Actinidine from the defensive secretions of dolichoderine ants

Wheeler, J. W.; Olagbemiro, T. O.; Nash, Anne D; Blum, Murray S.

doi:10.1007/bf00988439

Cited by 25 publications

(14 citation statements)

References 6 publications

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“…The mode of action of iridomyrmecin as repellent or insecticide and its physiological effects are unknown. Despite iridomyrmecin being a rather rare natural product, structurally related iridoids such as actinidine, iridodial, and nepetalactone are more widespread and are found in the defensive secretions of a number of insects (e.g., Wheeler et al, 1977;Jefson et al, 1983;Tomalski et al, 1987;Huth and Dettner, 1990) and plants (e.g., catnip Nepeta cataria, Schultz et al, 2004). Furthermore, iridoid-glycosides are common secondary plant metabolites, and are as such part of the plants' defense strategy against insect herbivores.…”

Section: Discussionmentioning

confidence: 99%

Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin

et al. 2012

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Chemical defense mechanisms are widespread among insects but have rarely been demonstrated in parasitoid wasps. Here, we show that the Drosophila parasitoid Leptopilina heterotoma (Hymenoptera, Figitidae) produces (−)-iridomyrmecin and (+)-isoiridomyrmecin in a cephalic gland, and that these chemicals have a highly repellent effect on ants. Stereoselective synthesis of 4 stereoisomers of iridomyrmecin allowed us to demonstrate that the repellent effect of iridomyrmecins depends on the stereochemistry. Potential food items impregnated with natural doses of (−)-iridomyrmecin were avoided by ants much longer than those impregnated with (+)-iridomyrmecin, (+)-isoiridomyrmecin, or (−)-isoiridomyrmecin, respectively. Quantitative headspace analyses revealed furthermore that females and males of L. heterotoma released iridomyrmecins in higher amounts when confronted with ants. This is the first time, that (−)-iridomyrmecin and (+)-isoiridomyrmecin are reported as natural products. Females synthesize more iridomyrmecins than males, and the most active (−)-iridomyrmecin is produced by females only. We, therefore, hypothesize that this defense mechanism is used mainly by female wasps when foraging for Drosophila larvae on rotten fruits, but also may protect male wasps during dispersal.

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Section: Discussionmentioning

confidence: 99%

Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin

et al. 2012

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“…The compound occurs not only in T. marum, but in a number of insects, including ants and a walking stick (Meinwald et al 1962;Cavill et al 1976;Cornelius et al 1995). Similarly, nepetalactone, or catnip, the familiar active principle of the mint plant, Nepeta cataria (Meinwald 1954;Eisner 1964;Bellesia et al 1984), is produced for defense also by a walking stick (Smith et al 1979), and the isoprenoid alkaloid actinidine, a product of some plants (Torssell & Wahlberg 1967;Johnson & Waller 1971), occurs in ants (Wheeler et al 1977;Cavill et al 1982), walking sticks (Chow & Lin 1986;Ho & Chow 1993), and staphilinid beetles as well (Dettner & Schwinger 1990;Huth & Dettner 1990). Some methylcyclopentanoid monoterpenes occur without parallel representation in other species, as for instance, chrysomelidial from chrysomelid beetles (Meinwald et al 1977).…”

Section: Discussionmentioning

confidence: 99%

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Eisner¹,

Eisner²,

Aneshansley³

et al. 2000

Chemoecology

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The mint plant, Teucrium marum (family Labiatae), sometimes called cat thyme, contains two methylcyclopentanoid monoterpenes, dolichodial and teucrein. The former compound is potently anti-insectan. It is repellent to ants (Monomorium pharaonis) and induces preening reflexes in flies (Phormia regina) and cockroaches (Periplaneta americana). Evidence is presented suggesting that dolichodial, which is presumed to be the plant's chief defensive agent, is stored in the tiny epidermal capsules that beset the leaves. It is only when the leaves are injured (and the capsules ruptured) that the leaves become repellent. Teucrein, in contrast, has no anti-insectan potency. It is present predominantly in the leaf buds, unlike dolichodial, which is present mostly in mature leaves. It is argued that teucrein is the storage compound from which dolichodial is generated during leaf development.

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“…We also identified actinidine in the pygidial gland secretions, but could not determine any behavior modifying function of this substance in P. marginata. Actinidine also occurs in the pygidial gland secretions of the termite hunting ponerine species Megaponera foetens, where it elicits alarm reactions (Janssen et al in press), and in several dolichoderine species it may function as a repellent substance (Wheeler et al 1977;Tomalski et al 1987).…”

Section: Discussionmentioning

confidence: 99%

Communication in the migratory termite-hunting ant Pachycondyla (= Termitopone) marginata (Formicidae, Ponerinae)

et al. 1996

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The Neotropical species Pachycondyla mar9inata conducts well-organized predatory raids on the termite species Neocapritermes opacus and frequently emigrates to new nest sites. During both activities the ants employ chemical trail communication. The trail pheromone orginates from the pygidial gland. Among the substances identified in the pygidial gland secretions, only citronellal was effective as a trail pheromone. Isopulegol elicited an increase in locomotory activity in the ants and may function as a synergist recruitment signal. The chemical signal is enhanced by a shaking display performed by the recruiting ant.

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Actinidine from the defensive secretions of dolichoderine ants

Cited by 25 publications

References 6 publications

Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin

Stereoselective Chemical Defense in the Drosophila Parasitoid Leptopilina heterotoma is Mediated by (−)-Iridomyrmecin and (+)-Isoiridomyrmecin

Chemical defense of the mint plant, Teucrium marum (Labiatae)

Communication in the migratory termite-hunting ant Pachycondyla (= Termitopone) marginata (Formicidae, Ponerinae)

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