable hemolymph constituents. Here we report a new, very strong feeding deterrent against ants released by larvae of the alder leaf beetle Agelastica alni when attacked. The larvae release a defensive fluid from openings of pairwise, dorsolaterally located tubercles on the first to the eighth abdominal segments. The fluid, consisting of hemolymph and probably a glandular cell secretion, has previously been shown to contain a very stable, non-volatile feeding deterrent. The major deterrent component was isolated by repeated HPLC separation and analyzed by NMR and MS. The compound proved to be gamma-L-glutamyl-L-2-furylalanine (1), a novel dipeptide containing the unusual amino acid L-2-furylalanine. This amino acid, although synthetically well known, has not previously been reported from natural sources. The absolute configuration of the natural compound was elucidated by enantioselective gas chromatography after derivatization. The structure of the dipeptide was verified by the synthesis of several isomeric dipeptides. In bioassays a concentration of 1 microg microL(-1) was sufficient to deter polyphagous Myrmica rubra ants from feeding.

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“…Saponins were found so far in most investigated Platyphora species, with the exception of one species feeding on Solanum (Termonia, unpublished result). Saponins were also observed in closely related outgroups such as Desmogramma subtropica (Plasman et al 2000b) and Leptinotarsa behrensi (Plasman et al 2001). Although the biosynthetic origin of beetles' saponins is still unknown, they are not present as such in the beetles' food plants, and their production seems largely independent of the plant families (five so far) on which the beetles specialized (for further discussion on the biosynthetic origin of the beetles' saponins, see Plasman et al 2001).…”

Section: Discussionmentioning

confidence: 99%

Pyrrolizidine alkaloids and pentacyclic triterpene saponins in the defensive secretions of Platyphora leaf beetles

et al. 2001

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Field collected exocrine defensive secretions of nine neotropical Platyphora species were analyzed for the presence of plant acquired pyrrolizidine alkaloids (PAs) and pentacyclic triterpene saponins. All species secrete saponins. In addition, five species feeding on Tournefortia (Boraginaceae), Koanophyllon (Asteraceae, tribe Eupatorieae) and Prestonia (Apocynaceae) were shown to sequester PAs of the lycopsamine type, which are characteristic for species of the three plant families. The PA sequestering species commonly store intermedine, lycopsamine and their O 3% -acetyl or propionyl esters as well as O 7 -and O 9 -hydroxyisovaleryl esters of retronecine. The latter as well as the O 3% -acyl esters were not found in the beetles' host plants, suggesting the ability of the beetles to esterify plant derived retronecine and intermedine or its stereoisomers. Despite the conformity of the beetles' PA patterns, considerable inconsistencies exist regarding the PA patterns of the respective host plants. One host plant was devoid of PAs, while another contained only simple necines. Since the previous history of the field collected beetles was unknown this discrepancy remains obscure. In contrast to the Palearctic chrysomeline leaf beetles, e.g. some Oreina species which ingest and store PAs as their non-toxic N-oxides, Platyphora leaf beetles absorb and store PAs as the toxic free base (tertiary PA), but apparently avoid to accumulate PAs in the haemolymph. This suggests that Chrysolina and Platyphora leaf beetles developed different lines of adaptations in their parallel evolution of PA mediated chemical defense.

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Chemical defense in Platyphora kollari Baly and Leptinotarsa behrensi Harold (Coleoptera: Chrysomelidae). Hypotheses on the origin and evolution of leaf beetles toxins

Cited by 20 publications

References 21 publications

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

The triterpene glycosides of Holothuria forskali: usefulness and efficiency as a chemical defense mechanism against predatory fish

How to Spoil the Taste of Insect Prey? A Novel Feeding Deterrent against Ants Released by Larvae of the Alder Leaf Beetle, Agelastica alni

Pyrrolizidine alkaloids and pentacyclic triterpene saponins in the defensive secretions of Platyphora leaf beetles

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