A major alkaloid, 217A, in skin extracts of a mantelline frog (Mantella baroni) was isolated by HPLC and the structure defined by 1H-NMR spectral analysis as (1R,4S,10S)- or (1R,4R,10R)- 1-methyl-4-(Z)-(1-pent-2-en-4-ynyl) quinolizidine (1). Four other alkaloids-207I (2), 231A (3), 233A (4), and 235E' (5)-detected in frog skin extracts are proposed to be 1,4-disubstituted quinolizidines based on diagnostic mass and FTIR spectra.
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http://dx.doi.org/10.1021/np9605100 | DOI Listing |
Org Biomol Chem
August 2017
Institute of Organic Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
Aliphatic macrolides are used by various organisms as semiochemicals or pheromones, e.g. by the endemic Madagascan frog family Mantellinae.
View Article and Find Full Text PDFChemistry
March 2014
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig (Germany).
Macrolide lactones, the so called cucujolides derived from unsaturated fatty acids, are aggregation pheromones of cucujid grain beetles. Thirty years ago, Oehlschlarger et al. showed that (3Z,6Z)-dodeca-3,6-dien-11-olide (4) and the respective 12-olide (7) attract the sawtoothed grain beetle Oryzaephilus surinamensis, whereas (5Z,8Z,13R)-tetradeca-5,8-dien-13-olide (5) increases the response synergistically.
View Article and Find Full Text PDFJ Nat Prod
September 2013
Institut für Organische Chemie, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany.
Acoustic and, to a lesser degree, visual signals are the predominant means of signaling in frogs. Nevertheless, certain lineages such as the mantelline frogs from Madagascar use the chemical communication channel as well. Males possess femoral glands on the hind legs, which recently have been shown to contain volatile compounds used in communication as pheromones.
View Article and Find Full Text PDFNaturwissenschaften
June 2010
Museo Regionale di Scienze Naturali, Via G. Giolitti, 36, 10123, Torino, Italy.
We describe a new mantelline frog of the genus Blommersia found in rainforest in North East Madagascar, from the protected areas of Ambatovaky, Betampona, Masoala, and Zahamena. Blommersia angolafa n.sp.
View Article and Find Full Text PDFToxicon
July 1997
Laboratory of Bioorganic Chemistry, National Institutes of Health, Bethesda, MD 20892, USA.
Mantelline frogs of the genus Mantella contain a variety of pumiliotoxin, allopumiliotoxin and homopumiliotoxin alkaloids in their skin. Pyrrolizidines, indolizidines and quinolizidines are also present. In contrast, captive-raised frogs (Mantella aurantiaca) have no alkaloids detectable in skin extracts.
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