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

doi:10.1021/np058089f

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

School of Chemistry and Chemical Engineering

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	1743-1748
Number of pages	6
Journal	Journal of Natural Products
Volume	68
Issue number	12
DOIs	https://doi.org/10.1021/np058089f
Publication status	Published - 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

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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.",

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

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A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar. / Andriamaharavo, N.R.; Andriantsiferana, M.; Stevenson, Paul; O'Mahony, G.; Yeh, H.J.C.; Kaneko, T.; Garraffo, H.M.; Spande, T.F.; Daly, J.W.

In: Journal of Natural Products, Vol. 68, No. 12, 12.2005, p. 1743-1748.

Research output: Contribution to journal › Article

TY - JOUR

T1 - A revised structure for alkaloid 235C isolated from skin extracts of mantellid (Mantella) frogs of Madagascar

AU - Andriamaharavo, N.R.

AU - Andriantsiferana, M.

AU - Stevenson, Paul

AU - O'Mahony, G.

AU - Yeh, H.J.C.

AU - Kaneko, T.

AU - Garraffo, H.M.

AU - Spande, T.F.

AU - Daly, J.W.

PY - 2005/12

Y1 - 2005/12

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AB - 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.

U2 - 10.1021/np058089f

DO - 10.1021/np058089f

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