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Literature DB >> 8482947

Alkaloids from bufonid toads (Melanophryniscus): decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines.

H M Garraffo¹, T F Spande, J W Daly, A Baldessari, E G Gros.

Abstract

Skins of bufonid toads of the genus Melanophryniscus contain several classes of alkaloids: decahydroquinolines, pumiliotoxins, allopumiliotoxins, homopumiliotoxins, both 3,5- and 5,8-disubstituted indolizidines, 3,5-disubstituted pyrrolizidines, and a 1,4-disubstituted quinolizidine. Tricyclic alkaloids, including precoccinelline [193A] and alkaloid 236, an oxime methyl ether, are present in one population of Melanophryniscus stelzneri.

Entities: Chemical Species

Mesh：

Substances：
Alkaloids

Year: 1993 PMID： 8482947 DOI： 10.1021/np50093a008

Source DB: PubMed Journal: J Nat Prod ISSN： 0163-3864 Impact factor: 4.050

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Cited

19 in total

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

Authors: Valerie C Clark; Christopher J Raxworthy; Valérie Rakotomalala; Petra Sierwald; Brian L Fisher
Journal: Proc Natl Acad Sci U S A Date: 2005-08-08 Impact factor: 11.205

2. Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.

Authors: John W Daly; Tetsuo Kaneko; Jason Wilham; H Martin Garraffo; Thomas F Spande; Alex Espinosa; Maureen A Donnelly
Journal: Proc Natl Acad Sci U S A Date: 2002-10-14 Impact factor: 11.205

3. Dietary sequestration of defensive steroids in nuchal glands of the Asian snake Rhabdophis tigrinus.

Authors: Deborah A Hutchinson; Akira Mori; Alan H Savitzky; Gordon M Burghardt; Xiaogang Wu; Jerrold Meinwald; Frank C Schroeder
Journal: Proc Natl Acad Sci U S A Date: 2007-02-06 Impact factor: 11.205

4. Individual and Geographic Variation of Skin Alkaloids in Three Swamp-Forest Species of Madagascan Poison Frogs (Mantella).

Authors: Nirina R Andriamaharavo; H Martin Garraffo; Thomas F Spande; Lesley-Ann Giddings; David R Vieites; Miguel Vences; Ralph A Saporito
Journal: J Chem Ecol Date: 2015-09-02 Impact factor: 2.626

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

Authors: Maggie M Hantak; Taran Grant; Sherri Reinsch; Dale McGinnity; Marjorie Loring; Naoki Toyooka; Ralph A Saporito
Journal: J Chem Ecol Date: 2013-11-06 Impact factor: 2.626

Alkaloids from bufonid toads (Melanophryniscus): decahydroquinolines, pumiliotoxins and homopumiliotoxins, indolizidines, pyrrolizidines, and quinolizidines.

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

2. Bioactive alkaloids of frog skin: combinatorial bioprospecting reveals that pumiliotoxins have an arthropod source.

3. Dietary sequestration of defensive steroids in nuchal glands of the Asian snake Rhabdophis tigrinus.

4. Individual and Geographic Variation of Skin Alkaloids in Three Swamp-Forest Species of Madagascan Poison Frogs (Mantella).

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

6. Contact toxicities of anuran skin alkaloids against the fire ant (Solenopsis invicta).

7. Evidence for an enantioselective pumiliotoxin 7-hydroxylase in dendrobatid poison frogs of the genus Dendrobates.

8. Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B.

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

10. N-methyldecahydroquinolines: an unexpected class of alkaloids from Amazonian poison frogs (Dendrobatidae).