Literature DB >> 18848574

Indolizidine 239Q and quinolizidine 275I. Major alkaloids in two Argentinian bufonid toads (Melanophryniscus).

John W Daly1, H Martin Garraffo, Thomas F Spande, Herman J C Yeh, Paola M Peltzer, Pedro M Cacivio, J Diego Baldo, Julián Faivovich.   

Abstract

Alkaloid profiles in skin of poison frogs/toads (Dendrobatidae, Mantellidae, Bufonidae, and Myobatrachidae) are highly dependent on diet and hence on the nature of habitat. Extracts of the two species of toads (Melanophryniscus klappenbachi and Melanophryniscus cupreuscapularis) from similar habitats in the Corrientes/Chaco Provinces of Argentina have similar profiles of alkaloids, which differ considerably in profiles from other Melanophryniscus species from Brazil, Uruguay and Argentina. Structures of two major alkaloids 239Q (1) and 275I (2) were determined by mass, FTIR, and NMR spectral analysis as 5Z,9Z-3-(1-hydroxybutyl)-5-propylindolizidine and 6Z,10E-4,6-di(pent-4-enyl) quinolizidine, respectively. A third alkaloid, 249F (3), is postulated to be a homopumiliotoxin with an unprecedented conjugated exocyclic diene moiety.

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Year:  2008        PMID： 18848574      PMCID： PMC2668131          DOI： 10.1016/j.toxicon.2008.08.016

Source DB:  PubMed          Journal:  Toxicon        ISSN： 0041-0101            Impact factor:   3.033


  37 in total

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6.  Geographic and seasonal variation in alkaloid-based chemical defenses of Dendrobates pumilio from Bocas del Toro, Panama.

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Journal:  J Chem Ecol       Date:  2006-05-05       Impact factor: 2.626

7.  Alkaloids in bufonid toads (melanophryniscus): temporal and geographic determinants for two argentinian species.

Authors:  J W Daly; J M Wilham; T F Spande; H M Garraffo; R R Gil; G L Silva; M Vaira
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8.  Evidence for biosynthesis of pseudophrynamine alkaloids by an Australian myobatrachid frog (pseudophryne) and for sequestration of dietary pumiliotoxins.

Authors:  B P Smith; M J Tyler; T Kaneko; H M Garraffo; T F Spande; J W Daly
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  9 in total

1.  Discovery of skin alkaloids in a miniaturized eleutherodactylid frog from Cuba.

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Authors:  Adriana M Jeckel; Taran Grant; Ralph A Saporito
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3.  Helminth community structure in the Argentinean bufonid Melanophryniscus klappenbachi: importance of habitat use and season.

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5.  Dietary alkaloid sequestration in a poison frog: an experimental test of alkaloid uptake in Melanophryniscus stelzneri (Bufonidae).

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6.  Caste-specific tyramides from Myrmicine ants.

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8.  Alkaloids from single skins of the Argentinian toad Melanophryniscus rubriventris (ANURA, BUFONIDAE): An unexpected variability in alkaloid profiles and a profusion of new structures.

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9.  Alkaloid defenses of co-mimics in a putative Müllerian mimetic radiation.

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