Latonduines A and B, new alkaloids isolated from the marine sponge Stylissa carteri: structure elucidation, synthesis, and biogenetic implications.
[structure: see text] Latonduines A (6) and B (7), two new alkaloids with unprecedented heterocyclic skeletons, have been isolated from the Indonesian marine sponge Stylissa carteri. The structures of the latonduines were elucidated by analysis of spectroscopic data and confirmed by the total synthesis of latonduine A (6). It is proposed that ornithine is the biogenetic precursor to the aminopyrimidine fragment of the latonduines.
Linington
Roger G
RG
Department of Chemistry, University of British Columbia, Vancouver, B.C., Canada V6T 1Z1.
Williams
David E
DE
Tahir
Akbar
A
van Soest
Rob
R
Andersen
Raymond J
RJ
D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009952:Ornithine / Q000737:chemistry; D011161:Porifera / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization
D000470:Alkaloids; D006575:Heterocyclic Compounds, 3-Ring; D011743:Pyrimidines; C478428:latonduine A; C478429:latonduine B; D009952:Ornithine