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

Author(s)

Daly, John W. ^[1] ; Garraffo, H. Martin ^[1] ; Spande, Thomas F. ^[1] ; Yeh, Herman J. C. ^[1] ; Peltzer, Paola M. ^[2] ; Cacivio, Pedro M. ^[3] ; Baldo, J. Diego ^[4] ; Faivovich, Julian ^[5]

Affiliation

^[1] NIDDKD, Bioorgan Chem Lab, NIH, DHHS, Bethesda, MD 20892 - USA

^[2] ESS FBCB UNL, Fac Bioquim & Ciencias Biol, CONICET, RA-3000 Santa Fe - Argentina

^[3] Consejo Nacl Invest Cient & Tecn, Museo Argentina Ciencias Nat, Div Herpetol, RA-1405 Buenos Aires, DF - Argentina

^[4] Univ Nacl Misiones, CONICET, Lab Genet Evolut, Fac Ciencias Exactas Quim & Nat, Dept Genet, Posadas, Misiones - Argentina

^[5] Univ Estadual Paulista, Inst Biociencias, Dept Zool, BR-13506900 Sao Paulo - Brazil

• Document type: Journal article
• Source: Toxicon; v. 52, n. 8, p. 858-870, DEC 15 2008.
• Web of Science Citations: 29

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 kiappenbachi 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 Metanophryniscus 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 5Z9Z-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. (C) 2008 Elsevier Ltd. All rights reserved. (AU)

• FAPESP's process: 05/56756-0 - Phylogenetic studies on hylid frogs: from the trunk to the tips
• Grantee: Julian Faivovich
• Support Opportunities: Research Grants - Young Investigators Grants