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

Clark, Valerie C.; Raxworthy, Christopher J.; Rakotomalala, Valérie; Sierwald, Petra; Fisher, Brian L.

doi:10.1073/pnas.0503502102

Cited by 114 publications

(96 citation statements)

References 66 publications

(78 reference statements)

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“…The spiropyrrolizidine alkaloid 236 was detected in a mixed oribatid mite sample (Tables 1 and 2) and has been identified previously in siphonotid millipedes (8,11). Spiropyrrolizidine 236 is found as a major alkaloid in some populations of O. pumilio, and spiropyrrolizidines are known from most poison frog families but do not make up a large percentage of known alkaloids.…”

Section: Resultsmentioning

confidence: 98%

“…Only two branched-chain izidines have been reported from ants: a 5,6,8-I detected in a mixed sample of myrmicine ants from Panama (8) (that sample probably also contained mites) and a 5,8-I from a Madagascan myrmicine ant of the genus Tetramorium (11). Although all unbranched-chain poison frog alkaloids have been presumed to derive from myrmicine ants (10), here we report one 3,5-disubstituted indolizidine (3,5-I) and one 4,6-disubstituted quinolizidine (4,6-Q) from oribatid mites (Tables 1 and 2).…”

Section: Resultsmentioning

confidence: 99%

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Oribatid mites as a major dietary source for alkaloids in poison frogs

Saporito

Donnelly²,

Norton³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

160

181

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Alkaloids in the skin glands of poison frogs serve as a chemical defense against predation, and almost all of these alkaloids appear to be sequestered from dietary arthropods. Certain alkaloid-containing ants have been considered the primary dietary source, but dietary sources for the majority of alkaloids remain unknown. Herein we report the presence of ≈80 alkaloids from extracts of oribatid mites collected throughout Costa Rica and Panama, which represent 11 of the ≈24 structural classes of alkaloids known in poison frogs. Forty-one of these alkaloids also occur in the dendrobatid poison frog, Oophaga pumilio , which co-occurs with the collected mites. These shared alkaloids include twenty-five 5,8-disubstituted or 5,6,8-trisubstituted indolizidines; one 1,4-disubstituted quinolizidine; three pumiliotoxins; and one homopumiliotoxin. All but the last of these alkaloid classes occur widely in poison frogs. In addition, nearly 40 alkaloids of unknown structure were detected in mites; none of these alkaloids have been identified in frog extracts. Two of these alkaloids are homopumiliotoxins, five appear to be izidines, four appear to be tricyclics, and six are related in structure to poison frog alkaloids that are currently unclassified as to structure. Mites are common in the diet of O. pumilio , as well as in the diets of other poison frogs. The results of this study indicate that mites are a significant arthropod repository of a variety of alkaloids and represent a major dietary source of alkaloids in poison frogs.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Oribatid mites as a major dietary source for alkaloids in poison frogs

Saporito

Donnelly²,

Norton³

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

160

181

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show abstract

“…The recent observation of defensive alkaloids from Mantella sp. poison frogs and Tetramorium electrum ants from southeastern Madagascar, including acetylenic 5,8-disubstituted indolizidine 21C, has been used to support convergent evolution of defensive alkaloid acquisition and/or biosynthetic pathways between Malagasy ant species and Neotropical ants [268]. Given the local distributions of the frog/ant ecosystems, it is tempting to consider that the acetylenic compound may be produced by an ant symbiont or local flora and acquired by the ants for their benefit.…”

Section: Acetylenic Alkaloidsmentioning

confidence: 99%

“…Compounds 21D and 21E were found in both dendrobatid frogs and virgin queens of Solenopsis azteca collected from a Puerto Rican hillside, while captive frogs are known not to accumulate the alkaloid toxins. The sequestration of groups of alkaloids in skin glands that mirror ant secondary metabolites suggests that frog alkaloids may not be chemically modified by the frogs [267]; an observation which has found few exceptions [268]. The formation of the bicyclic 2,5-disubstituted decahydroquinoline (e.g, 21G and 21H) and histrionicotoxin (THX) ring systems is presumed to occur from enamine 21F via electrophilic catalysis (Fig.…”

Section: Acetylenic Alkaloidsmentioning

confidence: 99%

Biosynthesis and function of polyacetylenes and allied natural products

Minto

Blacklock

2008

Progress in Lipid Research

291

228

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Polyacetylenic natural products are a substantial class of often unstable compounds containing a unique carbon-carbon triple bond functionality, that are intriguing for their wide variety of biochemical and ecological functions, economic potential, and surprising mode of biosynthesis. Isotopic tracer experiments between 1960 and 1990 demonstrated that the majority of these compounds are derived from fatty acid and polyketide precursors. During the past decade, research into the metabolism of polyacetylenes has swiftly advanced, driven by the cloning of the first genes responsible for polyacetylene biosynthesis in plants, moss, fungi, and actinomycetes, and the initial characterization of the gene products.The current state of knowledge of the biochemistry and molecular genetics of polyacetylenic secondary metabolic pathways will be presented together with an up-to-date survey of new terrestrial and marine natural products, their known biological activities, and a discussion of their likely metabolic origins.

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“…Among the most widespread forms of defensive chemicals are pyrrolidine alkaloids, a class of defense compounds that many arthropods acquire from their food or biosynthesize, which are toxic or unpalatable to a vast array of potential predators [1][2][3]. Producing these chemical defenses may be costly, perhaps reflected by the close link between their expression and the risk of predation at the population level [4] or following enemy attack at the individual level [5].…”

Section: Introductionmentioning

confidence: 99%

A novel property of spider silk: chemical defence against ants

et al. 2011

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Spider webs are made of silk, the properties of which ensure remarkable efficiency at capturing prey. However, remaining on, or near, the web exposes the resident spiders to many potential predators, such as ants. Surprisingly, ants are rarely reported foraging on the webs of orb-weaving spiders, despite the formidable capacity of ants to subdue prey and repel enemies, the diversity and abundance of orb-web spiders, and the nutritional value of the web and resident spider. We explain this paradox by reporting a novel property of the silk produced by the orb-web spider Nephila antipodiana (Walckenaer). These spiders deposit on the silk a pyrrolidine alkaloid (2-pyrrolidinone) that provides protection from ant invasion. Furthermore, the ontogenetic change in the production of 2-pyrrolidinone suggests that this compound represents an adaptive response to the threat of natural enemies, rather than a simple by-product of silk synthesis: while 2-pyrrolidinone occurs on the silk threads produced by adult and large juvenile spiders, it is absent on threads produced by small juvenile spiders, whose threads are sufficiently thin to be inaccessible to ants.

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

Cited by 114 publications

References 66 publications

Oribatid mites as a major dietary source for alkaloids in poison frogs

Oribatid mites as a major dietary source for alkaloids in poison frogs

Biosynthesis and function of polyacetylenes and allied natural products

A novel property of spider silk: chemical defence against ants

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