A distinctive structural twist in the aminoimidazole alkaloids from a calcareous marine sponge: isolation and characterization of leucosolenamines A and B

J Nat Prod. 2007 Jan;70(1):33-8. doi: 10.1021/np060462b.

Abstract

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.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Drug Screening Assays, Antitumor
  • Imidazoles / chemistry*
  • Imidazoles / isolation & purification*
  • Imidazoles / pharmacology
  • Marine Biology
  • Mice
  • Molecular Structure
  • Papua New Guinea
  • Porifera / chemistry*

Substances

  • Alkaloids
  • Antineoplastic Agents
  • Imidazoles
  • leucosolenamine A
  • leucosolenamine B