A distinctive structural twist in the aminoimidazole alkaloids from a calcareous marine sponge: isolation and characterization of leucosolenamines A and B.
Bioassay-guided fractionation of Papua New Guinea collections of Leucosolenia sp. resulted in the isolation of the novel compounds leucosolenamines A (5) and B (6) and the known compound thymidine (7). Compound 5 contains a 2-aminoimidazole core substituted at C-4 and C-5 by an N,N-dimethyl-5,6-diaminopyrimidine-2,4-dione and a benzyl group, respectively. Compound 6 retains the same core structure; however C-4 is substituted by a 5,6-diamino-1,3-dimethyl-4-(methylimino)-3,4-dihydropyrimidin-2(1H)-one moiety. This substitution pattern is unique and has never been observed in calcareous imidazole alkaloid chemistry. Leucosolenamine A (5) was mildly cytotoxic against the murine colon adenocarcinoma C-38 cell line.
Ralifo
Paul
P
Department of Chemistry and Biochemistry, Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Tenney
Karen
K
Valeriote
Frederick A
FA
Crews
Phillip
P
D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007093:Imidazoles / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D008386:Marine Biology; D051379:Mice; D015394:Molecular Structure; D010219:Papua New Guinea; D011161:Porifera / Q000737:chemistry*
D000470:Alkaloids; D000970:Antineoplastic Agents; D007093:Imidazoles; C517581:leucosolenamine A; C517582:leucosolenamine B