A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar

N.R. Andriamaharavo, M. Andriantsiferana, Paul Stevenson, G. O'Mahony, H.J.C. Yeh, T. Kaneko, H.M. Garraffo, T.F. Spande, J.W. Daly

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7 Citations (Scopus)

Abstract

Madagascan frogs of the mantellid genus Mantella have been a rich source of alkaloids derived from dietary arthropods. Two species of frogs, inhabiting swamp forest, contain a unique set of alkaloids, previously proposed, based only on GC-MS and GC-FTIR data, to represent dehydro analogues of the homopumiliotoxins. The major alkaloid of this set, alkaloid 235C (2), now has been isolated in sufficient quantities (ca. 0.3 mg) to allow determination of the structure by NMR analysis. The structure of alkaloid 235C proved to be a 7,8-dehydro-8-desmethylpumiliotoxin. A comparison is presented between the mass, infrared, and H-1 NMR spectra of 235C (2) and a synthetic dehydrohomopumiliotoxin (1), initially proposed incorrectly as the structure for 235C.
Original languageEnglish
Pages (from-to)1743-1748
Number of pages6
JournalJournal of Natural Products
Volume68
Issue number12
DOIs
Publication statusPublished - Dec 2005

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

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    Andriamaharavo, N. R., Andriantsiferana, M., Stevenson, P., O'Mahony, G., Yeh, H. J. C., Kaneko, T., Garraffo, H. M., Spande, T. F., & Daly, J. W. (2005). A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar. Journal of Natural Products, 68(12), 1743-1748. https://doi.org/10.1021/np058089f